# 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_mo_bly_2_180623_0m_pl
_database_code_depnum_ccdc_archive 'CCDC 1903596'
loop_
_audit_author_name
_audit_author_address
'Leyu Bi'
;Xi'an Jiaotong University
China
;
_audit_update_record             
;
2019-03-16 deposited with the CCDC.	2020-03-14 downloaded from the CCDC.
;
_audit_creation_date             2019-03-08
_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         'Bi Cu I8, 2(C6 H16 N2)'
_chemical_formula_sum            'C12 H32 Bi Cu I8 N4'
_chemical_formula_weight         1520.13
_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'

_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           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'

_cell_length_a                   8.474(4)
_cell_length_b                   10.137(5)
_cell_length_c                   18.767(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.642(7)
_cell_angle_gamma                90
_cell_volume                     1584.4(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5992
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.491
_cell_measurement_theta_min      2.208
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.019
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    3.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       bluk
_exptl_crystal_F_000             1336
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.23
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0321
_diffrn_reflns_av_unetI/netI     0.0255
_diffrn_reflns_Laue_measured_fraction_full 0.970
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12413
_diffrn_reflns_point_group_measured_fraction_full 0.970
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.009
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.970
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2560
_reflns_number_total             2780
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         2.234
_refine_diff_density_min         -0.967
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         2780
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.071
_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)+(0.0296P)²+9.3539P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0672
_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 C(H,H,H) groups
2. Others
 Fixed Sof: Cu1(0.25) Cu2(0.25)
3.a Ternary CH refined with riding coordinates:
 N1(H1), C4(H4)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2D,H2E), C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B)
3.c Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.7500 0.72574(4) 0.2500 0.01934(11) Uani 1 2 d S T P . .
I1 I 0.19053(5) 1.23547(5) 0.12244(2) 0.02475(13) Uani 1 1 d . . . . .
I2 I 0.48097(5) 0.93431(5) 0.23717(2) 0.02535(13) Uani 1 1 d . . . . .
I3 I 0.76389(5) 0.73181(5) 0.41560(2) 0.02167(12) Uani 1 1 d . . . . .
I4 I 1.00412(5) 0.50551(5) 0.26582(3) 0.02886(14) Uani 1 1 d . . . . .
Cu1 Cu 0.2500 1.1439(3) 0.2500 0.0415(7) Uani 0.5 2 d S T P . .
Cu2 Cu 1.2500 0.3092(4) 0.2500 0.0435(7) Uani 0.5 2 d S T P . .
N1 N 0.7711(7) 0.2258(6) 0.0805(3) 0.0248(13) Uani 1 1 d . . . . .
H1 H 0.8883 0.2292 0.0945 0.030 Uiso 1 1 calc R . . . .
N2 N 0.8296(8) 0.2968(8) -0.1368(3) 0.0397(18) Uani 1 1 d . . . . .
H2A H 0.8111 0.2295 -0.1677 0.048 Uiso 1 1 calc GR . . . .
H2B H 0.9349 0.3055 -0.1215 0.048 Uiso 1 1 calc GR . . . .
H2C H 0.7904 0.3705 -0.1590 0.048 Uiso 1 1 calc GR . . . .
C1 C 0.7037(10) 0.2028(10) 0.1483(4) 0.042(2) Uani 1 1 d . . . . .
H1A H 0.7378 0.2725 0.1823 0.063 Uiso 1 1 calc GR . . . .
H1B H 0.7419 0.1199 0.1695 0.063 Uiso 1 1 calc GR . . . .
H1C H 0.5886 0.2014 0.1364 0.063 Uiso 1 1 calc GR . . . .
C2 C 0.7165(9) 0.3558(7) 0.0477(4) 0.0268(16) Uani 1 1 d . . . . .
H2D H 0.7470 0.4251 0.0832 0.032 Uiso 1 1 calc R . . . .
H2E H 0.6004 0.3559 0.0339 0.032 Uiso 1 1 calc R . . . .
C3 C 0.7904(9) 0.3827(7) -0.0184(4) 0.0264(16) Uani 1 1 d . . . . .
H3A H 0.9061 0.3900 -0.0042 0.032 Uiso 1 1 calc R . . . .
H3B H 0.7497 0.4654 -0.0406 0.032 Uiso 1 1 calc R . . . .
C4 C 0.7488(8) 0.2707(7) -0.0726(4) 0.0243(16) Uani 1 1 d . . . . .
H4 H 0.6322 0.2680 -0.0892 0.029 Uiso 1 1 calc R . . . .
C5 C 0.8051(9) 0.1392(7) -0.0386(4) 0.0337(18) Uani 1 1 d . . . . .
H5A H 0.7741 0.0687 -0.0733 0.040 Uiso 1 1 calc R . . . .
H5B H 0.9212 0.1389 -0.0247 0.040 Uiso 1 1 calc R . . . .
C6 C 0.7309(9) 0.1176(8) 0.0266(4) 0.0353(18) Uani 1 1 d . . . . .
H6A H 0.6152 0.1120 0.0118 0.042 Uiso 1 1 calc R . . . .
H6B H 0.7685 0.0344 0.0491 0.042 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 I2 3.0859(12) 2_655 ?
Bi1 I2 3.0859(12) . ?
Bi1 I3 3.0890(15) 2_655 ?
Bi1 I3 3.0889(15) . ?
Bi1 I4 3.0778(12) 2_655 ?
Bi1 I4 3.0778(12) . ?
I1 Cu1 2.5301(17) . ?
I1 Cu2 2.4695(16) 1_465 ?
I2 Cu1 2.928(3) . ?
I4 Cu2 2.935(3) . ?
Cu1 I1 2.5302(17) 2 ?
Cu1 I2 2.928(3) 2 ?
Cu1 Cu2 1.676(5) 1_465 ?
Cu2 I1 2.4695(16) 2_645 ?
Cu2 I1 2.4695(16) 1_645 ?
Cu2 I4 2.935(3) 2_755 ?
Cu2 Cu1 1.676(5) 1_645 ?
N1 H1 0.9800 . ?
N1 C1 1.507(9) . ?
N1 C2 1.491(9) . ?
N1 C6 1.488(10) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
N2 C4 1.516(9) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2D 0.9700 . ?
C2 H2E 0.9700 . ?
C2 C3 1.514(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.521(10) . ?
C4 H4 0.9800 . ?
C4 C5 1.517(10) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 C6 1.491(11) . ?
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
I2 Bi1 I2 93.51(4) 2_655 . ?
I2 Bi1 I3 87.433(14) . . ?
I2 Bi1 I3 91.001(14) . 2_655 ?
I2 Bi1 I3 91.001(14) 2_655 . ?
I2 Bi1 I3 87.433(14) 2_655 2_655 ?
I3 Bi1 I3 177.72(2) . 2_655 ?
I4 Bi1 I2 89.76(4) . 2_655 ?
I4 Bi1 I2 176.491(15) . . ?
I4 Bi1 I2 89.76(4) 2_655 . ?
I4 Bi1 I2 176.491(15) 2_655 2_655 ?
I4 Bi1 I3 91.226(15) 2_655 2_655 ?
I4 Bi1 I3 90.431(14) 2_655 . ?
I4 Bi1 I3 91.227(15) . . ?
I4 Bi1 I3 90.430(14) . 2_655 ?
I4 Bi1 I4 87.01(4) . 2_655 ?
Cu2 I1 Cu1 39.16(11) 1_465 . ?
Cu1 I2 Bi1 170.38(2) . . ?
Cu2 I4 Bi1 168.22(3) . . ?
I1 Cu1 I1 136.94(14) . 2 ?
I1 Cu1 I2 108.95(4) 2 . ?
I1 Cu1 I2 101.99(4) 2 2 ?
I1 Cu1 I2 108.95(4) . 2 ?
I1 Cu1 I2 101.99(4) . . ?
I2 Cu1 I2 86.99(10) . 2 ?
Cu2 Cu1 I1 68.47(7) 1_465 . ?
Cu2 Cu1 I1 68.47(7) 1_465 2 ?
Cu2 Cu1 I2 136.50(5) 1_465 . ?
Cu2 Cu1 I2 136.50(5) 1_465 2 ?
I1 Cu2 I1 144.75(16) 1_645 2_645 ?
I1 Cu2 I4 97.40(4) 2_645 . ?
I1 Cu2 I4 106.36(5) 2_645 2_755 ?
I1 Cu2 I4 97.40(4) 1_645 2_755 ?
I1 Cu2 I4 106.36(5) 1_645 . ?
I4 Cu2 I4 94.65(11) . 2_755 ?
Cu1 Cu2 I1 72.38(8) 1_645 2_645 ?
Cu1 Cu2 I1 72.38(8) 1_645 1_645 ?
Cu1 Cu2 I4 132.67(5) 1_645 . ?
Cu1 Cu2 I4 132.67(6) 1_645 2_755 ?
C1 N1 H1 107.6 . . ?
C2 N1 H1 107.6 . . ?
C2 N1 C1 110.4(6) . . ?
C6 N1 H1 107.6 . . ?
C6 N1 C1 112.6(6) . . ?
C6 N1 C2 110.9(6) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C4 N2 H2A 109.5 . . ?
C4 N2 H2B 109.5 . . ?
C4 N2 H2C 109.5 . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2D 109.5 . . ?
N1 C2 H2E 109.5 . . ?
N1 C2 C3 110.7(6) . . ?
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 . . ?
C2 C3 C4 109.4(6) . . ?
H3A C3 H3B 108.2 . . ?
C4 C3 H3A 109.8 . . ?
C4 C3 H3B 109.8 . . ?
N2 C4 C3 108.5(6) . . ?
N2 C4 H4 109.2 . . ?
N2 C4 C5 109.6(6) . . ?
C3 C4 H4 109.2 . . ?
C5 C4 C3 111.0(6) . . ?
C5 C4 H4 109.2 . . ?
C4 C5 H5A 109.9 . . ?
C4 C5 H5B 109.9 . . ?
H5A C5 H5B 108.3 . . ?
C6 C5 C4 109.1(6) . . ?
C6 C5 H5A 109.9 . . ?
C6 C5 H5B 109.9 . . ?
N1 C6 C5 111.8(6) . . ?
N1 C6 H6A 109.3 . . ?
N1 C6 H6B 109.3 . . ?
C5 C6 H6A 109.3 . . ?
C5 C6 H6B 109.3 . . ?
H6A C6 H6B 107.9 . . ?

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
N1 C2 C3 C4 56.6(8) . . . . ?
N2 C4 C5 C6 177.3(6) . . . . ?
C1 N1 C2 C3 177.2(6) . . . . ?
C1 N1 C6 C5 -177.3(6) . . . . ?
C2 N1 C6 C5 58.4(8) . . . . ?
C2 C3 C4 N2 -177.6(6) . . . . ?
C2 C3 C4 C5 -57.2(8) . . . . ?
C3 C4 C5 C6 57.4(8) . . . . ?
C4 C5 C6 N1 -57.7(8) . . . . ?
C6 N1 C2 C3 -57.3(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
