# Electronic Supplementary Material (ESI) for Chemical Science.
# 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_sad1_a
_database_code_depnum_ccdc_archive 'CCDC 2169138'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_sad1_a              
;
PROBLEM: Check Calcd Resid. Dens.  2.44Ang From N2             -4.25 eA-3
RESPONSE: Many of the issues in the final refinement of this crystal structure are due to the modulated nature of this material. The effects of this modulation is  enhanced by the reduced temperature of this collection. This structure is  only the average structure for the modulated material and restraints were  required to model atomic displacements, likely caused by modulation, as  disorder.
;
# Added during the CSD deposition process: Wednesday 27 April 2022 08:10 PM
# end Validation Reply Form

_audit_creation_date             2022-04-27
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br4 Pb, C9 H13 N3'
_chemical_formula_sum            'C9 H13 Br4 N3 Pb'
_chemical_formula_weight         690.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.9594(5)
_cell_length_b                   30.9963(17)
_cell_length_c                   8.6387(5)
_cell_angle_alpha                90
_cell_angle_beta                 94.1860(10)
_cell_angle_gamma                90
_cell_volume                     3193.8(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.557
_exptl_absorpt_correction_T_max  0.4311
_exptl_absorpt_correction_T_min  0.2491
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
  wR2(int) was 0.1144 before and 0.0648 after correction. 
  The Ratio of minimum to maximum transmission is 0.5778. 
  The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.870
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2480
_exptl_crystal_preparation       
;
 'Crystals were prepared by dissolving the precursors in concentrated HBr
  at 100C and cooling the solution to room temperature at 2C/hr.'
;
_exptl_crystal_recrystallization_method 
"'Large colorless rectangular plates appear after cooling.   Small needles also appear after a few days.   These needles are not always observed and are a non-perovskite phase.'"
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0544
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            42973
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.485
_diffrn_reflns_theta_min         2.608
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3389
_reflns_number_total             3677
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         2.854
_refine_diff_density_min         -4.020
_refine_diff_density_rms         0.328
_refine_ls_extinction_coef       0.00010(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.247
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3677
_refine_ls_number_restraints     218
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      1.213
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+312.8122P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1433
_refine_ls_wR_factor_ref         0.1454
_refine_special_details          
;
Many of the issues in the final refinement of this crystal structure are due
to the modulated nature of this material. The effects of this modulation is 
enhanced by the reduced temperature of this collection. This structure is 
only the average structure for the modulated material and restraints were 
required to model atomic displacements, likely caused by modulation, as 
disorder.
;
_olex2_refinement_description    
;
1. Restrained distances
 C9-C8 \\sim C10-C8
 with sigma of 0.02
 C10-C8 \\sim C11-C8
 with sigma of 0.02
 C9-C8 \\sim C11-C8
 with sigma of 0.02
 N3-C9 \\sim N5-C10
 with sigma of 0.02
 N4-C11 \\sim N3-C9
 with sigma of 0.02
 N5-C10 \\sim N4-C11
 with sigma of 0.02
 N5-C10 \\sim N3-C9
 with sigma of 0.02
2. Rigid bond restraints
 N2, N1, C2, C3, C6, C4, C7, C1, C8, C5, N5, C10, N3, C9, N4, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N2 \\sim N1 \\sim C2 \\sim C3 \\sim C6 \\sim C4 \\sim C7 \\sim C1 \\sim C8
\\sim C5 \\sim N5 \\sim C10 \\sim N3 \\sim C9 \\sim N4 \\sim C11: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(N4) = Uanis(N5) = Uanis(N3)
Uanis(C10) = Uanis(C9) = Uanis(C11)
4. Others
 Sof(Br3)=1-FVAR(1)
 Sof(Br2)=FVAR(1)
 Sof(Br6)=1-FVAR(2)
 Sof(Br5)=FVAR(2)
 Fixed Sof: H8AB(0.3333) H8AA(0.3333) H8BD(0.3333) H8BC(0.3333) H8CF(0.3333)
 H8CE(0.3333) N5(0.3333) H5B(0.3333) H5C(0.3333) H5A(0.3333) C10(0.3333)
 H10B(0.3333) H10A(0.3333) N3(0.3333) H3B(0.3333) H3C(0.3333) H3A(0.3333)
 C9(0.3333) H9A(0.3333) H9B(0.3333) N4(0.3333) H4C(0.3333) H4A(0.3333)
 H4B(0.3333) C11(0.3333) H11B(0.3333) H11A(0.3333)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8AB,H8AA), C8(H8BD,H8BC), C8(H8CF,H8CE), C10(H10B,H10A), C9(H9A,H9B),
 C11(H11B,H11A)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C2(H2A), C3(H3), C4(H4), C5(H5)
5.c Idealised Me refined as rotating group:
 N5(H5B,H5C,H5A), N3(H3B,H3C,H3A), N4(H4C,H4A,H4B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.500000 0.67104(2) 0.750000 0.0251(2) Uani 1 2 d S T P . .
Pb2 Pb 1.000000 0.68530(3) 0.750000 0.0309(2) Uani 1 2 d S T P . .
Br1 Br 0.45683(13) 0.60690(5) 0.5198(2) 0.0396(4) Uani 1 1 d . . . . .
Br4 Br 0.99395(16) 0.62506(6) 0.4948(2) 0.0484(5) Uani 1 1 d . . . . .
Br2 Br 0.7492(2) 0.6722(2) 0.7372(5) 0.0366(15) Uani 0.471(12) 1 d . . P A 1
Br5 Br 0.9468(11) 0.7521(3) 1.0062(11) 0.022(3) Uani 0.30(3) 1 d . . P A 1
Br6 Br 0.9990(12) 0.75778(11) 0.9935(4) 0.052(2) Uani 0.70(3) 1 d . . P A 2
Br3 Br 0.7473(2) 0.6977(2) 0.7032(5) 0.0355(15) Uani 0.529(12) 1 d . . P A 2
N2 N 0.3303(11) 0.5719(5) 0.1585(16) 0.041(3) Uani 1 1 d . U . . .
H2 H 0.387245 0.575430 0.100765 0.049 Uiso 1 1 calc R U . . .
N1 N 0.1928(13) 0.5862(5) 0.2988(18) 0.049(4) Uani 1 1 d . U . . .
H1 H 0.144672 0.600759 0.350605 0.058 Uiso 1 1 calc R U . . .
C2 C 0.1355(15) 0.5100(6) 0.353(2) 0.048(4) Uani 1 1 d . U . . .
H2A H 0.075911 0.516495 0.416387 0.058 Uiso 1 1 calc R U . . .
C3 C 0.1657(16) 0.4680(6) 0.320(2) 0.053(4) Uani 1 1 d . U . . .
H3 H 0.122162 0.444906 0.356038 0.063 Uiso 1 1 calc R U . . .
C6 C 0.2869(15) 0.5327(6) 0.202(2) 0.044(3) Uani 1 1 d . U . . .
C4 C 0.2554(18) 0.4585(7) 0.237(3) 0.059(4) Uani 1 1 d . U . . .
H4 H 0.273934 0.429079 0.220686 0.070 Uiso 1 1 calc R U . . .
C7 C 0.2712(13) 0.6036(6) 0.219(2) 0.040(3) Uani 1 1 d . U . . .
C1 C 0.1972(11) 0.5412(6) 0.2894(19) 0.036(3) Uani 1 1 d . U . . .
C8 C 0.2918(18) 0.6499(6) 0.190(2) 0.057(4) Uani 1 1 d D U . . .
H8AB H 0.256054 0.657162 0.086498 0.069 Uiso 0.3333 1 calc R U P B 1
H8AA H 0.373550 0.653887 0.185272 0.069 Uiso 0.3333 1 calc R U P B 1
H8BD H 0.262433 0.657806 0.083875 0.069 Uiso 0.3333 1 calc R U P C 2
H8BC H 0.373255 0.655919 0.200435 0.069 Uiso 0.3333 1 calc R U P C 2
H8CF H 0.292026 0.654531 0.076858 0.069 Uiso 0.3333 1 calc R U P D 3
H8CE H 0.367255 0.657414 0.237067 0.069 Uiso 0.3333 1 calc R U P D 3
C5 C 0.3215(16) 0.4911(6) 0.175(2) 0.054(4) Uani 1 1 d . U . . .
H5 H 0.384795 0.484865 0.118041 0.065 Uiso 1 1 calc R U . . .
N5 N 0.241(3) 0.7214(11) 0.231(4) 0.031(4) Uani 0.3333 1 d D U P E 1
H5B H 0.211693 0.717554 0.131845 0.037 Uiso 0.3333 1 calc R U P E 1
H5C H 0.309082 0.734310 0.230543 0.037 Uiso 0.3333 1 calc R U P E 1
H5A H 0.193930 0.738494 0.282838 0.037 Uiso 0.3333 1 calc R U P E 1
C10 C 0.252(6) 0.6821(13) 0.304(4) 0.036(5) Uani 0.3333 1 d D U P E 1
H10B H 0.179131 0.672846 0.340534 0.043 Uiso 0.3333 1 calc R U P E 1
H10A H 0.306905 0.684237 0.395429 0.043 Uiso 0.3333 1 calc R U P E 1
N3 N 0.144(3) 0.6993(12) 0.245(4) 0.031(4) Uani 0.3333 1 d D U P E 2
H3B H 0.095965 0.681642 0.188263 0.037 Uiso 0.3333 1 calc R U P E 2
H3C H 0.168968 0.720330 0.182953 0.037 Uiso 0.3333 1 calc R U P E 2
H3A H 0.107605 0.711498 0.323068 0.037 Uiso 0.3333 1 calc R U P E 2
C9 C 0.233(5) 0.6756(17) 0.307(4) 0.036(5) Uani 0.3333 1 d D U P E 2
H9A H 0.206675 0.655689 0.386206 0.043 Uiso 0.3333 1 calc R U P E 2
H9B H 0.288218 0.695521 0.360903 0.043 Uiso 0.3333 1 calc R U P E 2
N4 N 0.228(3) 0.6943(12) 0.404(4) 0.031(4) Uani 0.3333 1 d D U P E 3
H4C H 0.292168 0.710384 0.411114 0.037 Uiso 0.3333 1 calc R U P E 3
H4A H 0.237006 0.671126 0.468382 0.037 Uiso 0.3333 1 calc R U P E 3
H4B H 0.169838 0.710615 0.431346 0.037 Uiso 0.3333 1 calc R U P E 3
C11 C 0.208(4) 0.6802(15) 0.254(5) 0.036(5) Uani 0.3333 1 d D U P E 3
H11B H 0.201164 0.705855 0.185213 0.043 Uiso 0.3333 1 calc R U P E 3
H11A H 0.133606 0.665650 0.245719 0.043 Uiso 0.3333 1 calc R U P E 3


_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 2.8325(17) 2_656 ?
Pb1 Br1 2.8326(17) . ?
Pb1 Br2 2.991(3) 2_656 ?
Pb1 Br2 2.991(3) . ?
Pb1 Br5 3.212(6) 7_667 ?
Pb1 Br5 3.212(6) 8_465 ?
Pb1 Br6 3.126(4) 7_667 ?
Pb1 Br6 3.126(4) 8_465 ?
Pb1 Br3 3.125(3) . ?
Pb1 Br3 3.125(3) 2_656 ?
Pb2 Br4 2.8859(19) . ?
Pb2 Br4 2.8858(19) 2_756 ?
Pb2 Br2 3.021(3) . ?
Pb2 Br2 3.021(3) 2_756 ?
Pb2 Br5 3.130(7) . ?
Pb2 Br5 3.130(7) 2_756 ?
Pb2 Br6 3.078(4) . ?
Pb2 Br6 3.078(4) 2_756 ?
Pb2 Br3 3.044(3) . ?
Pb2 Br3 3.044(3) 2_756 ?
N2 H2 0.8800 . ?
N2 C6 1.38(2) . ?
N2 C7 1.34(2) . ?
N1 H1 0.8800 . ?
N1 C7 1.32(2) . ?
N1 C1 1.40(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.39(3) . ?
C2 C1 1.36(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.36(3) . ?
C6 C1 1.38(2) . ?
C6 C5 1.38(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.42(3) . ?
C7 C8 1.48(3) . ?
C8 H8AB 0.9900 . ?
C8 H8AA 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 H8CF 0.9900 . ?
C8 H8CE 0.9900 . ?
C8 C10 1.50(3) . ?
C8 C9 1.50(3) . ?
C8 C11 1.51(3) . ?
C5 H5 0.9500 . ?
N5 H5B 0.9100 . ?
N5 H5C 0.9100 . ?
N5 H5A 0.9100 . ?
N5 C10 1.38(3) . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 H3A 0.9100 . ?
N3 C9 1.37(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N4 H4C 0.9100 . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 C11 1.38(3) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?

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 Br1 90.85(7) 2_656 . ?
Br1 Pb1 Br2 96.52(9) . . ?
Br1 Pb1 Br2 84.46(14) . 2_656 ?
Br1 Pb1 Br2 84.46(14) 2_656 . ?
Br1 Pb1 Br2 96.52(10) 2_656 2_656 ?
Br1 Pb1 Br5 92.45(19) 2_656 7_667 ?
Br1 Pb1 Br5 176.3(3) 2_656 8_465 ?
Br1 Pb1 Br5 92.45(19) . 8_465 ?
Br1 Pb1 Br5 176.3(3) . 7_667 ?
Br1 Pb1 Br6 169.7(3) . 7_667 ?
Br1 Pb1 Br6 90.38(7) . 8_465 ?
Br1 Pb1 Br6 169.7(3) 2_656 8_465 ?
Br1 Pb1 Br6 90.38(7) 2_656 7_667 ?
Br1 Pb1 Br3 98.67(12) . 2_656 ?
Br1 Pb1 Br3 102.74(7) . . ?
Br1 Pb1 Br3 102.73(7) 2_656 2_656 ?
Br1 Pb1 Br3 98.67(12) 2_656 . ?
Br2 Pb1 Br2 178.6(3) . 2_656 ?
Br2 Pb1 Br5 82.2(3) . 7_667 ?
Br2 Pb1 Br5 82.2(3) 2_656 8_465 ?
Br2 Pb1 Br5 96.7(3) 2_656 7_667 ?
Br2 Pb1 Br5 96.7(3) . 8_465 ?
Br2 Pb1 Br6 85.3(3) . 8_465 ?
Br2 Pb1 Br6 93.8(3) 2_656 8_465 ?
Br2 Pb1 Br6 93.8(3) . 7_667 ?
Br2 Pb1 Br6 85.3(3) 2_656 7_667 ?
Br2 Pb1 Br3 15.64(8) 2_656 2_656 ?
Br2 Pb1 Br3 163.1(2) . 2_656 ?
Br5 Pb1 Br5 84.3(4) 7_667 8_465 ?
Br3 Pb1 Br3 149.3(2) 2_656 . ?
Br4 Pb2 Br4 99.36(8) 2_756 . ?
Br4 Pb2 Br2 84.87(13) 2_756 . ?
Br4 Pb2 Br2 84.87(13) . 2_756 ?
Br4 Pb2 Br2 85.16(9) 2_756 2_756 ?
Br4 Pb2 Br2 85.16(9) . . ?
Br4 Pb2 Br5 83.3(2) . 2_756 ?
Br4 Pb2 Br5 166.7(2) . . ?
Br4 Pb2 Br5 166.7(2) 2_756 2_756 ?
Br4 Pb2 Br5 83.3(2) 2_756 . ?
Br4 Pb2 Br6 87.21(7) 2_756 . ?
Br4 Pb2 Br6 87.21(7) . 2_756 ?
Br4 Pb2 Br6 173.25(9) . . ?
Br4 Pb2 Br6 173.25(9) 2_756 2_756 ?
Br4 Pb2 Br3 98.77(13) . 2_756 ?
Br4 Pb2 Br3 98.77(13) 2_756 . ?
Br4 Pb2 Br3 90.63(8) . . ?
Br4 Pb2 Br3 90.63(8) 2_756 2_756 ?
Br2 Pb2 Br2 164.6(3) 2_756 . ?
Br2 Pb2 Br5 108.4(2) . 2_756 ?
Br2 Pb2 Br5 108.4(2) 2_756 . ?
Br2 Pb2 Br5 82.1(3) 2_756 2_756 ?
Br2 Pb2 Br5 82.1(3) . . ?
Br2 Pb2 Br6 97.3(3) . 2_756 ?
Br2 Pb2 Br6 94.0(3) 2_756 2_756 ?
Br2 Pb2 Br3 174.47(11) . 2_756 ?
Br2 Pb2 Br3 15.97(8) 2_756 2_756 ?
Br5 Pb2 Br5 97.1(5) . 2_756 ?
Br3 Pb2 Br6 82.5(3) 2_756 . ?
Br3 Pb2 Br6 86.9(3) . . ?
Br3 Pb2 Br3 165.5(2) . 2_756 ?
Pb1 Br2 Pb2 171.8(2) . . ?
Pb2 Br5 Pb1 156.0(5) . 7_667 ?
Pb2 Br6 Pb1 177.96(14) . 7_667 ?
Pb2 Br3 Pb1 152.8(2) . . ?
C6 N2 H2 125.7 . . ?
C7 N2 H2 125.7 . . ?
C7 N2 C6 108.6(14) . . ?
C7 N1 H1 124.9 . . ?
C7 N1 C1 110.3(14) . . ?
C1 N1 H1 124.9 . . ?
C3 C2 H2A 122.4 . . ?
C1 C2 H2A 122.4 . . ?
C1 C2 C3 115.3(19) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 123(2) . . ?
C4 C3 H3 118.7 . . ?
C1 C6 N2 107.6(15) . . ?
C5 C6 N2 130.6(18) . . ?
C5 C6 C1 121.8(19) . . ?
C3 C4 H4 119.1 . . ?
C3 C4 C5 121.9(18) . . ?
C5 C4 H4 119.1 . . ?
N2 C7 C8 123.2(16) . . ?
N1 C7 N2 108.6(16) . . ?
N1 C7 C8 128.1(15) . . ?
C2 C1 N1 131.5(16) . . ?
C2 C1 C6 123.6(17) . . ?
C6 C1 N1 104.8(15) . . ?
C7 C8 H8AB 107.8 . . ?
C7 C8 H8AA 107.8 . . ?
C7 C8 H8BD 110.1 . . ?
C7 C8 H8BC 110.1 . . ?
C7 C8 H8CF 108.6 . . ?
C7 C8 H8CE 108.6 . . ?
C7 C8 C10 118(2) . . ?
C7 C8 C9 108(3) . . ?
C7 C8 C11 115(3) . . ?
H8AB C8 H8AA 107.1 . . ?
H8BD C8 H8BC 108.4 . . ?
H8CF C8 H8CE 107.5 . . ?
C10 C8 H8AB 107.8 . . ?
C10 C8 H8AA 107.8 . . ?
C9 C8 H8BD 110.1 . . ?
C9 C8 H8BC 110.1 . . ?
C11 C8 H8CF 108.6 . . ?
C11 C8 H8CE 108.6 . . ?
C6 C5 C4 114.8(18) . . ?
C6 C5 H5 122.6 . . ?
C4 C5 H5 122.6 . . ?
H5B N5 H5C 109.5 . . ?
H5B N5 H5A 109.5 . . ?
H5C N5 H5A 109.5 . . ?
C10 N5 H5B 109.5 . . ?
C10 N5 H5C 109.5 . . ?
C10 N5 H5A 109.5 . . ?
C8 C10 H10B 110.0 . . ?
C8 C10 H10A 110.0 . . ?
N5 C10 C8 108(3) . . ?
N5 C10 H10B 110.0 . . ?
N5 C10 H10A 110.0 . . ?
H10B C10 H10A 108.4 . . ?
H3B N3 H3C 109.5 . . ?
H3B N3 H3A 109.5 . . ?
H3C N3 H3A 109.5 . . ?
C9 N3 H3B 109.5 . . ?
C9 N3 H3C 109.5 . . ?
C9 N3 H3A 109.5 . . ?
C8 C9 H9A 108.7 . . ?
C8 C9 H9B 108.7 . . ?
N3 C9 C8 114(3) . . ?
N3 C9 H9A 108.7 . . ?
N3 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
H4C N4 H4A 109.5 . . ?
H4C N4 H4B 109.5 . . ?
H4A N4 H4B 109.5 . . ?
C11 N4 H4C 109.5 . . ?
C11 N4 H4A 109.5 . . ?
C11 N4 H4B 109.5 . . ?
C8 C11 H11B 108.0 . . ?
C8 C11 H11A 108.0 . . ?
N4 C11 C8 117(3) . . ?
N4 C11 H11B 108.0 . . ?
N4 C11 H11A 108.0 . . ?
H11B C11 H11A 107.2 . . ?

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
N2 C6 C1 N1 -1.9(18) . . . . ?
N2 C6 C1 C2 -179.1(15) . . . . ?
N2 C6 C5 C4 -179.6(18) . . . . ?
N2 C7 C8 C10 -158(3) . . . . ?
N2 C7 C8 C9 -165(2) . . . . ?
N2 C7 C8 C11 173(2) . . . . ?
N1 C7 C8 C10 24(4) . . . . ?
N1 C7 C8 C9 18(3) . . . . ?
N1 C7 C8 C11 -4(3) . . . . ?
C2 C3 C4 C5 -2(3) . . . . ?
C3 C2 C1 N1 -178.9(17) . . . . ?
C3 C2 C1 C6 -3(3) . . . . ?
C3 C4 C5 C6 -1(3) . . . . ?
C6 N2 C7 N1 0(2) . . . . ?
C6 N2 C7 C8 -177.5(18) . . . . ?
C7 N2 C6 C1 1.1(19) . . . . ?
C7 N2 C6 C5 -177.1(19) . . . . ?
C7 N1 C1 C2 179.0(17) . . . . ?
C7 N1 C1 C6 2(2) . . . . ?
C7 C8 C10 N5 -158(4) . . . . ?
C7 C8 C9 N3 -112(5) . . . . ?
C7 C8 C11 N4 88(5) . . . . ?
C1 N1 C7 N2 -1(2) . . . . ?
C1 N1 C7 C8 176.1(18) . . . . ?
C1 C2 C3 C4 4(3) . . . . ?
C1 C6 C5 C4 2(3) . . . . ?
C5 C6 C1 N1 176.5(17) . . . . ?
C5 C6 C1 C2 -1(3) . . . . ?

_olex2_exptl_crystal_mounting_method 
;
 'Crystals were seperated from the mother liquor using paratone oil. 
  The crystal used for diffaction was placed on a kapton loop using 
  paratone to adhere it to the loop.'
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad_a
_database_code_depnum_ccdc_archive 'CCDC 2169139'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br4 Pb, C9 H13 N3'
_chemical_formula_sum            'C9 H13 Br4 N3 Pb'
_chemical_formula_weight         690.05
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   12.0291(2)
_cell_length_b                   31.1120(7)
_cell_length_c                   8.7353(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.0590(10)
_cell_angle_gamma                90
_cell_volume                     3260.98(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9623
_cell_measurement_temperature    300
_cell_measurement_theta_max      27.58
_cell_measurement_theta_min      2.62
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.134
_exptl_absorpt_correction_T_max  0.4306
_exptl_absorpt_correction_T_min  0.2524
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
  wR2(int) was 0.1344 before and 0.0717 after correction. 
  The Ratio of minimum to maximum transmission is 0.5862. 
  The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.811
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2480
_exptl_crystal_preparation       
;
 'Crystals were prepared by dissolving the precursors in concentrated HBr
  at 100C and cooling the solution to room temperature at 2C/hr.'
;
_exptl_crystal_recrystallization_method 
"'Large colorless rectangular plates appear after cooling.   Small needles also appear after a few days.   These needles are not always observed and are a non-perovskite phase.'"
_exptl_crystal_size_max          0.165
_exptl_crystal_size_mid          0.065
_exptl_crystal_size_min          0.015
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0270
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       38
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            38217
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         1.819
_diffrn_ambient_temperature      300.15
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2823
_reflns_number_total             3331
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.463
_refine_diff_density_min         -1.474
_refine_diff_density_rms         0.129
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     204
_refine_ls_number_reflns         3331
_refine_ls_number_restraints     218
_refine_ls_R_factor_all          0.0380
_refine_ls_R_factor_gt           0.0296
_refine_ls_restrained_S_all      0.995
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0273P)²+26.6161P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0684
_refine_ls_wR_factor_ref         0.0730
_refine_special_details          
;
Many of the issues in the final refinement of this crystal structure are due
to the modulated nature of this material. The effects of this modulation is 
reduced due to the vibrational energy of the atoms at 300K. This structure is 
only the average structure for the modulated material and restraints were 
required to model atomic displacements, likely caused by modulation, as 
disorder.
;
_olex2_refinement_description    
;
1. Restrained distances
 C8-C9 \\sim C8-C10
 with sigma of 0.02
 C8-C10 \\sim C8-C11
 with sigma of 0.02
 C8-C11 \\sim C8-C9
 with sigma of 0.02
 N3-C9 \\sim N4-C10
 with sigma of 0.02
 N3-C9 \\sim N5-C11
 with sigma of 0.02
 N5-C11 \\sim N4-C10
 with sigma of 0.02
2. Rigid bond restraints
 N1, N2, C7, C3, C6, C2, C5, C4, C1, C8, N3, C9, N4, C10, N5, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim N2 \\sim C7 \\sim C3 \\sim C6 \\sim C2 \\sim C5 \\sim C4 \\sim C1
\\sim C8 \\sim N3 \\sim C9 \\sim N4 \\sim C10 \\sim N5 \\sim C11: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(Br2)=1-FVAR(1)
 Sof(Br3)=FVAR(1)
 Fixed Sof: H8AA(0.3333) H8AB(0.3333) H8BC(0.3333) H8BD(0.3333) H8CE(0.3333)
 H8CF(0.3333) N3(0.3333) H3A(0.3333) H3B(0.3333) H3C(0.3333) C9(0.3333)
 H9A(0.3333) H9B(0.3333) N4(0.3333) H4A(0.3333) H4B(0.3333) H4C(0.3333)
 C10(0.3333) H10A(0.3333) H10B(0.3333) N5(0.3333) H5A(0.3333) H5B(0.3333)
 H5C(0.3333) C11(0.3333) H11A(0.3333) H11B(0.3333)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8AA,H8AB), C8(H8BC,H8BD), C8(H8CE,H8CF), C9(H9A,H9B), C10(H10A,H10B),
 C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), C2(H2A), C5(H5), C4(H4)
5.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N4(H4A,H4B,H4C), N5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.500000 0.32845(2) 0.250000 0.04008(10) Uani 1 2 d S T P . .
Pb2 Pb 0.000000 0.31593(2) 0.250000 0.04356(11) Uani 1 2 d S T P . .
Br4 Br 0.00493(8) 0.37634(3) 0.50188(10) 0.0769(3) Uani 1 1 d . . . . .
Br5 Br 0.01642(11) 0.24426(3) 0.00468(11) 0.0992(4) Uani 1 1 d . . . . .
Br1 Br 0.53870(7) 0.39265(3) 0.47870(10) 0.0727(2) Uani 1 1 d . . . . .
Br3 Br 0.25253(14) 0.3040(3) 0.2886(5) 0.0649(13) Uani 0.518(14) 1 d . . P A 1
Br2 Br 0.25033(15) 0.3269(3) 0.2615(4) 0.0585(13) Uani 0.482(14) 1 d . . P A 2
N1 N 0.8054(6) 0.4135(2) 0.7007(8) 0.0689(17) Uani 1 1 d . U . . .
H1 H 0.852620 0.399215 0.651518 0.083 Uiso 1 1 calc R U . . .
N2 N 0.6693(6) 0.4274(2) 0.8362(8) 0.0690(17) Uani 1 1 d . U . . .
H2 H 0.613403 0.423807 0.891047 0.083 Uiso 1 1 calc R U . . .
C7 C 0.7282(7) 0.3963(3) 0.7806(9) 0.0654(18) Uani 1 1 d . U . . .
C3 C 0.8292(10) 0.5320(3) 0.6801(13) 0.098(3) Uani 1 1 d . U . . .
H3 H 0.869494 0.554880 0.643863 0.118 Uiso 1 1 calc R U . . .
C6 C 0.7107(7) 0.4671(3) 0.7931(9) 0.0628(17) Uani 1 1 d . U . . .
C2 C 0.8620(8) 0.4906(3) 0.6480(11) 0.084(2) Uani 1 1 d . U . . .
H2A H 0.922358 0.484906 0.590261 0.100 Uiso 1 1 calc R U . . .
C5 C 0.6772(8) 0.5085(3) 0.8228(12) 0.087(3) Uani 1 1 d . U . . .
H5 H 0.616324 0.514333 0.879439 0.105 Uiso 1 1 calc R U . . .
C4 C 0.7397(10) 0.5405(4) 0.7631(13) 0.103(3) Uani 1 1 d . U . . .
H4 H 0.720503 0.568949 0.779752 0.124 Uiso 1 1 calc R U . . .
C1 C 0.8000(6) 0.4586(3) 0.7067(9) 0.0622(17) Uani 1 1 d . U . . .
C8 C 0.7058(9) 0.3496(3) 0.8063(12) 0.092(3) Uani 1 1 d D U . . .
H8AA H 0.716898 0.342896 0.914731 0.110 Uiso 0.3333 1 calc R U P B 1
H8AB H 0.629326 0.342852 0.772196 0.110 Uiso 0.3333 1 calc R U P B 1
H8BC H 0.690241 0.346639 0.913218 0.110 Uiso 0.3333 1 calc R U P C 2
H8BD H 0.637160 0.342823 0.746211 0.110 Uiso 0.3333 1 calc R U P C 2
H8CE H 0.738536 0.341631 0.906959 0.110 Uiso 0.3333 1 calc R U P D 3
H8CF H 0.625916 0.345475 0.806661 0.110 Uiso 0.3333 1 calc R U P D 3
N3 N 0.7571(17) 0.2789(6) 0.769(2) 0.078(6) Uani 0.3333 1 d D U P E 1
H3A H 0.787708 0.259901 0.708655 0.094 Uiso 0.3333 1 calc R U P E 1
H3B H 0.683572 0.275210 0.763680 0.094 Uiso 0.3333 1 calc R U P E 1
H3C H 0.784424 0.275052 0.865654 0.094 Uiso 0.3333 1 calc R U P E 1
C9 C 0.784(3) 0.3238(8) 0.718(4) 0.069(8) Uani 0.3333 1 d D U P E 1
H9A H 0.860778 0.331298 0.745528 0.083 Uiso 0.3333 1 calc R U P E 1
H9B H 0.768166 0.327318 0.608219 0.083 Uiso 0.3333 1 calc R U P E 1
N4 N 0.764(2) 0.3066(9) 0.607(3) 0.095(7) Uani 0.3333 1 d D U P E 2
H4A H 0.725279 0.328382 0.563438 0.114 Uiso 0.3333 1 calc R U P E 2
H4B H 0.724156 0.282483 0.594220 0.114 Uiso 0.3333 1 calc R U P E 2
H4C H 0.827791 0.303678 0.562868 0.114 Uiso 0.3333 1 calc R U P E 2
C10 C 0.787(3) 0.3153(11) 0.774(3) 0.084(7) Uani 0.3333 1 d D U P E 2
H10A H 0.774410 0.289749 0.834696 0.101 Uiso 0.3333 1 calc R U P E 2
H10B H 0.862805 0.325003 0.796507 0.101 Uiso 0.3333 1 calc R U P E 2
N5 N 0.8568(16) 0.3006(6) 0.755(2) 0.069(5) Uani 0.3333 1 d D U P E 3
H5A H 0.897690 0.293069 0.678208 0.083 Uiso 0.3333 1 calc R U P E 3
H5B H 0.842278 0.277494 0.809960 0.083 Uiso 0.3333 1 calc R U P E 3
H5C H 0.894243 0.319690 0.814508 0.083 Uiso 0.3333 1 calc R U P E 3
C11 C 0.749(3) 0.3203(11) 0.691(3) 0.063(6) Uani 0.3333 1 d D U P E 3
H11A H 0.761906 0.336112 0.597961 0.076 Uiso 0.3333 1 calc R U P E 3
H11B H 0.695392 0.297791 0.664985 0.076 Uiso 0.3333 1 calc R U P E 3


_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 Br5 3.1692(9) 8_556 ?
Pb1 Br5 3.1692(9) 7 ?
Pb1 Br1 2.8401(8) . ?
Pb1 Br1 2.8400(8) 2_655 ?
Pb1 Br3 3.114(3) 2_655 ?
Pb1 Br3 3.114(3) . ?
Pb1 Br2 3.0125(17) 2_655 ?
Pb1 Br2 3.0125(17) . ?
Pb2 Br4 2.8912(8) 2 ?
Pb2 Br4 2.8912(8) . ?
Pb2 Br5 3.1085(9) . ?
Pb2 Br5 3.1085(9) 2 ?
Pb2 Br3 3.055(2) . ?
Pb2 Br3 3.055(2) 2 ?
Pb2 Br2 3.0250(18) . ?
Pb2 Br2 3.0250(18) 2 ?
N1 H1 0.8600 . ?
N1 C7 1.315(10) . ?
N1 C1 1.405(10) . ?
N2 H2 0.8600 . ?
N2 C7 1.313(9) . ?
N2 C6 1.394(10) . ?
C7 C8 1.497(12) . ?
C3 H3 0.9300 . ?
C3 C2 1.381(13) . ?
C3 C4 1.365(14) . ?
C6 C5 1.379(11) . ?
C6 C1 1.381(11) . ?
C2 H2A 0.9300 . ?
C2 C1 1.366(12) . ?
C5 H5 0.9300 . ?
C5 C4 1.372(15) . ?
C4 H4 0.9300 . ?
C8 H8AA 0.9700 . ?
C8 H8AB 0.9700 . ?
C8 H8BC 0.9700 . ?
C8 H8BD 0.9700 . ?
C8 H8CE 0.9700 . ?
C8 H8CF 0.9700 . ?
C8 C9 1.489(19) . ?
C8 C10 1.486(19) . ?
C8 C11 1.484(19) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N3 C9 1.51(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N4 C10 1.50(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
N5 C11 1.50(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br5 Pb1 Br5 88.91(4) 7 8_556 ?
Br1 Pb1 Br5 174.15(3) . 7 ?
Br1 Pb1 Br5 90.53(3) 2_655 7 ?
Br1 Pb1 Br5 174.15(3) 2_655 8_556 ?
Br1 Pb1 Br5 90.53(3) . 8_556 ?
Br1 Pb1 Br1 90.61(4) 2_655 . ?
Br1 Pb1 Br3 101.87(8) . . ?
Br1 Pb1 Br3 97.90(16) . 2_655 ?
Br1 Pb1 Br3 101.87(8) 2_655 2_655 ?
Br1 Pb1 Br3 97.90(16) 2_655 . ?
Br1 Pb1 Br2 95.86(9) . . ?
Br1 Pb1 Br2 85.46(16) 2_655 . ?
Br1 Pb1 Br2 95.86(9) 2_655 2_655 ?
Br1 Pb1 Br2 85.46(16) . 2_655 ?
Br3 Pb1 Br5 83.65(9) 2_655 8_556 ?
Br3 Pb1 Br5 83.65(9) . 7 ?
Br3 Pb1 Br5 76.25(16) . 8_556 ?
Br3 Pb1 Br5 76.25(16) 2_655 7 ?
Br3 Pb1 Br3 151.8(3) 2_655 . ?
Br2 Pb1 Br2 178.1(3) . 2_655 ?
Br4 Pb2 Br4 98.90(4) . 2 ?
Br4 Pb2 Br5 86.59(3) 2 . ?
Br4 Pb2 Br5 172.78(3) 2 2 ?
Br4 Pb2 Br5 172.78(3) . . ?
Br4 Pb2 Br5 86.59(3) . 2 ?
Br4 Pb2 Br3 97.44(16) . 2 ?
Br4 Pb2 Br3 91.61(8) . . ?
Br4 Pb2 Br3 97.44(16) 2 . ?
Br4 Pb2 Br3 91.61(8) 2 2 ?
Br4 Pb2 Br2 85.35(15) 2 . ?
Br4 Pb2 Br2 86.26(8) . . ?
Br4 Pb2 Br2 85.35(15) . 2 ?
Br4 Pb2 Br2 86.26(8) 2 2 ?
Br5 Pb2 Br5 88.34(4) 2 . ?
Br3 Pb2 Br5 87.03(17) . 2 ?
Br3 Pb2 Br5 87.03(17) 2 . ?
Br3 Pb2 Br5 82.99(9) . . ?
Br3 Pb2 Br5 82.99(9) 2 2 ?
Br3 Pb2 Br3 166.1(3) . 2 ?
Br2 Pb2 Br5 89.54(10) . . ?
Br2 Pb2 Br5 99.75(16) 2 . ?
Br2 Pb2 Br2 167.1(3) 2 . ?
Pb2 Br5 Pb1 172.80(5) . 7 ?
Pb2 Br3 Pb1 155.4(4) . . ?
Pb1 Br2 Pb2 173.3(2) . . ?
C7 N1 H1 124.7 . . ?
C7 N1 C1 110.5(6) . . ?
C1 N1 H1 124.7 . . ?
C7 N2 H2 125.0 . . ?
C7 N2 C6 109.9(7) . . ?
C6 N2 H2 125.0 . . ?
N1 C7 C8 128.1(7) . . ?
N2 C7 N1 108.4(7) . . ?
N2 C7 C8 123.5(8) . . ?
C2 C3 H3 118.8 . . ?
C4 C3 H3 118.8 . . ?
C4 C3 C2 122.4(11) . . ?
C5 C6 N2 131.4(8) . . ?
C5 C6 C1 122.1(9) . . ?
C1 C6 N2 106.5(7) . . ?
C3 C2 H2A 122.2 . . ?
C1 C2 C3 115.6(9) . . ?
C1 C2 H2A 122.2 . . ?
C6 C5 H5 122.3 . . ?
C4 C5 C6 115.4(9) . . ?
C4 C5 H5 122.3 . . ?
C3 C4 C5 122.4(10) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C6 C1 N1 104.6(7) . . ?
C2 C1 N1 133.3(8) . . ?
C2 C1 C6 122.1(8) . . ?
C7 C8 H8AA 110.0 . . ?
C7 C8 H8AB 110.0 . . ?
C7 C8 H8BC 106.6 . . ?
C7 C8 H8BD 106.6 . . ?
C7 C8 H8CE 108.6 . . ?
C7 C8 H8CF 108.6 . . ?
H8AA C8 H8AB 108.4 . . ?
H8BC C8 H8BD 106.6 . . ?
H8CE C8 H8CF 107.5 . . ?
C9 C8 C7 108.6(13) . . ?
C9 C8 H8AA 110.0 . . ?
C9 C8 H8AB 110.0 . . ?
C10 C8 C7 123(2) . . ?
C10 C8 H8BC 106.6 . . ?
C10 C8 H8BD 106.6 . . ?
C11 C8 C7 114.8(17) . . ?
C11 C8 H8CE 108.6 . . ?
C11 C8 H8CF 108.6 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C9 N3 H3A 109.5 . . ?
C9 N3 H3B 109.5 . . ?
C9 N3 H3C 109.5 . . ?
C8 C9 N3 101.0(18) . . ?
C8 C9 H9A 111.6 . . ?
C8 C9 H9B 111.6 . . ?
N3 C9 H9A 111.6 . . ?
N3 C9 H9B 111.6 . . ?
H9A C9 H9B 109.4 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C10 N4 H4A 109.5 . . ?
C10 N4 H4B 109.5 . . ?
C10 N4 H4C 109.5 . . ?
C8 C10 N4 103.6(19) . . ?
C8 C10 H10A 111.0 . . ?
C8 C10 H10B 111.0 . . ?
N4 C10 H10A 111.0 . . ?
N4 C10 H10B 111.0 . . ?
H10A C10 H10B 109.0 . . ?
H5A N5 H5B 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C11 N5 H5A 109.5 . . ?
C11 N5 H5B 109.5 . . ?
C11 N5 H5C 109.5 . . ?
C8 C11 N5 109.5(18) . . ?
C8 C11 H11A 109.8 . . ?
C8 C11 H11B 109.8 . . ?
N5 C11 H11A 109.8 . . ?
N5 C11 H11B 109.8 . . ?
H11A C11 H11B 108.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 C9 -3(2) . . . . ?
N1 C7 C8 C10 15(2) . . . . ?
N1 C7 C8 C11 -21.4(18) . . . . ?
N2 C7 C8 C9 176(2) . . . . ?
N2 C7 C8 C10 -165.7(15) . . . . ?
N2 C7 C8 C11 157.6(14) . . . . ?
N2 C6 C5 C4 178.9(9) . . . . ?
N2 C6 C1 N1 1.1(8) . . . . ?
N2 C6 C1 C2 -178.6(8) . . . . ?
C7 N1 C1 C6 -1.8(9) . . . . ?
C7 N1 C1 C2 177.9(9) . . . . ?
C7 N2 C6 C5 179.9(9) . . . . ?
C7 N2 C6 C1 -0.1(9) . . . . ?
C7 C8 C9 N3 174.7(18) . . . . ?
C7 C8 C10 N4 -85(3) . . . . ?
C7 C8 C11 N5 100(2) . . . . ?
C3 C2 C1 N1 180.0(9) . . . . ?
C3 C2 C1 C6 -0.3(13) . . . . ?
C6 N2 C7 N1 -1.1(10) . . . . ?
C6 N2 C7 C8 179.8(8) . . . . ?
C6 C5 C4 C3 -0.1(15) . . . . ?
C2 C3 C4 C5 1.1(17) . . . . ?
C5 C6 C1 N1 -178.9(8) . . . . ?
C5 C6 C1 C2 1.4(13) . . . . ?
C4 C3 C2 C1 -0.9(15) . . . . ?
C1 N1 C7 N2 1.8(9) . . . . ?
C1 N1 C7 C8 -179.1(9) . . . . ?
C1 C6 C5 C4 -1.1(14) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_twin4_a
_database_code_depnum_ccdc_archive 'CCDC 2169142'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
'catena-[2-(2-ammonioethyl)-1H-imidazol-3-ium bis(mu-bromo)-dibromo-lead]'
_chemical_formula_moiety         'Cl4 Pb, C5 H11 N3'
_chemical_formula_sum            'C5 H11 Cl4 N3 Pb'
_chemical_formula_weight         462.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.6565(5)
_cell_length_b                   11.2444(5)
_cell_length_c                   11.4494(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.444(2)
_cell_angle_gamma                90
_cell_volume                     1192.34(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6248
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.27
_cell_measurement_theta_min      2.20
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.007
_exptl_absorpt_correction_T_max  0.431125
_exptl_absorpt_correction_T_min  0.220416
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 37258 reflections, Rint = 0.0662
 (20910 with I > 3sig(I), Rint = 0.0507)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_preparation       
'Slow cool in 6M HCl from 100C to 23C at 2C/hour.'
_exptl_crystal_recrystallization_method 
'Slow cool in 6M HCl from 100C to 23C at 2C/hour.'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0376
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5494
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.310
_diffrn_reflns_theta_min         2.199
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4918
_reflns_number_total             5494
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.722
_refine_diff_density_min         -1.801
_refine_diff_density_rms         0.265
_refine_ls_extinction_coef       0.00151(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         5494
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0335
_refine_ls_restrained_S_all      1.095
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0091P)²+16.0017P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0778
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.78241
 0.21759
2.a Secondary CH2 refined with riding coordinates:
 C5(H5A,H5B), C4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C1(H1A)
2.c Idealised Me refined as rotating group:
 N3(H3B,H3C,H3A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.51750(3) 0.70498(2) 0.22680(2) 0.00957(10) Uani 1 1 d . . . . .
Cl3 Cl 0.4853(2) 0.73221(16) 0.45068(15) 0.0134(4) Uani 1 1 d . . . . .
Cl1 Cl 0.2082(2) 0.75246(15) 0.12977(16) 0.0136(4) Uani 1 1 d . . . . .
Cl4 Cl 0.8107(2) 0.67511(16) 0.34622(16) 0.0142(3) Uani 1 1 d . . . . .
Cl2 Cl 0.5485(2) 0.95205(15) 0.23117(16) 0.0136(3) Uani 1 1 d . . . . .
N3 N 0.2797(7) 0.5062(6) 0.4753(6) 0.0128(13) Uani 1 1 d . . . . .
H3B H 0.250017 0.453537 0.523545 0.015 Uiso 1 1 calc R U . . .
H3C H 0.322794 0.569517 0.520772 0.015 Uiso 1 1 calc R U . . .
H3A H 0.343960 0.470118 0.442023 0.015 Uiso 1 1 calc R U . . .
N1 N -0.1736(8) 0.4298(6) 0.1671(6) 0.0141(13) Uani 1 1 d . . . . .
H1 H -0.199513 0.368669 0.204051 0.017 Uiso 1 1 calc R U . . .
N2 N -0.0461(8) 0.5671(6) 0.1179(6) 0.0155(14) Uani 1 1 d . . . . .
H2 H 0.027771 0.612718 0.117458 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1529(9) 0.5478(7) 0.3764(7) 0.0148(15) Uani 1 1 d . . . . .
H5A H 0.184560 0.605763 0.324093 0.018 Uiso 1 1 calc R U . . .
H5B H 0.083157 0.587945 0.412133 0.018 Uiso 1 1 calc R U . . .
C2 C -0.1818(9) 0.5751(7) 0.0371(7) 0.0150(16) Uani 1 1 d . . . . .
H2A H -0.212628 0.630326 -0.027810 0.018 Uiso 1 1 calc R U . . .
C1 C -0.2626(10) 0.4891(7) 0.0680(7) 0.0174(16) Uani 1 1 d . . . . .
H1A H -0.361372 0.472533 0.029285 0.021 Uiso 1 1 calc R U . . .
C3 C -0.0439(9) 0.4789(7) 0.1978(7) 0.0135(15) Uani 1 1 d . . . . .
C4 C 0.0807(9) 0.4415(7) 0.3002(7) 0.0144(15) Uani 1 1 d . . . . .
H4A H 0.152158 0.399925 0.267562 0.017 Uiso 1 1 calc R U . . .
H4B H 0.047208 0.384921 0.352699 0.017 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 Cl3 2.6855(16) . ?
Pb1 Cl3 3.1676(16) 4_575 ?
Pb1 Cl1 2.926(2) . ?
Pb1 Cl4 2.794(2) . ?
Pb1 Cl2 2.7931(17) . ?
Pb1 Cl2 2.9833(17) 2_645 ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 H3A 0.9100 . ?
N3 C5 1.489(10) . ?
N1 H1 0.8800 . ?
N1 C1 1.384(10) . ?
N1 C3 1.322(11) . ?
N2 H2 0.8800 . ?
N2 C2 1.376(11) . ?
N2 C3 1.345(10) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C5 C4 1.528(11) . ?
C2 H2A 0.9500 . ?
C2 C1 1.351(12) . ?
C1 H1A 0.9500 . ?
C3 C4 1.484(11) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
Cl3 Pb1 Cl3 157.22(4) . 4_575 ?
Cl3 Pb1 Cl1 87.71(6) . . ?
Cl3 Pb1 Cl4 85.52(6) . . ?
Cl3 Pb1 Cl2 84.85(5) . . ?
Cl3 Pb1 Cl2 82.36(5) . 2_645 ?
Cl1 Pb1 Cl3 77.24(5) . 4_575 ?
Cl1 Pb1 Cl2 89.63(5) . 2_645 ?
Cl4 Pb1 Cl3 108.34(5) . 4_575 ?
Cl4 Pb1 Cl1 172.66(5) . . ?
Cl4 Pb1 Cl2 92.27(5) . 2_645 ?
Cl2 Pb1 Cl3 114.11(5) 2_645 4_575 ?
Cl2 Pb1 Cl3 77.05(5) . 4_575 ?
Cl2 Pb1 Cl1 85.29(5) . . ?
Cl2 Pb1 Cl4 91.28(5) . . ?
Cl2 Pb1 Cl2 166.416(16) . 2_645 ?
Pb1 Cl2 Pb1 157.59(7) . 2_655 ?
H3B N3 H3C 109.5 . . ?
H3B N3 H3A 109.5 . . ?
H3C N3 H3A 109.5 . . ?
C5 N3 H3B 109.5 . . ?
C5 N3 H3C 109.5 . . ?
C5 N3 H3A 109.5 . . ?
C1 N1 H1 125.1 . . ?
C3 N1 H1 125.1 . . ?
C3 N1 C1 109.8(7) . . ?
C2 N2 H2 125.2 . . ?
C3 N2 H2 125.2 . . ?
C3 N2 C2 109.5(7) . . ?
N3 C5 H5A 109.8 . . ?
N3 C5 H5B 109.8 . . ?
N3 C5 C4 109.4(6) . . ?
H5A C5 H5B 108.2 . . ?
C4 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
N2 C2 H2A 126.6 . . ?
C1 C2 N2 106.7(7) . . ?
C1 C2 H2A 126.6 . . ?
N1 C1 H1A 126.6 . . ?
C2 C1 N1 106.8(7) . . ?
C2 C1 H1A 126.6 . . ?
N1 C3 N2 107.2(7) . . ?
N1 C3 C4 125.9(7) . . ?
N2 C3 C4 126.9(8) . . ?
C5 C4 H4A 109.3 . . ?
C5 C4 H4B 109.3 . . ?
C3 C4 C5 111.5(7) . . ?
C3 C4 H4A 109.3 . . ?
C3 C4 H4B 109.3 . . ?
H4A C4 H4B 108.0 . . ?

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
N3 C5 C4 C3 -178.2(6) . . . . ?
N1 C3 C4 C5 -132.4(8) . . . . ?
N2 C2 C1 N1 -0.4(9) . . . . ?
N2 C3 C4 C5 48.6(10) . . . . ?
C2 N2 C3 N1 1.4(9) . . . . ?
C2 N2 C3 C4 -179.4(7) . . . . ?
C1 N1 C3 N2 -1.7(9) . . . . ?
C1 N1 C3 C4 179.2(7) . . . . ?
C3 N1 C1 C2 1.3(9) . . . . ?
C3 N2 C2 C1 -0.6(9) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Mounted on MiTiGen Microloop with paratone oil.'
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.78241
2 0.21759

####################################################################### 
# 
# 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_twin4_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2169143'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Pb, C5 H11 N3'
_chemical_formula_sum            'C5 H11 Cl4 N3 Pb'
_chemical_formula_weight         462.16
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   9.7314(4)
_cell_length_b                   11.3143(4)
_cell_length_c                   11.5207(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.608(2)
_cell_angle_gamma                90
_cell_volume                     1215.56(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6251
_cell_measurement_temperature    300
_cell_measurement_theta_max      28.24
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.721
_exptl_absorpt_correction_T_max  0.431128
_exptl_absorpt_correction_T_min  0.228460
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.

Final HKLF 4 output contains 46179 reflections, Rint = 0.0634
 (25055 with I > 3sig(I), Rint = 0.0504)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.525
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
_exptl_crystal_preparation       
;
 'Crystals were prepared by dissolving precursors in 6M HCl 
  at 100C and cooling the solution to room temperature 
  at a rate of 2C/hr.'
;
_exptl_crystal_recrystallization_method 
"'Large crystals are light brown plates. Smaller crystals   or fragments of larger crystals appear colorless under   the microscope.'"
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0300
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4837
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.319
_diffrn_reflns_theta_min         2.578
_diffrn_ambient_temperature      300.15
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4225
_reflns_number_total             4837
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.993
_refine_diff_density_min         -1.928
_refine_diff_density_rms         0.276
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.163
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         4837
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0380
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0601P)²+9.5365P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1186
_refine_ls_wR_factor_ref         0.1267
_refine_special_details          'Refined as a 2-component twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.7776
 0.2224
2.a Secondary CH2 refined with riding coordinates:
 C00A(H00D,H00E), C00C(H00G,H00H)
2.b Aromatic/amide H refined with riding coordinates:
 N007(H007), N008(H008), C00B(H00F), C00D(H00I)
2.c Idealised Me refined as rotating group:
 N006(H00A,H00B,H00C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb01 Pb 0.51696(4) 0.29073(3) 0.23072(3) 0.02316(13) Uani 1 1 d . . . . .
Cl02 Cl 0.5451(3) 0.0432(2) 0.2334(2) 0.0357(6) Uani 1 1 d . . . . .
Cl03 Cl 0.4877(4) 0.2680(3) 0.4555(2) 0.0360(6) Uani 1 1 d . . . . .
Cl04 Cl 0.2065(4) 0.2463(2) 0.1327(3) 0.0345(6) Uani 1 1 d . . . . .
Cl05 Cl 0.8084(3) 0.3232(3) 0.3466(3) 0.0380(6) Uani 1 1 d . . . . .
N006 N 0.2769(11) 0.4921(10) 0.4752(9) 0.036(2) Uani 1 1 d . . . . .
H00A H 0.334894 0.532365 0.442338 0.044 Uiso 1 1 calc R U . . .
H00B H 0.322638 0.428946 0.513544 0.044 Uiso 1 1 calc R U . . .
H00C H 0.250325 0.538076 0.527737 0.044 Uiso 1 1 calc R U . . .
N007 N -0.1692(11) 0.5686(9) 0.1669(9) 0.035(2) Uani 1 1 d . . . . .
H007 H -0.193206 0.627913 0.203515 0.042 Uiso 1 1 calc R U . . .
N008 N -0.0468(11) 0.4321(9) 0.1177(9) 0.038(2) Uani 1 1 d . . . . .
H008 H 0.023531 0.386697 0.116199 0.045 Uiso 1 1 calc R U . . .
C009 C -0.0409(13) 0.5186(11) 0.1964(11) 0.034(2) Uani 1 1 d . . . . .
C00A C 0.0846(14) 0.5561(11) 0.2977(12) 0.042(3) Uani 1 1 d . . . . .
H00D H 0.054536 0.616689 0.344857 0.050 Uiso 1 1 calc R U . . .
H00E H 0.156863 0.590114 0.264684 0.050 Uiso 1 1 calc R U . . .
C00B C -0.2577(14) 0.5118(12) 0.0694(11) 0.042(3) Uani 1 1 d . . . . .
H00F H -0.353299 0.529603 0.031269 0.051 Uiso 1 1 calc R U . . .
C00C C 0.1489(13) 0.4541(10) 0.3793(11) 0.038(3) Uani 1 1 d . . . . .
H00G H 0.078423 0.422509 0.415871 0.045 Uiso 1 1 calc R U . . .
H00H H 0.175148 0.391836 0.331822 0.045 Uiso 1 1 calc R U . . .
C00D C -0.1809(15) 0.4260(12) 0.0397(11) 0.043(3) Uani 1 1 d . . . . .
H00I H -0.213023 0.371890 -0.022974 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
Pb01 Cl02 2.814(3) . ?
Pb01 Cl02 2.973(3) 2_655 ?
Pb01 Cl03 3.172(3) 4_565 ?
Pb01 Cl03 2.697(3) . ?
Pb01 Cl04 2.950(3) . ?
Pb01 Cl05 2.792(3) . ?
N006 H00A 0.8900 . ?
N006 H00B 0.8900 . ?
N006 H00C 0.8900 . ?
N006 C00C 1.473(14) . ?
N007 H007 0.8600 . ?
N007 C009 1.324(15) . ?
N007 C00B 1.365(15) . ?
N008 H008 0.8600 . ?
N008 C009 1.324(15) . ?
N008 C00D 1.359(16) . ?
C009 C00A 1.489(17) . ?
C00A H00D 0.9700 . ?
C00A H00E 0.9700 . ?
C00A C00C 1.507(16) . ?
C00B H00F 0.9300 . ?
C00B C00D 1.328(19) . ?
C00C H00G 0.9700 . ?
C00C H00H 0.9700 . ?
C00D H00I 0.9300 . ?

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
Cl02 Pb01 Cl02 167.97(2) . 2_655 ?
Cl02 Pb01 Cl03 77.47(8) . 4_565 ?
Cl02 Pb01 Cl03 112.12(7) 2_655 4_565 ?
Cl02 Pb01 Cl04 85.44(8) . . ?
Cl03 Pb01 Cl02 86.05(8) . . ?
Cl03 Pb01 Cl02 82.92(8) . 2_655 ?
Cl03 Pb01 Cl03 159.37(7) . 4_565 ?
Cl03 Pb01 Cl04 88.50(10) . . ?
Cl03 Pb01 Cl05 85.72(10) . . ?
Cl04 Pb01 Cl02 89.45(8) . 2_655 ?
Cl04 Pb01 Cl03 77.99(9) . 4_565 ?
Cl05 Pb01 Cl02 91.49(9) . 2_655 ?
Cl05 Pb01 Cl02 92.49(9) . . ?
Cl05 Pb01 Cl03 107.11(9) . 4_565 ?
Cl05 Pb01 Cl04 173.98(9) . . ?
Pb01 Cl02 Pb01 159.24(12) . 2_645 ?
H00A N006 H00B 109.5 . . ?
H00A N006 H00C 109.5 . . ?
H00B N006 H00C 109.5 . . ?
C00C N006 H00A 109.5 . . ?
C00C N006 H00B 109.5 . . ?
C00C N006 H00C 109.5 . . ?
C009 N007 H007 125.1 . . ?
C009 N007 C00B 109.7(10) . . ?
C00B N007 H007 125.1 . . ?
C009 N008 H008 125.2 . . ?
C009 N008 C00D 109.6(10) . . ?
C00D N008 H008 125.2 . . ?
N007 C009 N008 106.6(10) . . ?
N007 C009 C00A 125.6(12) . . ?
N008 C009 C00A 127.8(12) . . ?
C009 C00A H00D 109.2 . . ?
C009 C00A H00E 109.2 . . ?
C009 C00A C00C 111.9(10) . . ?
H00D C00A H00E 107.9 . . ?
C00C C00A H00D 109.2 . . ?
C00C C00A H00E 109.2 . . ?
N007 C00B H00F 126.7 . . ?
C00D C00B N007 106.7(11) . . ?
C00D C00B H00F 126.7 . . ?
N006 C00C C00A 110.8(10) . . ?
N006 C00C H00G 109.5 . . ?
N006 C00C H00H 109.5 . . ?
C00A C00C H00G 109.5 . . ?
C00A C00C H00H 109.5 . . ?
H00G C00C H00H 108.1 . . ?
N008 C00D H00I 126.3 . . ?
C00B C00D N008 107.3(11) . . ?
C00B C00D H00I 126.3 . . ?

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
N007 C009 C00A C00C 127.9(14) . . . . ?
N007 C00B C00D N008 -0.7(15) . . . . ?
N008 C009 C00A C00C -53.3(18) . . . . ?
C009 N007 C00B C00D -0.1(16) . . . . ?
C009 N008 C00D C00B 1.3(15) . . . . ?
C009 C00A C00C N006 177.2(11) . . . . ?
C00B N007 C009 N008 0.9(14) . . . . ?
C00B N007 C009 C00A 179.8(12) . . . . ?
C00D N008 C009 N007 -1.3(14) . . . . ?
C00D N008 C009 C00A 179.8(12) . . . . ?

_olex2_exptl_crystal_mounting_method 
;
 'Crystals were seperated from the mother liquor in paratone oil and placed
  on a kapton loop using the paratone to adhere the crystal to the loop.'
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.7776
2 0.2224

####################################################################### 
# 
# 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_sad_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2169140'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT972_sad_a               
;
PROBLEM: Check Calcd Resid. Dens.  2.28Ang From N1             -4.09 eA-3
RESPONSE: Many of the issues in the final refinement of this crystal structure are due to the modulated nature of this material. The effects of this modulation is  enhanced by the reduced temperature of this collection. This structure is  only the average structure for the modulated material and restraints were  required to model atomic displacements, likely caused by modulation, as  disorder.
;
# Added during the CSD deposition process: Wednesday 27 April 2022 08:10 PM
# end Validation Reply Form

_audit_creation_date             2021-04-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Pb, C9 H13 N3'
_chemical_formula_sum            'C9 H13 Cl4 N3 Pb'
_chemical_formula_weight         512.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.4666(6)
_cell_length_b                   30.4225(18)
_cell_length_c                   8.3667(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.590(2)
_cell_angle_gamma                90
_cell_volume                     2912.9(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8241
_cell_measurement_temperature    100
_cell_measurement_theta_max      25.16
_cell_measurement_theta_min      2.68
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.299
_exptl_absorpt_correction_T_max  0.4288
_exptl_absorpt_correction_T_min  0.3384
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
  wR2(int) was 0.0885 before and 0.0753 after correction. 
  The Ratio of minimum to maximum transmission is 0.7892. 
  The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1904
_exptl_crystal_preparation       'See crystallisation.'
_exptl_crystal_recrystallization_method 
"'Precursors were dissolved in 6M HCl and heated to 100C to dissolve.   Solution was then cooled to room temperature at 2C/hr.'"
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0730
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            26789
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.406
_diffrn_reflns_theta_min         1.901
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2395
_reflns_number_total             2686
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         2.142
_refine_diff_density_min         -3.600
_refine_diff_density_rms         0.224
_refine_ls_extinction_coef       0.00016(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.271
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     203
_refine_ls_number_reflns         2686
_refine_ls_number_restraints     152
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0487
_refine_ls_restrained_S_all      1.237
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+107.2131P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.0967
_refine_special_details          
;
Many of the issues in the final refinement of this crystal structure are due
to the modulated nature of this material. The effects of this modulation is 
enhanced by the reduced temperature of this collection. This structure is 
only the average structure for the modulated material and restraints were 
required to model atomic displacements, likely caused by modulation, as 
disorder.
;
_olex2_refinement_description    
;
1. Restrained distances
 N3-C9 \\sim N4-C11
 with sigma of 0.02
 C9-C8 \\sim C11-C8
 with sigma of 0.02
 N5-C11 \\sim N4-C10 \\sim N3-C9
 with sigma of 0.02
 C9-C8 \\sim C10-C8 \\sim C11-C8
 with sigma of 0.02
2. Rigid bond restraints
 C9, N1, C7, C1, N2, C8, C2, C6, C11, C3, C5, N4, N3, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
C11 \\sim N1 \\sim C7 \\sim C1 \\sim N2 \\sim C8 \\sim C2 \\sim C6 \\sim C9
\\sim C3 \\sim C5 \\sim N4 \\sim N3 \\sim C4: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
Uanis(C10) = Uanis(C11) = Uanis(C9)
4. Others
 Sof(Cl2)=1-FVAR(1)
 Sof(Cl3)=FVAR(1)
 Sof(Cl6)=1-FVAR(2)
 Sof(Cl5)=FVAR(2)
 Fixed Sof: H8CE(0.3333) H8CF(0.3333) H8AA(0.3333) H8AB(0.3333) H8BC(0.3333)
 H8BD(0.3333) C11(0.3333) H11A(0.3333) H11B(0.3333) N4(0.3333) H4A(0.3333)
 H4B(0.3333) H4C(0.3333) N3(0.3333) H3A(0.3333) H3B(0.3333) H3C(0.3333)
 C9(0.3333) H9A(0.3333) H9B(0.3333) N5(0.3333) H5A(0.3333) H5B(0.3333)
 H5C(0.3333) C10(0.3333) H10A(0.3333) H10B(0.3333)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8CE,H8CF), C8(H8AA,H8AB), C8(H8BC,H8BD), C11(H11A,H11B), C9(H9A,H9B),
 C10(H10A,H10B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C2(H2A), C3(H3), C5(H5), C4(H4)
5.c Idealised Me refined as rotating group:
 N4(H4A,H4B,H4C), N3(H3A,H3B,H3C), N5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.500000 0.67340(2) 0.750000 0.0276(2) Uani 1 2 d S T P . .
Pb2 Pb 1.000000 0.68640(2) 0.750000 0.0299(2) Uani 1 2 d S T P . .
Cl1 Cl 0.4566(3) 0.61078(10) 0.5255(4) 0.0416(7) Uani 1 1 d . . . . .
Cl4 Cl 0.9979(3) 0.62912(11) 0.4924(4) 0.0518(9) Uani 1 1 d . . . . .
Cl5 Cl 0.948(4) 0.7531(7) 1.005(2) 0.026(6) Uani 0.32(6) 1 d . . P A 1
Cl3 Cl 0.7486(6) 0.6980(9) 0.7056(19) 0.041(4) Uani 0.57(5) 1 d . . P A 1
N1 N 0.6595(8) 0.5720(4) 0.3369(12) 0.041(2) Uani 1 1 d . U . . .
H1 H 0.598910 0.575696 0.395096 0.049 Uiso 1 1 calc R U . . .
N2 N 0.8058(10) 0.5872(4) 0.1994(13) 0.047(3) Uani 1 1 d . U . . .
H2 H 0.858373 0.602275 0.150157 0.057 Uiso 1 1 calc R U . . .
C7 C 0.7225(11) 0.6041(5) 0.2804(16) 0.045(3) Uani 1 1 d . U . . .
C2 C 0.6693(12) 0.4886(5) 0.3141(17) 0.047(3) Uani 1 1 d . U . . .
H2A H 0.601592 0.481929 0.369257 0.057 Uiso 1 1 calc R U . . .
C1 C 0.7028(11) 0.5313(4) 0.2909(14) 0.038(2) Uani 1 1 d . U . . .
C6 C 0.7976(10) 0.5411(4) 0.2041(15) 0.038(2) Uani 1 1 d . U . . .
C3 C 0.7362(12) 0.4562(5) 0.2553(17) 0.048(3) Uani 1 1 d . U . . .
H3 H 0.715833 0.426454 0.272923 0.058 Uiso 1 1 calc R U . . .
C5 C 0.8667(12) 0.5097(4) 0.1420(17) 0.044(3) Uani 1 1 d . U . . .
H5 H 0.932375 0.517255 0.083817 0.053 Uiso 1 1 calc R U . . .
C4 C 0.8360(12) 0.4657(5) 0.1682(16) 0.048(3) Uani 1 1 d . U . . .
H4 H 0.881320 0.442443 0.128236 0.057 Uiso 1 1 calc R U . . .
C8 C 0.7019(13) 0.6513(5) 0.314(2) 0.061(4) Uani 1 1 d D U . . .
H8CE H 0.739376 0.658414 0.420641 0.073 Uiso 0.3333 1 calc R U P B 3
H8CF H 0.616781 0.655955 0.319458 0.073 Uiso 0.3333 1 calc R U P B 3
H8AA H 0.693447 0.654537 0.430429 0.073 Uiso 0.3333 1 calc R U P C 1
H8AB H 0.626340 0.659768 0.258785 0.073 Uiso 0.3333 1 calc R U P C 1
H8BC H 0.732090 0.658342 0.424446 0.073 Uiso 0.3333 1 calc R U P D 2
H8BD H 0.616909 0.657380 0.305553 0.073 Uiso 0.3333 1 calc R U P D 2
Cl2 Cl 0.7481(7) 0.6751(12) 0.7404(19) 0.041(6) Uani 0.43(5) 1 d . . P A 2
Cl6 Cl 1.001(3) 0.7564(2) 0.9901(11) 0.050(4) Uani 0.68(6) 1 d . . P A 2
C11 C 0.747(5) 0.6832(17) 0.192(4) 0.043(6) Uani 0.3333 1 d D U P E 3
H11A H 0.757692 0.667648 0.090441 0.051 Uiso 0.3333 1 calc R U P E 3
H11B H 0.689307 0.707039 0.171098 0.051 Uiso 0.3333 1 calc R U P E 3
N4 N 0.753(2) 0.7224(8) 0.273(3) 0.026(6) Uani 0.3333 1 d D U P E 2
H4A H 0.786481 0.743358 0.214225 0.032 Uiso 0.3333 1 calc R U P E 2
H4B H 0.789262 0.721385 0.373044 0.032 Uiso 0.3333 1 calc R U P E 2
H4C H 0.675785 0.729022 0.281558 0.032 Uiso 0.3333 1 calc R U P E 2
N3 N 0.764(3) 0.6942(11) 0.099(4) 0.046(7) Uani 0.3333 1 d D U P E 1
H3A H 0.759979 0.668869 0.040791 0.055 Uiso 0.3333 1 calc R U P E 1
H3B H 0.819738 0.712035 0.061055 0.055 Uiso 0.3333 1 calc R U P E 1
H3C H 0.693700 0.708024 0.090397 0.055 Uiso 0.3333 1 calc R U P E 1
C9 C 0.794(3) 0.6839(13) 0.266(4) 0.043(6) Uani 0.3333 1 d D U P E 1
H9A H 0.793132 0.710757 0.332137 0.051 Uiso 0.3333 1 calc R U P E 1
H9B H 0.873252 0.670626 0.278135 0.051 Uiso 0.3333 1 calc R U P E 1
N5 N 0.858(2) 0.7018(8) 0.254(3) 0.020(5) Uani 0.3333 1 d D . P E 3
H5A H 0.893730 0.714955 0.172836 0.024 Uiso 0.3333 1 calc R U P E 3
H5B H 0.904238 0.679956 0.296798 0.024 Uiso 0.3333 1 calc R U P E 3
H5C H 0.844600 0.721974 0.331034 0.024 Uiso 0.3333 1 calc R U P E 3
C10 C 0.762(6) 0.6799(13) 0.196(4) 0.043(6) Uani 0.3333 1 d D . P E 2
H10A H 0.845036 0.671127 0.187663 0.051 Uiso 0.3333 1 calc R U P E 2
H10B H 0.721338 0.679378 0.088466 0.051 Uiso 0.3333 1 calc R U P E 2


_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 Cl1 2.700(3) . ?
Pb1 Cl1 2.700(3) 2_656 ?
Pb1 Cl5 3.068(14) 7_667 ?
Pb1 Cl5 3.068(14) 8_465 ?
Pb1 Cl3 2.993(12) . ?
Pb1 Cl3 2.993(12) 2_656 ?
Pb1 Cl2 2.852(8) 2_656 ?
Pb1 Cl2 2.852(8) . ?
Pb1 Cl6 3.048(8) 7_667 ?
Pb1 Cl6 3.048(8) 8_465 ?
Pb2 Cl4 2.770(4) . ?
Pb2 Cl4 2.770(4) 2_756 ?
Pb2 Cl5 3.029(15) . ?
Pb2 Cl5 3.029(15) 2_756 ?
Pb2 Cl3 2.905(7) . ?
Pb2 Cl3 2.905(7) 2_756 ?
Pb2 Cl2 2.905(9) . ?
Pb2 Cl2 2.905(9) 2_756 ?
Pb2 Cl6 2.928(8) . ?
Pb2 Cl6 2.928(8) 2_756 ?
N1 H1 0.8800 . ?
N1 C7 1.320(15) . ?
N1 C1 1.398(17) . ?
N2 H2 0.8800 . ?
N2 C7 1.310(16) . ?
N2 C6 1.406(16) . ?
C7 C8 1.485(19) . ?
C2 H2A 0.9500 . ?
C2 C1 1.370(18) . ?
C2 C3 1.36(2) . ?
C1 C6 1.378(15) . ?
C6 C5 1.364(18) . ?
C3 H3 0.9500 . ?
C3 C4 1.42(2) . ?
C5 H5 0.9500 . ?
C5 C4 1.407(18) . ?
C4 H4 0.9500 . ?
C8 H8CE 0.9900 . ?
C8 H8CF 0.9900 . ?
C8 H8AA 0.9900 . ?
C8 H8AB 0.9900 . ?
C8 H8BC 0.9900 . ?
C8 H8BD 0.9900 . ?
C8 C11 1.52(2) . ?
C8 C9 1.53(2) . ?
C8 C10 1.52(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 N5 1.46(3) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
N4 C10 1.45(3) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C9 1.45(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
N5 H5A 0.9100 . ?
N5 H5B 0.9100 . ?
N5 H5C 0.9100 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?

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
Cl1 Pb1 Cl1 90.22(14) . 2_656 ?
Cl1 Pb1 Cl5 91.7(4) . 8_465 ?
Cl1 Pb1 Cl5 177.8(7) . 7_667 ?
Cl1 Pb1 Cl5 177.8(7) 2_656 8_465 ?
Cl1 Pb1 Cl5 91.7(4) 2_656 7_667 ?
Cl1 Pb1 Cl3 103.0(2) 2_656 2_656 ?
Cl1 Pb1 Cl3 97.3(6) 2_656 . ?
Cl1 Pb1 Cl3 97.3(6) . 2_656 ?
Cl1 Pb1 Cl3 103.0(2) . . ?
Cl1 Pb1 Cl2 97.7(4) 2_656 2_656 ?
Cl1 Pb1 Cl2 97.7(4) . . ?
Cl1 Pb1 Cl2 83.8(7) 2_656 . ?
Cl1 Pb1 Cl2 83.8(7) . 2_656 ?
Cl1 Pb1 Cl6 90.40(16) 2_656 7_667 ?
Cl1 Pb1 Cl6 169.0(7) 2_656 8_465 ?
Cl1 Pb1 Cl6 169.0(7) . 7_667 ?
Cl1 Pb1 Cl6 90.40(16) . 8_465 ?
Cl5 Pb1 Cl5 86.4(7) 7_667 8_465 ?
Cl3 Pb1 Cl5 83.2(9) 2_656 7_667 ?
Cl3 Pb1 Cl5 75.8(9) 2_656 8_465 ?
Cl3 Pb1 Cl5 83.2(9) . 8_465 ?
Cl3 Pb1 Cl5 75.8(9) . 7_667 ?
Cl3 Pb1 Cl3 151.0(10) 2_656 . ?
Cl3 Pb1 Cl6 71.9(8) . 8_465 ?
Cl3 Pb1 Cl6 87.8(7) 2_656 8_465 ?
Cl3 Pb1 Cl6 87.8(7) . 7_667 ?
Cl3 Pb1 Cl6 71.9(8) 2_656 7_667 ?
Cl2 Pb1 Cl6 85.3(10) . 8_465 ?
Cl2 Pb1 Cl6 93.3(8) 2_656 8_465 ?
Cl6 Pb1 Cl6 91.1(3) 7_667 8_465 ?
Cl4 Pb2 Cl4 102.05(15) . 2_756 ?
Cl4 Pb2 Cl5 82.3(5) 2_756 . ?
Cl4 Pb2 Cl5 167.5(6) 2_756 2_756 ?
Cl4 Pb2 Cl5 167.5(6) . . ?
Cl4 Pb2 Cl5 82.3(5) . 2_756 ?
Cl4 Pb2 Cl3 91.0(2) . . ?
Cl4 Pb2 Cl3 91.0(2) 2_756 2_756 ?
Cl4 Pb2 Cl3 97.8(6) . 2_756 ?
Cl4 Pb2 Cl3 97.8(6) 2_756 . ?
Cl4 Pb2 Cl2 86.8(3) . . ?
Cl4 Pb2 Cl2 84.7(7) . 2_756 ?
Cl4 Pb2 Cl2 86.8(3) 2_756 2_756 ?
Cl4 Pb2 Cl2 84.7(7) 2_756 . ?
Cl4 Pb2 Cl6 85.67(18) . 2_756 ?
Cl4 Pb2 Cl6 85.67(18) 2_756 . ?
Cl4 Pb2 Cl6 172.28(18) . . ?
Cl4 Pb2 Cl6 172.28(18) 2_756 2_756 ?
Cl5 Pb2 Cl5 95.9(12) 2_756 . ?
Cl3 Pb2 Cl5 76.8(7) 2_756 2_756 ?
Cl3 Pb2 Cl5 93.8(10) 2_756 . ?
Cl3 Pb2 Cl5 76.8(7) . . ?
Cl3 Pb2 Cl5 93.8(10) . 2_756 ?
Cl3 Pb2 Cl3 166.0(11) . 2_756 ?
Cl3 Pb2 Cl6 87.8(7) 2_756 2_756 ?
Cl3 Pb2 Cl6 82.0(9) . 2_756 ?
Cl2 Pb2 Cl2 166.4(15) 2_756 . ?
Cl2 Pb2 Cl6 93.9(8) . . ?
Cl2 Pb2 Cl6 96.0(10) 2_756 . ?
Pb2 Cl5 Pb1 157.0(16) . 7_667 ?
Pb2 Cl3 Pb1 154.0(12) . . ?
C7 N1 H1 124.9 . . ?
C7 N1 C1 110.2(10) . . ?
C1 N1 H1 124.9 . . ?
C7 N2 H2 125.5 . . ?
C7 N2 C6 108.9(10) . . ?
C6 N2 H2 125.5 . . ?
N1 C7 C8 123.4(12) . . ?
N2 C7 N1 109.2(12) . . ?
N2 C7 C8 127.3(11) . . ?
C1 C2 H2A 121.1 . . ?
C3 C2 H2A 121.1 . . ?
C3 C2 C1 117.7(12) . . ?
C2 C1 N1 133.8(12) . . ?
C2 C1 C6 121.2(13) . . ?
C6 C1 N1 105.0(11) . . ?
C1 C6 N2 106.7(12) . . ?
C5 C6 N2 130.3(11) . . ?
C5 C6 C1 123.0(12) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.0(13) . . ?
C4 C3 H3 119.0 . . ?
C6 C5 H5 121.6 . . ?
C6 C5 C4 116.8(12) . . ?
C4 C5 H5 121.6 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(14) . . ?
C5 C4 H4 120.4 . . ?
C7 C8 H8CE 108.5 . . ?
C7 C8 H8CF 108.5 . . ?
C7 C8 H8AA 108.0 . . ?
C7 C8 H8AB 108.0 . . ?
C7 C8 H8BC 109.6 . . ?
C7 C8 H8BD 109.6 . . ?
C7 C8 C11 115(3) . . ?
C7 C8 C9 117(2) . . ?
C7 C8 C10 110(2) . . ?
H8CE C8 H8CF 107.5 . . ?
H8AA C8 H8AB 107.2 . . ?
H8BC C8 H8BD 108.1 . . ?
C11 C8 H8CE 108.5 . . ?
C11 C8 H8CF 108.5 . . ?
C9 C8 H8AA 108.0 . . ?
C9 C8 H8AB 108.0 . . ?
C10 C8 H8BC 109.6 . . ?
C10 C8 H8BD 109.6 . . ?
Pb1 Cl2 Pb2 173.4(11) . . ?
Pb2 Cl6 Pb1 177.7(6) . 7_667 ?
C8 C11 H11A 109.7 . . ?
C8 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N5 C11 C8 110(3) . . ?
N5 C11 H11A 109.7 . . ?
N5 C11 H11B 109.7 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C10 N4 H4A 109.5 . . ?
C10 N4 H4B 109.5 . . ?
C10 N4 H4C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C9 N3 H3A 109.5 . . ?
C9 N3 H3B 109.5 . . ?
C9 N3 H3C 109.5 . . ?
C8 C9 H9A 110.6 . . ?
C8 C9 H9B 110.6 . . ?
N3 C9 C8 106(3) . . ?
N3 C9 H9A 110.6 . . ?
N3 C9 H9B 110.6 . . ?
H9A C9 H9B 108.8 . . ?
C11 N5 H5A 109.5 . . ?
C11 N5 H5B 109.5 . . ?
C11 N5 H5C 109.5 . . ?
H5A N5 H5B 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C8 C10 H10A 111.8 . . ?
C8 C10 H10B 111.8 . . ?
N4 C10 C8 100(2) . . ?
N4 C10 H10A 111.8 . . ?
N4 C10 H10B 111.8 . . ?
H10A C10 H10B 109.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C7 C8 C11 -157(2) . . . . ?
N1 C7 C8 C9 170(2) . . . . ?
N1 C7 C8 C10 -163(3) . . . . ?
N1 C1 C6 N2 -1.0(13) . . . . ?
N1 C1 C6 C5 177.8(12) . . . . ?
N2 C7 C8 C11 26(3) . . . . ?
N2 C7 C8 C9 -7(3) . . . . ?
N2 C7 C8 C10 20(3) . . . . ?
N2 C6 C5 C4 179.4(13) . . . . ?
C7 N1 C1 C2 -178.5(15) . . . . ?
C7 N1 C1 C6 0.7(13) . . . . ?
C7 N2 C6 C1 0.9(15) . . . . ?
C7 N2 C6 C5 -177.7(14) . . . . ?
C7 C8 C11 N5 -100(4) . . . . ?
C7 C8 C9 N3 86(4) . . . . ?
C7 C8 C10 N4 -168(3) . . . . ?
C2 C1 C6 N2 178.3(12) . . . . ?
C2 C1 C6 C5 -2.9(19) . . . . ?
C2 C3 C4 C5 0(2) . . . . ?
C1 N1 C7 N2 -0.1(15) . . . . ?
C1 N1 C7 C8 -177.4(14) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?
C1 C6 C5 C4 1.0(19) . . . . ?
C6 N2 C7 N1 -0.5(16) . . . . ?
C6 N2 C7 C8 176.6(14) . . . . ?
C6 C5 C4 C3 0.4(19) . . . . ?
C3 C2 C1 N1 -177.7(13) . . . . ?
C3 C2 C1 C6 3.3(19) . . . . ?

_olex2_exptl_crystal_mounting_method 
'Crystals were isolated in paratone and placed on a kapton loop. '
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2169141'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-03-31
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Pb, C9 H13 N3'
_chemical_formula_sum            'C9 H13 Cl4 N3 Pb'
_chemical_formula_weight         512.21
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.5223(3)
_cell_length_b                   30.5566(9)
_cell_length_c                   8.4574(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.4720(10)
_cell_angle_gamma                90
_cell_volume                     2972.24(14)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    300
_cell_measurement_theta_max      28.18
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    12.054
_exptl_absorpt_correction_T_max  0.4311
_exptl_absorpt_correction_T_min  0.3473
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
  wR2(int) was 0.1124 before and 0.0569 after correction. 
  The Ratio of minimum to maximum transmission is 0.8056. 
  The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1904
_exptl_crystal_preparation       
;
 'Crystals were prepared by dissolving precursors in 6M HCl at 100C. 
  Crystals were grown from this solution by cooling the solution to 
  room temperature at 2C/hr.'
;
_exptl_crystal_recrystallization_method 
"'Clear colorless plate-like crystals grew from the solution.   Additionally, there is a small amount of colorless needles   which grew as the solution was allowed to stand for a few days.   These crystals do not always appear from this crystallization.'"
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0460
_diffrn_reflns_av_unetI/netI     0.0177
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            41153
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.100
_diffrn_reflns_theta_min         1.892
_diffrn_ambient_temperature      300.15
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2989
_reflns_number_total             3284
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.999
_refine_diff_density_min         -1.276
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.000045(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         3284
_refine_ls_number_restraints     272
_refine_ls_R_factor_all          0.0291
_refine_ls_R_factor_gt           0.0245
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0142P)²+11.1897P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0481
_refine_special_details          
;
Many of the issues in the final refinement of this crystal structure are due
to the modulated nature of this material. The effects of this modulation is 
masked by the elevated temperature of this collection due to atomic motion. 
This structure is only the average structure for the modulated material 
and restraints were required to model atomic displacements, likely caused 
by modulation, as disorder.
;
_olex2_refinement_description    
;
1. Restrained distances
 C10-C8 \\sim C9-C8
 with sigma of 0.02
 N3-C9 \\sim N4-C10 \\sim N5-C10
 with sigma of 0.02
 N5-C11 \\sim N4-C10 \\sim N3-C9
 with sigma of 0.02
 C10-C8 \\sim C11-C8 \\sim C9-C8
 with sigma of 0.02
2. Rigid bond restraints
 N2, N1, C1, C2, C3, C7, C5, C6, C8, C4, H2A, H4, H2, H1, H5, H3, N3, C9, N4,
 C10, N5, C11
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3. Uiso/Uaniso restraints and constraints
N2 \\sim N1 \\sim C1 \\sim C2 \\sim C3 \\sim C7 \\sim C5 \\sim C6 \\sim C8
\\sim C4 \\sim H2A \\sim H4 \\sim H2 \\sim H1 \\sim H5 \\sim H3 \\sim N3 \\sim
C9 \\sim N4 \\sim C10 \\sim N5 \\sim C11: within 2A with sigma of 0.04 and
sigma for terminal atoms of 0.08 within 2A
4. Others
 Sof(Cl2)=1-FVAR(1)
 Sof(Cl3)=FVAR(1)
 Fixed Sof: H8BC(0.3333) H8BD(0.3333) H8AA(0.3333) H8AB(0.3333) H8CE(0.3333)
 H8CF(0.3333) N3(0.3333) H3A(0.3333) H3B(0.3333) H3C(0.3333) C9(0.3333)
 H9A(0.3333) H9B(0.3333) N4(0.3333) H4A(0.3333) H4B(0.3333) H4C(0.3333)
 C10(0.3333) H10A(0.3333) H10B(0.3333) N5(0.3333) H5A(0.3333) H5B(0.3333)
 H5C(0.3333) C11(0.3333) H11A(0.3333) H11B(0.3333)
5.a Secondary CH2 refined with riding coordinates:
 C8(H8BC,H8BD), C8(H8AA,H8AB), C8(H8CE,H8CF), C9(H9A,H9B), C10(H10A,H10B),
 C11(H11A,H11B)
5.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C2(H2A), C3(H3), C5(H5), C4(H4)
5.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N4(H4A,H4B,H4C), N5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.000000 0.67360(2) 0.750000 0.03878(8) Uani 1 2 d S T P . .
Pb2 Pb 0.500000 0.68530(2) 0.750000 0.04039(8) Uani 1 2 d S T P . .
Cl4 Cl 0.49977(14) 0.62761(5) 0.49693(17) 0.0744(4) Uani 1 1 d . . . . .
Cl5 Cl 0.48343(17) 0.75536(5) 0.99371(19) 0.0890(5) Uani 1 1 d . . . . .
Cl1 Cl -0.04047(13) 0.61117(5) 0.52663(16) 0.0705(4) Uani 1 1 d . . . . .
Cl3 Cl 0.2488(3) 0.6953(6) 0.7153(10) 0.071(2) Uani 0.61(3) 1 d . . P A 1
Cl2 Cl 0.2486(4) 0.6744(7) 0.7385(8) 0.055(3) Uani 0.39(3) 1 d . . P A 2
N2 N 0.8404(4) 0.57242(15) 0.1639(5) 0.0619(11) Uani 1 1 d . U . . .
H2 H 0.899458 0.575972 0.107687 0.074 Uiso 1 1 calc R U . . .
N1 N 0.6948(4) 0.58703(14) 0.3001(5) 0.0633(11) Uani 1 1 d . U . . .
H1 H 0.643824 0.601749 0.347823 0.076 Uiso 1 1 calc R U . . .
C1 C 0.7021(4) 0.54127(17) 0.2969(6) 0.0562(12) Uani 1 1 d . U . . .
C2 C 0.6359(5) 0.5094(2) 0.3573(7) 0.0719(14) Uani 1 1 d . U . . .
H2A H 0.571824 0.515989 0.414765 0.086 Uiso 1 1 calc R U . . .
C3 C 0.6679(6) 0.4664(2) 0.3297(8) 0.0809(16) Uani 1 1 d . U . . .
H3 H 0.624605 0.443459 0.368390 0.097 Uiso 1 1 calc R U . . .
C7 C 0.7775(5) 0.60414(19) 0.2194(6) 0.0615(13) Uani 1 1 d . U . . .
C5 C 0.8315(6) 0.4897(2) 0.1843(7) 0.0743(15) Uani 1 1 d . U . . .
H5 H 0.896787 0.483344 0.129100 0.089 Uiso 1 1 calc R U . . .
C6 C 0.7970(5) 0.53226(18) 0.2100(6) 0.0560(11) Uani 1 1 d . U . . .
C8 C 0.7993(6) 0.6513(2) 0.1882(8) 0.0852(19) Uani 1 1 d D U . . .
H8BC H 0.763069 0.658667 0.085045 0.102 Uiso 0.3333 1 calc R U P B 2
H8BD H 0.882399 0.655558 0.182768 0.102 Uiso 0.3333 1 calc R U P B 2
H8AA H 0.812940 0.654074 0.076551 0.102 Uiso 0.3333 1 calc R U P C 1
H8AB H 0.871473 0.659084 0.246462 0.102 Uiso 0.3333 1 calc R U P C 1
H8CE H 0.783418 0.657760 0.076632 0.102 Uiso 0.3333 1 calc R U P D 3
H8CF H 0.879893 0.658509 0.216533 0.102 Uiso 0.3333 1 calc R U P D 3
C4 C 0.7646(6) 0.4574(2) 0.2444(8) 0.0848(18) Uani 1 1 d . U . . .
H4 H 0.784556 0.428397 0.227399 0.102 Uiso 1 1 calc R U . . .
N3 N 0.7362(14) 0.6965(5) 0.3949(16) 0.065(4) Uani 0.3333 1 d D U P E 1
H3A H 0.686952 0.716995 0.424095 0.078 Uiso 0.3333 1 calc R U P E 1
H3B H 0.808746 0.706415 0.408897 0.078 Uiso 0.3333 1 calc R U P E 1
H3C H 0.728206 0.672616 0.453465 0.078 Uiso 0.3333 1 calc R U P E 1
C9 C 0.711(2) 0.6856(7) 0.225(2) 0.061(5) Uani 0.3333 1 d D U P E 1
H9A H 0.718753 0.711337 0.159476 0.074 Uiso 0.3333 1 calc R U P E 1
H9B H 0.632457 0.674271 0.207950 0.074 Uiso 0.3333 1 calc R U P E 1
N4 N 0.6433(12) 0.7008(4) 0.2418(16) 0.060(3) Uani 0.3333 1 d D U P E 2
H4A H 0.596229 0.705185 0.319834 0.072 Uiso 0.3333 1 calc R U P E 2
H4B H 0.610804 0.681700 0.172923 0.072 Uiso 0.3333 1 calc R U P E 2
H4C H 0.655434 0.725972 0.192779 0.072 Uiso 0.3333 1 calc R U P E 2
C10 C 0.7559(19) 0.6831(8) 0.308(2) 0.062(5) Uani 0.3333 1 d D U P E 2
H10A H 0.745428 0.668225 0.407645 0.074 Uiso 0.3333 1 calc R U P E 2
H10B H 0.811490 0.706613 0.327300 0.074 Uiso 0.3333 1 calc R U P E 2
N5 N 0.7454(12) 0.7225(4) 0.2269(19) 0.078(4) Uani 0.3333 1 d D U P E 3
H5A H 0.732479 0.742131 0.301449 0.093 Uiso 0.3333 1 calc R U P E 3
H5B H 0.699322 0.728017 0.140924 0.093 Uiso 0.3333 1 calc R U P E 3
H5C H 0.819333 0.723914 0.202555 0.093 Uiso 0.3333 1 calc R U P E 3
C11 C 0.720(3) 0.6779(6) 0.287(4) 0.070(7) Uani 0.3333 1 d D U P E 3
H11A H 0.639199 0.669958 0.265731 0.084 Uiso 0.3333 1 calc R U P E 3
H11B H 0.741009 0.675088 0.399046 0.084 Uiso 0.3333 1 calc R U P E 3


_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 Cl5 3.0654(14) 8_465 ?
Pb1 Cl5 3.0654(14) 7_567 ?
Pb1 Cl1 2.7054(13) . ?
Pb1 Cl1 2.7054(13) 2_556 ?
Pb1 Cl3 2.975(7) . ?
Pb1 Cl3 2.975(7) 2_556 ?
Pb1 Cl2 2.872(5) . ?
Pb1 Cl2 2.872(5) 2_556 ?
Pb2 Cl4 2.7727(13) 2_656 ?
Pb2 Cl4 2.7727(13) . ?
Pb2 Cl5 2.9859(14) . ?
Pb2 Cl5 2.9860(14) 2_656 ?
Pb2 Cl3 2.907(4) . ?
Pb2 Cl3 2.907(4) 2_656 ?
Pb2 Cl2 2.912(5) 2_656 ?
Pb2 Cl2 2.912(5) . ?
N2 H2 0.8600 . ?
N2 C7 1.314(6) . ?
N2 C6 1.390(7) . ?
N1 H1 0.8600 . ?
N1 C1 1.401(7) . ?
N1 C7 1.313(7) . ?
C1 C2 1.357(8) . ?
C1 C6 1.382(7) . ?
C2 H2A 0.9300 . ?
C2 C3 1.388(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(9) . ?
C7 C8 1.490(8) . ?
C5 H5 0.9300 . ?
C5 C6 1.380(7) . ?
C5 C4 1.369(9) . ?
C8 H8BC 0.9700 . ?
C8 H8BD 0.9700 . ?
C8 H8AA 0.9700 . ?
C8 H8AB 0.9700 . ?
C8 H8CE 0.9700 . ?
C8 H8CF 0.9700 . ?
C8 C9 1.509(15) . ?
C8 C10 1.510(15) . ?
C8 C11 1.508(15) . ?
C4 H4 0.9300 . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N3 C9 1.484(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
N4 H4C 0.8900 . ?
N4 C10 1.484(16) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
N5 H5A 0.8900 . ?
N5 H5B 0.8900 . ?
N5 H5C 0.8900 . ?
N5 C11 1.487(18) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl5 Pb1 Cl5 89.83(6) 7_567 8_465 ?
Cl1 Pb1 Cl5 173.64(5) 2_556 8_465 ?
Cl1 Pb1 Cl5 173.64(5) . 7_567 ?
Cl1 Pb1 Cl5 90.28(4) . 8_465 ?
Cl1 Pb1 Cl5 90.28(4) 2_556 7_567 ?
Cl1 Pb1 Cl1 90.31(7) . 2_556 ?
Cl1 Pb1 Cl3 102.40(16) 2_556 2_556 ?
Cl1 Pb1 Cl3 95.7(4) . 2_556 ?
Cl1 Pb1 Cl3 102.40(16) . . ?
Cl1 Pb1 Cl3 95.7(4) 2_556 . ?
Cl1 Pb1 Cl2 96.4(3) . . ?
Cl1 Pb1 Cl2 84.2(4) 2_556 . ?
Cl1 Pb1 Cl2 84.2(4) . 2_556 ?
Cl1 Pb1 Cl2 96.4(3) 2_556 2_556 ?
Cl3 Pb1 Cl5 83.84(17) 2_556 8_465 ?
Cl3 Pb1 Cl5 78.0(4) . 8_465 ?
Cl3 Pb1 Cl5 78.0(4) 2_556 7_567 ?
Cl3 Pb1 Cl5 83.84(17) . 7_567 ?
Cl3 Pb1 Cl3 154.2(7) . 2_556 ?
Cl2 Pb1 Cl2 179.1(8) 2_556 . ?
Cl4 Pb2 Cl4 101.05(7) . 2_656 ?
Cl4 Pb2 Cl5 85.42(4) . 2_656 ?
Cl4 Pb2 Cl5 172.56(5) . . ?
Cl4 Pb2 Cl5 85.42(4) 2_656 . ?
Cl4 Pb2 Cl5 172.56(5) 2_656 2_656 ?
Cl4 Pb2 Cl3 95.7(4) . 2_656 ?
Cl4 Pb2 Cl3 91.98(15) . . ?
Cl4 Pb2 Cl3 95.7(4) 2_656 . ?
Cl4 Pb2 Cl3 91.98(15) 2_656 2_656 ?
Cl4 Pb2 Cl2 87.0(2) . . ?
Cl4 Pb2 Cl2 84.7(3) 2_656 . ?
Cl4 Pb2 Cl2 84.7(3) . 2_656 ?
Cl4 Pb2 Cl2 87.0(2) 2_656 2_656 ?
Cl5 Pb2 Cl5 88.39(6) . 2_656 ?
Cl3 Pb2 Cl5 87.7(4) . 2_656 ?
Cl3 Pb2 Cl5 83.64(18) . . ?
Cl3 Pb2 Cl5 87.7(4) 2_656 . ?
Cl3 Pb2 Cl5 83.65(18) 2_656 2_656 ?
Cl3 Pb2 Cl3 167.9(8) 2_656 . ?
Cl3 Pb2 Cl2 13.21(9) 2_656 2_656 ?
Cl3 Pb2 Cl2 176.10(19) . 2_656 ?
Cl2 Pb2 Cl5 90.0(3) . . ?
Cl2 Pb2 Cl5 99.4(4) 2_656 . ?
Cl2 Pb2 Cl2 166.8(8) . 2_656 ?
Pb2 Cl5 Pb1 172.74(7) . 7_567 ?
Pb2 Cl3 Pb1 157.8(8) . . ?
Pb1 Cl2 Pb2 172.8(6) . . ?
C7 N2 H2 125.2 . . ?
C7 N2 C6 109.6(5) . . ?
C6 N2 H2 125.2 . . ?
C1 N1 H1 125.0 . . ?
C7 N1 H1 125.0 . . ?
C7 N1 C1 110.0(4) . . ?
C2 C1 N1 132.5(5) . . ?
C2 C1 C6 122.6(5) . . ?
C6 C1 N1 105.0(5) . . ?
C1 C2 H2A 121.4 . . ?
C1 C2 C3 117.1(6) . . ?
C3 C2 H2A 121.4 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.1(6) . . ?
C4 C3 H3 119.9 . . ?
N2 C7 C8 123.2(5) . . ?
N1 C7 N2 109.0(5) . . ?
N1 C7 C8 127.8(5) . . ?
C6 C5 H5 121.7 . . ?
C4 C5 H5 121.7 . . ?
C4 C5 C6 116.5(6) . . ?
C1 C6 N2 106.5(4) . . ?
C5 C6 N2 132.5(5) . . ?
C5 C6 C1 121.0(6) . . ?
C7 C8 H8BC 108.3 . . ?
C7 C8 H8BD 108.3 . . ?
C7 C8 H8AA 107.1 . . ?
C7 C8 H8AB 107.1 . . ?
C7 C8 H8CE 110.1 . . ?
C7 C8 H8CF 110.1 . . ?
C7 C8 C9 120.8(12) . . ?
C7 C8 C10 115.8(12) . . ?
C7 C8 C11 108.0(9) . . ?
H8BC C8 H8BD 107.4 . . ?
H8AA C8 H8AB 106.8 . . ?
H8CE C8 H8CF 108.4 . . ?
C9 C8 H8AA 107.1 . . ?
C9 C8 H8AB 107.1 . . ?
C10 C8 H8BC 108.3 . . ?
C10 C8 H8BD 108.3 . . ?
C11 C8 H8CE 110.1 . . ?
C11 C8 H8CF 110.1 . . ?
C3 C4 H4 118.7 . . ?
C5 C4 C3 122.6(6) . . ?
C5 C4 H4 118.7 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C9 N3 H3A 109.5 . . ?
C9 N3 H3B 109.5 . . ?
C9 N3 H3C 109.5 . . ?
C8 C9 H9A 110.7 . . ?
C8 C9 H9B 110.7 . . ?
N3 C9 C8 105.1(12) . . ?
N3 C9 H9A 110.7 . . ?
N3 C9 H9B 110.7 . . ?
H9A C9 H9B 108.8 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C10 N4 H4A 109.5 . . ?
C10 N4 H4B 109.5 . . ?
C10 N4 H4C 109.5 . . ?
C8 C10 H10A 110.3 . . ?
C8 C10 H10B 110.3 . . ?
N4 C10 C8 107.3(13) . . ?
N4 C10 H10A 110.3 . . ?
N4 C10 H10B 110.3 . . ?
H10A C10 H10B 108.5 . . ?
H5A N5 H5B 109.5 . . ?
H5A N5 H5C 109.5 . . ?
H5B N5 H5C 109.5 . . ?
C11 N5 H5A 109.5 . . ?
C11 N5 H5B 109.5 . . ?
C11 N5 H5C 109.5 . . ?
C8 C11 H11A 111.8 . . ?
C8 C11 H11B 111.8 . . ?
N5 C11 C8 99.7(13) . . ?
N5 C11 H11A 111.8 . . ?
N5 C11 H11B 111.8 . . ?
H11A C11 H11B 109.6 . . ?

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
N2 C7 C8 C9 167.3(9) . . . . ?
N2 C7 C8 C10 -155.8(10) . . . . ?
N2 C7 C8 C11 -173.1(16) . . . . ?
N1 C1 C2 C3 179.2(5) . . . . ?
N1 C1 C6 N2 -0.8(5) . . . . ?
N1 C1 C6 C5 179.0(5) . . . . ?
N1 C7 C8 C9 -11.2(12) . . . . ?
N1 C7 C8 C10 25.7(12) . . . . ?
N1 C7 C8 C11 8.5(18) . . . . ?
C1 N1 C7 N2 -0.7(6) . . . . ?
C1 N1 C7 C8 177.9(6) . . . . ?
C1 C2 C3 C4 0.4(9) . . . . ?
C2 C1 C6 N2 178.1(5) . . . . ?
C2 C1 C6 C5 -2.0(8) . . . . ?
C2 C3 C4 C5 -0.1(10) . . . . ?
C7 N2 C6 C1 0.5(6) . . . . ?
C7 N2 C6 C5 -179.4(6) . . . . ?
C7 N1 C1 C2 -177.8(6) . . . . ?
C7 N1 C1 C6 1.0(6) . . . . ?
C7 C8 C9 N3 85.7(18) . . . . ?
C7 C8 C10 N4 -99.2(17) . . . . ?
C7 C8 C11 N5 -174.3(15) . . . . ?
C6 N2 C7 N1 0.2(6) . . . . ?
C6 N2 C7 C8 -178.6(5) . . . . ?
C6 C1 C2 C3 0.6(8) . . . . ?
C6 C5 C4 C3 -1.2(9) . . . . ?
C4 C5 C6 N2 -177.9(5) . . . . ?
C4 C5 C6 C1 2.3(8) . . . . ?

_olex2_exptl_crystal_mounting_method 
;
 'Crystals were seperated from the mother liquor using paratone oil. 
  The crystal used for diffaction was placed on a kapton loop using 
  paratone to adhere it to the loop.'
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad1_a_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2169144'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-04-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Pb, 1(C4 H9 N3)'
_chemical_formula_sum            'C4 H9 Cl4 N3 Pb'
_chemical_formula_weight         448.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   15.7175(5)
_cell_length_b                   8.1812(2)
_cell_length_c                   17.2809(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2222.12(12)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7701
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.15
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    16.101
_exptl_absorpt_correction_T_max  0.4311
_exptl_absorpt_correction_T_min  0.3327
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. 
wR2(int) was 0.0913 before and 0.0681 after correction. 
The Ratio of minimum to maximum transmission is 0.7717. 
The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.679
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_preparation       
;
 'Crystals were prepared by dissolving the precursors in concentrated HCl 
at room temperature and diffusing in isopropanol in a closed vessel 
over several days.'
;
_exptl_crystal_recrystallization_method 
;
 'A mixture of large colorless plate-like crystals and colorless needles 
grew out of solution. The plates are the perovskite phase and the needles 
are another phase that sometimes grows from solution but not always.'
;
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0700
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            43232
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_min         2.592
_diffrn_ambient_temperature      100.15
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1825
_reflns_number_total             2456
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.559
_refine_diff_density_min         -1.131
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     144
_refine_ls_number_reflns         2456
_refine_ls_number_restraints     135
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0176
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0124P)²+3.6260P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0334
_refine_ls_wR_factor_ref         0.0390
_refine_special_details          
;
Restraints were required to properly model the disorder in the organic cations
due to the close proximity of the aromatic rings.
;
_olex2_refinement_description    
;
1. Restrained distances
 C2-C1
 1.35 with sigma of 0.02
 C6-C5
 1.35 with sigma of 0.02
 N5-C2 = N2-C6 = N4-C1 = N1-C5
 1.38 with sigma of 0.02
 N4-C2
 2.197 with sigma of 0.04
 N5-C1
 2.197 with sigma of 0.04
 N2-C5
 2.197 with sigma of 0.04
 N1-C6
 2.197 with sigma of 0.04
 N3-C8 \\sim N6-C4
 with sigma of 0.02
 C3-C4 \\sim C8-C7
 with sigma of 0.02
 N5-C3 \\sim N1-C7
 with sigma of 0.02
 N4-C3 \\sim N2-C7
 with sigma of 0.02
 N2-C6 \\sim N4-C1
 with sigma of 0.02
 N5-C2 \\sim N1-C5
 with sigma of 0.02
 C2-C1 \\sim C6-C5
 with sigma of 0.02
2. Restrained planarity
 N2, N1, C6, C7, C5
 with sigma of 0.1
 N4, N5, C3, C1, C2
 with sigma of 0.1
3. Rigid bond restraints
 N2, N1, N3, C6, C8, C7, C5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N4, N5, N6, C3, C1, C2, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
N2 \\sim N1 \\sim N3 \\sim C6 \\sim C8 \\sim C7 \\sim C5: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
N4 \\sim N5 \\sim N6 \\sim C3 \\sim C1 \\sim C2 \\sim C4: within 2A with sigma
of 0.04 and sigma for terminal atoms of 0.08 within 2A
Uanis(C7) = Uanis(C3)
Uanis(C6) = Uanis(C1)
Uanis(C2) = Uanis(C5)
Uanis(N2) = Uanis(N4)
Uanis(N5) = Uanis(N1)
5. Others
 Fixed Sof: N2(0.6667) H2(0.6667) N1(0.6667) H1(0.6667) N3(0.6667) H3A(0.6667)
 H3B(0.6667) H3C(0.6667) C6(0.6667) H6(0.6667) C8(0.6667) H8A(0.6667)
 H8B(0.6667) C7(0.6667) C5(0.6667) H5(0.6667) N4(0.3333) H4(0.3333) N5(0.3333)
 H5A(0.3333) N6(0.3333) H6A(0.3333) H6B(0.3333) H6C(0.3333) C3(0.3333)
 C1(0.3333) H1A(0.3333) C2(0.3333) H2A(0.3333) C4(0.3333) H4A(0.3333)
 H4B(0.3333)
6.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C4(H4A,H4B)
6.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C6(H6), C5(H5), N4(H4), N5(H5A), C1(H1A), C2(H2A)
6.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.62551(2) 0.12957(2) 0.73214(2) 0.01208(5) Uani 1 1 d . . . . .
Cl2 Cl 0.61616(7) 0.13040(16) 0.56862(6) 0.0289(2) Uani 1 1 d . . . . .
Cl4 Cl 0.66093(8) 0.12671(17) 0.89416(7) 0.0296(3) Uani 1 1 d . . . . .
Cl1 Cl 0.74651(7) 0.38490(15) 0.72602(6) 0.0220(2) Uani 1 1 d . . . . .
Cl3 Cl 0.50689(8) 0.39268(16) 0.74542(7) 0.0301(3) Uani 1 1 d . . . . .
N2 N 0.4517(10) 0.2689(11) 0.4953(7) 0.0167(19) Uani 0.6667 1 d D U P A 1
H2 H 0.504663 0.250328 0.509413 0.020 Uiso 0.6667 1 calc R U P A 1
N1 N 0.3163(9) 0.2604(10) 0.4906(6) 0.020(2) Uani 0.6667 1 d D U P A 1
H1 H 0.263192 0.234637 0.501045 0.024 Uiso 0.6667 1 calc R U P A 1
N3 N 0.3590(3) 0.1518(7) 0.6663(3) 0.0204(12) Uani 0.6667 1 d D U P A 1
H3A H 0.353527 0.071938 0.702559 0.024 Uiso 0.6667 1 calc R U P A 1
H3B H 0.308159 0.203404 0.659918 0.024 Uiso 0.6667 1 calc R U P A 1
H3C H 0.398804 0.225388 0.682037 0.024 Uiso 0.6667 1 calc R U P A 1
C6 C 0.4278(11) 0.371(2) 0.4362(7) 0.020(2) Uani 0.6667 1 d D U P A 1
H6 H 0.464351 0.433425 0.403705 0.024 Uiso 0.6667 1 calc R U P A 1
C8 C 0.3859(5) 0.0780(9) 0.5916(4) 0.0229(16) Uani 0.6667 1 d D U P A 1
H8A H 0.347181 -0.013290 0.578321 0.027 Uiso 0.6667 1 calc R U P A 1
H8B H 0.444088 0.033235 0.596866 0.027 Uiso 0.6667 1 calc R U P A 1
C7 C 0.3844(8) 0.2025(8) 0.5279(4) 0.0165(16) Uani 0.6667 1 d D U P A 1
C5 C 0.3418(11) 0.366(2) 0.4334(8) 0.021(2) Uani 0.6667 1 d D U P A 1
H5 H 0.305967 0.424123 0.398716 0.025 Uiso 0.6667 1 calc R U P A 1
N4 N 0.3137(19) 0.300(2) 0.4869(13) 0.0167(19) Uani 0.3333 1 d D U P B 2
H4 H 0.260027 0.284016 0.499264 0.020 Uiso 0.3333 1 calc R U P B 2
N5 N 0.451(2) 0.302(3) 0.4918(15) 0.020(2) Uani 0.3333 1 d D U P B 2
H5A H 0.503481 0.287639 0.508501 0.024 Uiso 0.3333 1 calc R U P B 2
N6 N 0.3463(8) 0.0159(13) 0.6096(7) 0.022(3) Uani 0.3333 1 d D U P B 2
H6A H 0.288422 0.015832 0.609605 0.027 Uiso 0.3333 1 calc R U P B 2
H6B H 0.365655 -0.034576 0.653088 0.027 Uiso 0.3333 1 calc R U P B 2
H6C H 0.365635 -0.038319 0.567114 0.027 Uiso 0.3333 1 calc R U P B 2
C3 C 0.3800(16) 0.2598(17) 0.5299(9) 0.0165(16) Uani 0.3333 1 d D U P B 2
C1 C 0.342(2) 0.371(5) 0.4199(18) 0.020(2) Uani 0.3333 1 d D U P B 2
H1A H 0.308159 0.413757 0.379283 0.024 Uiso 0.3333 1 calc R U P B 2
C2 C 0.428(2) 0.370(5) 0.4223(18) 0.021(2) Uani 0.3333 1 d D U P B 2
H2A H 0.465699 0.408679 0.383260 0.025 Uiso 0.3333 1 calc R U P B 2
C4 C 0.3779(10) 0.1878(16) 0.6079(8) 0.025(3) Uani 0.3333 1 d D U P B 2
H4A H 0.340810 0.255785 0.641251 0.030 Uiso 0.3333 1 calc R U P B 2
H4B H 0.435945 0.190862 0.630031 0.030 Uiso 0.3333 1 calc R U P B 2


_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 Cl2 2.8296(11) . ?
Pb1 Cl4 2.8548(11) . ?
Pb1 Cl1 2.8269(12) . ?
Pb1 Cl1 2.8397(11) 8_755 ?
Pb1 Cl3 2.8701(13) 3_646 ?
Pb1 Cl3 2.8570(13) . ?
N2 H2 0.8800 . ?
N2 C6 1.374(9) . ?
N2 C7 1.317(14) . ?
N1 H1 0.8800 . ?
N1 C7 1.336(13) . ?
N1 C5 1.372(9) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C8 1.486(8) . ?
C6 H6 0.9500 . ?
C6 C5 1.354(8) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C7 1.499(9) . ?
C5 H5 0.9500 . ?
N4 H4 0.8800 . ?
N4 C3 1.32(2) . ?
N4 C1 1.373(13) . ?
N5 H5A 0.8800 . ?
N5 C3 1.34(2) . ?
N5 C2 1.372(13) . ?
N6 H6A 0.9100 . ?
N6 H6B 0.9100 . ?
N6 H6C 0.9100 . ?
N6 C4 1.492(13) . ?
C3 C4 1.472(15) . ?
C1 H1A 0.9500 . ?
C1 C2 1.350(12) . ?
C2 H2A 0.9500 . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?

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
Cl2 Pb1 Cl4 171.73(3) . . ?
Cl2 Pb1 Cl1 90.08(3) . 8_755 ?
Cl2 Pb1 Cl3 95.67(3) . 3_646 ?
Cl2 Pb1 Cl3 92.55(4) . . ?
Cl4 Pb1 Cl3 90.19(4) . 3_646 ?
Cl4 Pb1 Cl3 93.13(4) . . ?
Cl1 Pb1 Cl2 89.76(3) . . ?
Cl1 Pb1 Cl4 84.93(3) . . ?
Cl1 Pb1 Cl4 83.84(4) 8_755 . ?
Cl1 Pb1 Cl1 92.463(6) . 8_755 ?
Cl1 Pb1 Cl3 175.09(3) 8_755 . ?
Cl1 Pb1 Cl3 92.44(3) 8_755 3_646 ?
Cl1 Pb1 Cl3 172.67(3) . 3_646 ?
Cl1 Pb1 Cl3 83.41(3) . . ?
Cl3 Pb1 Cl3 91.417(6) . 3_646 ?
Pb1 Cl1 Pb1 174.87(5) . 8_765 ?
Pb1 Cl3 Pb1 173.13(5) . 3_656 ?
C6 N2 H2 124.8 . . ?
C7 N2 H2 124.8 . . ?
C7 N2 C6 110.5(10) . . ?
C7 N1 H1 125.1 . . ?
C7 N1 C5 109.7(9) . . ?
C5 N1 H1 125.1 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C8 N3 H3A 109.5 . . ?
C8 N3 H3B 109.5 . . ?
C8 N3 H3C 109.5 . . ?
N2 C6 H6 126.9 . . ?
C5 C6 N2 106.2(9) . . ?
C5 C6 H6 126.9 . . ?
N3 C8 H8A 109.5 . . ?
N3 C8 H8B 109.5 . . ?
N3 C8 C7 110.9(6) . . ?
H8A C8 H8B 108.0 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
N2 C7 N1 106.9(8) . . ?
N2 C7 C8 125.6(9) . . ?
N1 C7 C8 127.4(9) . . ?
N1 C5 H5 126.7 . . ?
C6 C5 N1 106.6(8) . . ?
C6 C5 H5 126.7 . . ?
C3 N4 H4 125.7 . . ?
C3 N4 C1 108.7(18) . . ?
C1 N4 H4 125.7 . . ?
C3 N5 H5A 125.8 . . ?
C3 N5 C2 108.4(19) . . ?
C2 N5 H5A 125.8 . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C4 N6 H6A 109.5 . . ?
C4 N6 H6B 109.5 . . ?
C4 N6 H6C 109.5 . . ?
N4 C3 N5 108.6(17) . . ?
N4 C3 C4 126.6(19) . . ?
N5 C3 C4 124.8(19) . . ?
N4 C1 H1A 126.3 . . ?
C2 C1 N4 107.4(17) . . ?
C2 C1 H1A 126.3 . . ?
N5 C2 H2A 126.5 . . ?
C1 C2 N5 107.0(17) . . ?
C1 C2 H2A 126.5 . . ?
N6 C4 H4A 108.8 . . ?
N6 C4 H4B 108.8 . . ?
C3 C4 N6 113.7(12) . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?

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
N2 C6 C5 N1 -0.3(11) . . . . ?
N3 C8 C7 N2 107.2(9) . . . . ?
N3 C8 C7 N1 -76.9(10) . . . . ?
C6 N2 C7 N1 0.1(11) . . . . ?
C6 N2 C7 C8 176.7(10) . . . . ?
C7 N2 C6 C5 0.1(11) . . . . ?
C7 N1 C5 C6 0.3(11) . . . . ?
C5 N1 C7 N2 -0.2(11) . . . . ?
C5 N1 C7 C8 -176.8(11) . . . . ?
N4 C3 C4 N6 70(2) . . . . ?
N4 C1 C2 N5 -2(3) . . . . ?
N5 C3 C4 N6 -113.3(19) . . . . ?
C3 N4 C1 C2 1(3) . . . . ?
C3 N5 C2 C1 1(3) . . . . ?
C1 N4 C3 N5 -0.7(19) . . . . ?
C1 N4 C3 C4 177(2) . . . . ?
C2 N5 C3 N4 -0.3(19) . . . . ?
C2 N5 C3 C4 -178(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
;
 'Crystals were seperated from the mother liquor using paratone. 
  A plate-like crystal was selected and mounted on a kapton loop 
  using paratone to adhere the crystal.'
;
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_sad1_a_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2169145'
loop_
_audit_author_name
_audit_author_address
'Ethan Crace'
;Stanford University
United States of America
;
_audit_update_record             
;
2022-04-27 deposited with the CCDC.	2022-08-01 downloaded from the CCDC.
;
_audit_creation_date             2021-04-01
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Cl4 Pb, 1(C4 H9 N3)'
_chemical_formula_sum            'C4 H9 Cl4 N3 Pb'
_chemical_formula_weight         448.13
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
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'
'-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                   15.7952(8)
_cell_length_b                   8.1952(4)
_cell_length_c                   17.4241(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2255.5(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7381
_cell_measurement_temperature    300
_cell_measurement_theta_max      28.26
_cell_measurement_theta_min      2.34
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    15.863
_exptl_absorpt_correction_T_max  0.4311
_exptl_absorpt_correction_T_min  0.3324
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int)
  was 0.1301 before and 0.0721 after correction. The Ratio of minimum to 
  maximum transmission is 0.7711. The λ/2 correction factor is Not present.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.639
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1632
_exptl_crystal_preparation       
;
 'Crystals were prepared by dissolving the precursors in concentrated HCl 
  at room temperature and diffusing in isopropanol in a closed vessel 
  over several days.'
;
_exptl_crystal_recrystallization_method 
;
 'A mixture of large colorless plate-like crystals and colorless needles 
  grew out of solution. The plates are the perovskite phase and the needles 
  are another phase that sometimes grows from solution but not always.'
;
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0750
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            50954
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_min         2.338
_diffrn_ambient_temperature      300.15
_diffrn_detector                 'Bruker Photon II'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_detector_type            'CMOS area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.0
_diffrn_source_power             0.05
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1444
_reflns_number_total             2061
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.500
_refine_diff_density_min         -1.374
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.176
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     174
_refine_ls_number_reflns         2061
_refine_ls_number_restraints     329
_refine_ls_R_factor_all          0.0399
_refine_ls_R_factor_gt           0.0204
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0265P)²+0.2230P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0475
_refine_ls_wR_factor_ref         0.0576
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C5-N5
 2.164 with sigma of 0.04
 N4-C6
 2.164 with sigma of 0.04
 N1-C2
 2.164 with sigma of 0.04
 N2-C1
 2.164 with sigma of 0.04
 C8-C7 \\sim C4-C3
 with sigma of 0.02
 N3-C4 \\sim N6-C8
 with sigma of 0.02
 N5-C3 \\sim N5-C7
 with sigma of 0.02
 N4-C3 \\sim N4-C7
 with sigma of 0.02
 N4-C3 \\sim N1-C7
 with sigma of 0.02
 N4-C1 \\sim N1-C1
 with sigma of 0.02
 N2-C7 \\sim N5-C3
 with sigma of 0.02
 N2-C2 \\sim N5-C2
 with sigma of 0.02
 N5-C6 \\sim N2-C2
 with sigma of 0.02
 C1-C2 \\sim C5-C6
 with sigma of 0.02
 N4-C5 \\sim N1-C1
 with sigma of 0.02
 N5-C7 \\sim N4-C7
 with sigma of 0.02
 N1-C3 \\sim N2-C3
 with sigma of 0.02
 N5-C6 \\sim N4-C5
 with sigma of 0.02
 N1-C1 \\sim N2-C2
 with sigma of 0.02
2. Restrained planarity
 C1, C2, N4, N5, C7
 with sigma of 0.1
 N4, N5, C6, C5, C7
 with sigma of 0.1
 N1, N2, C1, C3, C2
 with sigma of 0.1
3. Rigid bond restraints
 N4, N5, H5, N6, H6A, H6B, H6C, C6, C5, H5A, C7, C8, H8A, H8B
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 H1A, N3, H3A, H3B, H3C, N1, H1, N2, H2, C4, H4A, H4B, C1, C3, C2, H2A
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
H1A \\sim N3 \\sim H3A \\sim H3B \\sim H3C \\sim N1 \\sim H1 \\sim N2 \\sim H2
\\sim C4 \\sim H4A \\sim H4B \\sim C1 \\sim C3 \\sim C2 \\sim H2A: within 2A
with sigma of 0.04 and sigma for terminal atoms of 0.08 within 2A
N4 \\sim N5 \\sim H5 \\sim N6 \\sim H6A \\sim H6B \\sim H6C \\sim C6 \\sim C5
\\sim H5A \\sim C7 \\sim C8 \\sim H8A \\sim H8B: within 2A with sigma of 0.04
and sigma for terminal atoms of 0.08 within 2A
5. Others
 Fixed Sof: N3(0.6667) H3A(0.6667) H3B(0.6667) H3C(0.6667) N1(0.6667)
 H1(0.6667) N2(0.6667) H2(0.6667) C4(0.6667) H4A(0.6667) H4B(0.6667) C1(0.6667)
 H1A(0.6667) C3(0.6667) C2(0.6667) H2A(0.6667) N4(0.3333) H4(0.3333) N5(0.3333)
 H5(0.3333) N6(0.3333) H6A(0.3333) H6B(0.3333) H6C(0.3333) C6(0.3333)
 H6(0.3333) C5(0.3333) H5A(0.3333) C7(0.3333) C8(0.3333) H8A(0.3333) H8B(0.3333)
6.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C8(H8A,H8B)
6.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C1(H1A), C2(H2A), N4(H4), N5(H5), C6(H6), C5(H5A)
6.c Idealised Me refined as rotating group:
 N3(H3A,H3B,H3C), N6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.37481(2) 0.86891(2) 0.73309(2) 0.02672(9) Uani 1 1 d . . . . .
Cl4 Cl 0.38690(11) 0.8662(2) 0.57013(11) 0.0572(5) Uani 1 1 d . . . . .
Cl2 Cl 0.34213(13) 0.8760(3) 0.89436(11) 0.0604(5) Uani 1 1 d . . . . .
Cl1 Cl 0.25446(11) 0.6119(2) 0.72898(11) 0.0481(4) Uani 1 1 d . . . . .
Cl3 Cl 0.49418(13) 0.6083(3) 0.74742(12) 0.0602(6) Uani 1 1 d . . . . .
N3 N 0.6410(5) 0.8425(10) 0.6623(5) 0.049(2) Uani 0.6667 1 d D U P A 1
H3A H 0.689287 0.787611 0.656847 0.059 Uiso 0.6667 1 calc R U P A 1
H3B H 0.600626 0.774986 0.678350 0.059 Uiso 0.6667 1 calc R U P A 1
H3C H 0.648131 0.921820 0.696608 0.059 Uiso 0.6667 1 calc R U P A 1
N1 N 0.5510(16) 0.728(2) 0.4902(13) 0.038(3) Uani 0.6667 1 d D U P A 1
H1 H 0.499004 0.745022 0.502341 0.045 Uiso 0.6667 1 calc R U P A 1
N2 N 0.6873(14) 0.739(2) 0.4890(11) 0.042(3) Uani 0.6667 1 d D U P A 1
H2 H 0.738535 0.764729 0.500704 0.050 Uiso 0.6667 1 calc R U P A 1
C4 C 0.6167(9) 0.9131(15) 0.5889(6) 0.050(3) Uani 0.6667 1 d D U P A 1
H4A H 0.654597 1.002819 0.577190 0.061 Uiso 0.6667 1 calc R U P A 1
H4B H 0.559945 0.957448 0.593365 0.061 Uiso 0.6667 1 calc R U P A 1
C1 C 0.5794(13) 0.628(3) 0.4326(12) 0.045(4) Uani 0.6667 1 d D U P A 1
H1A H 0.545660 0.565587 0.400043 0.054 Uiso 0.6667 1 calc R U P A 1
C3 C 0.6184(13) 0.7949(14) 0.5239(7) 0.037(3) Uani 0.6667 1 d D U P A 1
C2 C 0.6637(14) 0.635(3) 0.4314(10) 0.044(4) Uani 0.6667 1 d D U P A 1
H2A H 0.699568 0.579332 0.397953 0.053 Uiso 0.6667 1 calc R U P A 1
N4 N 0.552(3) 0.701(4) 0.498(3) 0.045(7) Uani 0.3333 1 d D U P B 2
H4 H 0.502588 0.713876 0.518426 0.054 Uiso 0.3333 1 calc R U P B 2
N5 N 0.682(3) 0.702(4) 0.485(2) 0.040(7) Uani 0.3333 1 d D U P B 2
H5 H 0.734534 0.714944 0.494591 0.048 Uiso 0.3333 1 calc R U P B 2
N6 N 0.6420(17) 0.984(2) 0.6074(12) 0.075(7) Uani 0.3333 1 d D U P B 2
H6A H 0.618886 1.028393 0.565693 0.090 Uiso 0.3333 1 calc R U P B 2
H6B H 0.697840 0.997861 0.606049 0.090 Uiso 0.3333 1 calc R U P B 2
H6C H 0.621067 1.032400 0.649060 0.090 Uiso 0.3333 1 calc R U P B 2
C6 C 0.650(3) 0.636(5) 0.419(2) 0.050(8) Uani 0.3333 1 d D U P B 2
H6 H 0.680631 0.598175 0.376627 0.060 Uiso 0.3333 1 calc R U P B 2
C5 C 0.566(3) 0.636(6) 0.427(3) 0.055(9) Uani 0.3333 1 d D U P B 2
H5A H 0.525368 0.600440 0.391674 0.066 Uiso 0.3333 1 calc R U P B 2
C7 C 0.622(3) 0.742(3) 0.5316(13) 0.035(6) Uani 0.3333 1 d D U P B 2
C8 C 0.6229(17) 0.814(2) 0.6096(14) 0.055(5) Uani 0.3333 1 d D U P B 2
H8A H 0.568053 0.798191 0.633610 0.066 Uiso 0.3333 1 calc R U P B 2
H8B H 0.664894 0.758236 0.640607 0.066 Uiso 0.3333 1 calc R U P B 2


_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 Cl4 2.8460(19) . ?
Pb1 Cl2 2.858(2) . ?
Pb1 Cl1 2.8529(18) 8_665 ?
Pb1 Cl1 2.8383(18) . ?
Pb1 Cl3 2.871(2) 3_656 ?
Pb1 Cl3 2.860(2) . ?
N3 H3A 0.8900 . ?
N3 H3B 0.8900 . ?
N3 H3C 0.8900 . ?
N3 C4 1.456(13) . ?
N1 H1 0.8600 . ?
N1 C1 1.373(12) . ?
N1 C3 1.33(2) . ?
N2 H2 0.8600 . ?
N2 C3 1.33(2) . ?
N2 C2 1.372(12) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C4 C3 1.491(14) . ?
C1 H1A 0.9300 . ?
C1 C2 1.333(14) . ?
C2 H2A 0.9300 . ?
N4 H4 0.8600 . ?
N4 C5 1.374(17) . ?
N4 C7 1.29(4) . ?
N5 H5 0.8600 . ?
N5 C6 1.375(16) . ?
N5 C7 1.29(4) . ?
N6 H6A 0.8900 . ?
N6 H6B 0.8900 . ?
N6 H6C 0.8900 . ?
N6 C8 1.428(17) . ?
C6 H6 0.9300 . ?
C6 C5 1.337(18) . ?
C5 H5A 0.9300 . ?
C7 C8 1.484(19) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl4 Pb1 Cl2 173.40(5) . . ?
Cl4 Pb1 Cl1 91.62(5) . 8_665 ?
Cl4 Pb1 Cl3 94.30(6) . 3_656 ?
Cl4 Pb1 Cl3 92.13(5) . . ?
Cl2 Pb1 Cl3 90.00(6) . 3_656 ?
Cl2 Pb1 Cl3 92.78(6) . . ?
Cl1 Pb1 Cl4 90.80(5) . . ?
Cl1 Pb1 Cl2 83.18(6) 8_665 . ?
Cl1 Pb1 Cl2 85.35(6) . . ?
Cl1 Pb1 Cl1 92.178(8) . 8_665 ?
Cl1 Pb1 Cl3 174.43(6) 8_665 . ?
Cl1 Pb1 Cl3 83.66(6) . . ?
Cl1 Pb1 Cl3 173.04(6) . 3_656 ?
Cl1 Pb1 Cl3 92.40(6) 8_665 3_656 ?
Cl3 Pb1 Cl3 91.420(8) . 3_656 ?
Pb1 Cl1 Pb1 175.35(7) . 8_655 ?
Pb1 Cl3 Pb1 174.63(10) . 3_646 ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C4 N3 H3A 109.5 . . ?
C4 N3 H3B 109.5 . . ?
C4 N3 H3C 109.5 . . ?
C1 N1 H1 126.1 . . ?
C3 N1 H1 126.1 . . ?
C3 N1 C1 107.9(16) . . ?
C3 N2 H2 125.5 . . ?
C3 N2 C2 109.1(14) . . ?
C2 N2 H2 125.5 . . ?
N3 C4 H4A 108.8 . . ?
N3 C4 H4B 108.8 . . ?
N3 C4 C3 113.9(11) . . ?
H4A C4 H4B 107.7 . . ?
C3 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
N1 C1 H1A 125.9 . . ?
C2 C1 N1 108.2(14) . . ?
C2 C1 H1A 125.9 . . ?
N1 C3 C4 125.9(17) . . ?
N2 C3 N1 108.2(15) . . ?
N2 C3 C4 125.9(16) . . ?
N2 C2 H2A 126.7 . . ?
C1 C2 N2 106.6(13) . . ?
C1 C2 H2A 126.7 . . ?
C5 N4 H4 124.1 . . ?
C7 N4 H4 124.1 . . ?
C7 N4 C5 112(3) . . ?
C6 N5 H5 124.4 . . ?
C7 N5 H5 124.4 . . ?
C7 N5 C6 111(3) . . ?
H6A N6 H6B 109.5 . . ?
H6A N6 H6C 109.5 . . ?
H6B N6 H6C 109.5 . . ?
C8 N6 H6A 109.5 . . ?
C8 N6 H6B 109.5 . . ?
C8 N6 H6C 109.5 . . ?
N5 C6 H6 127.2 . . ?
C5 C6 N5 106(2) . . ?
C5 C6 H6 127.2 . . ?
N4 C5 H5A 127.6 . . ?
C6 C5 N4 105(3) . . ?
C6 C5 H5A 127.6 . . ?
N4 C7 C8 122(3) . . ?
N5 C7 N4 106(3) . . ?
N5 C7 C8 132(3) . . ?
N6 C8 C7 112(2) . . ?
N6 C8 H8A 109.3 . . ?
N6 C8 H8B 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?

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
N3 C4 C3 N1 105.5(15) . . . . ?
N3 C4 C3 N2 -75.3(18) . . . . ?
N1 C1 C2 N2 0.4(15) . . . . ?
C1 N1 C3 N2 0.1(16) . . . . ?
C1 N1 C3 C4 179.4(15) . . . . ?
C3 N1 C1 C2 -0.3(15) . . . . ?
C3 N2 C2 C1 -0.4(16) . . . . ?
C2 N2 C3 N1 0.2(17) . . . . ?
C2 N2 C3 C4 -179.1(14) . . . . ?
N4 C7 C8 N6 -106(3) . . . . ?
N5 C6 C5 N4 -1(2) . . . . ?
N5 C7 C8 N6 76(4) . . . . ?
C6 N5 C7 N4 1(2) . . . . ?
C6 N5 C7 C8 179(3) . . . . ?
C5 N4 C7 N5 -1(3) . . . . ?
C5 N4 C7 C8 -180(3) . . . . ?
C7 N4 C5 C6 1(3) . . . . ?
C7 N5 C6 C5 0(2) . . . . ?

_olex2_exptl_crystal_mounting_method 
;
 'Crystals were seperated from the mother liquor using paratone. 
  A plate-like crystal was selected and mounted on a kapton loop 
  using paratone to adhere the crystal.'
;
_olex2_submission_special_instructions 'No special instructions were received'
