# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2016

####################################################################### 
# 
# 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_283k
_database_code_depnum_ccdc_archive 'CCDC 1479296'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_vrf_PLAT342_ALERT_3_B           
;

PROBLEM:Low Bond Precision on C-C Bonds ............... 0.02333 Ang.

RESPONSE:These alerts are generated because there is disorder in the structure.


# Added by publCIF


# publcif _publ_body_element loop end
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 Br3 N2 Pb'
_chemical_formula_weight         614.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4696(6)
_cell_length_b                   7.9769(5)
_cell_length_c                   23.0327(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.250(3)
_cell_angle_gamma                90
_cell_volume                     1642.57(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    283(2)
_cell_measurement_reflns_used    9985
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.51

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.484
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    17.550
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.021
_exptl_absorpt_correction_T_max  0.173
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      283(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21246
_diffrn_reflns_av_unetI/netI     0.0466
_diffrn_reflns_av_R_equivalents  0.0614
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.720
_diffrn_reflns_theta_max         27.564
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3782
_reflns_number_gt                3046
_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 APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0347P)²+29.4516P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0063(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3782
_refine_ls_number_parameters     148
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1247
_refine_ls_wR_factor_gt          0.1126
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_restrained_S_all      2.498
_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
N1 N 0.0642(11) 0.6603(12) 0.8407(5) 0.041(2) Uani 1 1 d . . . . .
N2 N 0.0759(12) 0.4238(13) 0.8852(5) 0.046(2) Uani 1 1 d . . . . .
C1 C 0.1016(19) 0.802(2) 0.8077(8) 0.069(3) Uani 1 1 d . U . . .
H1A H 0.2071 0.8018 0.8143 0.104 Uiso 1 1 calc R U . . .
H1B H 0.0742 0.9050 0.8226 0.104 Uiso 1 1 calc R U . . .
H1C H 0.0478 0.7914 0.7645 0.104 Uiso 1 1 calc R U . . .
C2 C -0.0576(19) 0.647(2) 0.8588(8) 0.069(2) Uani 1 1 d . U . . .
H2 H -0.1323 0.7274 0.8533 0.082 Uiso 1 1 calc R U . . .
C3 C -0.0507(19) 0.501(2) 0.8857(8) 0.070(2) Uani 1 1 d . U . . .
H3 H -0.1207 0.4585 0.9021 0.084 Uiso 1 1 calc R U . . .
C4 C 0.1449(19) 0.524(2) 0.8572(8) 0.070(2) Uani 1 1 d . U . . .
H4 H 0.2347 0.5023 0.8505 0.084 Uiso 1 1 calc R U . . .
C5 C 0.130(2) 0.255(2) 0.9109(8) 0.077(2) Uani 1 1 d . U . . .
H5A H 0.0575 0.1713 0.8888 0.093 Uiso 1 1 calc R U . . .
H5B H 0.2234 0.2311 0.9041 0.093 Uiso 1 1 calc R U . . .
C6 C 0.152(2) 0.240(2) 0.9775(8) 0.081(2) Uani 1 1 d . U . . .
H6A H 0.2359 0.3117 0.9991 0.097 Uiso 1 1 calc R U . . .
H6B H 0.0643 0.2875 0.9843 0.097 Uiso 1 1 calc R U . . .
C7 C 0.178(2) 0.079(2) 1.0067(10) 0.090(2) Uani 1 1 d D U . . .
H7A H 0.0826 0.0224 0.9955 0.108 Uiso 1 1 calc R U . . .
H7B H 0.2097 0.0987 1.0507 0.108 Uiso 1 1 calc DR U . . .
C8 C 0.284(2) -0.038(2) 0.9959(9) 0.090(2) Uani 1 1 d D U . . .
H8A H 0.3832 0.0104 1.0124 0.108 Uiso 1 1 calc R U . . .
H8B H 0.2615 -0.0485 0.9518 0.108 Uiso 1 1 calc R U . . .
C9 C 0.290(2) -0.2160(19) 1.0227(10) 0.094(3) Uani 1 1 d D U . . .
H9A H 0.3046 -0.2083 1.0663 0.113 Uiso 1 1 calc R U . . .
H9B H 0.1951 -0.2719 1.0030 0.113 Uiso 1 1 calc R U . . .
C10 C 0.402(2) -0.309(3) 1.0143(10) 0.100(4) Uani 1 1 d . U . . .
H10A H 0.3822 -0.3271 0.9711 0.150 Uiso 1 1 calc R U . . .
H10B H 0.4090 -0.4145 1.0348 0.150 Uiso 1 1 calc R U . . .
H10C H 0.4953 -0.2494 1.0309 0.150 Uiso 1 1 calc R U . . .
Pb1 Pb 0.50685(5) 0.39700(5) 0.75210(2) 0.03231(17) Uani 1 1 d . . . . .
Br1 Br 0.54113(14) 0.64913(16) 0.85340(5) 0.0438(3) Uani 1 1 d . . . . .
Br2 Br 0.24822(13) 0.58727(16) 0.68902(6) 0.0492(3) Uani 1 1 d . . . . .
Br3 Br 0.32344(15) 0.17049(15) 0.79708(6) 0.0482(3) Uani 1 1 d . . . . .


_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
N1 C4 1.308(18) . ?
N1 C2 1.354(18) . ?
N1 C1 1.469(17) . ?
N2 C4 1.328(18) . ?
N2 C3 1.352(18) . ?
N2 C5 1.491(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.31(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.48(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.43(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.450(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.542(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.36(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Pb1 Br2 2.8402(13) . ?
Pb1 Br3 2.9225(12) . ?
Pb1 Br1 3.0158(13) . ?
Pb1 Br1 3.0484(13) 2_646 ?
Pb1 Br3 3.1345(12) 2_656 ?
Br1 Pb1 3.0484(13) 2_656 ?
Br3 Pb1 3.1345(12) 2_646 ?

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
C4 N1 C2 108.8(12) . . ?
C4 N1 C1 124.8(12) . . ?
C2 N1 C1 126.4(12) . . ?
C4 N2 C3 107.9(12) . . ?
C4 N2 C5 125.5(12) . . ?
C3 N2 C5 126.6(12) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 107.4(14) . . ?
C3 C2 H2 126.3 . . ?
N1 C2 H2 126.3 . . ?
C2 C3 N2 108.0(14) . . ?
C2 C3 H3 126.0 . . ?
N2 C3 H3 126.0 . . ?
N1 C4 N2 108.0(13) . . ?
N1 C4 H4 126.0 . . ?
N2 C4 H4 126.0 . . ?
C6 C5 N2 113.3(14) . . ?
C6 C5 H5A 108.9 . . ?
N2 C5 H5A 108.9 . . ?
C6 C5 H5B 108.9 . . ?
N2 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 C5 119.8(17) . . ?
C7 C6 H6A 107.4 . . ?
C5 C6 H6A 107.4 . . ?
C7 C6 H6B 107.4 . . ?
C5 C6 H6B 107.4 . . ?
H6A C6 H6B 106.9 . . ?
C6 C7 C8 121.5(16) . . ?
C6 C7 H7A 107.0 . . ?
C8 C7 H7A 107.0 . . ?
C6 C7 H7B 107.0 . . ?
C8 C7 H7B 107.0 . . ?
H7A C7 H7B 106.7 . . ?
C7 C8 C9 117.5(14) . . ?
C7 C8 H8A 107.9 . . ?
C9 C8 H8A 107.9 . . ?
C7 C8 H8B 107.9 . . ?
C9 C8 H8B 107.9 . . ?
H8A C8 H8B 107.2 . . ?
C10 C9 C8 111.6(17) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br2 Pb1 Br3 89.92(4) . . ?
Br2 Pb1 Br1 83.92(4) . . ?
Br3 Pb1 Br1 93.61(4) . . ?
Br2 Pb1 Br1 93.56(4) . 2_646 ?
Br3 Pb1 Br1 86.09(4) . 2_646 ?
Br1 Pb1 Br1 177.46(3) . 2_646 ?
Br2 Pb1 Br3 84.35(4) . 2_656 ?
Br3 Pb1 Br3 173.62(3) . 2_656 ?
Br1 Pb1 Br3 83.00(3) . 2_656 ?
Br1 Pb1 Br3 97.05(3) 2_646 2_656 ?
Pb1 Br1 Pb1 82.30(3) . 2_656 ?
Pb1 Br3 Pb1 82.34(3) . 2_646 ?

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
C4 N1 C2 C3 -1(2) . . . . ?
C1 N1 C2 C3 178.9(15) . . . . ?
N1 C2 C3 N2 1(2) . . . . ?
C4 N2 C3 C2 -1(2) . . . . ?
C5 N2 C3 C2 179.9(16) . . . . ?
C2 N1 C4 N2 0.6(19) . . . . ?
C1 N1 C4 N2 -179.2(13) . . . . ?
C3 N2 C4 N1 0.0(18) . . . . ?
C5 N2 C4 N1 179.6(13) . . . . ?
C4 N2 C5 C6 121.9(17) . . . . ?
C3 N2 C5 C6 -59(2) . . . . ?
N2 C5 C6 C7 169.4(16) . . . . ?
C5 C6 C7 C8 46(3) . . . . ?
C6 C7 C8 C9 -172(2) . . . . ?
C7 C8 C9 C10 -174(2) . . . . ?

_refine_diff_density_max         2.647
_refine_diff_density_min         -2.242
_refine_diff_density_rms         0.253

####################################################################### 
# 
# 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_313k
_database_code_depnum_ccdc_archive 'CCDC 1479298'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_vrf_PLAT342_ALERT_3_B           
;

PROBLEM:Low Bond Precision on C-C Bonds ............... 0.04 Ang.

RESPONSE:These alerts are generated because there is disorder in the structure.

;

_vrf_PLAT411_ALERT_2_A           
;

PROBLEM:Short Inter H...H Contact H7A .. H7A .. 1.82 Ang.

RESPONSE:The disordered side-chains are very dynamic and may be considered as a
solvent. Short contacts between disordered fragments are to be expected.


#Added by publCIF


# publcif _publ_body_element loop end
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 Br3 N2 Pb'
_chemical_formula_weight         614.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4917(6)
_cell_length_b                   7.9842(5)
_cell_length_c                   23.0848(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.062(3)
_cell_angle_gamma                90
_cell_volume                     1653.52(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    313(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      27.51

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.467
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    17.433
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.021
_exptl_absorpt_correction_T_max  0.175
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      313(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6076
_diffrn_reflns_av_unetI/netI     0.0642
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.162
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.917
_diffrn_measured_fraction_theta_full 0.917
_diffrn_reflns_Laue_measured_fraction_max 0.917
_diffrn_reflns_Laue_measured_fraction_full 0.917
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_point_group_measured_fraction_full 0.917
_reflns_number_total             2674
_reflns_number_gt                2049
_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 APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.2000P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0072(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2674
_refine_ls_number_parameters     148
_refine_ls_number_restraints     203
_refine_ls_R_factor_all          0.1130
_refine_ls_R_factor_gt           0.0893
_refine_ls_wR_factor_ref         0.2773
_refine_ls_wR_factor_gt          0.2622
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      2.814
_refine_ls_shift/su_max          0.000
_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
N1 N 0.063(3) 0.658(3) 0.8395(12) 0.073(3) Uani 1 1 d . U . . .
N2 N 0.078(3) 0.425(3) 0.8851(12) 0.074(3) Uani 1 1 d . U . . .
C1 C 0.100(3) 0.795(3) 0.8049(14) 0.075(4) Uani 1 1 d . U . . .
H1A H 0.1869 0.7651 0.7945 0.113 Uiso 1 1 calc R U . . .
H1B H 0.1197 0.8944 0.8294 0.113 Uiso 1 1 calc R U . . .
H1C H 0.0180 0.8140 0.7681 0.113 Uiso 1 1 calc R U . . .
C2 C -0.060(3) 0.646(3) 0.8559(15) 0.074(3) Uani 1 1 d . U . . .
H2 H -0.1354 0.7248 0.8483 0.089 Uiso 1 1 calc R U . . .
C3 C -0.054(3) 0.501(3) 0.8849(14) 0.074(3) Uani 1 1 d . U . . .
H3 H -0.1235 0.4585 0.9015 0.089 Uiso 1 1 calc R U . . .
C4 C 0.146(3) 0.522(3) 0.8590(13) 0.074(3) Uani 1 1 d . U . . .
H4 H 0.2381 0.5005 0.8544 0.089 Uiso 1 1 calc R U . . .
C5 C 0.133(3) 0.253(3) 0.9116(14) 0.077(3) Uani 1 1 d . U . . .
H5A H 0.0626 0.1685 0.8892 0.093 Uiso 1 1 calc R U . . .
H5B H 0.2280 0.2305 0.9063 0.093 Uiso 1 1 calc R U . . .
C6 C 0.149(3) 0.242(3) 0.9775(14) 0.079(3) Uani 1 1 d . U . . .
H6A H 0.2292 0.3160 0.9997 0.095 Uiso 1 1 calc R U . . .
H6B H 0.0581 0.2849 0.9826 0.095 Uiso 1 1 calc R U . . .
C7 C 0.178(3) 0.080(3) 1.0068(15) 0.084(3) Uani 1 1 d D U . . .
H7A H 0.0862 0.0163 0.9914 0.101 Uiso 1 1 calc R U . . .
H7B H 0.1945 0.0988 1.0500 0.101 Uiso 1 1 calc DR U . . .
C8 C 0.301(3) -0.033(3) 1.0032(14) 0.085(3) Uani 1 1 d D U . . .
H8A H 0.3953 0.0146 1.0273 0.102 Uiso 1 1 calc R U . . .
H8B H 0.2986 -0.0382 0.9609 0.102 Uiso 1 1 calc R U . . .
C9 C 0.291(3) -0.213(3) 1.0257(15) 0.089(3) Uani 1 1 d D U . . .
H9A H 0.3070 -0.2111 1.0694 0.107 Uiso 1 1 calc R U . . .
H9B H 0.1923 -0.2575 1.0052 0.107 Uiso 1 1 calc R U . . .
C10 C 0.407(3) -0.326(3) 1.0130(17) 0.096(5) Uani 1 1 d D U . . .
H10A H 0.3730 -0.3584 0.9706 0.144 Uiso 1 1 calc R U . . .
H10B H 0.4207 -0.4244 1.0382 0.144 Uiso 1 1 calc R U . . .
H10C H 0.4996 -0.2671 1.0222 0.144 Uiso 1 1 calc R U . . .
Pb1 Pb 0.50621(8) 0.39563(9) 0.75194(4) 0.0358(5) Uani 1 1 d . . . . .
Br1 Br 0.5408(3) 0.6476(3) 0.85329(11) 0.0492(7) Uani 1 1 d . . . . .
Br2 Br 0.2487(2) 0.5863(3) 0.68929(13) 0.0547(8) Uani 1 1 d . . . . .
Br3 Br 0.3235(3) 0.1683(3) 0.79694(13) 0.0545(8) Uani 1 1 d . . . . .


_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
N1 C4 1.33(3) . ?
N1 C2 1.34(3) . ?
N1 C1 1.46(3) . ?
N2 C4 1.28(3) . ?
N2 C3 1.38(3) . ?
N2 C5 1.53(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.33(3) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.48(4) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.44(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.498(17) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.536(18) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.523(18) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Pb1 Br2 2.842(2) . ?
Pb1 Br3 2.925(2) . ?
Pb1 Br1 3.021(2) . ?
Pb1 Br1 3.052(2) 2_646 ?
Pb1 Br3 3.133(2) 2_656 ?
Br1 Pb1 3.052(2) 2_656 ?
Br3 Pb1 3.133(2) 2_646 ?

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
C4 N1 C2 109(2) . . ?
C4 N1 C1 125(2) . . ?
C2 N1 C1 126(2) . . ?
C4 N2 C3 109(2) . . ?
C4 N2 C5 125(2) . . ?
C3 N2 C5 126(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 108(3) . . ?
C3 C2 H2 126.1 . . ?
N1 C2 H2 126.1 . . ?
C2 C3 N2 106(2) . . ?
C2 C3 H3 127.1 . . ?
N2 C3 H3 127.1 . . ?
N2 C4 N1 108(3) . . ?
N2 C4 H4 125.9 . . ?
N1 C4 H4 125.9 . . ?
C6 C5 N2 112(2) . . ?
C6 C5 H5A 109.2 . . ?
N2 C5 H5A 109.2 . . ?
C6 C5 H5B 109.2 . . ?
N2 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 118(3) . . ?
C7 C6 H6A 107.7 . . ?
C5 C6 H6A 107.7 . . ?
C7 C6 H6B 107.7 . . ?
C5 C6 H6B 107.7 . . ?
H6A C6 H6B 107.1 . . ?
C6 C7 C8 123(2) . . ?
C6 C7 H7A 106.5 . . ?
C8 C7 H7A 106.5 . . ?
C6 C7 H7B 106.5 . . ?
C8 C7 H7B 106.5 . . ?
H7A C7 H7B 106.5 . . ?
C7 C8 C9 114.3(16) . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 111(2) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br2 Pb1 Br3 90.10(7) . . ?
Br2 Pb1 Br1 83.99(7) . . ?
Br3 Pb1 Br1 93.73(7) . . ?
Br2 Pb1 Br1 93.71(7) . 2_646 ?
Br3 Pb1 Br1 86.02(7) . 2_646 ?
Br1 Pb1 Br1 177.68(4) . 2_646 ?
Br2 Pb1 Br3 84.47(7) . 2_656 ?
Br3 Pb1 Br3 173.92(6) . 2_656 ?
Br1 Pb1 Br3 82.98(6) . 2_656 ?
Br1 Pb1 Br3 97.05(7) 2_646 2_656 ?
Pb1 Br1 Pb1 82.24(6) . 2_656 ?
Pb1 Br3 Pb1 82.41(5) . 2_646 ?

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
C4 N1 C2 C3 -1(4) . . . . ?
C1 N1 C2 C3 178(3) . . . . ?
N1 C2 C3 N2 0(4) . . . . ?
C4 N2 C3 C2 1(4) . . . . ?
C5 N2 C3 C2 -178(3) . . . . ?
C3 N2 C4 N1 -2(4) . . . . ?
C5 N2 C4 N1 178(3) . . . . ?
C2 N1 C4 N2 2(4) . . . . ?
C1 N1 C4 N2 -177(3) . . . . ?
C4 N2 C5 C6 123(3) . . . . ?
C3 N2 C5 C6 -58(4) . . . . ?
N2 C5 C6 C7 171(2) . . . . ?
C5 C6 C7 C8 51(4) . . . . ?
C6 C7 C8 C9 -168(3) . . . . ?
C7 C8 C9 C10 173(3) . . . . ?

_refine_diff_density_max         6.897
_refine_diff_density_min         -5.440
_refine_diff_density_rms         0.498

####################################################################### 
# 
# 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_173k
_database_code_depnum_ccdc_archive 'CCDC 1479305'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;
#Added by publCIF


# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 Br3 N2 Pb'
_chemical_formula_weight         614.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.389(4)
_cell_length_b                   7.955(3)
_cell_length_c                   22.888(8)
_cell_angle_alpha                90
_cell_angle_beta                 109.638(15)
_cell_angle_gamma                90
_cell_volume                     1610.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9776
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.52

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.534
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   0.019
_exptl_transmission_factor_max   0.167
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    17.904
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.019
_exptl_absorpt_correction_T_max  0.167
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27388
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_av_R_equivalents  0.0606
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.729
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3682
_reflns_number_gt                3278
_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 APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0370P)²+18.7489P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00352(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3682
_refine_ls_number_parameters     148
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0382
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0920
_refine_ls_goodness_of_fit_ref   1.118
_refine_ls_restrained_S_all      2.542
_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
N1 N 0.0660(7) 0.6686(8) 0.8412(3) 0.0270(14) Uani 1 1 d . . . . .
N2 N 0.0804(8) 0.4298(9) 0.8864(3) 0.0304(15) Uani 1 1 d . . . . .
C1 C 0.1024(12) 0.8119(13) 0.8083(5) 0.0432(19) Uani 1 1 d . U . . .
H1A H 0.2096 0.8162 0.8168 0.065 Uiso 1 1 calc R U . . .
H1B H 0.0697 0.9141 0.8221 0.065 Uiso 1 1 calc R U . . .
H1C H 0.0517 0.7990 0.7645 0.065 Uiso 1 1 calc R U . . .
C2 C -0.0599(11) 0.6529(12) 0.8587(5) 0.0372(14) Uani 1 1 d . U . . .
H2 H -0.1371 0.7313 0.8524 0.045 Uiso 1 1 calc R U . . .
C3 C -0.0503(11) 0.5047(12) 0.8863(4) 0.0378(13) Uani 1 1 d . U . . .
H3 H -0.1203 0.4598 0.9026 0.045 Uiso 1 1 calc R U . . .
C4 C 0.1483(11) 0.5319(12) 0.8586(4) 0.0381(13) Uani 1 1 d . U . . .
H4 H 0.2396 0.5106 0.8524 0.046 Uiso 1 1 calc R U . . .
C5 C 0.1322(13) 0.2610(14) 0.9117(5) 0.0482(14) Uani 1 1 d . U . . .
H5A H 0.2290 0.2377 0.9068 0.058 Uiso 1 1 calc R U . . .
H5B H 0.0605 0.1777 0.8880 0.058 Uiso 1 1 calc R U . . .
C6 C 0.1484(13) 0.2453(14) 0.9793(5) 0.0492(14) Uani 1 1 d . U . . .
H6A H 0.2326 0.3149 1.0032 0.059 Uiso 1 1 calc R U . . .
H6B H 0.0579 0.2907 0.9849 0.059 Uiso 1 1 calc R U . . .
C7 C 0.1724(15) 0.0749(14) 1.0055(6) 0.0640(17) Uani 1 1 d D U . . .
H7A H 0.1964 0.0867 1.0500 0.077 Uiso 1 1 calc R U . . .
H7B H 0.0758 0.0176 0.9901 0.077 Uiso 1 1 calc DR U . . .
C8 C 0.2828(15) -0.0370(14) 0.9964(6) 0.0623(17) Uani 1 1 d D U . . .
H8A H 0.3818 0.0119 1.0167 0.075 Uiso 1 1 calc R U . . .
H8B H 0.2672 -0.0404 0.9523 0.075 Uiso 1 1 calc R U . . .
C9 C 0.2870(16) -0.2195(14) 1.0192(6) 0.066(2) Uani 1 1 d D U . . .
H9A H 0.2891 -0.2184 1.0619 0.080 Uiso 1 1 calc R U . . .
H9B H 0.1949 -0.2760 0.9945 0.080 Uiso 1 1 calc R U . . .
C10 C 0.4132(17) -0.3126(18) 1.0159(7) 0.073(3) Uani 1 1 d . U . . .
H10A H 0.4074 -0.3225 0.9734 0.110 Uiso 1 1 calc R U . . .
H10B H 0.4125 -0.4226 1.0331 0.110 Uiso 1 1 calc R U . . .
H10C H 0.5048 -0.2555 1.0391 0.110 Uiso 1 1 calc R U . . .
Pb1 Pb 0.50893(3) 0.40448(3) 0.75247(2) 0.02048(12) Uani 1 1 d . . . . .
Br1 Br 0.54186(9) 0.65484(10) 0.85411(3) 0.02640(19) Uani 1 1 d . . . . .
Br2 Br 0.24628(9) 0.59345(10) 0.68761(4) 0.0313(2) Uani 1 1 d . . . . .
Br3 Br 0.32311(10) 0.17996(10) 0.79763(4) 0.0298(2) Uani 1 1 d . . . . .


_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
N1 C4 1.317(11) . ?
N1 C2 1.376(11) . ?
N1 C1 1.468(11) . ?
N2 C4 1.320(12) . ?
N2 C3 1.363(11) . ?
N2 C5 1.478(13) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.325(13) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.510(14) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.468(15) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.434(13) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.539(13) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.420(17) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Pb1 Br2 2.8432(12) . ?
Pb1 Br3 2.9179(11) . ?
Pb1 Br1 2.9985(11) . ?
Pb1 Br1 3.0561(11) 2_646 ?
Pb1 Br3 3.1337(11) 2_656 ?
Br1 Pb1 3.0562(11) 2_656 ?
Br3 Pb1 3.1337(11) 2_646 ?

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
C4 N1 C2 108.1(7) . . ?
C4 N1 C1 125.7(7) . . ?
C2 N1 C1 126.3(7) . . ?
C4 N2 C3 108.1(7) . . ?
C4 N2 C5 126.7(8) . . ?
C3 N2 C5 125.1(8) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 107.0(8) . . ?
C3 C2 H2 126.5 . . ?
N1 C2 H2 126.5 . . ?
C2 C3 N2 107.9(8) . . ?
C2 C3 H3 126.1 . . ?
N2 C3 H3 126.1 . . ?
N1 C4 N2 109.0(8) . . ?
N1 C4 H4 125.5 . . ?
N2 C4 H4 125.5 . . ?
N2 C5 C6 112.5(9) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 116.3(10) . . ?
C7 C6 H6A 108.2 . . ?
C5 C6 H6A 108.2 . . ?
C7 C6 H6B 108.2 . . ?
C5 C6 H6B 108.2 . . ?
H6A C6 H6B 107.4 . . ?
C8 C7 C6 122.3(11) . . ?
C8 C7 H7A 106.8 . . ?
C6 C7 H7A 106.8 . . ?
C8 C7 H7B 106.8 . . ?
C6 C7 H7B 106.8 . . ?
H7A C7 H7B 106.6 . . ?
C7 C8 C9 118.3(10) . . ?
C7 C8 H8A 107.7 . . ?
C9 C8 H8A 107.7 . . ?
C7 C8 H8B 107.7 . . ?
C9 C8 H8B 107.7 . . ?
H8A C8 H8B 107.1 . . ?
C10 C9 C8 113.6(11) . . ?
C10 C9 H9A 108.8 . . ?
C8 C9 H9A 108.8 . . ?
C10 C9 H9B 108.8 . . ?
C8 C9 H9B 108.8 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br2 Pb1 Br3 89.52(4) . . ?
Br2 Pb1 Br1 84.21(3) . . ?
Br3 Pb1 Br1 92.85(3) . . ?
Br2 Pb1 Br1 92.96(3) . 2_646 ?
Br3 Pb1 Br1 86.19(3) . 2_646 ?
Br1 Pb1 Br1 177.016(14) . 2_646 ?
Br2 Pb1 Br3 83.92(4) . 2_656 ?
Br3 Pb1 Br3 172.76(2) . 2_656 ?
Br1 Pb1 Br3 83.46(3) . 2_656 ?
Br1 Pb1 Br3 97.18(3) 2_646 2_656 ?
Pb1 Br1 Pb1 82.22(3) . 2_656 ?
Pb1 Br3 Pb1 82.19(3) . 2_646 ?

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
C4 N1 C2 C3 -0.4(11) . . . . ?
C1 N1 C2 C3 179.2(9) . . . . ?
N1 C2 C3 N2 0.6(11) . . . . ?
C4 N2 C3 C2 -0.5(11) . . . . ?
C5 N2 C3 C2 -178.6(9) . . . . ?
C2 N1 C4 N2 0.1(11) . . . . ?
C1 N1 C4 N2 -179.5(8) . . . . ?
C3 N2 C4 N1 0.2(11) . . . . ?
C5 N2 C4 N1 178.3(9) . . . . ?
C4 N2 C5 C6 124.4(10) . . . . ?
C3 N2 C5 C6 -57.9(13) . . . . ?
N2 C5 C6 C7 169.3(10) . . . . ?
C5 C6 C7 C8 48.1(18) . . . . ?
C6 C7 C8 C9 -173.1(12) . . . . ?
C7 C8 C9 C10 -171.6(13) . . . . ?

_refine_diff_density_max         2.037
_refine_diff_density_min         -3.263
_refine_diff_density_rms         0.240


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_223k
_database_code_depnum_ccdc_archive 'CCDC 1479306'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_vrf_PLAT342_ALERT_3_B           
;

PROBLEM:Low Bond Precision on C-C Bonds ............... 0.02333 Ang.

RESPONSE:These alerts are generated because there is disorder in the structure.


# Added by publCIF


# publcif _publ_body_element loop end
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 Br3 N2 Pb'
_chemical_formula_weight         614.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4198(13)
_cell_length_b                   7.9592(11)
_cell_length_c                   22.961(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.524(6)
_cell_angle_gamma                90
_cell_volume                     1622.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.51

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.514
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    17.767
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.020
_exptl_absorpt_correction_T_max  0.169
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20543
_diffrn_reflns_av_unetI/netI     0.0415
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.177
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3713
_reflns_number_gt                3178
_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 APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0799P)²+25.3728P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3713
_refine_ls_number_parameters     147
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0566
_refine_ls_wR_factor_ref         0.1569
_refine_ls_wR_factor_gt          0.1467
_refine_ls_goodness_of_fit_ref   1.128
_refine_ls_restrained_S_all      2.549
_refine_ls_shift/su_max          0.000
_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
N1 N 0.0659(11) 0.6643(12) 0.8413(5) 0.030(2) Uani 1 1 d . . . . .
N2 N 0.0786(11) 0.4265(13) 0.8861(5) 0.032(2) Uani 1 1 d . . . . .
C1 C 0.1029(18) 0.807(2) 0.8083(8) 0.051(3) Uani 1 1 d . U . . .
H1A H 0.2037 0.7939 0.8076 0.077 Uiso 1 1 calc R U . . .
H1B H 0.0956 0.9094 0.8290 0.077 Uiso 1 1 calc R U . . .
H1C H 0.0337 0.8097 0.7667 0.077 Uiso 1 1 calc R U . . .
C2 C -0.0595(18) 0.6514(19) 0.8582(8) 0.0485(19) Uani 1 1 d . U . . .
H2 H -0.1362 0.7303 0.8515 0.058 Uiso 1 1 calc R U . . .
C3 C -0.0504(17) 0.5036(19) 0.8862(7) 0.0493(18) Uani 1 1 d . U . . .
H3 H -0.1199 0.4604 0.9030 0.059 Uiso 1 1 calc R U . . .
C4 C 0.1462(18) 0.5284(19) 0.8581(7) 0.0493(18) Uani 1 1 d . U . . .
H4 H 0.2366 0.5065 0.8515 0.059 Uiso 1 1 calc R U . . .
C5 C 0.130(2) 0.258(2) 0.9111(8) 0.0570(18) Uani 1 1 d . U . . .
H5A H 0.2261 0.2347 0.9057 0.068 Uiso 1 1 calc R U . . .
H5B H 0.0583 0.1752 0.8878 0.068 Uiso 1 1 calc R U . . .
C6 C 0.148(2) 0.242(2) 0.9786(8) 0.0591(19) Uani 1 1 d . U . . .
H6A H 0.2313 0.3136 1.0017 0.071 Uiso 1 1 calc R U . . .
H6B H 0.0579 0.2881 0.9842 0.071 Uiso 1 1 calc R U . . .
C7 C 0.173(2) 0.078(2) 1.0068(10) 0.069(2) Uani 1 1 d D U . . .
H7B H 0.1985 0.0927 1.0506 0.083 Uiso 1 1 d R U . . .
H7A H 0.0783 0.0206 0.9920 0.083 Uiso 1 1 d DR U . . .
C8 C 0.284(2) -0.036(2) 0.9964(9) 0.068(2) Uani 1 1 d D U . . .
H8A H 0.3834 0.0123 1.0154 0.082 Uiso 1 1 calc R U . . .
H8B H 0.2658 -0.0421 0.9523 0.082 Uiso 1 1 calc R U . . .
C9 C 0.288(2) -0.2176(19) 1.0208(10) 0.072(3) Uani 1 1 d D U . . .
H9A H 0.2935 -0.2137 1.0638 0.086 Uiso 1 1 calc R U . . .
H9B H 0.1944 -0.2738 0.9977 0.086 Uiso 1 1 calc R U . . .
C10 C 0.409(2) -0.311(3) 1.0160(10) 0.077(3) Uani 1 1 d . U . . .
H10A H 0.3927 -0.3354 0.9733 0.116 Uiso 1 1 calc R U . . .
H10B H 0.4182 -0.4135 1.0387 0.116 Uiso 1 1 calc R U . . .
H10C H 0.5002 -0.2464 1.0326 0.116 Uiso 1 1 calc R U . . .
Pb1 Pb 0.50807(4) 0.40053(5) 0.75235(2) 0.02325(16) Uani 1 1 d . . . . .
Br1 Br 0.54188(13) 0.65193(15) 0.85387(5) 0.0320(3) Uani 1 1 d . . . . .
Br2 Br 0.24699(13) 0.59035(15) 0.68831(6) 0.0368(3) Uani 1 1 d . . . . .
Br3 Br 0.32343(15) 0.17511(15) 0.79744(6) 0.0358(3) Uani 1 1 d . . . . .


_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
N1 C4 1.302(18) . ?
N1 C2 1.365(17) . ?
N1 C1 1.468(17) . ?
N2 C4 1.323(18) . ?
N2 C3 1.362(17) . ?
N2 C5 1.473(19) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.33(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.51(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.44(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.464(15) . ?
C7 H7B 0.9601 . ?
C7 H7A 0.9600 . ?
C8 C9 1.543(15) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.40(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Pb1 Br2 2.8418(13) . ?
Pb1 Br3 2.9188(12) . ?
Pb1 Br1 3.0071(13) . ?
Pb1 Br1 3.0523(13) 2_646 ?
Pb1 Br3 3.1329(12) 2_656 ?
Br1 Pb1 3.0524(13) 2_656 ?
Br3 Pb1 3.1329(12) 2_646 ?

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
C4 N1 C2 109.0(12) . . ?
C4 N1 C1 125.4(11) . . ?
C2 N1 C1 125.6(11) . . ?
C4 N2 C3 107.4(11) . . ?
C4 N2 C5 126.6(11) . . ?
C3 N2 C5 125.9(12) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 106.4(13) . . ?
C3 C2 H2 126.8 . . ?
N1 C2 H2 126.8 . . ?
C2 C3 N2 108.1(13) . . ?
C2 C3 H3 125.9 . . ?
N2 C3 H3 125.9 . . ?
N1 C4 N2 109.1(12) . . ?
N1 C4 H4 125.5 . . ?
N2 C4 H4 125.5 . . ?
N2 C5 C6 112.7(13) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 118.8(16) . . ?
C7 C6 H6A 107.6 . . ?
C5 C6 H6A 107.6 . . ?
C7 C6 H6B 107.6 . . ?
C5 C6 H6B 107.6 . . ?
H6A C6 H6B 107.0 . . ?
C6 C7 C8 120.7(15) . . ?
C6 C7 H7B 107.8 . . ?
C8 C7 H7B 107.8 . . ?
C6 C7 H7A 106.1 . . ?
C8 C7 H7A 106.1 . . ?
H7B C7 H7A 107.7 . . ?
C7 C8 C9 116.8(13) . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C10 C9 C8 112.5(16) . . ?
C10 C9 H9A 109.1 . . ?
C8 C9 H9A 109.1 . . ?
C10 C9 H9B 109.1 . . ?
C8 C9 H9B 109.1 . . ?
H9A C9 H9B 107.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br2 Pb1 Br3 89.72(4) . . ?
Br2 Pb1 Br1 84.06(4) . . ?
Br3 Pb1 Br1 93.17(4) . . ?
Br2 Pb1 Br1 93.19(4) . 2_646 ?
Br3 Pb1 Br1 86.21(4) . 2_646 ?
Br1 Pb1 Br1 177.18(2) . 2_646 ?
Br2 Pb1 Br3 84.07(4) . 2_656 ?
Br3 Pb1 Br3 173.14(3) . 2_656 ?
Br1 Pb1 Br3 83.30(3) . 2_656 ?
Br1 Pb1 Br3 97.02(3) 2_646 2_656 ?
Pb1 Br1 Pb1 82.18(3) . 2_656 ?
Pb1 Br3 Pb1 82.23(3) . 2_646 ?

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
C4 N1 C2 C3 0.6(19) . . . . ?
C1 N1 C2 C3 179.3(14) . . . . ?
N1 C2 C3 N2 -0.4(18) . . . . ?
C4 N2 C3 C2 0.1(18) . . . . ?
C5 N2 C3 C2 -178.4(15) . . . . ?
C2 N1 C4 N2 -0.5(18) . . . . ?
C1 N1 C4 N2 -179.3(13) . . . . ?
C3 N2 C4 N1 0.3(17) . . . . ?
C5 N2 C4 N1 178.7(13) . . . . ?
C4 N2 C5 C6 124.1(16) . . . . ?
C3 N2 C5 C6 -58(2) . . . . ?
N2 C5 C6 C7 169.8(15) . . . . ?
C5 C6 C7 C8 46(3) . . . . ?
C6 C7 C8 C9 -171.7(19) . . . . ?
C7 C8 C9 C10 -172(2) . . . . ?

_refine_diff_density_max         3.088
_refine_diff_density_min         -4.259
_refine_diff_density_rms         0.383


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_243K
_database_code_depnum_ccdc_archive 'CCDC 1479307'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_vrf_PLAT342_ALERT_3_B           
;

PROBLEM:Low Bond Precision on C-C Bonds ............... 0.025 Ang.

RESPONSE:These alerts are generated because there is disorder in the structure.


# Added by publCIF


# publcif _publ_body_element loop end
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 Br3 N2 Pb'
_chemical_formula_weight         614.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4442(6)
_cell_length_b                   7.9704(5)
_cell_length_c                   22.9992(14)
_cell_angle_alpha                90
_cell_angle_beta                 109.466(3)
_cell_angle_gamma                90
_cell_volume                     1632.28(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    243(2)
_cell_measurement_reflns_used    9970
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.56

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.499
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    17.660
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.020
_exptl_absorpt_correction_T_max  0.171
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      243(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20908
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.723
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3778
_reflns_number_gt                3184
_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 APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0832P)²+27.0776P] 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         3778
_refine_ls_number_parameters     147
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1631
_refine_ls_wR_factor_gt          0.1527
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      2.489
_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
N1 N 0.0647(11) 0.6627(13) 0.8410(5) 0.033(2) Uani 1 1 d . . . . .
N2 N 0.0779(12) 0.4250(14) 0.8857(5) 0.038(2) Uani 1 1 d . . . . .
C1 C 0.102(2) 0.804(2) 0.8083(8) 0.058(3) Uani 1 1 d . U . . .
H1A H 0.1651 0.7654 0.7859 0.086 Uiso 1 1 calc R U . . .
H1B H 0.1535 0.8880 0.8374 0.086 Uiso 1 1 calc R U . . .
H1C H 0.0112 0.8500 0.7800 0.086 Uiso 1 1 calc R U . . .
C2 C -0.059(2) 0.650(2) 0.8581(8) 0.055(2) Uani 1 1 d . U . . .
H2 H -0.1346 0.7295 0.8517 0.066 Uiso 1 1 calc R U . . .
C3 C -0.0505(19) 0.503(2) 0.8859(8) 0.056(2) Uani 1 1 d . U . . .
H3 H -0.1203 0.4599 0.9025 0.067 Uiso 1 1 calc R U . . .
C4 C 0.146(2) 0.528(2) 0.8579(8) 0.056(2) Uani 1 1 d . U . . .
H4 H 0.2367 0.5066 0.8515 0.067 Uiso 1 1 calc R U . . .
C5 C 0.130(2) 0.257(2) 0.9105(8) 0.0627(19) Uani 1 1 d . U . . .
H5A H 0.2246 0.2333 0.9044 0.075 Uiso 1 1 calc R U . . .
H5B H 0.0574 0.1742 0.8876 0.075 Uiso 1 1 calc R U . . .
C6 C 0.150(2) 0.241(2) 0.9787(9) 0.066(2) Uani 1 1 d . U . . .
H6A H 0.2334 0.3130 1.0011 0.079 Uiso 1 1 calc R U . . .
H6B H 0.0609 0.2866 0.9848 0.079 Uiso 1 1 calc R U . . .
C7 C 0.177(2) 0.079(2) 1.0070(10) 0.074(2) Uani 1 1 d D U . . .
H7A H 0.0815 0.0206 0.9942 0.088 Uiso 1 1 calc DR U . . .
H7B H 0.2049 0.0967 1.0511 0.088 Uiso 1 1 calc R U . . .
C8 C 0.288(2) -0.037(2) 0.9974(10) 0.073(2) Uani 1 1 d D U . . .
H8A H 0.3872 0.0101 1.0170 0.088 Uiso 1 1 calc R U . . .
H8B H 0.2715 -0.0430 0.9535 0.088 Uiso 1 1 calc R U . . .
C9 C 0.287(2) -0.218(2) 1.0216(10) 0.077(3) Uani 1 1 d D U . . .
H9A H 0.2932 -0.2138 1.0645 0.093 Uiso 1 1 calc R U . . .
H9B H 0.1941 -0.2726 0.9983 0.093 Uiso 1 1 calc R U . . .
C10 C 0.410(3) -0.311(3) 1.0164(11) 0.081(3) Uani 1 1 d . U . . .
H10A H 0.3972 -0.3270 0.9736 0.122 Uiso 1 1 calc R U . . .
H10B H 0.4133 -0.4183 1.0359 0.122 Uiso 1 1 calc R U . . .
H10C H 0.5014 -0.2515 1.0362 0.122 Uiso 1 1 calc R U . . .
Pb1 Pb 0.50766(5) 0.39921(5) 0.75228(2) 0.02570(16) Uani 1 1 d . . . . .
Br1 Br 0.54169(14) 0.65094(16) 0.85372(6) 0.0355(3) Uani 1 1 d . . . . .
Br2 Br 0.24735(14) 0.58916(16) 0.68855(7) 0.0402(3) Uani 1 1 d . . . . .
Br3 Br 0.32346(16) 0.17352(15) 0.79728(7) 0.0397(3) Uani 1 1 d . . . . .


_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
N1 C4 1.304(19) . ?
N1 C2 1.352(19) . ?
N1 C1 1.458(19) . ?
N2 C4 1.33(2) . ?
N2 C3 1.363(18) . ?
N2 C5 1.47(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.33(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.52(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.43(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.470(16) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.545(16) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.41(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Pb1 Br2 2.8430(13) . ?
Pb1 Br3 2.9212(13) . ?
Pb1 Br1 3.0120(13) . ?
Pb1 Br1 3.0526(13) 2_646 ?
Pb1 Br3 3.1361(13) 2_656 ?
Br1 Pb1 3.0527(13) 2_656 ?
Br3 Pb1 3.1361(13) 2_646 ?

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
C4 N1 C2 109.4(13) . . ?
C4 N1 C1 124.7(13) . . ?
C2 N1 C1 125.8(12) . . ?
C4 N2 C3 107.2(12) . . ?
C4 N2 C5 126.3(12) . . ?
C3 N2 C5 126.4(13) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 106.7(14) . . ?
C3 C2 H2 126.7 . . ?
N1 C2 H2 126.7 . . ?
C2 C3 N2 108.1(14) . . ?
C2 C3 H3 126.0 . . ?
N2 C3 H3 126.0 . . ?
N1 C4 N2 108.6(13) . . ?
N1 C4 H4 125.7 . . ?
N2 C4 H4 125.7 . . ?
N2 C5 C6 112.7(14) . . ?
N2 C5 H5A 109.1 . . ?
C6 C5 H5A 109.1 . . ?
N2 C5 H5B 109.1 . . ?
C6 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 119.1(17) . . ?
C7 C6 H6A 107.5 . . ?
C5 C6 H6A 107.5 . . ?
C7 C6 H6B 107.5 . . ?
C5 C6 H6B 107.5 . . ?
H6A C6 H6B 107.0 . . ?
C6 C7 C8 121.8(16) . . ?
C6 C7 H7A 106.9 . . ?
C8 C7 H7A 106.9 . . ?
C6 C7 H7B 106.9 . . ?
C8 C7 H7B 106.9 . . ?
H7A C7 H7B 106.7 . . ?
C7 C8 C9 116.3(14) . . ?
C7 C8 H8A 108.2 . . ?
C9 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
C9 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 111.1(17) . . ?
C10 C9 H9A 109.4 . . ?
C8 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
C8 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br2 Pb1 Br3 89.76(4) . . ?
Br2 Pb1 Br1 83.99(4) . . ?
Br3 Pb1 Br1 93.33(4) . . ?
Br2 Pb1 Br1 93.31(4) . 2_646 ?
Br3 Pb1 Br1 86.18(4) . 2_646 ?
Br1 Pb1 Br1 177.27(2) . 2_646 ?
Br2 Pb1 Br3 84.17(4) . 2_656 ?
Br3 Pb1 Br3 173.28(4) . 2_656 ?
Br1 Pb1 Br3 83.18(3) . 2_656 ?
Br1 Pb1 Br3 97.04(4) 2_646 2_656 ?
Pb1 Br1 Pb1 82.23(3) . 2_656 ?
Pb1 Br3 Pb1 82.27(3) . 2_646 ?

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
C4 N1 C2 C3 0(2) . . . . ?
C1 N1 C2 C3 179.2(15) . . . . ?
N1 C2 C3 N2 0(2) . . . . ?
C4 N2 C3 C2 0(2) . . . . ?
C5 N2 C3 C2 -178.5(16) . . . . ?
C2 N1 C4 N2 0.3(19) . . . . ?
C1 N1 C4 N2 -179.1(14) . . . . ?
C3 N2 C4 N1 -0.3(19) . . . . ?
C5 N2 C4 N1 178.4(14) . . . . ?
C4 N2 C5 C6 122.9(18) . . . . ?
C3 N2 C5 C6 -59(2) . . . . ?
N2 C5 C6 C7 170.2(16) . . . . ?
C5 C6 C7 C8 47(3) . . . . ?
C6 C7 C8 C9 -170(2) . . . . ?
C7 C8 C9 C10 -173(2) . . . . ?

_refine_diff_density_max         3.384
_refine_diff_density_min         -4.411
_refine_diff_density_rms         0.378

####################################################################### 
# 
# 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_263k
_database_code_depnum_ccdc_archive 'CCDC 1479308'
_audit_update_record             
;
2016-08-09 deposited with the CCDC.
2016-08-22 downloaded from the CCDC.
;

_vrf_PLAT342_ALERT_3_B           
;

PROBLEM:Low Bond Precision on C-C Bonds ............... 0.02333 Ang.

RESPONSE:These alerts are generated because there is disorder in the structure.


# Added by publCIF


# publcif _publ_body_element loop end
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H19 Br3 N2 Pb'
_chemical_formula_weight         614.19

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4561(6)
_cell_length_b                   7.9720(5)
_cell_length_c                   23.0041(12)
_cell_angle_alpha                90
_cell_angle_beta                 109.354(3)
_cell_angle_gamma                90
_cell_volume                     1636.14(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    263(2)
_cell_measurement_reflns_used    9983
_cell_measurement_theta_min      2.98
_cell_measurement_theta_max      27.54

_exptl_crystal_description       bulk
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.493
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   0.02
_exptl_transmission_factor_max   0.172
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    17.619
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.020
_exptl_absorpt_correction_T_max  0.172
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      263(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21092
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.171
_diffrn_reflns_theta_max         27.585
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3772
_reflns_number_gt                3105
_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 APEXII'
_computing_cell_refinement       'Bruker APEXII'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (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)+(0.0370P)²+30.4706P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0045(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3772
_refine_ls_number_parameters     148
_refine_ls_number_restraints     136
_refine_ls_R_factor_all          0.0682
_refine_ls_R_factor_gt           0.0508
_refine_ls_wR_factor_ref         0.1196
_refine_ls_wR_factor_gt          0.1095
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      2.411
_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
N1 N 0.0648(10) 0.6618(12) 0.8411(4) 0.038(2) Uani 1 1 d . . . . .
N2 N 0.0772(11) 0.4246(12) 0.8855(5) 0.041(2) Uani 1 1 d . . . . .
C1 C 0.1010(17) 0.8032(19) 0.8075(7) 0.064(3) Uani 1 1 d . U . . .
H1A H 0.2060 0.8014 0.8128 0.095 Uiso 1 1 calc R U . . .
H1B H 0.0765 0.9066 0.8233 0.095 Uiso 1 1 calc R U . . .
H1C H 0.0440 0.7939 0.7645 0.095 Uiso 1 1 calc R U . . .
C2 C -0.0578(17) 0.6483(18) 0.8590(7) 0.061(2) Uani 1 1 d . U . . .
H2 H -0.1328 0.7282 0.8535 0.074 Uiso 1 1 calc R U . . .
C3 C -0.0505(17) 0.5005(19) 0.8859(7) 0.0632(19) Uani 1 1 d . U . . .
H3 H -0.1205 0.4566 0.9022 0.076 Uiso 1 1 calc R U . . .
C4 C 0.1455(17) 0.5251(19) 0.8578(7) 0.0621(19) Uani 1 1 d . U . . .
H4 H 0.2356 0.5029 0.8513 0.075 Uiso 1 1 calc R U . . .
C5 C 0.1283(19) 0.256(2) 0.9106(8) 0.0703(18) Uani 1 1 d . U . . .
H5A H 0.2215 0.2297 0.9035 0.084 Uiso 1 1 calc R U . . .
H5B H 0.0544 0.1734 0.8885 0.084 Uiso 1 1 calc R U . . .
C6 C 0.152(2) 0.241(2) 0.9779(8) 0.074(2) Uani 1 1 d . U . . .
H6A H 0.2367 0.3117 0.9996 0.089 Uiso 1 1 calc R U . . .
H6B H 0.0646 0.2890 0.9851 0.089 Uiso 1 1 calc R U . . .
C7 C 0.178(2) 0.0776(19) 1.0062(9) 0.084(2) Uani 1 1 d D U . . .
H7A H 0.0820 0.0198 0.9934 0.101 Uiso 1 1 calc R U . . .
H7B H 0.2056 0.0947 1.0504 0.101 Uiso 1 1 calc DR U . . .
C8 C 0.286(2) -0.0368(19) 0.9963(9) 0.084(2) Uani 1 1 d D U . . .
H8A H 0.3851 0.0118 1.0147 0.100 Uiso 1 1 calc R U . . .
H8B H 0.2674 -0.0447 0.9523 0.100 Uiso 1 1 calc R U . . .
C9 C 0.289(2) -0.2169(18) 1.0219(9) 0.088(3) Uani 1 1 d D U . . .
H9A H 0.3008 -0.2112 1.0653 0.105 Uiso 1 1 calc R U . . .
H9B H 0.1947 -0.2718 1.0007 0.105 Uiso 1 1 calc R U . . .
C10 C 0.404(2) -0.310(3) 1.0145(10) 0.095(3) Uani 1 1 d . U . . .
H10A H 0.3861 -0.3294 0.9714 0.142 Uiso 1 1 calc R U . . .
H10B H 0.4104 -0.4161 1.0352 0.142 Uiso 1 1 calc R U . . .
H10C H 0.4972 -0.2508 1.0318 0.142 Uiso 1 1 calc R U . . .
Pb1 Pb 0.50725(4) 0.39810(4) 0.75217(2) 0.02936(16) Uani 1 1 d . . . . .
Br1 Br 0.54155(13) 0.64997(15) 0.85353(5) 0.0397(3) Uani 1 1 d . . . . .
Br2 Br 0.24780(12) 0.58831(14) 0.68886(6) 0.0451(3) Uani 1 1 d . . . . .
Br3 Br 0.32342(14) 0.17189(14) 0.79716(6) 0.0443(3) Uani 1 1 d . . . . .


_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
N1 C4 1.313(17) . ?
N1 C2 1.358(16) . ?
N1 C1 1.468(16) . ?
N2 C4 1.317(17) . ?
N2 C3 1.354(16) . ?
N2 C5 1.482(18) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.32(2) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C5 C6 1.50(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.44(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.448(15) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.548(15) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.38(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
Pb1 Br2 2.8410(12) . ?
Pb1 Br3 2.9220(11) . ?
Pb1 Br1 3.0122(12) . ?
Pb1 Br1 3.0486(12) 2_646 ?
Pb1 Br3 3.1337(11) 2_656 ?
Br1 Pb1 3.0487(12) 2_656 ?
Br3 Pb1 3.1336(11) 2_646 ?

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
C4 N1 C2 108.4(11) . . ?
C4 N1 C1 125.3(11) . . ?
C2 N1 C1 126.3(11) . . ?
C4 N2 C3 108.3(11) . . ?
C4 N2 C5 126.3(11) . . ?
C3 N2 C5 125.4(11) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 N1 107.2(12) . . ?
C3 C2 H2 126.4 . . ?
N1 C2 H2 126.4 . . ?
C2 C3 N2 107.6(13) . . ?
C2 C3 H3 126.2 . . ?
N2 C3 H3 126.2 . . ?
N1 C4 N2 108.5(12) . . ?
N1 C4 H4 125.8 . . ?
N2 C4 H4 125.8 . . ?
N2 C5 C6 113.0(13) . . ?
N2 C5 H5A 109.0 . . ?
C6 C5 H5A 109.0 . . ?
N2 C5 H5B 109.0 . . ?
C6 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 C5 118.7(15) . . ?
C7 C6 H6A 107.6 . . ?
C5 C6 H6A 107.6 . . ?
C7 C6 H6B 107.6 . . ?
C5 C6 H6B 107.6 . . ?
H6A C6 H6B 107.1 . . ?
C6 C7 C8 121.5(15) . . ?
C6 C7 H7A 107.0 . . ?
C8 C7 H7A 107.0 . . ?
C6 C7 H7B 107.0 . . ?
C8 C7 H7B 107.0 . . ?
H7A C7 H7B 106.7 . . ?
C7 C8 C9 116.7(13) . . ?
C7 C8 H8A 108.1 . . ?
C9 C8 H8A 108.1 . . ?
C7 C8 H8B 108.1 . . ?
C9 C8 H8B 108.1 . . ?
H8A C8 H8B 107.3 . . ?
C10 C9 C8 111.8(16) . . ?
C10 C9 H9A 109.3 . . ?
C8 C9 H9A 109.3 . . ?
C10 C9 H9B 109.3 . . ?
C8 C9 H9B 109.3 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
Br2 Pb1 Br3 89.82(4) . . ?
Br2 Pb1 Br1 83.92(3) . . ?
Br3 Pb1 Br1 93.51(3) . . ?
Br2 Pb1 Br1 93.48(4) . 2_646 ?
Br3 Pb1 Br1 86.07(3) . 2_646 ?
Br1 Pb1 Br1 177.38(2) . 2_646 ?
Br2 Pb1 Br3 84.30(4) . 2_656 ?
Br3 Pb1 Br3 173.47(3) . 2_656 ?
Br1 Pb1 Br3 83.06(3) . 2_656 ?
Br1 Pb1 Br3 97.10(3) 2_646 2_656 ?
Pb1 Br1 Pb1 82.30(3) . 2_656 ?
Pb1 Br3 Pb1 82.31(3) . 2_646 ?

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
C4 N1 C2 C3 -1.0(18) . . . . ?
C1 N1 C2 C3 178.0(14) . . . . ?
N1 C2 C3 N2 1.1(18) . . . . ?
C4 N2 C3 C2 -0.8(18) . . . . ?
C5 N2 C3 C2 -179.4(14) . . . . ?
C2 N1 C4 N2 0.5(17) . . . . ?
C1 N1 C4 N2 -178.5(12) . . . . ?
C3 N2 C4 N1 0.2(17) . . . . ?
C5 N2 C4 N1 178.8(12) . . . . ?
C4 N2 C5 C6 121.4(16) . . . . ?
C3 N2 C5 C6 -60(2) . . . . ?
N2 C5 C6 C7 170.0(14) . . . . ?
C5 C6 C7 C8 48(3) . . . . ?
C6 C7 C8 C9 -172.2(18) . . . . ?
C7 C8 C9 C10 -174.9(19) . . . . ?

_refine_diff_density_max         2.833
_refine_diff_density_min         -2.348
_refine_diff_density_rms         0.255

