# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry A.
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1955022'
loop_
_audit_author_name
_audit_author_address
'Leyu Bi'
;Xian Jiaotong University
China
;
_audit_update_record             
;
2019-09-21 deposited with the CCDC.	2020-03-14 downloaded from the CCDC.
;
_audit_creation_date             2019-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '0.1(Bi2 Cu2 I16), 0.1(H4 O2), 0.4(C6 H16 N2)'
_chemical_formula_sum            'C2.40 H6.80 Bi0.20 Cu0.20 I1.60 N0.80 O0.20'
_chemical_formula_weight         307.63
_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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.259(13)
_cell_length_b                   8.575(5)
_cell_length_c                   19.643(12)
_cell_angle_alpha                90
_cell_angle_beta                 119.160(6)
_cell_angle_gamma                90
_cell_volume                     3274(3)
_cell_formula_units_Z            20
_cell_measurement_reflns_used    4542
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.91
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.100
_shelx_estimated_absorpt_T_min   0.083
_exptl_absorpt_coefficient_mu    13.572
_exptl_absorpt_correction_T_max  0.100
_exptl_absorpt_correction_T_min  0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    3.120
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       bulk
_exptl_crystal_F_000             2712
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   0.100
_exptl_transmission_factor_min   0.083
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            18155
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.542
_diffrn_reflns_theta_min         2.095
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2824
_reflns_number_total             3739
_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 v8.27A (Bruker, 2012)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.394
_refine_diff_density_min         -3.292
_refine_diff_density_rms         0.281
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         3739
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.013
_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)+(0.0520P)²+39.8890P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1058
_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,H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Others
 Fixed Sof: H1D(0.5) H1E(0.5)
3.a Free rotating group:
 O1(H1D,H1E)
3.b Ternary CH refined with riding coordinates:
 C1(H1), C5(H5)
3.c Secondary CH2 refined with riding coordinates:
 C2(H2D,H2E), C3(H3A,H3B), C4(H4A,H4B), C6(H6A,H6B)
3.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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 0.5000 0.5000 0.5000 0.02943(13) Uani 1 2 d S T P . .
I1 I 0.65627(3) 0.49081(8) 0.55481(4) 0.03920(17) Uani 1 1 d . . . . .
I2 I 0.51403(3) 0.19788(8) 0.59150(4) 0.03922(17) Uani 1 1 d . . . . .
I3 I 0.52125(3) 0.70366(7) 0.63941(3) 0.03571(16) Uani 1 1 d . . . . .
I4 I 0.62429(3) 0.98522(8) 0.82960(4) 0.04263(18) Uani 1 1 d . . . . .
Cu1 Cu 0.5000 0.9264(4) 0.7500 0.164(2) Uani 1 2 d S T P . .
O1 O 0.5000 0.3565(13) 0.7500 0.046(2) Uani 1 2 d S T P . .
H1D H 0.4862 0.4453 0.7289 0.069 Uiso 0.5 1 d G . . . .
H1E H 0.5090 0.2995 0.7207 0.069 Uiso 0.5 1 d G . . . .
N1 N 0.6222(4) 0.5382(11) 0.8482(5) 0.048(2) Uani 1 1 d . . . . .
H1A H 0.5851 0.4888 0.8124 0.057 Uiso 1 1 calc GR . . . .
H1B H 0.6219 0.6362 0.8331 0.057 Uiso 1 1 calc GR . . . .
H1C H 0.6221 0.5377 0.8934 0.057 Uiso 1 1 calc GR . . . .
N2 N 0.8731(4) 0.5647(11) 0.9860(5) 0.042(2) Uani 1 1 d . . . . .
H2A H 0.8692 0.6634 0.9705 0.051 Uiso 1 1 calc GR . . . .
H2B H 0.9114 0.5238 0.9901 0.051 Uiso 1 1 calc GR . . . .
H2C H 0.8746 0.5610 1.0322 0.051 Uiso 1 1 calc GR . . . .
C1 C 0.6852(5) 0.4578(14) 0.8577(6) 0.043(2) Uani 1 1 d . . . . .
H1 H 0.6870 0.3528 0.8784 0.051 Uiso 1 1 calc R . . . .
C2 C 0.6848(6) 0.4440(16) 0.7805(6) 0.053(3) Uani 1 1 d . . . . .
H2D H 0.6800 0.5469 0.7579 0.063 Uiso 1 1 calc R . . . .
H2E H 0.6457 0.3816 0.7447 0.063 Uiso 1 1 calc R . . . .
C3 C 0.7510(6) 0.3689(17) 0.7916(7) 0.059(3) Uani 1 1 d . . . . .
H3A H 0.7537 0.2622 0.8093 0.071 Uiso 1 1 calc R . . . .
H3B H 0.7511 0.3671 0.7423 0.071 Uiso 1 1 calc R . . . .
C4 C 0.8120(6) 0.4605(15) 0.8508(6) 0.051(3) Uani 1 1 d . . . . .
H4A H 0.8111 0.5641 0.8305 0.062 Uiso 1 1 calc R . . . .
H4B H 0.8540 0.4097 0.8591 0.062 Uiso 1 1 calc R . . . .
C5 C 0.8127(5) 0.4742(13) 0.9281(6) 0.043(2) Uani 1 1 d . . . . .
H5 H 0.8152 0.3689 0.9488 0.051 Uiso 1 1 calc R . . . .
C6 C 0.7473(5) 0.5498(13) 0.9167(6) 0.042(2) Uani 1 1 d . . . . .
H6A H 0.7448 0.6558 0.8983 0.050 Uiso 1 1 calc R . . . .
H6B H 0.7474 0.5536 0.9660 0.050 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
Bi1 I1 3.101(2) 5_666 ?
Bi1 I1 3.101(2) . ?
Bi1 I2 3.0810(15) . ?
Bi1 I2 3.0810(15) 5_666 ?
Bi1 I3 3.0838(15) . ?
Bi1 I3 3.0839(15) 5_666 ?
I3 Cu1 3.097(3) . ?
I4 Cu1 2.4775(17) . ?
Cu1 I3 3.097(3) 2_656 ?
Cu1 I4 2.4775(16) 2_656 ?
O1 H1D 0.8499 . ?
O1 H1E 0.8499 . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C1 1.490(13) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C5 1.488(13) . ?
C1 H1 0.9800 . ?
C1 C2 1.517(14) . ?
C1 C6 1.522(14) . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C2 C3 1.523(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.509(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C5 1.515(14) . ?
C5 H5 0.9800 . ?
C5 C6 1.506(14) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?

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
I1 Bi1 I1 180.0 . 5_666 ?
I2 Bi1 I1 89.907(19) 5_666 5_666 ?
I2 Bi1 I1 89.908(19) . . ?
I2 Bi1 I1 90.092(19) . 5_666 ?
I2 Bi1 I1 90.092(19) 5_666 . ?
I2 Bi1 I2 180.0 . 5_666 ?
I2 Bi1 I3 91.72(5) 5_666 5_666 ?
I2 Bi1 I3 88.28(5) . 5_666 ?
I2 Bi1 I3 91.72(5) . . ?
I2 Bi1 I3 88.28(5) 5_666 . ?
I3 Bi1 I1 87.401(18) . 5_666 ?
I3 Bi1 I1 92.599(18) . . ?
I3 Bi1 I1 92.600(18) 5_666 5_666 ?
I3 Bi1 I1 87.401(19) 5_666 . ?
I3 Bi1 I3 180.0 . 5_666 ?
Bi1 I3 Cu1 164.22(3) . . ?
I3 Cu1 I3 103.86(12) 2_656 . ?
I4 Cu1 I3 93.62(5) . . ?
I4 Cu1 I3 100.85(6) 2_656 . ?
I4 Cu1 I3 93.62(5) 2_656 2_656 ?
I4 Cu1 I3 100.84(6) . 2_656 ?
I4 Cu1 I4 156.49(17) . 2_656 ?
H1D O1 H1E 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C5 N2 H2A 109.5 . . ?
C5 N2 H2B 109.5 . . ?
C5 N2 H2C 109.5 . . ?
N1 C1 H1 108.8 . . ?
N1 C1 C2 111.3(9) . . ?
N1 C1 C6 107.8(9) . . ?
C2 C1 H1 108.8 . . ?
C2 C1 C6 111.2(9) . . ?
C6 C1 H1 108.8 . . ?
C1 C2 H2D 109.5 . . ?
C1 C2 H2E 109.5 . . ?
C1 C2 C3 110.9(9) . . ?
H2D C2 H2E 108.1 . . ?
C3 C2 H2D 109.5 . . ?
C3 C2 H2E 109.5 . . ?
C2 C3 H3A 109.8 . . ?
C2 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 C2 109.6(10) . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
C3 C4 H4A 109.2 . . ?
C3 C4 H4B 109.2 . . ?
C3 C4 C5 112.2(10) . . ?
H4A C4 H4B 107.9 . . ?
C5 C4 H4A 109.2 . . ?
C5 C4 H4B 109.2 . . ?
N2 C5 C4 111.8(9) . . ?
N2 C5 H5 108.3 . . ?
N2 C5 C6 109.6(8) . . ?
C4 C5 H5 108.3 . . ?
C6 C5 C4 110.3(9) . . ?
C6 C5 H5 108.3 . . ?
C1 C6 H6A 109.6 . . ?
C1 C6 H6B 109.6 . . ?
C5 C6 C1 110.1(9) . . ?
C5 C6 H6A 109.6 . . ?
C5 C6 H6B 109.6 . . ?
H6A C6 H6B 108.2 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
