# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2098407'
loop_
_audit_author_name
_audit_author_address
'Magali Allain'
;UNIV Angers, UMR CNRS
France
;
_audit_update_record             
;
2021-07-22 deposited with the CCDC.	2022-06-20 downloaded from the CCDC.
;

_audit_creation_date             2019-03-19T16:35:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         '2(C6 H14 N O2), Br4 Pb'
_chemical_formula_sum            'C12 H28 Br4 N2 O4 Pb'
_chemical_formula_weight         791.19
_chemical_absolute_configuration ad

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Ccm21
_symmetry_space_group_name_Hall  'C 2c -2c'
_symmetry_Int_Tables_number      36
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, z+1/2'
'x, -y, z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z'

_cell_length_a                   8.2708(8)
_cell_length_b                   34.825(3)
_cell_length_c                   8.2264(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2369.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4903
_cell_measurement_theta_min      2.531
_cell_measurement_theta_max      27.494

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.335
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.055
_exptl_crystal_density_diffrn    2.218
_exptl_crystal_F_000             1472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    13.881
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 '(SADABS (Sheldrick, Bruker, 2008))'
;
_exptl_absorpt_correction_T_min  0.298
_exptl_absorpt_correction_T_max  0.466

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_detector_area_resol_mean 9
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_number            12795
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.531
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        27.494
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_Friedel_coverage         0.865
_reflns_number_total             2687
_reflns_number_gt                2111
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Collect (Hooft, 2008)'
_computing_cell_refinement       'Dirax (Duisenberg, 1992)'
_computing_data_reduction        'EvalCCD (Duisenberg et al., 2000)'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2016/4 (Sheldrick, 2016)'
_computing_molecular_graphics    'DIAMOND 3.2k (Crystal Impact GbR, 2014)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     patterson
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0230P)²+2.8990P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2687
_refine_ls_number_parameters     112
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.066
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0705
_refine_ls_wR_factor_gt          0.0632
_refine_ls_goodness_of_fit_ref   1.09
_refine_ls_restrained_S_all      1.09
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.041(17)
_refine_diff_density_max         0.89
_refine_diff_density_min         -0.893
_refine_diff_density_rms         0.187

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pb Pb -3.3944 10.1111 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.2400(16) 0.4056(5) 0.9676(17) 0.069(5) Uani 1 1 d . . . . .
H1A H 0.342402 0.41896 0.978447 0.083 Uiso 1 1 calc R U . . .
H1B H 0.185125 0.406993 1.071682 0.083 Uiso 1 1 calc R U . . .
C2 C 0.2715(16) 0.3654(4) 0.929(3) 0.077(4) Uani 1 1 d . . . . .
H2A H 0.343884 0.364344 0.836226 0.093 Uiso 1 1 calc R U . . .
H2B H 0.170569 0.353412 0.897014 0.093 Uiso 1 1 calc R U . . .
C3 C 0.3452(19) 0.3423(5) 1.067(2) 0.081(5) Uani 1 1 d . . . . .
H3A H 0.394743 0.319419 1.021897 0.097 Uiso 1 1 calc R U . . .
H3B H 0.430172 0.357453 1.116905 0.097 Uiso 1 1 calc R U . . .
C4 C 0.229(2) 0.3308(5) 1.1936(19) 0.073(4) Uani 1 1 d . . . . .
C5 C 0.194(3) 0.2992(8) 1.449(3) 0.128(7) Uani 1 1 d . . . . .
H5A H 0.164355 0.321675 1.511684 0.153 Uiso 1 1 calc R U . . .
H5B H 0.095779 0.288218 1.40465 0.153 Uiso 1 1 calc R U . . .
C6 C 0.264(3) 0.2734(9) 1.548(4) 0.176(14) Uani 1 1 d . . . . .
H6A H 0.29953 0.251652 1.485557 0.264 Uiso 1 1 calc R U . . .
H6B H 0.18772 0.265174 1.628393 0.264 Uiso 1 1 calc R U . . .
H6C H 0.355745 0.28495 1.600671 0.264 Uiso 1 1 calc R U . . .
N1 N 0.1408(13) 0.4256(4) 0.8443(11) 0.071(4) Uani 1 1 d . . . . .
H1C H 0.036775 0.420399 0.861415 0.106 Uiso 1 1 calc R U . . .
H1D H 0.168907 0.417504 0.745594 0.106 Uiso 1 1 calc R U . . .
H1E H 0.156931 0.450763 0.851631 0.106 Uiso 1 1 calc R U . . .
O1 O 0.3001(15) 0.3115(4) 1.3114(15) 0.091(4) Uani 1 1 d . . . . .
O2 O 0.0866(14) 0.3377(5) 1.1920(14) 0.121(6) Uani 1 1 d . . . . .
BR1 Br 1.05247(17) 0.5 1.1210(2) 0.0412(4) Uani 1 2 d S T P . .
BR2 Br 0.5868(2) 0.5 1.2597(3) 0.0656(6) Uani 1 2 d S T P . .
BR3 Br 0.74134(14) 0.41367(4) 0.9522(2) 0.0560(5) Uani 1 1 d . . . . .
PB1 Pb 0.72839(5) 0.5 0.92892(5) 0.03415(18) Uani 1 2 d S T P . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.46(2) . ?
C1 N1 1.478(16) . ?
C1 H1A 0.97 . ?
C1 H1B 0.97 . ?
C2 C3 1.52(2) . ?
C2 H2A 0.97 . ?
C2 H2B 0.97 . ?
C3 C4 1.47(2) . ?
C3 H3A 0.97 . ?
C3 H3B 0.97 . ?
C4 O2 1.203(16) . ?
C4 O1 1.317(19) . ?
C5 C6 1.35(3) . ?
C5 O1 1.49(2) . ?
C5 H5A 0.97 . ?
C5 H5B 0.97 . ?
C6 H6A 0.96 . ?
C6 H6B 0.96 . ?
C6 H6C 0.96 . ?
N1 H1C 0.89 . ?
N1 H1D 0.89 . ?
N1 H1E 0.89 . ?
BR1 PB1 3.1114(17) . ?
BR1 PB1 3.115(2) 2_765 ?
BR2 PB1 2.9550(18) 2_665 ?
BR2 PB1 2.962(2) . ?
BR3 PB1 3.0144(14) . ?
PB1 BR2 2.9550(18) 2_664 ?
PB1 BR3 3.0143(14) 4_565 ?
PB1 BR1 3.115(2) 2_764 ?

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
C2 C1 N1 113.6(14) . . ?
C2 C1 H1A 108.9 . . ?
N1 C1 H1A 108.9 . . ?
C2 C1 H1B 108.9 . . ?
N1 C1 H1B 108.9 . . ?
H1A C1 H1B 107.7 . . ?
C1 C2 C3 114.6(18) . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2B 108.6 . . ?
C3 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C4 C3 C2 114.3(13) . . ?
C4 C3 H3A 108.7 . . ?
C2 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C2 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
O2 C4 O1 123.3(16) . . ?
O2 C4 C3 125.1(16) . . ?
O1 C4 C3 111.6(14) . . ?
C6 C5 O1 113.4(19) . . ?
C6 C5 H5A 108.9 . . ?
O1 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
O1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 N1 H1C 109.5 . . ?
C1 N1 H1D 109.5 . . ?
H1C N1 H1D 109.5 . . ?
C1 N1 H1E 109.5 . . ?
H1C N1 H1E 109.5 . . ?
H1D N1 H1E 109.5 . . ?
C4 O1 C5 116.1(14) . . ?
PB1 BR1 PB1 156.10(7) . 2_765 ?
PB1 BR2 PB1 141.40(8) 2_665 . ?
BR2 PB1 BR2 94.82(3) 2_664 . ?
BR2 PB1 BR3 93.51(3) 2_664 4_565 ?
BR2 PB1 BR3 87.46(4) . 4_565 ?
BR2 PB1 BR3 93.51(3) 2_664 . ?
BR2 PB1 BR3 87.47(4) . . ?
BR3 PB1 BR3 171.66(7) 4_565 . ?
BR2 PB1 BR1 177.59(7) 2_664 . ?
BR2 PB1 BR1 82.78(6) . . ?
BR3 PB1 BR1 86.40(3) 4_565 . ?
BR3 PB1 BR1 86.40(3) . . ?
BR2 PB1 BR1 97.47(7) 2_664 2_764 ?
BR2 PB1 BR1 167.71(6) . 2_764 ?
BR3 PB1 BR1 91.77(3) 4_565 2_764 ?
BR3 PB1 BR1 91.77(3) . 2_764 ?
BR1 PB1 BR1 84.934(19) . 2_764 ?



# The following lines are used to test the character set of files sent by
# network email or other means. They are not part of the CIF data set
# abcdefghijklmnopqrstuvwxyzABCDEFGHIJKLMNOPQRSTUVWXYZ0123456789
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# END of CIF
