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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_PPDBiI5
_database_code_depnum_ccdc_archive 'CCDC 2180531'
loop_
_audit_author_name
_audit_author_address
'Julia Payne'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi I5, C6 H10 N2'
_chemical_formula_sum            'C6 H10 Bi I5 N2'
_chemical_formula_weight         953.64

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'
Bi Bi -4.1077 10.2566 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   10.0586(4)
_cell_length_b                   8.4358(3)
_cell_length_c                   10.8613(5)
_cell_angle_alpha                90
_cell_angle_beta                 107.582(4)
_cell_angle_gamma                90
_cell_volume                     878.55(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6970
_cell_measurement_theta_min      2.4120
_cell_measurement_theta_max      28.8810

_exptl_crystal_description       chip
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.605
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.050
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    18.796
_shelx_estimated_absorpt_T_min   0.453
_shelx_estimated_absorpt_T_max   0.705
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59196
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_source_type              'Rigaku FR-X'
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11474
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.967
_diffrn_reflns_theta_max         29.028
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_point_group_measured_fraction_full 0.967
_reflns_number_total             3734
_reflns_number_gt                3514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.728
_reflns_Friedel_fraction_max     0.717
_reflns_Friedel_fraction_full    0.936

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Rigaku CrystalClear-SM Expert 2.1 b45'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Crystalmaker (2021)'
_computing_publication_material  'WinGX (Farrugia, 2012),enCIFer(Towler, 2004)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0110P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1383 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(3)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         3734
_refine_ls_number_parameters     145
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0235
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_ref         0.0363
_refine_ls_wR_factor_gt          0.0357
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.39910(3) 0.45568(3) 0.27077(2) 0.01750(7) Uani 1 1 d . . . . .
I2 I 0.31256(5) 0.66144(7) 0.04610(5) 0.02341(12) Uani 1 1 d . . . . .
I3 I 0.48418(5) 0.78016(6) 0.43977(5) 0.02369(13) Uani 1 1 d . . . . .
I4 I 0.35244(5) 0.14578(6) 0.13553(5) 0.02386(12) Uani 1 1 d . . . . .
I5 I 0.70991(5) 0.45319(7) 0.26231(5) 0.02438(12) Uani 1 1 d . . . . .
I6 I 0.11053(5) 0.44661(7) 0.28892(6) 0.03261(14) Uani 1 1 d . . . . .
N7 N 0.8001(7) 0.5614(9) 0.5908(7) 0.0252(16) Uani 1 1 d D . . . .
N8 N 1.3523(6) 0.3543(8) 0.8260(6) 0.0256(16) Uani 1 1 d D . . . .
C1 C 0.9425(8) 0.5011(9) 0.6502(7) 0.0226(19) Uani 1 1 d . . . . .
C6 C 1.2082(7) 0.4043(9) 0.7609(8) 0.0191(18) Uani 1 1 d . . . . .
C2 C 0.9690(8) 0.3945(10) 0.7481(8) 0.029(2) Uani 1 1 d . . . . .
H4 H 0.894949 0.354653 0.776656 0.035 Uiso 1 1 calc R U . . .
C3 C 1.1025(8) 0.3447(11) 0.8053(9) 0.032(2) Uani 1 1 d . . . . .
H5 H 1.122678 0.270546 0.874308 0.038 Uiso 1 1 calc R U . . .
C4 C 1.0461(8) 0.5604(10) 0.6048(8) 0.030(2) Uani 1 1 d . . . . .
H7 H 1.024768 0.633883 0.535287 0.036 Uiso 1 1 calc R U . . .
C5 C 1.1825(9) 0.5110(11) 0.6625(8) 0.029(2) Uani 1 1 d . . . . .
H6 H 1.256341 0.550847 0.633778 0.034 Uiso 1 1 calc R U . . .
H1 H 0.731(6) 0.504(9) 0.616(7) 0.043 Uiso 1 1 d D U . . .
H2 H 0.777(9) 0.553(11) 0.4996(18) 0.043 Uiso 1 1 d D U . . .
H3 H 0.797(9) 0.672(3) 0.605(8) 0.043 Uiso 1 1 d D U . . .
H8 H 1.360(7) 0.2416(17) 0.827(5) 0.043 Uiso 1 1 d D U . . .
H9 H 1.387(6) 0.393(6) 0.912(2) 0.043 Uiso 1 1 d D U . . .
H10 H 1.407(6) 0.397(6) 0.776(5) 0.043 Uiso 1 1 d D 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
Bi1 I2 2.9055(6) . ?
Bi1 I4 2.9658(6) . ?
Bi1 I6 2.9691(5) . ?
Bi1 I5 3.1554(5) . ?
Bi1 I3 3.2627(6) . ?
Bi1 I3 3.3504(6) 2_646 ?
N7 C1 1.473(10) . ?
N7 H1 0.948(14) . ?
N7 H2 0.949(13) . ?
N7 H3 0.948(14) . ?
N8 C6 1.469(9) . ?
N8 H8 0.953(13) . ?
N8 H9 0.951(13) . ?
N8 H10 0.954(13) . ?
C1 C2 1.357(11) . ?
C1 C4 1.374(11) . ?
C6 C5 1.361(11) . ?
C6 C3 1.388(11) . ?
C2 C3 1.364(11) . ?
C2 H4 0.9500 . ?
C3 H5 0.9500 . ?
C4 C5 1.389(11) . ?
C4 H7 0.9500 . ?
C5 H6 0.9500 . ?

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 Bi1 I4 98.522(17) . . ?
I2 Bi1 I6 91.162(17) . . ?
I4 Bi1 I6 89.918(17) . . ?
I2 Bi1 I5 91.583(16) . . ?
I4 Bi1 I5 89.408(15) . . ?
I6 Bi1 I5 177.241(19) . . ?
I2 Bi1 I3 86.124(16) . . ?
I4 Bi1 I3 173.479(17) . . ?
I6 Bi1 I3 94.579(17) . . ?
I5 Bi1 I3 85.878(15) . . ?
I2 Bi1 I3 169.508(18) . 2_646 ?
I4 Bi1 I3 91.913(16) . 2_646 ?
I6 Bi1 I3 89.931(16) . 2_646 ?
I5 Bi1 I3 87.418(15) . 2_646 ?
I3 Bi1 I3 83.387(8) . 2_646 ?
Bi1 I3 Bi1 148.947(19) . 2_656 ?
C1 N7 H1 114(5) . . ?
C1 N7 H2 109(5) . . ?
H1 N7 H2 107(7) . . ?
C1 N7 H3 110(5) . . ?
H1 N7 H3 113(8) . . ?
H2 N7 H3 104(7) . . ?
C6 N8 H8 111(4) . . ?
C6 N8 H9 113(4) . . ?
H8 N8 H9 109.0(16) . . ?
C6 N8 H10 106(4) . . ?
H8 N8 H10 108.6(16) . . ?
H9 N8 H10 108.8(17) . . ?
C2 C1 C4 122.2(8) . . ?
C2 C1 N7 120.4(7) . . ?
C4 C1 N7 117.4(7) . . ?
C5 C6 C3 121.9(7) . . ?
C5 C6 N8 119.6(7) . . ?
C3 C6 N8 118.5(7) . . ?
C1 C2 C3 119.6(8) . . ?
C1 C2 H4 120.2 . . ?
C3 C2 H4 120.2 . . ?
C2 C3 C6 118.9(8) . . ?
C2 C3 H5 120.6 . . ?
C6 C3 H5 120.6 . . ?
C1 C4 C5 118.8(8) . . ?
C1 C4 H7 120.6 . . ?
C5 C4 H7 120.6 . . ?
C6 C5 C4 118.7(8) . . ?
C6 C5 H6 120.6 . . ?
C4 C5 H6 120.6 . . ?

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
C3 H5 I4 0.95 3.25 4.069(8) 146.0 1_656 yes
N7 H1 I3 0.948(14) 2.80(4) 3.652(7) 150(6) 2_646 yes
N7 H1 I4 0.948(14) 3.29(8) 3.802(7) 116(6) 2_656 yes
N7 H2 I5 0.949(13) 2.60(3) 3.525(7) 165(7) . yes
N7 H3 I6 0.948(14) 2.63(4) 3.517(7) 156(7) 2_656 yes
N8 H8 I5 0.953(13) 2.64(3) 3.521(7) 154(5) 2_746 yes
N8 H9 I2 0.951(13) 2.91(5) 3.629(7) 133(5) 1_656 yes
N8 H9 I4 0.951(13) 3.30(5) 3.794(7) 114(4) 1_656 yes
N8 H10 I3 0.954(13) 3.03(4) 3.781(7) 137(4) 2_746 yes
N8 H10 I4 0.954(13) 3.13(4) 3.781(7) 127(4) 2_756 yes

_refine_diff_density_max         0.673
_refine_diff_density_min         -0.883
_refine_diff_density_rms         0.165

####################################################################### 
# 
# 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_PPDBi2Br8-2H2O
_database_code_depnum_ccdc_archive 'CCDC 2180532'
loop_
_audit_author_name
_audit_author_address
'Julia Payne'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'Bi Br4, 0.5(C6 H10 N2), H2 O'
_chemical_formula_sum            'C3 H7 Bi Br4 N O'
_chemical_formula_weight         601.72

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.2340(17)
_cell_length_b                   12.090(3)
_cell_length_c                   12.753(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.210(6)
_cell_angle_gamma                90
_cell_volume                     1103.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2987
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      27.4

_exptl_crystal_description       Prism
_exptl_crystal_colour            Yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.620
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    30.397
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_source_type              'Rigaku FR-X'
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            13096
_diffrn_reflns_av_unetI/netI     0.0441
_diffrn_reflns_av_R_equivalents  0.0770
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.333
_diffrn_reflns_theta_max         25.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2018
_reflns_number_gt                1667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.

 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.1 b45
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b45
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b45
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Crystalmaker (2021)'
_computing_publication_material  'WinGX (Farrugia, 2012),enCIFer(Towler, 2004)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0428P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2018
_refine_ls_number_parameters     106
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0320
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0738
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.72704(4) 0.51368(3) 0.90589(2) 0.02663(13) Uani 1 1 d . . . . .
Br2 Br 1.03763(12) 0.37016(7) 0.90050(7) 0.0323(2) Uani 1 1 d . . . . .
Br3 Br 0.39644(12) 0.64225(7) 0.92163(7) 0.0345(2) Uani 1 1 d . . . . .
Br4 Br 0.85116(12) 0.66453(7) 0.78023(7) 0.0373(2) Uani 1 1 d . . . . .
Br5 Br 0.54047(13) 0.39416(8) 0.75021(8) 0.0429(3) Uani 1 1 d . . . . .
O6 O 0.5530(10) 0.6112(7) 0.5495(6) 0.064(2) Uani 1 1 d D . . . .
C7 C 0.0510(12) 0.4644(7) 0.6026(7) 0.035(2) Uani 1 1 d . . . . .
H7 H 0.085578 0.440613 0.673699 0.042 Uiso 1 1 calc R U . . .
C8 C 0.1148(11) 0.5633(7) 0.5693(7) 0.0331(18) Uani 1 1 d D . . . .
C9 C 0.0640(12) 0.6002(7) 0.4681(7) 0.0328(19) Uani 1 1 d . . . . .
H9 H 0.107399 0.669602 0.446660 0.039 Uiso 1 1 calc R U . . .
N1 N 0.2414(10) 0.6318(7) 0.6437(6) 0.0404(18) Uani 1 1 d D . . . .
H11 H 0.357(3) 0.640(4) 0.616(3) 0.061 Uiso 1 1 d D U . . .
H12 H 0.178(8) 0.701(3) 0.640(5) 0.061 Uiso 1 1 d D U . . .
H13 H 0.268(7) 0.609(6) 0.716(2) 0.061 Uiso 1 1 d D U . . .
H101 H 0.645(10) 0.624(7) 0.611(4) 0.061 Uiso 1 1 d D U . . .
H102 H 0.544(12) 0.673(5) 0.500(5) 0.061 Uiso 1 1 d D 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
Bi1 Br5 2.6619(11) . ?
Bi1 Br4 2.6667(10) . ?
Bi1 Br2 2.8474(10) . ?
Bi1 Br3 2.8832(10) . ?
Bi1 Br3 3.1228(10) 3_667 ?
Bi1 Br2 3.1251(11) 3_767 ?
O6 H101 0.97(2) . ?
O6 H102 0.97(2) . ?
C7 C8 1.371(12) . ?
C7 C9 1.379(13) 3_566 ?
C7 H7 0.9500 . ?
C8 C9 1.365(12) . ?
C8 N1 1.474(11) . ?
C9 H9 0.9500 . ?
N1 H11 0.955(10) . ?
N1 H12 0.950(10) . ?
N1 H13 0.952(10) . ?

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 Bi1 Br4 95.82(4) . . ?
Br5 Bi1 Br2 88.22(3) . . ?
Br4 Bi1 Br2 93.88(3) . . ?
Br5 Bi1 Br3 90.42(3) . . ?
Br4 Bi1 Br3 91.55(3) . . ?
Br2 Bi1 Br3 174.51(3) . . ?
Br5 Bi1 Br3 91.84(3) . 3_667 ?
Br4 Bi1 Br3 172.26(3) . 3_667 ?
Br2 Bi1 Br3 87.43(3) . 3_667 ?
Br3 Bi1 Br3 87.30(3) . 3_667 ?
Br5 Bi1 Br2 173.81(3) . 3_767 ?
Br4 Bi1 Br2 88.59(3) . 3_767 ?
Br2 Bi1 Br2 87.15(3) . 3_767 ?
Br3 Bi1 Br2 93.81(3) . 3_767 ?
Br3 Bi1 Br2 83.86(3) 3_667 3_767 ?
Bi1 Br2 Bi1 92.85(3) . 3_767 ?
Bi1 Br3 Bi1 92.70(3) . 3_667 ?
H101 O6 H102 112(2) . . ?
C8 C7 C9 119.3(9) . 3_566 ?
C8 C7 H7 120.3 . . ?
C9 C7 H7 120.3 3_566 . ?
C9 C8 C7 121.3(8) . . ?
C9 C8 N1 118.9(8) . . ?
C7 C8 N1 119.7(8) . . ?
C8 C9 C7 119.3(8) . 3_566 ?
C8 C9 H9 120.3 . . ?
C7 C9 H9 120.3 3_566 . ?
C8 N1 H11 108.7(11) . . ?
C8 N1 H12 102(4) . . ?
H11 N1 H12 108.9(13) . . ?
C8 N1 H13 119(4) . . ?
H11 N1 H13 108.7(13) . . ?
H12 N1 H13 109.2(13) . . ?

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
C7 H7 Br2 0.95 3.08 3.980(9) 158.4 1_455 yes
C9 H9 Br3 0.95 3.14 4.030(8) 157.3 4_575 yes
N1 H11 O6 0.955(10) 1.793(19) 2.713(10) 161(3) . yes
N1 H12 Br2 0.950(10) 2.582(17) 3.518(8) 168(6) 2_656 yes
N1 H13 Br3 0.952(10) 2.69(4) 3.564(8) 154(6) . yes
O6 H101 Br4 0.97(2) 2.49(2) 3.451(8) 173(8) . yes
O6 H102 Br3 0.97(2) 2.61(5) 3.508(8) 153(8) 4_575 yes

_refine_diff_density_max         1.680
_refine_diff_density_min         -1.815
_refine_diff_density_rms         0.244

####################################################################### 
# 
# 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_PPD2BiCl7_H2O
_database_code_depnum_ccdc_archive 'CCDC 2180533'
loop_
_audit_author_name
_audit_author_address
'Julia Payne'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2022-06-20 deposited with the CCDC.	2022-11-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H10 N2), Bi Cl6, Cl, H2 O '
_chemical_formula_sum            'C12 H22 Bi Cl7 N4 O'
_chemical_formula_weight         695.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.505(2)
_cell_length_b                   10.376(2)
_cell_length_c                   13.322(3)
_cell_angle_alpha                99.260(4)
_cell_angle_beta                 110.582(4)
_cell_angle_gamma                105.1820(10)
_cell_volume                     1139.6(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    4110
_cell_measurement_theta_min      2.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_F_000             664
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    8.566
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Rotating Anode'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_source_type              'Rigaku FR-X'
_diffrn_measurement_device       'AFC10: Fixed χ 3 circle'
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            4063
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_av_R_equivalents  0.046
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.701
_diffrn_reflns_theta_max         25.376
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             4063
_reflns_number_gt                3941
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       
;
Rigaku CrystalClear-SM Expert 2.1 b45
;
_computing_cell_refinement       
;
Rigaku CrystalClear-SM Expert 2.1 b45
;
_computing_data_reduction        
;
Rigaku CrystalClear-SM Expert 2.1 b45
;
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Crystalmaker (2021)'
_computing_publication_material  'WinGX (Farrugia, 2012),enCIFer(Towler, 2004)'
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0441P)²+18.6669P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4063
_refine_ls_number_parameters     269
_refine_ls_number_restraints     82
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1307
_refine_ls_wR_factor_gt          0.1300
_refine_ls_goodness_of_fit_ref   1.180
_refine_ls_restrained_S_all      1.168
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi01 Bi 0.04525(4) 0.13401(4) 0.77200(3) 0.01611(14) Uani 1 1 d . . . . .
Cl2 Cl -0.0920(3) 0.1101(3) 0.9144(2) 0.0219(5) Uani 1 1 d . . . . .
Cl8 Cl -0.5354(3) -0.1331(3) 0.7544(2) 0.0261(6) Uani 1 1 d . . . . .
Cl3 Cl 0.2926(3) 0.1129(3) 0.9197(2) 0.0228(6) Uani 1 1 d . . . . .
Cl6 Cl 0.1551(3) 0.3998(3) 0.8511(2) 0.0231(6) Uani 1 1 d . . . . .
Cl5 Cl -0.2680(3) 0.1280(3) 0.6179(2) 0.0242(6) Uani 1 1 d . . . . .
Cl7 Cl -0.0876(3) -0.1618(3) 0.6890(2) 0.0239(6) Uani 1 1 d . . . . .
Cl4 Cl 0.1989(4) 0.1340(3) 0.6316(2) 0.0304(6) Uani 1 1 d . . . . .
N1 N 0.5923(12) 0.2059(10) 0.8433(10) 0.030(2) Uani 1 1 d D . . . .
C1 C 0.6381(13) 0.3547(11) 0.8465(10) 0.020(2) Uani 1 1 d . . . . .
C2 C 0.5359(13) 0.4227(11) 0.8548(10) 0.022(2) Uani 1 1 d . . . . .
H2 H 0.438129 0.375179 0.857951 0.026 Uiso 1 1 calc R U . . .
C3 C 0.5776(13) 0.5631(11) 0.8586(10) 0.022(2) Uani 1 1 d . . . . .
H3 H 0.507211 0.612312 0.861844 0.026 Uiso 1 1 calc R U . . .
C4 C 0.7226(12) 0.6290(10) 0.8576(8) 0.017(2) Uani 1 1 d . . . . .
C5 C 0.8274(14) 0.5590(12) 0.8504(11) 0.027(3) Uani 1 1 d . . . . .
H5 H 0.926621 0.606104 0.849038 0.033 Uiso 1 1 calc R U . . .
C6 C 0.7831(14) 0.4207(12) 0.8453(11) 0.028(3) Uani 1 1 d . . . . .
H6 H 0.852161 0.370479 0.840974 0.034 Uiso 1 1 calc R U . . .
N2 N 0.7692(11) 0.7754(9) 0.8628(8) 0.0209(19) Uani 1 1 d D . . . .
C7 C -0.5837(14) 0.4196(12) 0.5487(10) 0.028(3) Uani 1 1 d . . . . .
H7 H -0.638600 0.363737 0.582517 0.033 Uiso 1 1 calc R U . . .
C8 C -0.5216(12) 0.3634(10) 0.4810(9) 0.019(2) Uani 1 1 d D . . . .
C9 C -0.5647(14) 0.5575(12) 0.5662(11) 0.029(3) Uani 1 1 d . . . . .
H9 H -0.609926 0.598603 0.610130 0.034 Uiso 1 1 calc R U . . .
N4 N -0.1249(11) 0.2062(9) 0.4373(8) 0.021(2) Uani 1 1 d D . . . .
C10 C -0.0584(14) 0.4262(12) 0.3885(10) 0.025(2) Uani 1 1 d . . . . .
H10 H -0.099068 0.374051 0.312692 0.029 Uiso 1 1 calc R U . . .
C11 C -0.0602(12) 0.3604(11) 0.4710(9) 0.019(2) Uani 1 1 d . . . . .
C12 C -0.0038(16) 0.4312(12) 0.5805(10) 0.028(3) Uani 1 1 d . . . . .
H12 H -0.007536 0.382566 0.634690 0.034 Uiso 1 1 calc R U . . .
O1 O 0.7027(12) 0.1981(10) 1.0648(9) 0.042(2) Uani 1 1 d D . . . .
N3 N -0.5470(12) 0.2123(9) 0.4578(9) 0.026(2) Uani 1 1 d D . . . .
H53 H -0.153(10) 0.174(10) 0.493(5) 0.040 Uiso 1 1 d D U . . .
H52 H -0.219(6) 0.187(10) 0.372(4) 0.040 Uiso 1 1 d D U . . .
H51 H -0.059(9) 0.160(9) 0.419(7) 0.040 Uiso 1 1 d D U . . .
H101 H 0.699(14) 0.215(13) 1.136(4) 0.040 Uiso 1 1 d D U . . .
H102 H 0.755(12) 0.132(9) 1.059(8) 0.040 Uiso 1 1 d D U . . .
H21 H 0.482(3) 0.155(10) 0.799(6) 0.040 Uiso 1 1 d D U . . .
H22 H 0.619(10) 0.200(11) 0.918(3) 0.040 Uiso 1 1 d D U . . .
H23 H 0.654(8) 0.168(10) 0.813(6) 0.040 Uiso 1 1 d D U . . .
H32 H 0.685(7) 0.798(10) 0.876(7) 0.040 Uiso 1 1 d D U . . .
H31 H 0.791(10) 0.818(9) 0.809(6) 0.040 Uiso 1 1 d D U . . .
H33 H 0.863(5) 0.809(10) 0.931(3) 0.040 Uiso 1 1 d D U . . .
H41 H -0.641(5) 0.165(2) 0.465(7) 0.040 Uiso 1 1 d D U . . .
H43 H -0.458(6) 0.199(10) 0.510(6) 0.040 Uiso 1 1 d D U . . .
H42 H -0.558(9) 0.175(9) 0.384(3) 0.040 Uiso 1 1 d D 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
Bi01 Cl6 2.567(3) . ?
Bi01 Cl3 2.569(3) . ?
Bi01 Cl2 2.662(3) . ?
Bi01 Cl4 2.747(3) . ?
Bi01 Cl7 2.852(3) . ?
Bi01 Cl5 2.941(3) . ?
N1 C1 1.479(14) . ?
N1 H21 0.950(5) . ?
N1 H22 0.950(5) . ?
N1 H23 0.950(5) . ?
C1 C2 1.364(15) . ?
C1 C6 1.376(15) . ?
C2 C3 1.393(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.375(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(15) . ?
C4 N2 1.449(13) . ?
C5 C6 1.369(16) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N2 H32 0.950(5) . ?
N2 H31 0.950(5) . ?
N2 H33 0.950(5) . ?
C7 C9 1.365(17) . ?
C7 C8 1.374(17) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(17) 2_466 ?
C8 N3 1.485(13) . ?
C9 H9 0.9500 . ?
N4 C11 1.483(13) . ?
N4 H53 0.949(5) . ?
N4 H52 0.950(5) . ?
N4 H51 0.949(5) . ?
C10 C12 1.372(16) 2_566 ?
C10 C11 1.386(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.362(16) . ?
C12 H12 0.9500 . ?
O1 H101 0.950(5) . ?
O1 H102 0.950(5) . ?
N3 H41 0.951(5) . ?
N3 H43 0.950(5) . ?
N3 H42 0.950(5) . ?

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
Cl6 Bi01 Cl3 91.23(9) . . ?
Cl6 Bi01 Cl2 90.41(9) . . ?
Cl3 Bi01 Cl2 87.67(8) . . ?
Cl6 Bi01 Cl4 94.29(9) . . ?
Cl3 Bi01 Cl4 87.50(9) . . ?
Cl2 Bi01 Cl4 173.33(9) . . ?
Cl6 Bi01 Cl7 177.19(8) . . ?
Cl3 Bi01 Cl7 89.49(9) . . ?
Cl2 Bi01 Cl7 86.90(8) . . ?
Cl4 Bi01 Cl7 88.46(8) . . ?
Cl6 Bi01 Cl5 93.79(8) . . ?
Cl3 Bi01 Cl5 170.59(8) . . ?
Cl2 Bi01 Cl5 84.35(8) . . ?
Cl4 Bi01 Cl5 100.03(9) . . ?
Cl7 Bi01 Cl5 85.12(8) . . ?
C1 N1 H21 113(7) . . ?
C1 N1 H22 108(7) . . ?
H21 N1 H22 109.3(13) . . ?
C1 N1 H23 107(7) . . ?
H21 N1 H23 109.4(13) . . ?
H22 N1 H23 109.3(12) . . ?
C2 C1 C6 122.4(10) . . ?
C2 C1 N1 118.1(10) . . ?
C6 C1 N1 119.5(10) . . ?
C1 C2 C3 118.8(10) . . ?
C1 C2 H2 120.6 . . ?
C3 C2 H2 120.6 . . ?
C4 C3 C2 118.7(10) . . ?
C4 C3 H3 120.7 . . ?
C2 C3 H3 120.7 . . ?
C3 C4 C5 122.1(10) . . ?
C3 C4 N2 119.6(9) . . ?
C5 C4 N2 118.3(9) . . ?
C6 C5 C4 118.2(10) . . ?
C6 C5 H5 120.9 . . ?
C4 C5 H5 120.9 . . ?
C5 C6 C1 119.8(10) . . ?
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C4 N2 H32 100(6) . . ?
C4 N2 H31 128(6) . . ?
H32 N2 H31 109.6(12) . . ?
C4 N2 H33 98(6) . . ?
H32 N2 H33 109.4(12) . . ?
H31 N2 H33 109.4(13) . . ?
C9 C7 C8 118.5(11) . . ?
C9 C7 H7 120.8 . . ?
C8 C7 H7 120.8 . . ?
C7 C8 C9 122.4(10) . 2_466 ?
C7 C8 N3 118.9(10) . . ?
C9 C8 N3 118.6(10) 2_466 . ?
C7 C9 C8 119.0(11) . 2_466 ?
C7 C9 H9 120.5 . . ?
C8 C9 H9 120.5 2_466 . ?
C11 N4 H53 110(6) . . ?
C11 N4 H52 102(6) . . ?
H53 N4 H52 109.3(12) . . ?
C11 N4 H51 117(6) . . ?
H53 N4 H51 109.6(12) . . ?
H52 N4 H51 109.3(12) . . ?
C12 C10 C11 118.1(11) 2_566 . ?
C12 C10 H10 120.9 2_566 . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 122.9(10) . . ?
C12 C11 N4 119.3(10) . . ?
C10 C11 N4 117.9(10) . . ?
C11 C12 C10 119.0(11) . 2_566 ?
C11 C12 H12 120.5 . . ?
C10 C12 H12 120.5 2_566 . ?
H101 O1 H102 109.4(12) . . ?
C8 N3 H41 109.2(13) . . ?
C8 N3 H43 109(6) . . ?
H41 N3 H43 109.2(12) . . ?
C8 N3 H42 111(6) . . ?
H41 N3 H42 109.1(12) . . ?
H43 N3 H42 109.5(12) . . ?

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
C2 H2 Cl6 0.95 2.74 3.547(11) 143.3 . yes
C6 H6 Cl6 0.95 2.77 3.574(12) 143.3 1_655 yes
C7 H7 Cl4 0.95 2.79 3.705(12) 162.1 1_455 yes
C9 H9 Cl8 0.95 2.87 3.623(12) 137.0 1_565 yes
C12 H12 Cl6 0.95 2.70 3.492(12) 141.2 . yes
N4 H53 Cl5 0.949(5) 2.34(3) 3.263(10) 165(8) . yes
N4 H52 Cl8 0.950(5) 2.20(2) 3.133(10) 167(7) 2_456 yes
N4 H51 Cl7 0.949(5) 2.33(6) 3.123(10) 140(7) 2_556 yes
N4 H51 Cl4 0.949(5) 2.84(9) 3.317(9) 112(7) 2_556 yes
O1 H101 Cl8 0.950(5) 2.56(8) 3.381(10) 144(10) 2_557 yes
O1 H102 Cl2 0.950(5) 2.81(9) 3.428(10) 124(8) 1_655 yes
O1 H102 Cl3 0.950(5) 2.55(8) 3.278(10) 134(8) 2_657 yes
N1 H21 Cl3 0.950(5) 2.80(8) 3.316(11) 115(6) . yes
N1 H21 Cl4 0.950(5) 2.75(6) 3.597(11) 149(9) . yes
N1 H22 O1 0.950(5) 1.84(2) 2.786(16) 171(8) . yes
N1 H23 Cl2 0.950(5) 2.59(7) 3.280(11) 130(6) 1_655 yes
N1 H23 Cl5 0.950(5) 2.94(6) 3.744(11) 143(7) 1_655 yes
N2 H32 Cl8 0.950(5) 2.51(7) 3.211(10) 131(6) 1_665 yes
N2 H32 Cl3 0.950(5) 2.65(7) 3.249(10) 122(6) 2_667 yes
N2 H31 Cl7 0.950(5) 2.29(5) 3.142(10) 149(8) 1_665 yes
N2 H33 Cl2 0.950(5) 2.243(12) 3.192(10) 177(7) 2_667 yes
N3 H41 Cl5 0.951(5) 2.85(2) 3.307(9) 111(2) 2_456 yes
N3 H41 Cl7 0.951(5) 2.66(7) 3.179(10) 115(5) 2_456 yes
N3 H43 Cl5 0.950(5) 2.25(2) 3.190(10) 170(8) . yes
N3 H42 Cl8 0.950(5) 2.35(3) 3.230(11) 155(6) 2_456 yes

_refine_diff_density_max         2.968
_refine_diff_density_min         -1.945
_refine_diff_density_rms         0.267

