# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2021

####################################################################### 
# 
# 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_808
_database_code_depnum_ccdc_archive 'CCDC 2055290'
loop_
_audit_author_name
_audit_author_address
'shichao wu'
;Shanxi University
China
;
_audit_update_record             
;
2021-01-11 deposited with the CCDC.	2021-06-09 downloaded from the CCDC.
;
_audit_creation_date             2021-01-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Ag Bi I8, 2(C6 H10 N2), H2 O'
_chemical_formula_sum            'C12 H22 Ag Bi I8 N4 O'
_chemical_formula_weight         1570.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   8.5258(4)
_cell_length_b                   9.7136(5)
_cell_length_c                   18.5101(10)
_cell_angle_alpha                86.146(2)
_cell_angle_beta                 88.192(2)
_cell_angle_gamma                88.857(2)
_cell_volume                     1528.46(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9820
_cell_measurement_temperature    200.02
_cell_measurement_theta_max      27.50
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.480
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3995
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1545 before and 0.0830 after correction.
The Ratio of minimum to maximum transmission is 0.5358.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'blackish red'
_exptl_crystal_colour_modifier   blackish
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    3.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.0360
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            55189
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_min         2.102
_diffrn_ambient_temperature      200.02
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6234
_reflns_number_total             7023
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.905
_refine_diff_density_min         -2.392
_refine_diff_density_rms         0.257
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         7023
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0302
_refine_ls_restrained_S_all      1.082
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0205P)²+5.9428P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0644
_refine_ls_wR_factor_ref         0.0675
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O1(H1D,H1E)
2.b Secondary CH2 refined with riding coordinates:
 C6(H6A,H6B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 N4(H4A), N2(H2), C1(H1), C3(H3), C4(H4), C7(H7), C9(H9), C8(H8), C10(H10),
 C2(H2A)
2.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N3(H3A,H3B,H3C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.87629(2) 0.21674(2) 0.75897(2) 0.01859(6) Uani 1 1 d . . . . .
I8 I 0.62971(4) -0.00941(4) 0.77636(2) 0.02446(9) Uani 1 1 d . . . . .
I6 I 1.12812(4) 0.01490(4) 0.80260(2) 0.02412(9) Uani 1 1 d . . . . .
I7 I 0.92619(5) 0.14106(4) 0.59870(2) 0.02626(9) Uani 1 1 d . . . . .
I1 I 0.39656(5) 0.67840(4) 0.88860(2) 0.02706(9) Uani 1 1 d . . . . .
I5 I 1.12044(5) 0.44680(4) 0.73591(3) 0.02853(10) Uani 1 1 d . . . . .
I2 I 0.33295(5) 0.80524(4) 0.61123(2) 0.02863(10) Uani 1 1 d . . . . .
I4 I 0.82080(5) 0.28583(4) 0.91591(2) 0.02979(10) Uani 1 1 d . . . . .
I3 I 0.60527(5) 0.43536(4) 0.71868(3) 0.03021(10) Uani 1 1 d . . . . .
Ag1 Ag 0.38758(8) 0.68169(8) 0.74285(3) 0.05193(17) Uani 1 1 d . . . . .
N1 N 0.3527(6) 1.1603(5) 0.6523(3) 0.0256(11) Uani 1 1 d . . . . .
H1A H 0.263490 1.114486 0.644381 0.031 Uiso 1 1 calc GR . . . .
H1B H 0.327408 1.240769 0.672730 0.031 Uiso 1 1 calc GR . . . .
H1C H 0.414276 1.107031 0.682712 0.031 Uiso 1 1 calc GR . . . .
N4 N 0.3401(7) 1.3238(6) -0.0635(3) 0.0359(13) Uani 1 1 d . . . . .
H4A H 0.379898 1.388317 -0.093977 0.043 Uiso 1 1 calc R . . . .
C11 C 0.1853(7) 1.2647(6) 0.0409(3) 0.0249(13) Uani 1 1 d . . . . .
N3 N 0.1815(7) 1.3438(6) 0.1647(3) 0.0365(14) Uani 1 1 d . . . . .
H3A H 0.238677 1.420027 0.151363 0.044 Uiso 1 1 calc GR . . . .
H3B H 0.247509 1.271517 0.176313 0.044 Uiso 1 1 calc GR . . . .
H3C H 0.118383 1.360833 0.203741 0.044 Uiso 1 1 calc GR . . . .
N2 N 0.1827(7) 1.3140(6) 0.4302(3) 0.0337(13) Uani 1 1 d . . . . .
H2 H 0.137837 1.277851 0.393939 0.040 Uiso 1 1 calc R . . . .
C1 C 0.2692(8) 1.2328(7) 0.4748(3) 0.0293(14) Uani 1 1 d . . . . .
H1 H 0.280702 1.137396 0.467047 0.035 Uiso 1 1 calc R . . . .
C3 C 0.2301(8) 1.5062(7) 0.4952(4) 0.0340(15) Uani 1 1 d . . . . .
H3 H 0.215653 1.601760 0.501909 0.041 Uiso 1 1 calc R . . . .
C5 C 0.3413(7) 1.2847(6) 0.5315(3) 0.0224(12) Uani 1 1 d . . . . .
C4 C 0.3199(7) 1.4246(6) 0.5423(3) 0.0273(13) Uani 1 1 d . . . . .
H4 H 0.366978 1.463448 0.581888 0.033 Uiso 1 1 calc R . . . .
C7 C 0.2481(7) 1.3624(7) -0.0082(4) 0.0289(14) Uani 1 1 d . . . . .
H7 H 0.226240 1.457515 -0.002917 0.035 Uiso 1 1 calc R . . . .
C6 C 0.4400(8) 1.1909(7) 0.5819(4) 0.0289(14) Uani 1 1 d . . . . .
H6A H 0.465056 1.103692 0.558877 0.035 Uiso 1 1 calc R . . . .
H6B H 0.539915 1.236299 0.590648 0.035 Uiso 1 1 calc R . . . .
C9 C 0.3137(9) 1.0901(8) -0.0269(4) 0.0423(19) Uani 1 1 d . . . . .
H9 H 0.337330 0.995627 -0.033322 0.051 Uiso 1 1 calc R . . . .
C8 C 0.3746(9) 1.1910(8) -0.0746(4) 0.0436(19) Uani 1 1 d . . . . .
H8 H 0.439766 1.167433 -0.114682 0.052 Uiso 1 1 calc R . . . .
C10 C 0.2182(9) 1.1265(7) 0.0304(4) 0.0366(17) Uani 1 1 d . . . . .
H10 H 0.174393 1.056726 0.062912 0.044 Uiso 1 1 calc R . . . .
C2 C 0.1620(8) 1.4488(8) 0.4390(4) 0.0350(16) Uani 1 1 d . . . . .
H2A H 0.100228 1.504326 0.406194 0.042 Uiso 1 1 calc R . . . .
C12 C 0.0836(8) 1.3098(8) 0.1036(4) 0.0353(16) Uani 1 1 d . . . . .
H12A H 0.019731 1.391798 0.087501 0.042 Uiso 1 1 calc R . . . .
H12B H 0.011049 1.234921 0.120029 0.042 Uiso 1 1 calc R . . . .
O1 O 0.0615(6) 1.2196(5) 0.3094(3) 0.0366(11) Uani 1 1 d . . . . .
H1D H -0.036946 1.202911 0.319718 0.055 Uiso 1 1 d G . . . .
H1E H 0.102464 1.138712 0.301518 0.055 Uiso 1 1 d G . . . .


_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
Bi1 I8 3.0652(4) . ?
Bi1 I6 2.9722(4) . ?
Bi1 I7 3.1183(5) . ?
Bi1 I5 3.0839(4) . ?
Bi1 I4 3.0456(5) . ?
Bi1 I3 3.1788(4) . ?
I8 Ag1 3.7719(9) 1_545 ?
I1 Ag1 2.6995(8) . ?
I5 Ag1 3.2672(9) 1_655 ?
I2 Ag1 2.6923(7) . ?
I3 Ag1 3.0470(8) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C6 1.496(8) . ?
N4 H4A 0.8800 . ?
N4 C7 1.339(9) . ?
N4 C8 1.346(9) . ?
C11 C7 1.374(9) . ?
C11 C10 1.391(9) . ?
C11 C12 1.510(9) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C12 1.485(9) . ?
N2 H2 0.8800 . ?
N2 C1 1.332(9) . ?
N2 C2 1.338(9) . ?
C1 H1 0.9500 . ?
C1 C5 1.363(9) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(9) . ?
C3 C2 1.363(10) . ?
C5 C4 1.394(9) . ?
C5 C6 1.520(9) . ?
C4 H4 0.9500 . ?
C7 H7 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C8 1.373(12) . ?
C9 C10 1.377(11) . ?
C8 H8 0.9500 . ?
C10 H10 0.9500 . ?
C2 H2A 0.9500 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
O1 H1D 0.8706 . ?
O1 H1E 0.8726 . ?

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
I8 Bi1 I7 87.595(13) . . ?
I8 Bi1 I5 177.948(14) . . ?
I8 Bi1 I3 89.135(12) . . ?
I6 Bi1 I8 90.958(12) . . ?
I6 Bi1 I7 89.557(12) . . ?
I6 Bi1 I5 90.256(13) . . ?
I6 Bi1 I4 90.634(13) . . ?
I6 Bi1 I3 177.783(14) . . ?
I7 Bi1 I3 92.661(13) . . ?
I5 Bi1 I7 90.761(13) . . ?
I5 Bi1 I3 89.716(13) . . ?
I4 Bi1 I8 91.007(13) . . ?
I4 Bi1 I7 178.591(13) . . ?
I4 Bi1 I5 90.634(13) . . ?
I4 Bi1 I3 87.149(13) . . ?
Bi1 I8 Ag1 161.980(18) . 1_545 ?
Bi1 I5 Ag1 169.68(2) . 1_655 ?
Ag1 I3 Bi1 155.34(2) . . ?
I1 Ag1 I6 73.556(19) . 1_465 ?
I1 Ag1 I5 96.89(2) . 1_455 ?
I1 Ag1 I3 98.87(2) . . ?
I5 Ag1 I6 102.143(19) 1_455 1_465 ?
I2 Ag1 I6 80.298(19) . 1_465 ?
I2 Ag1 I1 152.85(3) . . ?
I2 Ag1 I5 95.60(2) . 1_455 ?
I2 Ag1 I3 106.72(3) . . ?
I3 Ag1 I6 171.75(2) . 1_465 ?
I3 Ag1 I5 81.76(2) . 1_455 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C6 N1 H1A 109.5 . . ?
C6 N1 H1B 109.5 . . ?
C6 N1 H1C 109.5 . . ?
C7 N4 H4A 118.5 . . ?
C7 N4 C8 123.0(6) . . ?
C8 N4 H4A 118.5 . . ?
C7 C11 C10 118.0(6) . . ?
C7 C11 C12 119.5(6) . . ?
C10 C11 C12 122.5(6) . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C12 N3 H3A 109.5 . . ?
C12 N3 H3B 109.5 . . ?
C12 N3 H3C 109.5 . . ?
C1 N2 H2 119.0 . . ?
C1 N2 C2 122.0(6) . . ?
C2 N2 H2 119.0 . . ?
N2 C1 H1 119.6 . . ?
N2 C1 C5 120.9(6) . . ?
C5 C1 H1 119.6 . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.6(7) . . ?
C1 C5 C4 118.2(6) . . ?
C1 C5 C6 120.3(6) . . ?
C4 C5 C6 121.5(6) . . ?
C3 C4 C5 119.7(6) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
N4 C7 C11 120.1(6) . . ?
N4 C7 H7 119.9 . . ?
C11 C7 H7 119.9 . . ?
N1 C6 C5 110.2(5) . . ?
N1 C6 H6A 109.6 . . ?
N1 C6 H6B 109.6 . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.1 . . ?
C8 C9 H9 120.2 . . ?
C8 C9 C10 119.7(7) . . ?
C10 C9 H9 120.2 . . ?
N4 C8 C9 118.7(7) . . ?
N4 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.5(7) . . ?
C9 C10 H10 119.8 . . ?
N2 C2 C3 119.7(6) . . ?
N2 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
N3 C12 C11 110.7(5) . . ?
N3 C12 H12A 109.5 . . ?
N3 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
H1D O1 H1E 104.1 . . ?

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 C1 C5 C4 1.1(9) . . . . ?
N2 C1 C5 C6 -179.8(6) . . . . ?
C1 N2 C2 C3 -0.4(10) . . . . ?
C1 C5 C4 C3 -1.2(9) . . . . ?
C1 C5 C6 N1 -104.7(7) . . . . ?
C4 C3 C2 N2 0.2(11) . . . . ?
C4 C5 C6 N1 74.3(7) . . . . ?
C7 N4 C8 C9 -0.5(11) . . . . ?
C7 C11 C10 C9 1.4(10) . . . . ?
C7 C11 C12 N3 -84.6(8) . . . . ?
C6 C5 C4 C3 179.7(6) . . . . ?
C8 N4 C7 C11 0.7(10) . . . . ?
C8 C9 C10 C11 -1.2(11) . . . . ?
C10 C11 C7 N4 -1.1(9) . . . . ?
C10 C11 C12 N3 95.7(7) . . . . ?
C10 C9 C8 N4 0.7(11) . . . . ?
C2 N2 C1 C5 -0.3(10) . . . . ?
C2 C3 C4 C5 0.6(10) . . . . ?
C12 C11 C7 N4 179.2(6) . . . . ?
C12 C11 C10 C9 -178.9(6) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
