# 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_e4317a_b
_database_code_depnum_ccdc_archive 'CCDC 2167649'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Pb, C4 H12 N'
_chemical_formula_sum            'C4 H12 Br3 N Pb'
_chemical_formula_weight         521.07

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8483(3)
_cell_length_b                   7.9539(3)
_cell_length_c                   17.8105(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1111.81(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    14000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       colorless
_exptl_crystal_colour            prism
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.113
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    25.894
_shelx_estimated_absorpt_T_min   0.204
_shelx_estimated_absorpt_T_max   0.204
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_T_max  0.224
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14387
_diffrn_reflns_av_unetI/netI     0.0758
_diffrn_reflns_av_R_equivalents  0.0831
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         30.150
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3178
_reflns_number_gt                2854
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.727
_reflns_Friedel_fraction_max     0.962
_reflns_Friedel_fraction_full    0.992

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0007P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0065(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1111 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3178
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0707
_refine_ls_wR_factor_gt          0.0692
_refine_ls_goodness_of_fit_ref   0.921
_refine_ls_restrained_S_all      0.921
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Pb1 Pb 0.38209(3) 0.75314(4) 0.49041(2) 0.01794(12) Uani 1 1 d . . . . .
Br1 Br 0.17779(11) 0.70629(11) 0.62625(5) 0.0221(2) Uani 1 1 d . . . . .
Br2 Br 0.60952(10) 0.48349(12) 0.54674(6) 0.0242(2) Uani 1 1 d . . . . .
Br3 Br 0.58332(10) 0.99935(13) 0.56444(6) 0.0232(2) Uani 1 1 d . . . . .
C1 C 0.1548(12) 0.1989(12) 0.6658(6) 0.027(2) Uani 1 1 d . . . . .
H1 H 0.1692 0.0742 0.6632 0.032 Uiso 1 1 calc R U . . .
N1 N 0.2428(9) 0.2753(10) 0.5993(4) 0.0242(18) Uani 1 1 d . . . . .
H1A H 0.2387 0.3894 0.6029 0.036 Uiso 1 1 calc R U . . .
H1B H 0.1897 0.2419 0.5564 0.036 Uiso 1 1 calc R U . . .
H1C H 0.3534 0.2411 0.5983 0.036 Uiso 1 1 calc R U . . .
C2 C -0.0341(13) 0.2387(15) 0.6599(7) 0.057(4) Uani 1 1 d . . . . .
H2A H -0.0762 0.2044 0.6104 0.085 Uiso 1 1 calc R U . . .
H2B H -0.0516 0.3598 0.6664 0.085 Uiso 1 1 calc R U . . .
H2C H -0.0962 0.1776 0.6990 0.085 Uiso 1 1 calc R U . . .
C3 C 0.2377(12) 0.2605(15) 0.7366(6) 0.037(3) Uani 1 1 d . . . . .
H3A H 0.2285 0.3846 0.7384 0.045 Uiso 1 1 calc R U . . .
H3B H 0.1741 0.2150 0.7801 0.045 Uiso 1 1 calc R U . . .
C4 C 0.4217(14) 0.2125(17) 0.7443(7) 0.053(4) Uani 1 1 d . . . . .
H4A H 0.4630 0.2455 0.7941 0.079 Uiso 1 1 calc R U . . .
H4B H 0.4887 0.2702 0.7056 0.079 Uiso 1 1 calc R U . . .
H4C H 0.4336 0.0906 0.7382 0.079 Uiso 1 1 calc R U . . .


_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
Pb1 Br3 2.8404(10) . ?
Pb1 Br1 2.9262(10) . ?
Pb1 Br2 2.9652(10) . ?
Pb1 Br2 3.0662(9) 4_466 ?
Pb1 Br1 3.1317(9) 4_566 ?
Pb1 Br3 3.2382(9) 4_466 ?
Br1 Pb1 3.1316(9) 4_466 ?
Br2 Pb1 3.0662(9) 4_566 ?
Br3 Pb1 3.2382(9) 4_566 ?
C1 N1 1.499(12) . ?
C1 C3 1.501(14) . ?
C1 C2 1.520(13) . ?
C1 H1 1.0000 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.500(13) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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
Br3 Pb1 Br1 90.50(3) . . ?
Br3 Pb1 Br2 90.40(3) . . ?
Br1 Pb1 Br2 87.59(3) . . ?
Br3 Pb1 Br2 90.98(3) . 4_466 ?
Br1 Pb1 Br2 83.29(3) . 4_466 ?
Br2 Pb1 Br2 170.79(2) . 4_466 ?
Br3 Pb1 Br1 79.92(3) . 4_566 ?
Br1 Pb1 Br1 165.40(3) . 4_566 ?
Br2 Pb1 Br1 81.54(3) . 4_566 ?
Br2 Pb1 Br1 107.66(3) 4_466 4_566 ?
Br3 Pb1 Br3 166.00(2) . 4_466 ?
Br1 Pb1 Br3 76.92(3) . 4_466 ?
Br2 Pb1 Br3 95.13(3) . 4_466 ?
Br2 Pb1 Br3 81.57(3) 4_466 4_466 ?
Br1 Pb1 Br3 113.60(3) 4_566 4_466 ?
Pb1 Br1 Pb1 81.05(2) . 4_466 ?
Pb1 Br2 Pb1 81.54(2) . 4_566 ?
Pb1 Br3 Pb1 80.50(2) . 4_566 ?
N1 C1 C3 109.4(8) . . ?
N1 C1 C2 108.1(8) . . ?
C3 C1 C2 114.4(9) . . ?
N1 C1 H1 108.3 . . ?
C3 C1 H1 108.3 . . ?
C2 C1 H1 108.3 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 114.3(9) . . ?
C4 C3 H3A 108.7 . . ?
C1 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         2.015
_refine_diff_density_min         -2.608
_refine_diff_density_rms         0.336

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_ea_e
_database_code_depnum_ccdc_archive 'CCDC 2167651'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H13 N, Br3 Pb'
_chemical_formula_sum            'C9 H13 Br3 N Pb'
_chemical_formula_weight         582.12

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   8.0192(7)
_cell_length_b                   8.1450(6)
_cell_length_c                   21.301(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1391.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1511
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      26.46

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.779
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    20.709
_shelx_estimated_absorpt_T_min   0.174
_shelx_estimated_absorpt_T_max   0.257
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.556
_exptl_absorpt_correction_T_max  0.668
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5225
_diffrn_reflns_av_unetI/netI     0.0975
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.677
_diffrn_reflns_theta_max         28.035
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1772
_reflns_number_gt                1366
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0108P)²+2.9047P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1772
_refine_ls_number_parameters     93
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0486
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1123
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.040
_refine_ls_shift/su_mean         0.004

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
Pb1 Pb 0.14499(7) 0.750000 0.26014(2) 0.0258(2) Uani 1 2 d S T P A 4
Br1 Br 0.3218(2) 0.750000 0.14468(8) 0.0647(6) Uani 1 2 d S T P A 4
Br2 Br -0.06964(14) 0.49345(11) 0.20854(6) 0.0349(3) Uani 1 1 d . . . A 4
C1 C 0.364(3) 0.250000 0.1228(10) 0.139(15) Uani 1 2 d S T P B 4
N1 N 0.2668(18) 0.250000 0.1699(6) 0.061(5) Uani 1 2 d S T P B 4
H1A H 0.308112 0.250000 0.208207 0.074 Uiso 1 2 calc R U P B 4
H1B H 0.158116 0.250000 0.164259 0.074 Uiso 1 2 calc R U P B 4
C2 C 0.2780(15) 0.274(2) 0.0581(4) 0.040(6) Uani 0.5 1 d G . P C -1
C3 C 0.1605(16) 0.3884(16) 0.0386(6) 0.034(5) Uani 0.5 1 d G . P C -1
H3 H 0.134028 0.479243 0.064683 0.041 Uiso 0.5 1 calc R U P C -1
C4 C 0.0818(14) 0.3701(18) -0.0192(6) 0.042(6) Uani 0.5 1 d G . P C -1
H4 H 0.001577 0.448460 -0.032492 0.051 Uiso 0.5 1 calc R U P C -1
C5 C 0.1206(15) 0.237(2) -0.0574(4) 0.032(4) Uani 0.5 1 d G . P C -1
H5 H 0.066833 0.224624 -0.096825 0.038 Uiso 0.5 1 calc R U P C -1
C6 C 0.2380(17) 0.1224(17) -0.0379(6) 0.032(4) Uani 0.5 1 d G . P C -1
H6 H 0.264541 0.031570 -0.063984 0.038 Uiso 0.5 1 calc R U P C -1
C7 C 0.3167(14) 0.1407(17) 0.0199(6) 0.037(5) Uani 0.5 1 d G . P C -1
H7 H 0.396994 0.062351 0.033191 0.044 Uiso 0.5 1 calc R U P C -1
C8 C 0.544(2) 0.250000 0.1273(8) 0.051(5) Uani 1 2 d S T P . .
C9 C 0.647(3) 0.165(3) 0.0781(15) 0.066(8) Uani 0.5 1 d . . P B -1
H9A H 0.655327 0.048047 0.088108 0.099 Uiso 0.5 1 calc R U P B -1
H9B H 0.758941 0.213559 0.077267 0.099 Uiso 0.5 1 calc R U P B -1
H9C H 0.594257 0.178818 0.036966 0.099 Uiso 0.5 1 calc R U P B -1


_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
Pb1 Br1 2.8387(17) . ?
Pb1 Br2 2.9218(11) 8_575 ?
Pb1 Br2 2.9218(11) . ?
Pb1 Br2 3.1699(12) 3_565 ?
Pb1 Br2 3.1699(12) 6_656 ?
C1 N1 1.27(2) . ?
C1 C8 1.44(3) . ?
N1 H1A 0.8800 . ?
N1 H1B 0.8800 . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 C7 1.3900 . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.50(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
Br1 Pb1 Br2 88.19(4) . 8_575 ?
Br1 Pb1 Br2 88.19(4) . . ?
Br2 Pb1 Br2 91.32(5) 8_575 . ?
N1 C1 C8 124.0(19) . . ?
C1 N1 H1A 120.0 . . ?
C1 N1 H1B 120.0 . . ?
H1A N1 H1B 120.0 . . ?
C3 C2 C7 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

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
C7 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?

_refine_diff_density_max         2.721
_refine_diff_density_min         -2.607
_refine_diff_density_rms         0.308


####################################################################### 
# 
# 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_e4897a_a
_database_code_depnum_ccdc_archive 'CCDC 2167653'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Pb, C4 H12 N '
_chemical_formula_sum            'C4 H12 Br3 N Pb'
_chemical_formula_weight         521.07

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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9713(7)
_cell_length_b                   7.9116(7)
_cell_length_c                   17.6232(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.932(4)
_cell_angle_gamma                90
_cell_volume                     1111.27(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1902
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      24.05

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.114
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    25.907
_shelx_estimated_absorpt_T_min   0.112
_shelx_estimated_absorpt_T_max   0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.469
_exptl_absorpt_correction_T_max  0.514
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10108
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  0.0853
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.312
_diffrn_reflns_theta_max         27.943
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2658
_reflns_number_gt                1984
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0439P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2658
_refine_ls_number_parameters     85
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1048
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Pb1 Pb 0.75257(4) 0.38985(4) 0.24064(2) 0.02416(16) Uani 1 1 d . . . . .
Br1 Br 0.70984(13) 0.18626(13) 0.37715(6) 0.0306(3) Uani 1 1 d . . . . .
Br2 Br 0.48580(13) 0.62044(11) 0.29697(6) 0.0304(3) Uani 1 1 d . . . . .
Br3 Br 1.00099(13) 0.58767(12) 0.31536(6) 0.0309(3) Uani 1 1 d . . . . .
C1 C 0.2005(19) 0.1664(18) 0.4145(7) 0.079(5) Uani 1 1 d D . . . .
H1 H 0.079286 0.199178 0.413396 0.095 Uiso 1 1 calc R U . . .
N1 N 0.2799(10) 0.2512(10) 0.3499(4) 0.0298(19) Uani 1 1 d . . . . .
H1A H 0.263067 0.364743 0.353308 0.045 Uiso 1 1 calc R U . . .
H1B H 0.233751 0.212172 0.305732 0.045 Uiso 1 1 calc R U . . .
H1C H 0.391965 0.229245 0.350845 0.045 Uiso 1 1 calc R U . . .
C2 C 0.274(2) 0.2311(18) 0.4864(9) 0.111(7) Uani 1 1 d D . . . .
H2A H 0.392265 0.194369 0.490496 0.133 Uiso 1 1 calc R U . . .
H2B H 0.212845 0.180651 0.529351 0.133 Uiso 1 1 calc R U . . .
C3 C 0.2664(19) 0.4215(14) 0.4927(8) 0.062(4) Uani 1 1 d D . . . .
H3A H 0.318978 0.472416 0.448357 0.093 Uiso 1 1 calc R U . . .
H3B H 0.326408 0.457600 0.538913 0.093 Uiso 1 1 calc R U . . .
H3C H 0.149054 0.457775 0.495035 0.093 Uiso 1 1 calc R U . . .
C4 C 0.208(2) -0.0321(14) 0.4100(9) 0.082(5) Uani 1 1 d D . . . .
H4A H 0.324952 -0.069399 0.413721 0.123 Uiso 1 1 calc R U . . .
H4B H 0.158774 -0.069891 0.361530 0.123 Uiso 1 1 calc R U . . .
H4C H 0.144482 -0.080715 0.451872 0.123 Uiso 1 1 calc R U . . .


_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
Pb1 Br3 2.8320(11) . ?
Pb1 Br1 2.9197(11) . ?
Pb1 Br2 2.9840(10) . ?
Pb1 Br2 3.0622(10) 2_645 ?
Pb1 Br1 3.1495(11) 2_655 ?
C1 N1 1.473(14) . ?
C1 C2 1.478(15) . ?
C1 C4 1.574(14) . ?
C1 H1 1.0000 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 C3 1.512(14) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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
Br3 Pb1 Br1 90.68(3) . . ?
Br3 Pb1 Br2 90.24(3) . . ?
Br1 Pb1 Br2 88.27(3) . . ?
Br3 Pb1 Br2 90.68(3) . 2_645 ?
Br1 Pb1 Br2 83.30(3) . 2_645 ?
Br2 Pb1 Br2 171.53(2) . 2_645 ?
Br3 Pb1 Br1 79.73(3) . 2_655 ?
Br1 Pb1 Br1 165.35(3) . 2_655 ?
Br2 Pb1 Br1 80.79(3) . 2_655 ?
Br2 Pb1 Br1 107.65(3) 2_645 2_655 ?
Pb1 Br1 Pb1 81.61(3) . 2_645 ?
Pb1 Br2 Pb1 82.07(3) . 2_655 ?
N1 C1 C2 109.6(11) . . ?
N1 C1 C4 113.5(11) . . ?
C2 C1 C4 112.0(12) . . ?
N1 C1 H1 107.1 . . ?
C2 C1 H1 107.1 . . ?
C4 C1 H1 107.1 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 C2 C3 113.1(14) . . ?
C1 C2 H2A 109.0 . . ?
C3 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C3 C2 H2B 109.0 . . ?
H2A C2 H2B 107.8 . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         1.992
_refine_diff_density_min         -2.613
_refine_diff_density_rms         0.477


####################################################################### 
# 
# 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_e4324a_b
_database_code_depnum_ccdc_archive 'CCDC 2167650'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Pb, C4 H12 N '
_chemical_formula_sum            'C8 H12 Br3 N Pb'
_chemical_formula_weight         569.11

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.9016(5)
_cell_length_b                   8.0986(4)
_cell_length_c                   20.2960(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1298.78(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    8000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.910
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    22.181
_shelx_estimated_absorpt_T_min   0.194
_shelx_estimated_absorpt_T_max   0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.184
_exptl_absorpt_correction_T_max  0.224
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8107
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.766
_diffrn_reflns_theta_max         30.108
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             3700
_reflns_number_gt                3237
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.723
_reflns_Friedel_fraction_max     0.960
_reflns_Friedel_fraction_full    0.988

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0001P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3700
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0720
_refine_ls_wR_factor_gt          0.0695
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_restrained_S_all      0.935
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Pb1 Pb 0.78391(4) 0.24296(5) 0.48638(2) 0.02078(9) Uani 1 1 d . . . . .
Br1 Br 0.98865(14) -0.00809(11) 0.54866(5) 0.0217(2) Uani 1 1 d . . . . .
Br2 Br 1.00657(14) 0.51833(11) 0.53015(5) 0.0234(2) Uani 1 1 d . . . . .
Br3 Br 0.62054(14) 0.29276(11) 0.61014(5) 0.0230(2) Uani 1 1 d . . . . .
C1 C 0.6737(13) 0.7902(11) 0.7057(5) 0.023(2) Uani 1 1 d . . . . .
C2 C 0.6796(15) 0.6499(12) 0.7438(5) 0.030(3) Uani 1 1 d . . . . .
H2 H 0.6089 0.5588 0.7332 0.036 Uiso 1 1 calc R U . . .
C3 C 0.7868(17) 0.6399(13) 0.7970(5) 0.034(3) Uani 1 1 d . . . . .
H3 H 0.7894 0.5421 0.8228 0.041 Uiso 1 1 calc R U . . .
C4 C 0.8902(15) 0.7701(15) 0.8132(5) 0.037(3) Uani 1 1 d . . . . .
H4 H 0.9654 0.7623 0.8495 0.045 Uiso 1 1 calc R U . . .
C5 C 0.8831(17) 0.9144(14) 0.7754(5) 0.037(3) Uani 1 1 d . . . . .
H5 H 0.9513 1.0067 0.7867 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7778(16) 0.9220(12) 0.7220(5) 0.032(2) Uani 1 1 d . . . . .
H6 H 0.7759 1.0190 0.6957 0.038 Uiso 1 1 calc R U . . .
C7 C 0.5634(13) 0.8005(11) 0.6447(5) 0.022(2) Uani 1 1 d . . . . .
H7 H 0.5486 0.9199 0.6336 0.027 Uiso 1 1 calc R U . . .
N1 N 0.6575(11) 0.7199(9) 0.5879(4) 0.0244(18) Uani 1 1 d . . . . .
H1A H 0.6630 0.6089 0.5947 0.037 Uiso 1 1 calc R U . . .
H1B H 0.7641 0.7619 0.5854 0.037 Uiso 1 1 calc R U . . .
H1C H 0.6017 0.7404 0.5495 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3933(14) 0.7267(15) 0.6507(5) 0.039(3) Uani 1 1 d . . . . .
H8A H 0.3240 0.7596 0.6129 0.058 Uiso 1 1 calc R U . . .
H8B H 0.3398 0.7654 0.6915 0.058 Uiso 1 1 calc R U . . .
H8C H 0.4031 0.6061 0.6518 0.058 Uiso 1 1 calc R U . . .


_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
Pb1 Br3 2.8528(10) . ?
Pb1 Br1 2.8894(11) . ?
Pb1 Br2 2.9762(11) . ?
Pb1 Br2 3.0647(11) 4_456 ?
Br2 Pb1 3.0647(11) 4_556 ?
C1 C2 1.375(13) . ?
C1 C6 1.388(14) . ?
C1 C7 1.517(14) . ?
C2 C3 1.375(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.399(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.367(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.477(15) . ?
C7 N1 1.519(12) . ?
C7 H7 1.0000 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
Br3 Pb1 Br1 88.15(3) . . ?
Br3 Pb1 Br2 84.19(3) . . ?
Br1 Pb1 Br2 93.77(3) . . ?
Br3 Pb1 Br2 82.56(3) . 4_456 ?
Br1 Pb1 Br2 87.84(3) . 4_456 ?
Br2 Pb1 Br2 166.59(3) . 4_456 ?
Pb1 Br2 Pb1 82.68(2) . 4_556 ?
C2 C1 C6 118.8(10) . . ?
C2 C1 C7 121.6(9) . . ?
C6 C1 C7 119.5(8) . . ?
C1 C2 C3 120.7(11) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.6(10) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.1(10) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 119.8(11) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C1 121.0(10) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
C8 C7 C1 115.6(8) . . ?
C8 C7 N1 109.6(8) . . ?
C1 C7 N1 108.4(8) . . ?
C8 C7 H7 107.7 . . ?
C1 C7 H7 107.7 . . ?
N1 C7 H7 107.7 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         2.054
_refine_diff_density_min         -1.855
_refine_diff_density_rms         0.246

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4305a_b
_database_code_depnum_ccdc_archive 'CCDC 2167656'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Pb, C9 H14 N'
_chemical_formula_sum            'C9 H14 Br3 N Pb'
_chemical_formula_weight         583.13

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1743(4)
_cell_length_b                   8.2125(4)
_cell_length_c                   20.4992(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1376.14(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    15000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.815
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    20.937
_shelx_estimated_absorpt_T_min   0.188
_shelx_estimated_absorpt_T_max   0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.171
_exptl_absorpt_correction_T_max  0.234
_exptl_absorpt_process_details   sadbs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15012
_diffrn_reflns_av_unetI/netI     0.0691
_diffrn_reflns_av_R_equivalents  0.0704
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         1.987
_diffrn_reflns_theta_max         30.130
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4032
_reflns_number_gt                3426
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.986
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0424P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1314 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.001(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4032
_refine_ls_number_parameters     111
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0965
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.082
_refine_ls_shift/su_mean         0.010

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
Pb1 Pb 0.50777(5) 0.46763(5) 0.76178(2) 0.02491(13) Uani 1 1 d . . . . .
Br1 Br 0.23809(13) 0.24214(14) 0.72320(6) 0.0255(3) Uani 1 1 d . . . . .
Br2 Br 0.75016(14) 0.26731(15) 0.70152(7) 0.0276(3) Uani 1 1 d . . . . .
Br3 Br 0.45156(14) 0.62548(16) 0.64193(7) 0.0283(3) Uani 1 1 d . . . . .
C1 C 0.9481(12) 0.5369(12) 0.5490(5) 0.031(3) Uani 1 1 d G . . . .
C2 C 1.0999(10) 0.483(2) 0.5274(6) 0.159(18) Uani 1 1 d G . . . .
H2 H 1.1959 0.5092 0.5514 0.191 Uiso 1 1 calc R U . . .
C3 C 1.1114(11) 0.391(2) 0.4708(7) 0.17(2) Uani 1 1 d G . . . .
H3 H 1.2151 0.3539 0.4560 0.210 Uiso 1 1 calc R U . . .
C4 C 0.9710(15) 0.3523(13) 0.4357(5) 0.056(5) Uani 1 1 d G . . . .
H4 H 0.9788 0.2893 0.3970 0.068 Uiso 1 1 calc R U . . .
C5 C 0.8192(11) 0.406(2) 0.4573(7) 0.113(12) Uani 1 1 d G . . . .
H5 H 0.7233 0.3800 0.4334 0.136 Uiso 1 1 calc R U . . .
C6 C 0.8078(9) 0.498(2) 0.5140(7) 0.137(15) Uani 1 1 d G . . . .
H6 H 0.7040 0.5353 0.5288 0.164 Uiso 1 1 calc R U . . .
C7 C 0.9347(15) 0.6422(15) 0.6090(7) 0.034(3) Uani 1 1 d D . . . .
H7 H 0.8171 0.6461 0.6224 0.041 Uiso 1 1 calc R U . . .
N1 N 1.0311(12) 0.5687(13) 0.6642(6) 0.031(2) Uani 1 1 d . . . . .
H1A H 1.0050 0.4615 0.6682 0.046 Uiso 1 1 calc R U . . .
H1B H 1.0067 0.6216 0.7019 0.046 Uiso 1 1 calc R U . . .
H1C H 1.1399 0.5786 0.6557 0.046 Uiso 1 1 calc R U . . .
C8 C 0.983(5) 0.814(2) 0.5821(13) 0.168(12) Uani 1 1 d D . . . .
H8A H 1.0924 0.8110 0.5611 0.201 Uiso 1 1 calc R U . . .
H8B H 0.9021 0.8534 0.5499 0.201 Uiso 1 1 calc R U . . .
C9 C 0.986(4) 0.921(3) 0.6399(15) 0.168(12) Uani 1 1 d D . . . .
H9A H 0.8809 0.9778 0.6437 0.252 Uiso 1 1 calc R U . . .
H9B H 1.0743 1.0008 0.6355 0.252 Uiso 1 1 calc R U . . .
H9C H 1.0042 0.8549 0.6791 0.252 Uiso 1 1 calc R U . . .


_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
Pb1 Br3 2.8156(14) . ?
Pb1 Br2 2.8563(13) . ?
Pb1 Br1 2.9857(12) . ?
Pb1 Br1 3.0810(12) 3_656 ?
Br1 Pb1 3.0810(12) 3_646 ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.508(16) . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.504(17) . ?
C7 C8 1.570(19) . ?
C7 H7 1.0000 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C8 C9 1.473(17) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
Br3 Pb1 Br2 90.06(4) . . ?
Br3 Pb1 Br1 86.21(4) . . ?
Br2 Pb1 Br1 92.31(4) . . ?
Br3 Pb1 Br1 81.97(4) . 3_656 ?
Br2 Pb1 Br1 89.82(3) . 3_656 ?
Br1 Pb1 Br1 167.99(3) . 3_656 ?
Pb1 Br1 Pb1 85.96(3) . 3_646 ?
C2 C1 C6 120.0 . . ?
C2 C1 C7 120.5(8) . . ?
C6 C1 C7 119.4(8) . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 120.0 . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
C1 C7 N1 110.1(10) . . ?
C1 C7 C8 102.2(13) . . ?
N1 C7 C8 119.5(16) . . ?
C1 C7 H7 108.2 . . ?
N1 C7 H7 108.2 . . ?
C8 C7 H7 108.1 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 C8 C7 104.8(18) . . ?
C9 C8 H8A 110.7 . . ?
C7 C8 H8A 110.7 . . ?
C9 C8 H8B 111.0 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.8 . . ?
C8 C9 H9A 109.3 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.6 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         2.235
_refine_diff_density_min         -1.816
_refine_diff_density_rms         0.293

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4306a_b
_database_code_depnum_ccdc_archive 'CCDC 2167655'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Pb, C9 H14 N'
_chemical_formula_sum            'C9 H14 Br3 N Pb'
_chemical_formula_weight         583.13

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.1770(4)
_cell_length_b                   8.2177(4)
_cell_length_c                   20.5239(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1379.13(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    13000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.808
_exptl_crystal_F_000             1048
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    20.892
_shelx_estimated_absorpt_T_min   0.207
_shelx_estimated_absorpt_T_max   0.229
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.198
_exptl_absorpt_correction_T_max  0.236
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13637
_diffrn_reflns_av_unetI/netI     0.0689
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.670
_diffrn_reflns_theta_max         31.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4470
_reflns_number_gt                3899
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.750
_reflns_Friedel_fraction_max     0.999
_reflns_Friedel_fraction_full    0.999

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0431P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1487 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.000(10)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4470
_refine_ls_number_parameters     105
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0412
_refine_ls_wR_factor_ref         0.1026
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.013

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
Pb1 Pb 0.49231(5) 0.53246(5) 0.23826(2) 0.01935(11) Uani 1 1 d . . . . .
Br1 Br 0.76183(13) 0.75815(13) 0.27689(5) 0.0200(2) Uani 1 1 d . . . . .
Br2 Br 0.25003(14) 0.73294(14) 0.29846(6) 0.0220(2) Uani 1 1 d . . . . .
Br3 Br 0.54849(14) 0.37496(15) 0.35800(6) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.0513(12) 0.4639(12) 0.4508(4) 0.027(2) Uani 1 1 d G . . . .
C2 C -0.1011(10) 0.510(2) 0.4745(6) 0.19(2) Uani 1 1 d G . . . .
H2 H -0.1975 0.4791 0.4518 0.232 Uiso 1 1 calc R U . . .
C3 C -0.1125(11) 0.600(2) 0.5315(6) 0.20(3) Uani 1 1 d G . . . .
H3 H -0.2167 0.6316 0.5478 0.238 Uiso 1 1 calc R U . . .
C4 C 0.0285(15) 0.6450(14) 0.5648(4) 0.052(5) Uani 1 1 d G . . . .
H4 H 0.0207 0.7069 0.6038 0.062 Uiso 1 1 calc R U . . .
C5 C 0.1809(12) 0.599(2) 0.5411(7) 0.121(14) Uani 1 1 d G . . . .
H5 H 0.2773 0.6298 0.5639 0.146 Uiso 1 1 calc R U . . .
C6 C 0.1923(9) 0.509(2) 0.4841(7) 0.133(15) Uani 1 1 d G . . . .
H6 H 0.2965 0.4773 0.4679 0.160 Uiso 1 1 calc R U . . .
C7 C 0.063(3) 0.359(2) 0.3884(10) 0.071(3) Uani 1 1 d D . . . .
H7 H 0.1803 0.3537 0.3750 0.085 Uiso 1 1 calc R U . . .
N1 N -0.0303(11) 0.4304(12) 0.3348(5) 0.024(2) Uani 1 1 d . . . . .
H1A H -0.0010 0.3818 0.2967 0.036 Uiso 1 1 calc R U . . .
H1B H -0.0089 0.5389 0.3324 0.036 Uiso 1 1 calc R U . . .
H1C H -0.1390 0.4149 0.3419 0.036 Uiso 1 1 calc R U . . .
C8 C 0.011(3) 0.1908(18) 0.4106(9) 0.071(3) Uani 1 1 d D . . . .
H8A H 0.0875 0.1559 0.4453 0.085 Uiso 1 1 calc R U . . .
H8B H -0.0985 0.2010 0.4309 0.085 Uiso 1 1 calc R U . . .
C9 C 0.003(3) 0.0634(18) 0.3637(10) 0.071(3) Uani 1 1 d D . . . .
H9A H -0.0924 -0.0056 0.3728 0.106 Uiso 1 1 calc R U . . .
H9B H 0.1025 -0.0022 0.3658 0.106 Uiso 1 1 calc R U . . .
H9C H -0.0082 0.1104 0.3200 0.106 Uiso 1 1 calc R U . . .


_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
Pb1 Br3 2.8153(12) . ?
Pb1 Br2 2.8575(12) . ?
Pb1 Br1 2.9875(12) . ?
Pb1 Br1 3.0817(12) 3_645 ?
Br1 Pb1 3.0817(12) 3_655 ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C1 C7 1.55(2) . ?
C2 C3 1.3900 . ?
C2 H2 0.9500 . ?
C3 C4 1.3900 . ?
C3 H3 0.9500 . ?
C4 C5 1.3900 . ?
C4 H4 0.9500 . ?
C5 C6 1.3900 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.46(2) . ?
C7 C8 1.517(18) . ?
C7 H7 1.0000 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C8 C9 1.425(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?

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
Br3 Pb1 Br2 90.04(4) . . ?
Br3 Pb1 Br1 86.18(3) . . ?
Br2 Pb1 Br1 92.23(3) . . ?
Br3 Pb1 Br1 82.06(3) . 3_645 ?
Br2 Pb1 Br1 89.87(3) . 3_645 ?
Br1 Pb1 Br1 168.06(3) . 3_645 ?
Pb1 Br1 Pb1 85.98(3) . 3_655 ?
C2 C1 C6 120.0 . . ?
C2 C1 C7 119.7(11) . . ?
C6 C1 C7 120.2(11) . . ?
C3 C2 C1 120.0 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 H2 120.0 . . ?
C2 C3 C4 120.0 . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 H6 120.0 . . ?
C1 C6 H6 120.0 . . ?
N1 C7 C1 111.6(14) . . ?
N1 C7 C8 116.5(16) . . ?
C1 C7 C8 103.9(14) . . ?
N1 C7 H7 108.2 . . ?
C1 C7 H7 108.2 . . ?
C8 C7 H7 108.1 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 C8 C7 118.7(17) . . ?
C9 C8 H8A 107.8 . . ?
C7 C8 H8A 107.8 . . ?
C9 C8 H8B 107.5 . . ?
C7 C8 H8B 107.5 . . ?
H8A C8 H8B 107.1 . . ?
C8 C9 H9A 109.6 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?

_refine_diff_density_max         2.507
_refine_diff_density_min         -2.409
_refine_diff_density_rms         0.285

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4323a_b
_database_code_depnum_ccdc_archive 'CCDC 2167654'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Pb, C4 H12 N'
_chemical_formula_sum            'C4 H12 Br3 N Pb'
_chemical_formula_weight         521.07

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8629(6)
_cell_length_b                   7.9677(7)
_cell_length_c                   17.8420(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1117.79(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.096
_exptl_crystal_F_000             920
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    25.756
_shelx_estimated_absorpt_T_min   0.148
_shelx_estimated_absorpt_T_max   0.183
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.135
_exptl_absorpt_correction_T_max  0.192
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6811
_diffrn_reflns_av_unetI/netI     0.0840
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.800
_diffrn_reflns_theta_max         30.175
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3257
_reflns_number_gt                2816
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.710
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.994

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0007P)²+0.1100P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0026(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1025 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.013(17)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3257
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0953
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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
Pb1 Pb 0.61785(5) 0.24681(7) 0.50962(2) 0.02557(15) Uani 1 1 d . . . . .
Br1 Br 0.82185(15) 0.29424(18) 0.37386(7) 0.0296(3) Uani 1 1 d . . . . .
Br2 Br 0.39074(16) 0.51690(19) 0.45331(8) 0.0321(3) Uani 1 1 d . . . . .
Br3 Br 0.41665(15) 0.0007(2) 0.43542(7) 0.0312(3) Uani 1 1 d . . . . .
C1 C 0.8437(16) 0.805(2) 0.3348(8) 0.036(3) Uani 1 1 d . . . . .
H1 H 0.8299 0.9291 0.3387 0.043 Uiso 1 1 calc R U . . .
N1 N 0.7576(12) 0.7231(16) 0.4015(5) 0.031(3) Uani 1 1 d . . . . .
H1A H 0.7692 0.6097 0.3984 0.047 Uiso 1 1 calc R U . . .
H1B H 0.6451 0.7502 0.4015 0.047 Uiso 1 1 calc R U . . .
H1C H 0.8066 0.7605 0.4445 0.047 Uiso 1 1 calc R U . . .
C2 C 1.0311(17) 0.762(3) 0.3388(9) 0.060(5) Uani 1 1 d . . . . .
H2A H 1.0815 0.8166 0.3828 0.090 Uiso 1 1 calc R U . . .
H2B H 1.0880 0.8029 0.2934 0.090 Uiso 1 1 calc R U . . .
H2C H 1.0452 0.6406 0.3427 0.090 Uiso 1 1 calc R U . . .
C3 C 0.7617(16) 0.745(3) 0.2628(7) 0.049(4) Uani 1 1 d . . . . .
H3A H 0.8229 0.7957 0.2199 0.059 Uiso 1 1 calc R U . . .
H3B H 0.7750 0.6218 0.2592 0.059 Uiso 1 1 calc R U . . .
C4 C 0.579(2) 0.787(3) 0.2563(9) 0.069(7) Uani 1 1 d . . . . .
H4A H 0.5308 0.7291 0.2126 0.104 Uiso 1 1 calc R U . . .
H4B H 0.5658 0.9082 0.2502 0.104 Uiso 1 1 calc R U . . .
H4C H 0.5194 0.7503 0.3017 0.104 Uiso 1 1 calc R U . . .


_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
Pb1 Br3 2.8461(15) . ?
Pb1 Br1 2.9297(13) . ?
Pb1 Br2 2.9715(15) . ?
Pb1 Br2 3.0751(15) 4_556 ?
Pb1 Br1 3.1379(13) 4_456 ?
Br1 Pb1 3.1378(12) 4_556 ?
Br2 Pb1 3.0751(15) 4_456 ?
C1 C2 1.513(19) . ?
C1 N1 1.515(16) . ?
C1 C3 1.514(19) . ?
C1 H1 1.0000 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 C4 1.48(2) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?

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
Br3 Pb1 Br1 90.50(4) . . ?
Br3 Pb1 Br2 90.44(4) . . ?
Br1 Pb1 Br2 87.48(4) . . ?
Br3 Pb1 Br2 90.98(4) . 4_556 ?
Br1 Pb1 Br2 83.34(4) . 4_556 ?
Br2 Pb1 Br2 170.72(3) . 4_556 ?
Br3 Pb1 Br1 79.87(4) . 4_456 ?
Br1 Pb1 Br1 165.32(4) . 4_456 ?
Br2 Pb1 Br1 81.59(4) . 4_456 ?
Br2 Pb1 Br1 107.69(4) 4_556 4_456 ?
Pb1 Br1 Pb1 81.08(3) . 4_556 ?
Pb1 Br2 Pb1 81.48(4) . 4_456 ?
C2 C1 N1 107.7(12) . . ?
C2 C1 C3 112.6(13) . . ?
N1 C1 C3 110.0(12) . . ?
C2 C1 H1 108.8 . . ?
N1 C1 H1 108.8 . . ?
C3 C1 H1 108.8 . . ?
C1 N1 H1A 109.5 . . ?
C1 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C1 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C4 C3 C1 114.2(14) . . ?
C4 C3 H3A 108.7 . . ?
C1 C3 H3A 108.7 . . ?
C4 C3 H3B 108.7 . . ?
C1 C3 H3B 108.7 . . ?
H3A C3 H3B 107.6 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?

_refine_diff_density_max         1.843
_refine_diff_density_min         -1.869
_refine_diff_density_rms         0.292

_shelxl_version_number           2014/6



####################################################################### 
# 
# 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_e4318a_b
_database_code_depnum_ccdc_archive 'CCDC 2167652'
loop_
_audit_author_name
_audit_author_address
'Nathalie GRUBER'
;CNRS
France
;
_audit_update_record             
;
2022-04-20 deposited with the CCDC.	2022-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Br3 Pb, C8 H12 N'
_chemical_formula_sum            'C8 H12 Br3 N Pb'
_chemical_formula_weight         569.11

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8860(4)
_cell_length_b                   8.0842(4)
_cell_length_c                   20.2617(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1291.72(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    100000
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      none
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.926
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    22.302
_shelx_estimated_absorpt_T_min   0.214
_shelx_estimated_absorpt_T_max   0.268
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.204
_exptl_absorpt_correction_T_max  0.270
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            104048
_diffrn_reflns_av_unetI/netI     0.0229
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.010
_diffrn_reflns_theta_max         30.138
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3807
_reflns_number_gt                3638
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0100P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.00413(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1500 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3807
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0165
_refine_ls_wR_factor_ref         0.0363
_refine_ls_wR_factor_gt          0.0360
_refine_ls_goodness_of_fit_ref   1.308
_refine_ls_restrained_S_all      1.308
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

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
Pb1 Pb 0.21614(2) 0.24301(2) 0.48637(2) 0.01824(5) Uani 1 1 d . . . . .
Br1 Br 0.01140(5) -0.00812(5) 0.54857(2) 0.01871(10) Uani 1 1 d . . . . .
Br2 Br 0.37959(6) 0.29274(5) 0.61014(2) 0.02034(10) Uani 1 1 d . . . . .
Br3 Br -0.00662(5) 0.51820(5) 0.53017(2) 0.02069(11) Uani 1 1 d . . . . .
C1 C 0.3266(5) 0.7901(5) 0.7054(2) 0.0187(9) Uani 1 1 d . . . . .
C2 C 0.3218(7) 0.6495(6) 0.7438(2) 0.0283(11) Uani 1 1 d . . . . .
H2 H 0.3933 0.5585 0.7336 0.034 Uiso 1 1 calc R U . . .
C3 C 0.2123(7) 0.6411(6) 0.7974(2) 0.0332(12) Uani 1 1 d . . . . .
H3 H 0.2081 0.5430 0.8231 0.040 Uiso 1 1 calc R U . . .
C4 C 0.1097(6) 0.7729(6) 0.8136(2) 0.0296(11) Uani 1 1 d . . . . .
H4 H 0.0349 0.7655 0.8502 0.036 Uiso 1 1 calc R U . . .
C5 C 0.1163(7) 0.9146(6) 0.7768(3) 0.0346(12) Uani 1 1 d . . . . .
H5 H 0.0485 1.0072 0.7886 0.041 Uiso 1 1 calc R U . . .
C6 C 0.2237(7) 0.9227(6) 0.7216(2) 0.0289(11) Uani 1 1 d . . . . .
H6 H 0.2258 1.0199 0.6953 0.035 Uiso 1 1 calc R U . . .
C7 C 0.4368(5) 0.8016(5) 0.6441(2) 0.0202(9) Uani 1 1 d . . . . .
H7 H 0.4517 0.9212 0.6329 0.024 Uiso 1 1 calc R U . . .
N1 N 0.3426(5) 0.7197(4) 0.58810(18) 0.0209(8) Uani 1 1 d . . . . .
H1A H 0.4000 0.7362 0.5497 0.031 Uiso 1 1 calc R U . . .
H1B H 0.2370 0.7643 0.5847 0.031 Uiso 1 1 calc R U . . .
H1C H 0.3339 0.6092 0.5961 0.031 Uiso 1 1 calc R U . . .
C8 C 0.6085(6) 0.7250(7) 0.6500(2) 0.0346(12) Uani 1 1 d . . . . .
H8A H 0.6685 0.7736 0.6876 0.052 Uiso 1 1 calc R U . . .
H8B H 0.6730 0.7457 0.6095 0.052 Uiso 1 1 calc R U . . .
H8C H 0.5967 0.6055 0.6567 0.052 Uiso 1 1 calc R U . . .


_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
Pb1 Br2 2.8483(5) . ?
Pb1 Br1 2.8839(5) . ?
Pb1 Br3 2.9703(5) . ?
Pb1 Br3 3.0579(5) 4_556 ?
Br3 Pb1 3.0579(5) 4_456 ?
C1 C2 1.378(6) . ?
C1 C6 1.384(6) . ?
C1 C7 1.518(6) . ?
C2 C3 1.388(7) . ?
C2 H2 0.9500 . ?
C3 C4 1.379(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.367(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.405(7) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.494(6) . ?
C7 N1 1.509(5) . ?
C7 H7 1.0000 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?

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
Br2 Pb1 Br1 88.161(13) . . ?
Br2 Pb1 Br3 84.195(13) . . ?
Br1 Pb1 Br3 93.758(13) . . ?
Br2 Pb1 Br3 82.552(13) . 4_556 ?
Br1 Pb1 Br3 87.826(13) . 4_556 ?
Br3 Pb1 Br3 166.595(10) . 4_556 ?
Pb1 Br3 Pb1 82.699(11) . 4_456 ?
C2 C1 C6 119.2(4) . . ?
C2 C1 C7 121.9(4) . . ?
C6 C1 C7 118.9(4) . . ?
C1 C2 C3 120.0(5) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.7(5) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 119.7(5) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 120.5(5) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 N1 108.9(4) . . ?
C8 C7 C1 115.4(4) . . ?
N1 C7 C1 107.8(3) . . ?
C8 C7 H7 108.2 . . ?
N1 C7 H7 108.2 . . ?
C1 C7 H7 108.2 . . ?
C7 N1 H1A 109.5 . . ?
C7 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C7 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?

_refine_diff_density_max         1.273
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.126

_shelxl_version_number           2014/6



