# 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_p-1_pl
_database_code_depnum_ccdc_archive 'CCDC 1903595'
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         '0.5(Bi2 Cu2 I16), 0.5(H4 O2), 4(C6 H14 N)'
_chemical_formula_sum            'C24 H58 Bi Cu I8 N4 O'
_chemical_formula_weight         1706.46
_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        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   19.688(3)
_cell_length_b                   8.6011(16)
_cell_length_c                   26.531(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.146(15)
_cell_angle_gamma                90
_cell_volume                     4489.6(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      26.349
_cell_measurement_theta_min      2.488
_shelx_estimated_absorpt_T_max   0.0431
_shelx_estimated_absorpt_T_min   0.0122
_exptl_absorpt_coefficient_mu    9.911
_exptl_absorpt_correction_T_max  0.0431
_exptl_absorpt_correction_T_min  0.0122
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            black
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    2.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       flake
_exptl_crystal_F_000             3096
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.484
_exptl_crystal_size_min          0.318
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            20928
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         2.070
_diffrn_ambient_temperature      150.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_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                3326
_reflns_number_total             3947
_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         1.817
_refine_diff_density_min         -0.905
_refine_diff_density_rms         0.217
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     188
_refine_ls_number_reflns         3947
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.101
_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)+(0.0509P)²+62.8387P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1050
_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. Restrained distances
 H1D-H2C_$1
 2.4 with sigma of 0.02
 H1E-H2C_$1
 2.4 with sigma of 0.02
3. Others
 Fixed Sof: Cu1(0.5) H1D(0.5) H1E(0.5)
4.a Free rotating group:
 O1(H1D,H1E)
4.b Ternary CH refined with riding coordinates:
 C1(H1), C7(H7)
4.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C8(H8A,H8B),
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B)
4.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2C,H2D,H2E)
;
_atom_sites_solution_hydrogens   mixed
_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 0.0000 0.5000 0.0000 0.02333(14) Uani 1 2 d S T P . .
I1 I -0.02660(3) 0.51756(7) 0.11471(2) 0.03070(17) Uani 1 1 d . . . . .
I2 I 0.08619(3) 0.79653(6) 0.00893(2) 0.02967(17) Uani 1 1 d . . . . .
I3 I 0.12572(3) 0.29098(6) 0.01762(2) 0.02695(16) Uani 1 1 d . . . . .
I4 I 0.26642(3) 0.00448(7) 0.08990(3) 0.03545(18) Uani 1 1 d . . . . .
Cu1 Cu 0.21587(19) 0.0513(4) 0.00467(12) 0.0707(10) Uani 0.5 1 d . . . . .
O1 O -0.2500 0.3677(10) 0.0000 0.035(2) Uani 1 2 d S T P . .
H1D H -0.2815 0.3012 0.0029 0.052 Uiso 0.5 1 d DG . . . .
H1E H -0.2147 0.3137 -0.0049 0.052 Uiso 0.5 1 d DG . . . .
N1 N -0.0508(4) -0.0661(9) 0.0907(3) 0.0298(17) Uani 1 1 d . . . . .
H1A H -0.0355 -0.0332 0.0615 0.036 Uiso 1 1 calc GR . . . .
H1B H -0.0960 -0.0601 0.0900 0.036 Uiso 1 1 calc GR . . . .
H1C H -0.0381 -0.1644 0.0959 0.036 Uiso 1 1 calc GR . . . .
C1 C -0.0216(5) 0.0346(11) 0.1331(4) 0.036(2) Uani 1 1 d . . . . .
H1 H -0.0361 0.1423 0.1272 0.043 Uiso 1 1 calc R . . . .
C2 C 0.0549(5) 0.0275(13) 0.1327(4) 0.042(3) Uani 1 1 d . . . . .
H2A H 0.0704 0.0667 0.1008 0.051 Uiso 1 1 calc R . . . .
H2B H 0.0699 -0.0795 0.1363 0.051 Uiso 1 1 calc R . . . .
C3 C 0.0855(6) 0.1260(14) 0.1764(4) 0.051(3) Uani 1 1 d . . . . .
H3A H 0.1346 0.1147 0.1775 0.062 Uiso 1 1 calc R . . . .
H3B H 0.0750 0.2347 0.1703 0.062 Uiso 1 1 calc R . . . .
C4 C 0.0587(5) 0.0785(16) 0.2262(4) 0.055(3) Uani 1 1 d . . . . .
H4A H 0.0759 0.1491 0.2522 0.066 Uiso 1 1 calc R . . . .
H4B H 0.0748 -0.0252 0.2347 0.066 Uiso 1 1 calc R . . . .
C5 C -0.0178(6) 0.080(2) 0.2253(5) 0.074(4) Uani 1 1 d . . . . .
H5A H -0.0338 0.1860 0.2213 0.088 Uiso 1 1 calc R . . . .
H5B H -0.0333 0.0410 0.2572 0.088 Uiso 1 1 calc R . . . .
C6 C -0.0484(6) -0.0199(15) 0.1823(4) 0.052(3) Uani 1 1 d . . . . .
H6A H -0.0364 -0.1281 0.1878 0.062 Uiso 1 1 calc R . . . .
H6B H -0.0976 -0.0113 0.1815 0.062 Uiso 1 1 calc R . . . .
N2 N 0.2841(4) 0.4446(10) 0.0867(3) 0.0378(19) Uani 1 1 d . . . . .
H2C H 0.2705 0.5011 0.0601 0.045 Uiso 1 1 calc DGR . . . .
H2D H 0.2643 0.3516 0.0850 0.045 Uiso 1 1 calc GR . . . .
H2E H 0.3290 0.4331 0.0868 0.045 Uiso 1 1 calc GR . . . .
C7 C 0.2645(5) 0.5260(11) 0.1345(4) 0.034(2) Uani 1 1 d . . . . .
H7 H 0.2912 0.6216 0.1381 0.041 Uiso 1 1 calc R . . . .
C8 C 0.2833(5) 0.4182(13) 0.1793(4) 0.045(3) Uani 1 1 d . . . . .
H8A H 0.2591 0.3204 0.1754 0.054 Uiso 1 1 calc R . . . .
H8B H 0.3316 0.3963 0.1799 0.054 Uiso 1 1 calc R . . . .
C9 C 0.2650(7) 0.4944(15) 0.2285(4) 0.055(3) Uani 1 1 d . . . . .
H9A H 0.2742 0.4226 0.2562 0.065 Uiso 1 1 calc R . . . .
H9B H 0.2931 0.5858 0.2342 0.065 Uiso 1 1 calc R . . . .
C10 C 0.1915(6) 0.5406(15) 0.2277(4) 0.051(3) Uani 1 1 d . . . . .
H10A H 0.1821 0.5958 0.2586 0.062 Uiso 1 1 calc R . . . .
H10B H 0.1634 0.4479 0.2263 0.062 Uiso 1 1 calc R . . . .
C11 C 0.1729(6) 0.6441(13) 0.1825(4) 0.048(3) Uani 1 1 d . . . . .
H11A H 0.1244 0.6649 0.1818 0.058 Uiso 1 1 calc R . . . .
H11B H 0.1965 0.7426 0.1861 0.058 Uiso 1 1 calc R . . . .
C12 C 0.1916(5) 0.5677(13) 0.1334(4) 0.044(3) Uani 1 1 d . . . . .
H12A H 0.1643 0.4748 0.1280 0.053 Uiso 1 1 calc R . . . .
H12B H 0.1817 0.6385 0.1057 0.053 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 3.1112(7) 5_565 ?
Bi1 I1 3.1111(7) . ?
Bi1 I2 3.0677(7) 5_565 ?
Bi1 I2 3.0677(7) . ?
Bi1 I3 3.0806(6) . ?
Bi1 I3 3.0806(6) 5_565 ?
I3 Cu1 2.750(3) . ?
I4 Cu1 2.470(3) . ?
I4 Cu1 2.578(3) 2 ?
Cu1 I4 2.578(3) 2 ?
Cu1 Cu1 1.376(8) 2 ?
N1 C1 1.515(12) . ?
C1 C2 1.508(14) . ?
C1 C6 1.502(15) . ?
C2 C3 1.541(14) . ?
C3 C4 1.499(16) . ?
C4 C5 1.505(15) . ?
C5 C6 1.532(16) . ?
N2 C7 1.512(12) . ?
C7 C8 1.543(14) . ?
C7 C12 1.479(13) . ?
C8 C9 1.516(15) . ?
C9 C10 1.501(17) . ?
C10 C11 1.525(16) . ?
C11 C12 1.516(15) . ?

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_565 ?
I2 Bi1 I1 90.175(18) . 5_565 ?
I2 Bi1 I1 90.172(18) 5_565 . ?
I2 Bi1 I1 89.827(18) 5_565 5_565 ?
I2 Bi1 I1 89.826(18) . . ?
I2 Bi1 I2 180.0 5_565 . ?
I2 Bi1 I3 91.977(19) . . ?
I2 Bi1 I3 88.023(19) 5_565 . ?
I2 Bi1 I3 91.978(19) 5_565 5_565 ?
I2 Bi1 I3 88.023(19) . 5_565 ?
I3 Bi1 I1 92.497(19) 5_565 5_565 ?
I3 Bi1 I1 87.502(19) 5_565 . ?
I3 Bi1 I1 87.501(19) . 5_565 ?
I3 Bi1 I1 92.500(19) . . ?
I3 Bi1 I3 180.0 5_565 . ?
Cu1 I3 Bi1 159.57(7) . . ?
Cu1 I4 Cu1 31.54(17) . 2 ?
I4 Cu1 I3 104.35(11) . . ?
I4 Cu1 I3 110.51(11) 2 . ?
I4 Cu1 I4 143.25(14) . 2 ?
Cu1 Cu1 I3 131.45(9) 2 . ?
Cu1 Cu1 I4 69.9(3) 2 2 ?
Cu1 Cu1 I4 78.6(3) 2 . ?
C2 C1 N1 108.9(8) . . ?
C6 C1 N1 109.3(8) . . ?
C6 C1 C2 112.1(9) . . ?
C1 C2 C3 109.6(9) . . ?
C4 C3 C2 111.9(9) . . ?
C3 C4 C5 111.7(10) . . ?
C4 C5 C6 111.9(10) . . ?
C1 C6 C5 109.4(10) . . ?
N2 C7 C8 107.9(8) . . ?
C12 C7 N2 112.0(8) . . ?
C12 C7 C8 111.4(9) . . ?
C9 C8 C7 110.3(9) . . ?
C10 C9 C8 111.2(10) . . ?
C9 C10 C11 111.7(9) . . ?
C12 C11 C10 111.3(9) . . ?
C7 C12 C11 110.8(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 C1 C2 C3 -178.5(8) . . . . ?
N1 C1 C6 C5 178.9(9) . . . . ?
C1 C2 C3 C4 54.7(13) . . . . ?
C2 C1 C6 C5 58.1(12) . . . . ?
C2 C3 C4 C5 -53.8(15) . . . . ?
C3 C4 C5 C6 54.6(17) . . . . ?
C4 C5 C6 C1 -55.9(16) . . . . ?
C6 C1 C2 C3 -57.5(12) . . . . ?
N2 C7 C8 C9 179.7(9) . . . . ?
N2 C7 C12 C11 178.0(9) . . . . ?
C7 C8 C9 C10 55.1(13) . . . . ?
C8 C7 C12 C11 57.0(12) . . . . ?
C8 C9 C10 C11 -54.8(14) . . . . ?
C9 C10 C11 C12 54.6(13) . . . . ?
C10 C11 C12 C7 -55.7(13) . . . . ?
C12 C7 C8 C9 -56.9(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
