# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_shi_5165_ilgu_autored
_database_code_depnum_ccdc_archive 'CCDC 2207739'
loop_
_audit_author_name
_audit_author_address
'Ilya Guralskiy'
;Taras Shevchenko National University of Kyiv
Ukraine
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-22
_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         'I4 Pb, 2(C6 H10 N3 O2), H0.44 O0.22'
_chemical_formula_sum            'C12 H20.44 I4 N6 O4.22 Pb'
_chemical_formula_weight         1031.09
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C10H10N2O4Pb1I2
_chemical_oxdiff_usercomment     SV354
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x, y, -z+1/2'
'x, -y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z+1/2'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3053(15)
_cell_length_b                   9.5330(18)
_cell_length_c                   30.667(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2428.0(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1352
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.8380
_cell_measurement_theta_min      2.6240
_shelx_estimated_absorpt_T_max   0.794
_shelx_estimated_absorpt_T_min   0.644
_exptl_absorpt_coefficient_mu    12.063
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.115a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light red'
_exptl_crystal_density_diffrn    2.821
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1849
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.855
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            6398
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.825
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.448
_diffrn_reflns_theta_min         2.657
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.855
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  14.00   1.00  100.00    --  -15.13 107.00   5.00   56
  2  ω      8.00  86.00   1.00  100.00    --   17.71  28.00 167.00   78
  3  ω     -8.00  54.00   1.00  100.00    --   17.71 -99.00   0.00   62
  4  ω     -2.00  37.00   1.00  100.00    --   17.71  77.00-120.00   39
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0602789000
_diffrn_orient_matrix_UB_12      0.0526138000
_diffrn_orient_matrix_UB_13      0.0010323000
_diffrn_orient_matrix_UB_21      0.0554602000
_diffrn_orient_matrix_UB_22      -0.0496076000
_diffrn_orient_matrix_UB_23      0.0084676000
_diffrn_orient_matrix_UB_31      0.0248047000
_diffrn_orient_matrix_UB_32      -0.0170540000
_diffrn_orient_matrix_UB_33      -0.0214891000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.706
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.787
_reflns_number_gt                1752
_reflns_number_total             2787
_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       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.115a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.921
_refine_diff_density_min         -1.472
_refine_diff_density_rms         0.248
_refine_ls_abs_structure_details 
;
 Flack x determined using 503 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     105
_refine_ls_number_reflns         2787
_refine_ls_number_restraints     29
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0524
_refine_ls_restrained_S_all      0.989
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0794
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 C6-C4 = N3-C6 = N3-C5 = N2-C5 = N2-C4
 1.35 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(O3) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C6) \\sim Ueq, Uanis(C4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C4) = Uanis(N2) = Uanis(C5) = Uanis(N3) = Uanis(C6)
3. Others
 Fixed Sof: O3(0.11) H3C(0.22)
4.a Riding coordinates:
 O1(H1), O3(H3C)
4.b Ternary CH refined with riding coordinates:
 C2(H2)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
4.d Aromatic/amide H refined with riding coordinates:
 N3(H3), C5(H5), C6(H6)
4.e Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_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 1.09217(9) 0.500000 0.500000 0.0261(2) Uani 1 2 d S T P . .
I2 I 1.34977(13) 0.25755(12) 0.50090(9) 0.0496(3) Uani 1 1 d . . . . .
I1 I 1.09908(15) 0.5009(3) 0.39523(3) 0.0531(4) Uani 1 1 d . . . . .
N1 N 0.9011(18) 0.3871(15) 0.2965(4) 0.035(4) Uani 1 1 d . . . . .
H1A H 0.869868 0.449494 0.276657 0.042 Uiso 1 1 calc R U . . .
H1B H 0.991481 0.345808 0.287720 0.042 Uiso 1 1 calc R U . . .
H1C H 0.918454 0.430511 0.321802 0.042 Uiso 1 1 calc R U . . .
O1 O 0.8283(18) 0.2302(16) 0.2267(4) 0.059(5) Uani 1 1 d . . . . .
H1 H 0.810882 0.180569 0.205607 0.088 Uiso 1 1 d R U . . .
C2 C 0.772(2) 0.2788(19) 0.3023(5) 0.033(5) Uani 1 1 d . . . . .
H2 H 0.800744 0.219362 0.327202 0.039 Uiso 1 1 calc R U . . .
O2 O 0.681(2) 0.0806(15) 0.2647(4) 0.081(6) Uani 1 1 d . . . . .
C1 C 0.759(3) 0.184(2) 0.2607(7) 0.042(6) Uani 1 1 d . . . . .
O3 O 0.701(7) 0.500000 0.500000 0.032(14) Uani 0.22 2 d S TU P . .
H3C H 0.761556 0.429850 0.504670 0.048 Uiso 0.22 1 d R U P . .
C4 C 0.605(4) 0.429(2) 0.3535(7) 0.052(2) Uani 1 1 d D U . . .
N2 N 0.631(3) 0.574(2) 0.3501(5) 0.052(2) Uani 1 1 d D . . . .
N3 N 0.5979(18) 0.5239(17) 0.4164(4) 0.052(2) Uani 1 1 d D U . . .
H3 H 0.586553 0.533930 0.444145 0.062 Uiso 1 1 calc R U . . .
C5 C 0.623(3) 0.625(2) 0.3915(6) 0.052(2) Uani 1 1 d D . . . .
H5 H 0.634965 0.718471 0.399658 0.062 Uiso 1 1 calc R U . . .
C3 C 0.608(2) 0.350(2) 0.3118(6) 0.039(5) Uani 1 1 d . . . . .
H3A H 0.582065 0.413368 0.288078 0.047 Uiso 1 1 calc R U . . .
H3B H 0.524663 0.278350 0.312709 0.047 Uiso 1 1 calc R U . . .
C6 C 0.589(3) 0.394(2) 0.3961(7) 0.052(2) Uani 1 1 d D U . . .
H6 H 0.576251 0.305762 0.408503 0.062 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 I2 3.1496(13) 4_566 ?
Pb1 I2 3.1496(12) . ?
Pb1 I2 3.1752(12) 8_456 ?
Pb1 I2 3.1752(12) 5_455 ?
Pb1 I1 3.2133(11) 4_566 ?
Pb1 I1 3.2134(11) . ?
I2 H3C 1.94(2) 8_556 ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
N1 C2 1.50(2) . ?
O1 H1 0.8143 . ?
O1 C1 1.27(2) . ?
C2 H2 0.9800 . ?
C2 C1 1.57(2) . ?
C2 C3 1.55(2) . ?
O2 C1 1.19(2) . ?
O3 H3C 0.8469 . ?
O3 H3C 0.8469 4_566 ?
C4 N2 1.397(16) . ?
C4 C3 1.48(2) . ?
C4 C6 1.357(18) . ?
N2 C5 1.360(16) . ?
N3 H3 0.8600 . ?
N3 C5 1.250(17) . ?
N3 C6 1.387(18) . ?
C5 H5 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C6 H6 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
I2 Pb1 I2 94.43(5) 4_566 . ?
I2 Pb1 I2 82.145(15) 4_566 5_455 ?
I2 Pb1 I2 176.42(5) . 5_455 ?
I2 Pb1 I2 82.144(15) . 8_456 ?
I2 Pb1 I2 176.42(5) 4_566 8_456 ?
I2 Pb1 I2 101.30(5) 8_456 5_455 ?
I2 Pb1 I1 89.91(6) 4_566 4_566 ?
I2 Pb1 I1 91.03(6) 8_456 4_566 ?
I2 Pb1 I1 88.70(6) 4_566 . ?
I2 Pb1 I1 89.91(6) . . ?
I2 Pb1 I1 90.27(6) 5_455 4_566 ?
I2 Pb1 I1 88.70(6) . 4_566 ?
I2 Pb1 I1 90.27(6) 8_456 . ?
I2 Pb1 I1 91.03(6) 5_455 . ?
I1 Pb1 I1 177.95(5) 4_566 . ?
Pb1 I2 Pb1 176.42(5) . 5_545 ?
Pb1 I2 H3C 114.8(15) . 8_556 ?
Pb1 I2 H3C 61.7(15) 5_545 8_556 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
C1 O1 H1 111.9 . . ?
N1 C2 H2 108.6 . . ?
N1 C2 C1 110.5(14) . . ?
N1 C2 C3 110.5(15) . . ?
C1 C2 H2 108.6 . . ?
C3 C2 H2 108.6 . . ?
C3 C2 C1 110.1(16) . . ?
O1 C1 C2 116.1(17) . . ?
O2 C1 O1 128(2) . . ?
O2 C1 C2 115.6(19) . . ?
H3C O3 H3C 107.7 . 4_566 ?
N2 C4 C3 116(2) . . ?
C6 C4 N2 109(2) . . ?
C6 C4 C3 135(2) . . ?
C5 N2 C4 106(2) . . ?
C5 N3 H3 122.5 . . ?
C5 N3 C6 114.9(14) . . ?
C6 N3 H3 122.5 . . ?
N2 C5 H5 126.2 . . ?
N3 C5 N2 107.5(18) . . ?
N3 C5 H5 126.2 . . ?
C2 C3 H3A 108.9 . . ?
C2 C3 H3B 108.9 . . ?
C4 C3 C2 113.5(18) . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
C4 C6 N3 101.9(18) . . ?
C4 C6 H6 129.0 . . ?
N3 C6 H6 129.0 . . ?

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
N1 C2 C1 O1 -15(3) . . . . ?
N1 C2 C1 O2 167.3(19) . . . . ?
N1 C2 C3 C4 -64(2) . . . . ?
C1 C2 C3 C4 173.8(17) . . . . ?
C4 N2 C5 N3 1(3) . . . . ?
N2 C4 C3 C2 97(3) . . . . ?
N2 C4 C6 N3 3(3) . . . . ?
C5 N3 C6 C4 -3(3) . . . . ?
C3 C2 C1 O1 107(2) . . . . ?
C3 C2 C1 O2 -70(2) . . . . ?
C3 C4 N2 C5 179.9(19) . . . . ?
C3 C4 C6 N3 180(3) . . . . ?
C6 C4 N2 C5 -3(4) . . . . ?
C6 C4 C3 C2 -79(4) . . . . ?
C6 N3 C5 N2 1(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.272
_oxdiff_exptl_absorpt_empirical_full_min 0.760
####################################################################### 
# 
# 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_shi_5670_ilgu
_database_code_depnum_ccdc_archive 'CCDC 2207740'
loop_
_audit_author_name
_audit_author_address
'Ilya Guralskiy'
;Taras Shevchenko National University of Kyiv
Ukraine
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-02-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Br4 Pb, 2(C6 H10 N3 O2)'
_chemical_formula_sum            'C12 H20 Br4 N6 O4 Pb'
_chemical_formula_weight         839.17
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C12H16Br4N6O4Pb
_chemical_oxdiff_usercomment     SV_405
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'
O O 0.0106 0.0060 '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           20
_space_group_name_H-M_alt        'C 2 2 21'
_space_group_name_Hall           'C 2c 2'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, 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'
'x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, -z+1/2'

_cell_length_a                   9.2006(6)
_cell_length_b                   7.8434(6)
_cell_length_c                   29.935(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2160.2(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1303
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0080
_cell_measurement_theta_min      2.7180
_shelx_estimated_absorpt_T_max   0.750
_shelx_estimated_absorpt_T_min   0.311
_exptl_absorpt_coefficient_mu    15.239
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.93a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.580
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             1552
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.1237
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            5265
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.834
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.330
_diffrn_reflns_theta_min         2.041
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -32.00  47.50   0.75  175.00    --  -15.29  66.00 164.00  106
  2  ω      4.00  39.25   0.75  175.00    --   17.71-132.00 -29.00   47
  3  ω     -9.00  30.00   0.75  175.00    --   17.71  77.00  30.00   52
  4  ω      6.00  38.25   0.75  175.00    --   17.71  77.00-120.00   43
  5  ω     -9.00  31.50   0.75  175.00    --   17.71  77.00 150.00   54
  6  ω    -65.00 -61.25   0.75  175.00    --  -15.29 139.00-143.00    5
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0075521590
_diffrn_orient_matrix_UB_12      -0.0015998729
_diffrn_orient_matrix_UB_13      0.0235774342
_diffrn_orient_matrix_UB_21      0.0581544505
_diffrn_orient_matrix_UB_22      0.0588330015
_diffrn_orient_matrix_UB_23      0.0020289137
_diffrn_orient_matrix_UB_31      -0.0500166064
_diffrn_orient_matrix_UB_32      0.0686882423
_diffrn_orient_matrix_UB_33      -0.0011950239
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.715
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                1744
_reflns_number_total             2482
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.41.93a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         4.696
_refine_diff_density_min         -3.274
_refine_diff_density_rms         0.340
_refine_ls_abs_structure_details 
;
 Flack x determined using 474 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.157
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     92
_refine_ls_number_reflns         2482
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.1264
_refine_ls_R_factor_gt           0.0875
_refine_ls_restrained_S_all      1.151
_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)+(0.0835P)²+2.6954P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1883
_refine_ls_wR_factor_ref         0.2121
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.969(4)
 0.031(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Uiso/Uaniso restraints and constraints
Uanis(C5) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(O2) \\sim
Ueq, Uanis(O1) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma
of 0.01 and sigma for terminal atoms of 0.02
Uanis(N3) = Uanis(C5) = Uanis(N2) = Uanis(C4) = Uanis(C6)
4.a Riding coordinates:
 O1(H1)
4.b Ternary CH refined with riding coordinates:
 C2(H2)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
4.d Aromatic/amide H refined with riding coordinates:
 C6(H6), N3(H3), C5(H5)
4.e Fitted pentagon refined as free rotating group:
 C4(C6,N3,C5,N2)
4.f Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Pb1 Pb 0.500000 1.05633(17) 0.250000 0.0210(4) Uani 1 2 d S T P . .
Br2 Br 0.7670(3) 0.8154(4) 0.2495(3) 0.0396(8) Uani 1 1 d . . . . .
Br1 Br 0.5021(6) 1.0636(5) 0.35026(9) 0.0493(9) Uani 1 1 d . . . . .
C4 C 0.427(3) 0.582(3) 0.3961(6) 0.050(4) Uani 1 1 d G . . . .
C6 C 0.384(2) 0.548(4) 0.3514(8) 0.050(4) Uani 1 1 d G U . . .
H6 H 0.291157 0.519255 0.341923 0.060 Uiso 1 1 calc R U . . .
N3 N 0.508(3) 0.567(3) 0.3237(5) 0.050(4) Uani 1 1 d G U . . .
H3 H 0.510826 0.553556 0.295184 0.060 Uiso 1 1 calc R U . . .
C5 C 0.628(2) 0.613(4) 0.3513(8) 0.050(4) Uani 1 1 d G U . . .
H5 H 0.722454 0.632603 0.341702 0.060 Uiso 1 1 calc R U . . .
N2 N 0.577(3) 0.622(3) 0.3960(6) 0.050(4) Uani 1 1 d G U . . .
C3 C 0.338(3) 0.597(5) 0.4372(11) 0.036(10) Uani 1 1 d . . . . .
H3A H 0.399507 0.573362 0.462748 0.044 Uiso 1 1 calc R U . . .
H3B H 0.262590 0.511094 0.436370 0.044 Uiso 1 1 calc R U . . .
O2 O 0.056(3) 0.685(4) 0.4800(9) 0.076(9) Uani 1 1 d . U . . .
C1 C 0.170(4) 0.758(5) 0.4854(13) 0.040(9) Uani 1 1 d . . . . .
C2 C 0.267(3) 0.769(4) 0.4439(11) 0.025(7) Uani 1 1 d . U . . .
H2 H 0.208313 0.798089 0.417774 0.030 Uiso 1 1 calc R U . . .
N1 N 0.380(2) 0.905(3) 0.4512(8) 0.027(6) Uani 1 1 d . . . . .
H1A H 0.444706 0.868545 0.471281 0.032 Uiso 1 1 calc R U . . .
H1B H 0.337649 0.999225 0.461176 0.032 Uiso 1 1 calc R U . . .
H1C H 0.425358 0.926610 0.425560 0.032 Uiso 1 1 calc R U . . .
O1 O 0.221(3) 0.818(3) 0.5219(8) 0.045(7) Uani 1 1 d . U . . .
H1 H 0.154712 0.812260 0.540438 0.067 Uiso 1 1 d R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pb1 Br2 2.953(3) 8_655 ?
Pb1 Br2 3.100(3) 4_655 ?
Pb1 Br2 2.953(3) 5_455 ?
Pb1 Br2 3.100(3) . ?
Pb1 Br1 3.002(3) . ?
Pb1 Br1 3.002(3) 4_655 ?
C4 C6 1.4200 . ?
C4 N2 1.4200 . ?
C4 C3 1.48(3) . ?
C6 H6 0.9300 . ?
C6 N3 1.4200 . ?
N3 H3 0.8600 . ?
N3 C5 1.4200 . ?
C5 H5 0.9300 . ?
C5 N2 1.4200 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.51(4) . ?
O2 C1 1.21(4) . ?
C1 C2 1.53(4) . ?
C1 O1 1.28(4) . ?
C2 H2 0.9800 . ?
C2 N1 1.50(4) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
O1 H1 0.8248 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br2 Pb1 Br2 93.07(12) 8_655 5_455 ?
Br2 Pb1 Br2 174.08(12) 5_455 . ?
Br2 Pb1 Br2 81.039(8) 8_655 . ?
Br2 Pb1 Br2 174.07(12) 8_655 4_655 ?
Br2 Pb1 Br2 104.86(11) 4_655 . ?
Br2 Pb1 Br2 81.039(8) 5_455 4_655 ?
Br2 Pb1 Br1 88.66(19) 5_455 4_655 ?
Br2 Pb1 Br1 89.8(2) 5_455 . ?
Br2 Pb1 Br1 89.8(2) 8_655 4_655 ?
Br2 Pb1 Br1 88.66(19) 8_655 . ?
Br1 Pb1 Br2 90.7(2) . 4_655 ?
Br1 Pb1 Br2 90.7(2) 4_655 4_655 ?
Br1 Pb1 Br2 90.7(2) . . ?
Br1 Pb1 Br2 90.7(2) 4_655 . ?
Br1 Pb1 Br1 177.83(14) 4_655 . ?
Pb1 Br2 Pb1 174.08(12) 5_545 . ?
C6 C4 N2 108.0 . . ?
C6 C4 C3 130(2) . . ?
N2 C4 C3 121(2) . . ?
C4 C6 H6 126.0 . . ?
C4 C6 N3 108.0 . . ?
N3 C6 H6 126.0 . . ?
C6 N3 H3 126.0 . . ?
C5 N3 C6 108.0 . . ?
C5 N3 H3 126.0 . . ?
N3 C5 H5 126.0 . . ?
N3 C5 N2 108.0 . . ?
N2 C5 H5 126.0 . . ?
C4 N2 C5 108.0 . . ?
C4 C3 H3A 108.6 . . ?
C4 C3 H3B 108.6 . . ?
C4 C3 C2 115(3) . . ?
H3A C3 H3B 107.5 . . ?
C2 C3 H3A 108.6 . . ?
C2 C3 H3B 108.6 . . ?
O2 C1 C2 115(3) . . ?
O2 C1 O1 127(3) . . ?
O1 C1 C2 117(3) . . ?
C3 C2 C1 108(3) . . ?
C3 C2 H2 109.7 . . ?
C1 C2 H2 109.7 . . ?
N1 C2 C3 111(2) . . ?
N1 C2 C1 109(3) . . ?
N1 C2 H2 109.7 . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O1 H1 106.8 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1 H1A O2 0.89 1.83 2.71(3) 169.3 7_566 yes
N1 H1B O1 0.89 1.86 2.74(3) 170.6 3_576 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C6 N3 C5 0.0 . . . . ?
C4 C3 C2 C1 175(3) . . . . ?
C4 C3 C2 N1 -65(3) . . . . ?
C6 C4 N2 C5 0.0 . . . . ?
C6 C4 C3 C2 -82(3) . . . . ?
C6 N3 C5 N2 0.0 . . . . ?
N3 C5 N2 C4 0.0 . . . . ?
N2 C4 C6 N3 0.0 . . . . ?
N2 C4 C3 C2 90(3) . . . . ?
C3 C4 C6 N3 173(3) . . . . ?
C3 C4 N2 C5 -174(3) . . . . ?
O2 C1 C2 C3 -77(4) . . . . ?
O2 C1 C2 N1 163(3) . . . . ?
O1 C1 C2 C3 100(4) . . . . ?
O1 C1 C2 N1 -20(4) . . . . ?

_olex2_date_sample_data_collection 2022-02-12
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.488
_oxdiff_exptl_absorpt_empirical_full_min 0.844
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.969(4)
2 0.031(4)

####################################################################### 
# 
# 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_shi_5959_ilgu_twin1_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2207741'
loop_
_audit_author_name
_audit_author_address
'Ilya Guralskiy'
;Taras Shevchenko National University of Kyiv
Ukraine
;
_audit_update_record             
;
2022-09-16 deposited with the CCDC.	2022-10-05 downloaded from the CCDC.
;
_audit_creation_date             2022-08-11
_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         'Br0.4 I3.6 Pb, 2(C6 H10 N3 O2)'
_chemical_formula_sum            'C12 H20 Br0.40 I3.60 N6 O4 Pb'
_chemical_formula_weight         1008.33
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         C11H22I4N6O6Pb
_chemical_oxdiff_usercomment     SV_383
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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   8.1236(9)
_cell_length_b                   9.4686(9)
_cell_length_c                   15.3633(19)
_cell_angle_alpha                90
_cell_angle_beta                 95.658(11)
_cell_angle_gamma                90
_cell_volume                     1176.0(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2234
_cell_measurement_temperature    227(40)
_cell_measurement_theta_max      26.7270
_cell_measurement_theta_min      2.6440
_shelx_estimated_absorpt_T_max   0.787
_shelx_estimated_absorpt_T_min   0.338
_exptl_absorpt_coefficient_mu    12.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59225
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.848
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             906
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0078
0 0 -1 0.0078
3 -1 -1 0.0358
-3 1 1 0.0358
8 10 1 0.0451
-7 -11 0 0.0352
-4 11 -7 0.0406

_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.0000 -0.0000 0.9996 0.0377 -0.0183 0.0199
0.0000 0.0000 -0.9996 -0.0377 0.0183 -0.0199
3.0000 -0.9993 -1.0145 -0.1232 0.0560 0.2372
-3.0000 0.9993 1.0145 0.1232 -0.0560 -0.2372
7.8262 9.6287 1.1133 -0.4627 -0.7613 0.4543
-6.8550 -10.6705 -0.1129 0.4895 0.8043 -0.3369
-4.1468 11.4609 -6.9749 -0.3787 -0.6145 -0.6921

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.870
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3232
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.831
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.425
_diffrn_reflns_theta_min         2.665
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      227(40)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1593
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.870
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  15.00   1.00   50.00    --  -15.29 106.00 -58.00   71
  2  ω     20.00  56.00   1.00   50.00    --   17.71-106.00-157.00   36
  3  ω    -85.00 -40.00   1.00   50.00    --  -15.29-178.00 -30.00   45
  4  ω     -8.00  38.00   1.00   50.00    --  -15.29  77.00-120.00   46
  5  ω    -49.00   0.00   1.00   50.00    --   17.71 -57.00 150.00   49
  6  ω     -9.00  28.00   1.00   50.00    --   17.71  77.00 120.00   37
  7  ω      1.00  79.00   1.00   50.00    --   17.71  38.00-180.00   78
  8  ω     44.00  90.00   1.00   50.00    --   17.71 178.00-150.00   46
  9  ω     39.00  67.00   1.00   50.00    --   17.71 178.00 150.00   28
 10  ω     -9.00  33.00   1.00   50.00    --   17.71  77.00 -60.00   42
 11  ω     -5.00  22.00   1.00   50.00    --   17.71  77.00  90.00   27
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0360265000
_diffrn_orient_matrix_UB_12      -0.0231292000
_diffrn_orient_matrix_UB_13      0.0377031000
_diffrn_orient_matrix_UB_21      -0.0103560000
_diffrn_orient_matrix_UB_22      -0.0685273000
_diffrn_orient_matrix_UB_23      -0.0183483000
_diffrn_orient_matrix_UB_31      0.0792839000
_diffrn_orient_matrix_UB_32      -0.0195702000
_diffrn_orient_matrix_UB_33      0.0199385000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.996
_reflns_Friedel_fraction_max     0.788
_reflns_number_gt                2167
_reflns_number_total             3232
_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       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         2.007
_refine_diff_density_min         -2.000
_refine_diff_density_rms         0.267
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.935
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     126
_refine_ls_number_reflns         3232
_refine_ls_number_restraints     74
_refine_ls_R_factor_all          0.0798
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      0.930
_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)+(0.0579P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1112
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.60112
 0.39888
2. Shared sites
{I1, Br1}
{I2, Br2}
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(C3) \\sim Ueq, Uanis(C2) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C4) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C5) \\sim
Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of
0.02
Uanis(I2) = Uanis(Br2)
Uanis(I1) = Uanis(Br1)
5. Others
 Fixed Sof: I2(0.9) I1(0.9) Br2(0.1) Br1(0.1)
6.a Ternary CH refined with riding coordinates:
 C2(H2)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
6.c Aromatic/amide H refined with riding coordinates:
 C5(H5), N2(H2A), C6(H6)
6.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C)
6.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     heavy
_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 0.4984(2) 0.000000 0.0218(3) Uani 1 2 d S TU P . .
I2 I 0.5450(3) 0.5025(6) 0.20843(9) 0.0400(4) Uani 0.9 1 d . U P A 2
I1 I 0.7488(9) 0.7525(6) -0.0023(3) 0.0423(4) Uani 0.9 1 d . U P A 2
O1 O 0.336(3) 0.771(2) 0.5463(14) 0.048(6) Uani 1 1 d . U . . .
H1 H 0.301597 0.807965 0.589946 0.072 Uiso 1 1 calc R U . . .
C2 C 0.251(4) 0.722(3) 0.392(2) 0.030(6) Uani 1 1 d . U . . .
H2 H 0.269963 0.783369 0.342238 0.036 Uiso 1 1 calc R U . . .
C4 C 0.058(5) 0.565(4) 0.296(3) 0.027(6) Uani 1 1 d . U . . .
C5 C 0.032(5) 0.615(4) 0.213(2) 0.029(7) Uani 1 1 d . U . . .
H5 H 0.013196 0.710570 0.198159 0.035 Uiso 1 1 calc R U . . .
C3 C 0.083(4) 0.652(3) 0.3751(17) 0.032(6) Uani 1 1 d . U . . .
H3A H 0.064711 0.592913 0.425651 0.039 Uiso 1 1 calc R U . . .
H3B H -0.001645 0.726296 0.371248 0.039 Uiso 1 1 calc R U . . .
N2 N 0.036(4) 0.517(4) 0.1610(14) 0.057(7) Uani 1 1 d . U . . .
H2A H 0.022574 0.527721 0.104492 0.068 Uiso 1 1 calc R U . . .
C6 C 0.063(5) 0.393(5) 0.199(3) 0.036(8) Uani 1 1 d . U . . .
H6 H 0.060961 0.303597 0.173133 0.043 Uiso 1 1 calc R U . . .
N3 N 0.096(4) 0.425(4) 0.288(2) 0.040(7) Uani 1 1 d . U . . .
N1 N 0.391(3) 0.615(2) 0.4057(13) 0.027(5) Uani 1 1 d . U . . .
H1A H 0.396089 0.564365 0.356454 0.033 Uiso 1 1 calc R U . . .
H1B H 0.373113 0.556729 0.450035 0.033 Uiso 1 1 calc R U . . .
H1C H 0.487636 0.660889 0.418602 0.033 Uiso 1 1 calc R U . . .
C1 C 0.254(5) 0.815(3) 0.479(2) 0.033(7) Uani 1 1 d . U . . .
O2 O 0.177(3) 0.923(3) 0.4693(16) 0.063(8) Uani 1 1 d . U . . .
Br2 Br 0.5450(3) 0.5025(6) 0.20843(9) 0.0400(4) Uani 0.1 1 d . U P A 1
Br1 Br 0.7488(9) 0.7525(6) -0.0023(3) 0.0423(4) Uani 0.1 1 d . U P A 1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pb1 I2 3.1872(14) . ?
Pb1 I2 3.1872(14) 2_655 ?
Pb1 I1 3.145(6) . ?
Pb1 I1 3.145(6) 2_655 ?
Pb1 I1 3.094(6) 3_445 ?
Pb1 I1 3.094(6) 4_645 ?
Pb1 Br2 3.1872(14) . ?
Pb1 Br1 3.145(6) . ?
O1 H1 0.8300 . ?
O1 C1 1.25(4) . ?
C2 H2 0.9900 . ?
C2 C3 1.52(4) . ?
C2 N1 1.52(3) . ?
C2 C1 1.60(4) . ?
C4 C5 1.36(5) . ?
C4 C3 1.46(5) . ?
C4 N3 1.37(3) . ?
C5 H5 0.9400 . ?
C5 N2 1.24(4) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
N2 H2A 0.8700 . ?
N2 C6 1.32(5) . ?
C6 H6 0.9400 . ?
C6 N3 1.39(5) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C1 O2 1.20(4) . ?

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
I2 Pb1 I2 178.6(2) 2_655 . ?
I1 Pb1 I2 91.76(11) 3_445 . ?
I1 Pb1 I2 89.41(11) 2_655 . ?
I1 Pb1 I2 89.53(14) . . ?
I1 Pb1 I2 89.29(13) 4_645 . ?
I1 Pb1 I1 98.741(8) 4_645 . ?
I1 Pb1 I1 82.4(3) 3_445 4_645 ?
I1 Pb1 I1 178.3(2) 3_445 . ?
Br1 Pb1 I2 89.41(11) . 2_655 ?
Br1 Pb1 I1 80.2(3) . 2_655 ?
Br1 Pb1 Br2 89.53(14) . . ?
Pb1 I1 Pb1 178.3(2) 3 . ?
C1 O1 H1 109.5 . . ?
C3 C2 H2 109.1 . . ?
C3 C2 N1 113(2) . . ?
C3 C2 C1 109(2) . . ?
N1 C2 H2 109.1 . . ?
N1 C2 C1 108(2) . . ?
C1 C2 H2 109.1 . . ?
C5 C4 C3 125(3) . . ?
C5 C4 N3 105(4) . . ?
N3 C4 C3 128(4) . . ?
C4 C5 H5 125.2 . . ?
N2 C5 C4 110(3) . . ?
N2 C5 H5 125.2 . . ?
C2 C3 H3A 108.3 . . ?
C2 C3 H3B 108.3 . . ?
C4 C3 C2 116(3) . . ?
C4 C3 H3A 108.3 . . ?
C4 C3 H3B 108.3 . . ?
H3A C3 H3B 107.4 . . ?
C5 N2 H2A 123.5 . . ?
C5 N2 C6 113(2) . . ?
C6 N2 H2A 123.5 . . ?
N2 C6 H6 127.7 . . ?
N2 C6 N3 105(3) . . ?
N3 C6 H6 127.7 . . ?
C4 N3 C6 106(4) . . ?
C2 N1 H1A 109.5 . . ?
C2 N1 H1B 109.5 . . ?
C2 N1 H1C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O1 C1 C2 118(3) . . ?
O2 C1 O1 128(3) . . ?
O2 C1 C2 114(3) . . ?
Pb1 Br1 Pb1 178.3(2) 3 . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 N3 0.83 2.27 2.94(4) 138.5 4_556 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 C5 N2 C6 0(5) . . . . ?
C5 C4 C3 C2 -75(5) . . . . ?
C5 C4 N3 C6 -10(5) . . . . ?
C5 N2 C6 N3 -7(5) . . . . ?
C3 C2 C1 O1 107(4) . . . . ?
C3 C2 C1 O2 -74(4) . . . . ?
C3 C4 C5 N2 172(4) . . . . ?
C3 C4 N3 C6 -175(4) . . . . ?
N2 C6 N3 C4 10(5) . . . . ?
N3 C4 C5 N2 6(5) . . . . ?
N3 C4 C3 C2 87(5) . . . . ?
N1 C2 C3 C4 -62(4) . . . . ?
N1 C2 C1 O1 -15(4) . . . . ?
N1 C2 C1 O2 163(3) . . . . ?
C1 C2 C3 C4 178(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.635
_oxdiff_exptl_absorpt_empirical_full_min 0.665
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               2
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.60112 484 5731 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.39888 485 5731 nmt 1.0010 -0.0001 0.0007 0.0002 -1.0005 0.0002 -0.3717
-0.0030 -1.0016

_twin_special_details            
;
Component 2 rotated by -179.9063° 
around [0.98 0.00 -0.18] (reciprocal) or [1.00 -0.00 0.00] (direct)
;
