# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_compound1b
_database_code_depnum_ccdc_archive 'CCDC 1554513'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2018/1


_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Bi Cl3 N2'
_chemical_formula_sum            'C10 H8 Bi Cl3 N2'
_chemical_formula_weight         471.51
_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'
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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1976(16)
_cell_length_b                   8.6395(17)
_cell_length_c                   9.7726(19)
_cell_angle_alpha                66.75(3)
_cell_angle_beta                 88.28(3)
_cell_angle_gamma                87.94(3)
_cell_volume                     635.4(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3228
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.258
_cell_measurement_theta_min      2.487
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    14.477
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4906
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1171 before and 0.0540 after correction.
The Ratio of minimum to maximum transmission is 0.6579.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.465
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.218
_exptl_crystal_size_mid          0.144
_exptl_crystal_size_min          0.133
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9078
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.343
_diffrn_reflns_theta_min         2.269
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2797
_reflns_number_total             3159
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.236
_refine_diff_density_min         -1.856
_refine_diff_density_rms         0.258
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.003
_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)+(0.0280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0654
_refine_ls_wR_factor_ref         0.0684
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C1(H1), C6(H6), C4(H4), C10(H10), C9(H9), C5(H5), C2(H2)
;
_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
Bi1 Bi 1.03565(3) 0.59622(3) 0.26666(2) 0.00958(7) Uani 1 1 d . . . . .
Cl2 Cl 1.22319(17) 0.50322(18) 0.10519(16) 0.0143(3) Uani 1 1 d . . . . .
Cl1 Cl 0.88109(18) 0.80936(18) 0.05048(17) 0.0168(3) Uani 1 1 d . . . . .
Cl3 Cl 1.17538(18) 0.31949(18) 0.52244(17) 0.0166(3) Uani 1 1 d . . . . .
N1 N 0.8387(6) 0.3830(6) 0.2755(6) 0.0134(10) Uani 1 1 d . . . . .
C8 C 0.4830(7) 0.0363(7) 0.2712(7) 0.0125(12) Uani 1 1 d . . . . .
C7 C 0.5128(8) -0.0707(7) 0.1962(7) 0.0151(12) Uani 1 1 d . . . . .
H7 H 0.614627 -0.068504 0.146533 0.018 Uiso 1 1 calc R . . . .
N2 N 0.2492(6) -0.1901(6) 0.2615(6) 0.0142(10) Uani 1 1 d . . . . .
C3 C 0.6061(7) 0.1548(7) 0.2738(6) 0.0126(12) Uani 1 1 d . . . . .
C1 C 0.8843(8) 0.2515(7) 0.2440(7) 0.0153(12) Uani 1 1 d . . . . .
H1 H 0.995970 0.236561 0.221871 0.018 Uiso 1 1 calc R . . . .
C6 C 0.3951(7) -0.1787(7) 0.1945(7) 0.0172(13) Uani 1 1 d . . . . .
H6 H 0.418792 -0.249519 0.142466 0.021 Uiso 1 1 calc R . . . .
C4 C 0.5629(7) 0.2952(7) 0.3078(7) 0.0151(12) Uani 1 1 d . . . . .
H4 H 0.452542 0.314666 0.330439 0.018 Uiso 1 1 calc R . . . .
C10 C 0.2183(7) -0.0861(7) 0.3332(7) 0.0152(12) Uani 1 1 d . . . . .
H10 H 0.115062 -0.090956 0.381387 0.018 Uiso 1 1 calc R . . . .
C9 C 0.3290(7) 0.0259(7) 0.3396(7) 0.0149(12) Uani 1 1 d . . . . .
H9 H 0.301111 0.096835 0.390703 0.018 Uiso 1 1 calc R . . . .
C5 C 0.6814(7) 0.4036(7) 0.3080(7) 0.0138(12) Uani 1 1 d . . . . .
H5 H 0.650575 0.496990 0.332137 0.017 Uiso 1 1 calc R . . . .
C2 C 0.7717(7) 0.1347(7) 0.2428(7) 0.0141(12) Uani 1 1 d . . . . .
H2 H 0.807385 0.041097 0.220831 0.017 Uiso 1 1 calc R . . . .


_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 Cl2 2.5032(15) . ?
Bi1 Cl1 2.5260(18) . ?
Bi1 Cl3 2.921(2) . ?
Bi1 Cl3 2.9413(16) 2_766 ?
Bi1 N1 2.467(5) . ?
Bi1 N2 2.575(5) 1_665 ?
N1 C1 1.329(7) . ?
N1 C5 1.342(7) . ?
C8 C7 1.399(7) . ?
C8 C3 1.472(8) . ?
C8 C9 1.399(8) . ?
C7 H7 0.9500 . ?
C7 C6 1.371(8) . ?
N2 C6 1.334(8) . ?
N2 C10 1.354(7) . ?
C3 C4 1.409(7) . ?
C3 C2 1.401(8) . ?
C1 H1 0.9500 . ?
C1 C2 1.396(8) . ?
C6 H6 0.9500 . ?
C4 H4 0.9500 . ?
C4 C5 1.374(8) . ?
C10 H10 0.9500 . ?
C10 C9 1.370(8) . ?
C9 H9 0.9500 . ?
C5 H5 0.9500 . ?
C2 H2 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
Cl2 Bi1 Cl1 94.26(5) . . ?
Cl2 Bi1 Cl3 175.24(4) . 2_766 ?
Cl2 Bi1 Cl3 87.41(5) . . ?
Cl2 Bi1 N2 88.93(12) . 1_665 ?
Cl1 Bi1 Cl3 171.98(4) . . ?
Cl1 Bi1 Cl3 90.36(5) . 2_766 ?
Cl1 Bi1 N2 93.22(12) . 1_665 ?
Cl3 Bi1 Cl3 87.85(5) . 2_766 ?
N1 Bi1 Cl2 89.94(12) . . ?
N1 Bi1 Cl1 88.66(12) . . ?
N1 Bi1 Cl3 89.02(12) . 2_766 ?
N1 Bi1 Cl3 83.50(12) . . ?
N1 Bi1 N2 177.87(15) . 1_665 ?
N2 Bi1 Cl3 94.65(12) 1_665 . ?
N2 Bi1 Cl3 91.96(12) 1_665 2_766 ?
Bi1 Cl3 Bi1 92.15(5) . 2_766 ?
C1 N1 Bi1 121.3(4) . . ?
C1 N1 C5 119.4(5) . . ?
C5 N1 Bi1 119.2(4) . . ?
C7 C8 C3 121.3(6) . . ?
C9 C8 C7 116.0(5) . . ?
C9 C8 C3 122.6(5) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 120.0(6) . . ?
C6 C7 H7 120.0 . . ?
C6 N2 Bi1 123.2(4) . 1_445 ?
C6 N2 C10 116.7(5) . . ?
C10 N2 Bi1 120.1(4) . 1_445 ?
C4 C3 C8 121.4(5) . . ?
C2 C3 C8 122.1(5) . . ?
C2 C3 C4 116.5(5) . . ?
N1 C1 H1 119.3 . . ?
N1 C1 C2 121.4(6) . . ?
C2 C1 H1 119.3 . . ?
C7 C6 H6 118.1 . . ?
N2 C6 C7 123.9(5) . . ?
N2 C6 H6 118.1 . . ?
C3 C4 H4 120.2 . . ?
C5 C4 C3 119.6(5) . . ?
C5 C4 H4 120.2 . . ?
N2 C10 H10 118.5 . . ?
N2 C10 C9 123.0(6) . . ?
C9 C10 H10 118.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(5) . . ?
C10 C9 H9 119.8 . . ?
N1 C5 C4 122.7(5) . . ?
N1 C5 H5 118.6 . . ?
C4 C5 H5 118.6 . . ?
C3 C2 H2 119.8 . . ?
C1 C2 C3 120.4(5) . . ?
C1 C2 H2 119.8 . . ?

_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_compound3
_database_code_depnum_ccdc_archive 'CCDC 1554522'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2016-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Bi I3 N2'
_chemical_formula_sum            'C10 H8 Bi I3 N2'
_chemical_formula_weight         745.86
_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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6526(15)
_cell_length_b                   10.094(2)
_cell_length_c                   10.841(2)
_cell_angle_alpha                117.34(3)
_cell_angle_beta                 91.13(3)
_cell_angle_gamma                94.78(3)
_cell_volume                     739.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4679
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.309
_cell_measurement_theta_min      2.284
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    18.157
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3589
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1281 before and 0.0420 after correction.
The Ratio of minimum to maximum transmission is 0.4813.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    3.349
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.161
_exptl_crystal_size_min          0.153
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_unetI/netI     0.0389
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10057
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.323
_diffrn_reflns_theta_min         2.677
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3385
_reflns_number_total             3675
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         1.105
_refine_diff_density_min         -1.371
_refine_diff_density_rms         0.223
_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     145
_refine_ls_number_reflns         3675
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.051
_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)+(0.0153P)²+0.5582P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0485
_refine_ls_wR_factor_ref         0.0499
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C2(H2), C1(H1), C7(H7), C6(H6), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Bi1 Bi 0.45002(2) 0.39895(2) 0.25956(2) 0.00810(5) Uani 1 1 d . . . . .
I3 I 0.26670(4) 0.63747(4) 0.52307(3) 0.01237(7) Uani 1 1 d . . . . .
I2 I 0.20698(4) 0.44218(3) 0.07938(3) 0.01164(7) Uani 1 1 d . . . . .
I1 I 0.64714(4) 0.20503(4) 0.02862(4) 0.01449(8) Uani 1 1 d . . . . .
N1 N 0.6458(5) 0.6261(4) 0.2868(4) 0.0101(8) Uani 1 1 d . . . . .
C4 C 0.9381(6) 0.7392(5) 0.3058(5) 0.0126(10) Uani 1 1 d . . . . .
H4 H 1.0607 0.7364 0.3186 0.015 Uiso 1 1 calc R . . . .
C5 C 0.8188(6) 0.6268(6) 0.3034(5) 0.0130(10) Uani 1 1 d . . . . .
H5 H 0.8623 0.5469 0.3140 0.016 Uiso 1 1 calc R . . . .
C2 C 0.6940(6) 0.8582(5) 0.2767(5) 0.0107(10) Uani 1 1 d . . . . .
H2 H 0.6467 0.9386 0.2694 0.013 Uiso 1 1 calc R . . . .
C3 C 0.8763(6) 0.8558(5) 0.2892(5) 0.0094(9) Uani 1 1 d . . . . .
C1 C 0.5843(6) 0.7417(5) 0.2752(5) 0.0126(10) Uani 1 1 d . . . . .
H1 H 0.4609 0.7429 0.2657 0.015 Uiso 1 1 calc R . . . .
C8 C 1.0000(6) 0.9718(5) 0.2800(5) 0.0099(9) Uani 1 1 d . . . . .
C7 C 0.9538(6) 1.0392(5) 0.1990(5) 0.0138(10) Uani 1 1 d . . . . .
H7 H 0.8422 1.0126 0.1493 0.017 Uiso 1 1 calc R . . . .
C6 C 1.0740(6) 1.1460(6) 0.1920(6) 0.0154(11) Uani 1 1 d . . . . .
H6 H 1.0413 1.1922 0.1371 0.019 Uiso 1 1 calc R . . . .
N2 N 1.2342(5) 1.1875(4) 0.2589(4) 0.0113(8) Uani 1 1 d . . . . .
C10 C 1.2774(6) 1.1206(5) 0.3353(5) 0.0120(10) Uani 1 1 d . . . . .
H10 H 1.3908 1.1478 0.3823 0.014 Uiso 1 1 calc R . . . .
C9 C 1.1669(6) 1.0149(6) 0.3494(5) 0.0137(10) Uani 1 1 d . . . . .
H9 H 1.2033 0.9714 0.4057 0.016 Uiso 1 1 calc R . . . .


_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 I3 3.3339(10) 2_666 ?
Bi1 I3 3.2137(14) . ?
Bi1 I2 2.8706(9) . ?
Bi1 I1 2.9178(13) . ?
Bi1 N1 2.525(4) . ?
Bi1 N2 2.585(4) 1_445 ?
I3 Bi1 3.3340(10) 2_666 ?
N1 C5 1.331(6) . ?
N1 C1 1.350(6) . ?
C4 C5 1.386(6) . ?
C4 C3 1.388(6) . ?
C2 C3 1.403(6) . ?
C2 C1 1.380(6) . ?
C3 C8 1.484(6) . ?
C8 C7 1.391(6) . ?
C8 C9 1.399(6) . ?
C7 C6 1.388(6) . ?
C6 N2 1.343(6) . ?
N2 Bi1 2.585(4) 1_665 ?
N2 C10 1.338(6) . ?
C10 C9 1.372(6) . ?

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
I3 Bi1 I3 89.21(3) . 2_666 ?
I2 Bi1 I3 89.12(3) . . ?
I2 Bi1 I3 177.846(11) . 2_666 ?
I2 Bi1 I1 92.85(3) . . ?
I1 Bi1 I3 174.215(11) . . ?
I1 Bi1 I3 88.69(3) . 2_666 ?
N1 Bi1 I3 84.21(10) . . ?
N1 Bi1 I3 88.50(10) . 2_666 ?
N1 Bi1 I2 89.98(10) . . ?
N1 Bi1 I1 90.34(10) . . ?
N1 Bi1 N2 173.19(13) . 1_445 ?
N2 Bi1 I3 90.60(9) 1_445 2_666 ?
N2 Bi1 I3 89.03(10) 1_445 . ?
N2 Bi1 I2 90.73(9) 1_445 . ?
N2 Bi1 I1 96.38(10) 1_445 . ?
Bi1 I3 Bi1 90.79(3) . 2_666 ?
C5 N1 Bi1 118.4(3) . . ?
C5 N1 C1 118.5(4) . . ?
C1 N1 Bi1 123.0(3) . . ?
C5 C4 C3 119.2(4) . . ?
N1 C5 C4 122.8(4) . . ?
C1 C2 C3 118.9(4) . . ?
C4 C3 C2 118.2(4) . . ?
C4 C3 C8 120.8(4) . . ?
C2 C3 C8 121.0(4) . . ?
N1 C1 C2 122.5(4) . . ?
C7 C8 C3 120.6(4) . . ?
C7 C8 C9 117.9(4) . . ?
C9 C8 C3 121.6(4) . . ?
C6 C7 C8 118.7(4) . . ?
N2 C6 C7 123.3(4) . . ?
C6 N2 Bi1 123.4(3) . 1_665 ?
C10 N2 Bi1 119.3(3) . 1_665 ?
C10 N2 C6 117.2(4) . . ?
N2 C10 C9 123.6(4) . . ?
C10 C9 C8 119.2(4) . . ?

_shelx_SHELXL_version_number     2014/7
_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_compound2
_database_code_depnum_ccdc_archive 'CCDC 1554523'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2016-06-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Bi Br3 N2'
_chemical_formula_sum            'C10 H8 Bi Br3 N2'
_chemical_formula_weight         604.89
_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'
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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0006(16)
_cell_length_b                   9.1231(18)
_cell_length_c                   10.094(2)
_cell_angle_alpha                114.97(3)
_cell_angle_beta                 92.83(3)
_cell_angle_gamma                90.59(3)
_cell_volume                     666.7(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7361
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.471
_cell_measurement_theta_min      2.464
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    22.186
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4472
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1155 before and 0.0337 after correction.
The Ratio of minimum to maximum transmission is 0.5997.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    3.013
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             540
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.205
_exptl_crystal_size_mid          0.091
_exptl_crystal_size_min          0.067
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_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       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10278
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.485
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_special_details          ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3162
_reflns_number_total             3379
_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 v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.260
_refine_diff_density_min         -0.956
_refine_diff_density_rms         0.163
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         3379
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0189
_refine_ls_restrained_S_all      1.066
_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)+(0.0161P)²+0.5493P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0407
_refine_ls_wR_factor_ref         0.0415
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C6(H6), C2(H2), C9(H9), C1(H1), C10(H10), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_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
Bi1 Bi -0.04721(2) 0.39861(2) 0.26227(2) 0.00864(4) Uani 1 1 d . . . . .
Br3 Br -0.18993(4) 0.66991(4) 0.52251(4) 0.01325(8) Uani 1 1 d . . . . .
Br2 Br -0.25770(4) 0.47096(4) 0.09022(4) 0.01272(7) Uani 1 1 d . . . . .
Br1 Br 0.12425(5) 0.19824(4) 0.04125(4) 0.01543(8) Uani 1 1 d . . . . .
N2 N 0.7388(4) 1.1824(3) 0.2604(3) 0.0133(6) Uani 1 1 d . . . . .
N1 N 0.1476(4) 0.6169(3) 0.2810(3) 0.0110(6) Uani 1 1 d . . . . .
C4 C 0.4307(4) 0.7129(4) 0.3070(4) 0.0125(7) Uani 1 1 d . . . . .
H4 H 0.5458 0.6988 0.3248 0.015 Uiso 1 1 calc R . . . .
C8 C 0.5055(4) 0.9620(4) 0.2750(4) 0.0111(7) Uani 1 1 d . . . . .
C7 C 0.4679(5) 1.0535(4) 0.1991(4) 0.0162(8) Uani 1 1 d . . . . .
H7 H 0.3606 1.0422 0.1504 0.019 Uiso 1 1 calc R . . . .
C3 C 0.3808(4) 0.8456(4) 0.2826(4) 0.0101(7) Uani 1 1 d . . . . .
C6 C 0.5859(5) 1.1614(4) 0.1941(4) 0.0163(8) Uani 1 1 d . . . . .
H6 H 0.5576 1.2236 0.1413 0.020 Uiso 1 1 calc R . . . .
C2 C 0.2098(4) 0.8620(4) 0.2609(4) 0.0121(7) Uani 1 1 d . . . . .
H2 H 0.1703 0.9518 0.2456 0.014 Uiso 1 1 calc R . . . .
C9 C 0.6654(4) 0.9824(4) 0.3436(4) 0.0126(7) Uani 1 1 d . . . . .
H9 H 0.6970 0.9212 0.3965 0.015 Uiso 1 1 calc R . . . .
C1 C 0.0985(4) 0.7456(4) 0.2620(4) 0.0115(7) Uani 1 1 d . . . . .
H1 H -0.0180 0.7582 0.2485 0.014 Uiso 1 1 calc R . . . .
C10 C 0.7768(4) 1.0929(4) 0.3331(4) 0.0129(7) Uani 1 1 d . . . . .
H10 H 0.8856 1.1061 0.3797 0.015 Uiso 1 1 calc R . . . .
C5 C 0.3116(4) 0.6028(4) 0.3049(4) 0.0128(7) Uani 1 1 d . . . . .
H5 H 0.3469 0.5123 0.3211 0.015 Uiso 1 1 calc R . . . .


_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 Br3 3.0325(14) . ?
Bi1 Br3 3.0779(9) 2_566 ?
Bi1 Br2 2.6437(8) . ?
Bi1 Br1 2.6667(12) . ?
Bi1 N2 2.592(3) 1_445 ?
Bi1 N1 2.454(3) . ?
Br3 Bi1 3.0780(9) 2_566 ?
N2 Bi1 2.592(3) 1_665 ?
N2 C6 1.337(5) . ?
N2 C10 1.337(4) . ?
N1 C1 1.327(4) . ?
N1 C5 1.339(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.392(5) . ?
C4 C5 1.370(5) . ?
C8 C7 1.377(5) . ?
C8 C3 1.478(5) . ?
C8 C9 1.397(5) . ?
C7 H7 0.9500 . ?
C7 C6 1.375(5) . ?
C3 C2 1.394(5) . ?
C6 H6 0.9500 . ?
C2 H2 0.9500 . ?
C2 C1 1.383(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.379(5) . ?
C1 H1 0.9500 . ?
C10 H10 0.9500 . ?
C5 H5 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
Br3 Bi1 Br3 88.54(3) . 2_566 ?
Br2 Bi1 Br3 88.23(3) . . ?
Br2 Bi1 Br3 176.767(11) . 2_566 ?
Br2 Bi1 Br1 93.82(3) . . ?
Br1 Bi1 Br3 89.36(3) . 2_566 ?
Br1 Bi1 Br3 169.588(13) . . ?
N2 Bi1 Br3 93.86(7) 1_445 . ?
N2 Bi1 Br3 90.29(7) 1_445 2_566 ?
N2 Bi1 Br2 89.97(7) 1_445 . ?
N2 Bi1 Br1 96.35(7) 1_445 . ?
N1 Bi1 Br3 88.99(7) . 2_566 ?
N1 Bi1 Br3 82.02(7) . . ?
N1 Bi1 Br2 90.52(7) . . ?
N1 Bi1 Br1 87.75(7) . . ?
N1 Bi1 N2 175.83(9) . 1_445 ?
Bi1 Br3 Bi1 91.46(3) . 2_566 ?
C6 N2 Bi1 122.1(2) . 1_665 ?
C6 N2 C10 117.8(3) . . ?
C10 N2 Bi1 120.0(2) . 1_665 ?
C1 N1 Bi1 122.8(2) . . ?
C1 N1 C5 118.3(3) . . ?
C5 N1 Bi1 118.8(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.1(3) . . ?
C7 C8 C3 121.0(3) . . ?
C7 C8 C9 117.7(3) . . ?
C9 C8 C3 121.3(3) . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.9(3) . . ?
C6 C7 H7 120.1 . . ?
C4 C3 C8 121.0(3) . . ?
C4 C3 C2 117.8(3) . . ?
C2 C3 C8 121.2(3) . . ?
N2 C6 C7 122.7(3) . . ?
N2 C6 H6 118.6 . . ?
C7 C6 H6 118.6 . . ?
C3 C2 H2 120.5 . . ?
C1 C2 C3 119.0(3) . . ?
C1 C2 H2 120.5 . . ?
C8 C9 H9 120.6 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 H9 120.6 . . ?
N1 C1 C2 122.7(3) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
N2 C10 C9 123.0(3) . . ?
N2 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
N1 C5 C4 123.0(3) . . ?
N1 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?

_shelx_SHELXL_version_number     2014/7
_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_compound6
_database_code_depnum_ccdc_archive 'CCDC 1554515'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2016-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014/6

# start Validation Reply Form
_vrf_PLAT094_compound6           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density .... 5.09 Report
RESPONSE: The maximum residual density is located next to the Bi atom.
There are no hints for twinning or any remaining solvent molecules in 
the final structure.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C10 H8 Cl4 N2 Sm), 4(C5 H5.5 N)'
_chemical_formula_sum            'C40 H38 Cl8 N8 Sm2'
_chemical_formula_weight         1215.08
_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'
Sm Sm -0.1638 3.4418 '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           12
_space_group_name_H-M_alt        'C 1 2/m 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'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.205(4)
_cell_length_b                   12.340(4)
_cell_length_c                   8.1926(16)
_cell_angle_alpha                90
_cell_angle_beta                 121.97(3)
_cell_angle_gamma                90
_cell_volume                     1132.5(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.01
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.079
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5679
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   '(BRUKER SADABS,2011)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.782
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             594
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6951
_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         27.036
_diffrn_reflns_theta_min         2.456
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1310
_reflns_number_total             1312
_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 v7.53A (Bruker, 2008)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.165
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0157
_refine_ls_R_factor_gt           0.0157
_refine_ls_restrained_S_all      1.120
_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)+(0.0242P)²+0.8449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0406
_refine_ls_wR_factor_ref         0.0406
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H2A(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C1(H1), N2(H2A), C4(H4), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Sm1 Sm 0.5000 0.5000 0.0000 0.02090(7) Uani 1 4 d S T P . .
Cl1 Cl 0.32119(6) 0.5000 0.06134(9) 0.03088(14) Uani 1 2 d S T P . .
Cl2 Cl 0.66722(6) 0.5000 0.37376(8) 0.03095(14) Uani 1 2 d S T P . .
N1 N 0.5000 0.28994(17) 0.0000 0.0248(4) Uani 1 2 d S T P . .
C3 C 0.5000 0.06028(19) 0.0000 0.0216(5) Uani 1 2 d S T P . .
C2 C 0.41110(17) 0.12016(16) -0.1539(3) 0.0321(4) Uani 1 1 d . . . . .
H2 H 0.3478 0.0840 -0.2625 0.038 Uiso 1 1 calc R . . . .
C1 C 0.41511(17) 0.23236(16) -0.1486(3) 0.0318(4) Uani 1 1 d . . . . .
H1 H 0.3541 0.2708 -0.2567 0.038 Uiso 1 1 calc R . . . .
N2 N 0.5000 0.89443(19) 0.5000 0.0352(5) Uani 1 2 d S T P . .
H2A H 0.5000 0.9657 0.5000 0.042 Uiso 0.25 1 calc RS T P A -1
C4 C 0.40764(19) 0.84047(19) 0.3578(3) 0.0404(5) Uani 1 1 d . . . . .
H4 H 0.3423 0.8798 0.2578 0.048 Uiso 1 1 calc R . . . .
C5 C 0.4053(2) 0.7291(2) 0.3536(4) 0.0489(6) Uani 1 1 d . . . . .
H5 H 0.3395 0.6915 0.2512 0.059 Uiso 1 1 calc R . . . .
C6 C 0.5000 0.6730(3) 0.5000 0.0507(9) Uani 1 2 d S T P . .
H6 H 0.5000 0.5960 0.5000 0.061 Uiso 1 2 calc RS T P . .


_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
Sm1 Cl1 2.6616(10) . ?
Sm1 Cl1 2.6616(10) 5_665 ?
Sm1 Cl2 2.6631(13) . ?
Sm1 Cl2 2.6631(13) 5_665 ?
Sm1 N1 2.592(2) 5_665 ?
Sm1 N1 2.592(2) . ?
N1 C1 1.341(2) . ?
N1 C1 1.341(2) 2_655 ?
C3 C3 1.488(5) 5_655 ?
C3 C2 1.395(2) . ?
C3 C2 1.395(2) 2_655 ?
C2 H2 0.9500 . ?
C2 C1 1.385(3) . ?
C1 H1 0.9500 . ?
N2 H2A 0.8800 . ?
N2 C4 1.335(3) . ?
N2 C4 1.335(3) 2_656 ?
C4 H4 0.9500 . ?
C4 C5 1.375(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.376(3) . ?
C6 C5 1.376(3) 2_656 ?
C6 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
Cl1 Sm1 Cl1 180.00(2) . 5_665 ?
Cl1 Sm1 Cl2 86.49(4) . 5_665 ?
Cl1 Sm1 Cl2 93.51(4) 5_665 5_665 ?
Cl1 Sm1 Cl2 93.51(3) . . ?
Cl1 Sm1 Cl2 86.49(4) 5_665 . ?
Cl2 Sm1 Cl2 180.0 . 5_665 ?
N1 Sm1 Cl1 90.0 . . ?
N1 Sm1 Cl1 90.0 5_665 5_665 ?
N1 Sm1 Cl1 90.0 . 5_665 ?
N1 Sm1 Cl1 90.0 5_665 . ?
N1 Sm1 Cl2 90.0 . . ?
N1 Sm1 Cl2 90.0 5_665 . ?
N1 Sm1 Cl2 90.0 5_665 5_665 ?
N1 Sm1 Cl2 90.0 . 5_665 ?
N1 Sm1 N1 180.0 5_665 . ?
C1 N1 Sm1 121.99(11) 2_655 . ?
C1 N1 Sm1 121.99(11) . . ?
C1 N1 C1 116.0(2) . 2_655 ?
C2 C3 C3 121.98(12) 2_655 5_655 ?
C2 C3 C3 121.98(11) . 5_655 ?
C2 C3 C2 116.0(2) . 2_655 ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.07(18) . . ?
C1 C2 H2 120.0 . . ?
N1 C1 C2 123.90(18) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C4 N2 H2A 119.9 . . ?
C4 N2 H2A 119.9 2_656 . ?
C4 N2 C4 120.2(3) . 2_656 ?
N2 C4 H4 119.4 . . ?
N2 C4 C5 121.2(2) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.9(2) . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C5 119.6(3) . 2_656 ?
C5 C6 H6 120.2 . . ?
C5 C6 H6 120.2 2_656 . ?

_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_compound7
_database_code_depnum_ccdc_archive 'CCDC 1554516'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2016-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014/6


# start Validation Reply Form
_vrf_PLAT110_compound7           
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ... ? Check  
RESPONSE: The ADDSYM routine was performed with PLATON and 
revealed no need for a space group change.
;

_vrf_PLAT112_compound7           
;
PROBLEM: ADDSYM Detects Potential Lattice Translation ... ? Check  
RESPONSE: The ADDSYM routine was performed with PLATON and 
revealed no need for a space group change.
;

# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Cl4 N2 Tb, 2(C5 H5.5 N)'
_chemical_formula_sum            'C20 H19 Cl4 N4 Tb'
_chemical_formula_weight         616.11
_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'
Tb Tb -0.1723 4.1537 '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                   14.5387(4)
_cell_length_b                   12.2326(3)
_cell_length_c                   13.1136(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.7010(10)
_cell_angle_gamma                90
_cell_volume                     2221.79(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      30.07
_cell_measurement_theta_min      2.48
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.679
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0490 before and 0.0395 after correction. The Ratio of minimum to maximum transmission is 0.8724. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.842
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.339
_exptl_crystal_size_mid          0.321
_exptl_crystal_size_min          0.200
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0278
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17699
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.074
_diffrn_reflns_theta_min         2.221
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2998
_reflns_number_total             3180
_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 V8.18C (?, 2016)'
_computing_data_collection       'APEX2 ver. 7.68A (Bruker AXS)'
_computing_data_reduction        'SAINT V8.18C (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         0.562
_refine_diff_density_min         -0.914
_refine_diff_density_rms         0.108
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         3180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0193
_refine_ls_R_factor_gt           0.0169
_refine_ls_restrained_S_all      1.094
_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)+(0.0229P)²+0.7524P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0414
_refine_ls_wR_factor_ref         0.0425
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H3(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C5(H5), C1(H1), C6(H6), C11(H11), C10(H10), C7(H7), C9(H9),
 C8(H8)
;
_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
Tb1 Tb 0.5000 0.76661(2) 0.2500 0.00751(4) Uani 1 2 d S T P . .
Cl1 Cl 0.68538(3) 0.76649(3) 0.27022(4) 0.01328(8) Uani 1 1 d . . . . .
Cl2 Cl 0.52951(3) 0.76173(3) 0.45743(3) 0.01385(9) Uani 1 1 d . . . . .
N1 N 0.5000 0.55921(16) 0.2500 0.0105(4) Uani 1 2 d S T P . .
N3 N 0.74291(10) 0.35585(13) 0.49205(11) 0.0161(3) Uani 1 1 d . . . . .
H3 H 0.7474 0.2841 0.4954 0.019 Uiso 0.5 1 calc R . . A -1
N2 N 0.5000 -0.02556(16) 0.2500 0.0110(4) Uani 1 2 d S T P . .
C4 C 0.5000 0.20605(19) 0.2500 0.0093(4) Uani 1 2 d S T P . .
C3 C 0.5000 0.32788(19) 0.2500 0.0095(4) Uani 1 2 d S T P . .
C2 C 0.42609(12) 0.38754(14) 0.27139(14) 0.0117(3) Uani 1 1 d . . . . .
H2 H 0.3745 0.3507 0.2871 0.014 Uiso 1 1 calc R . . . .
C5 C 0.41711(12) 0.14599(15) 0.24573(14) 0.0137(3) Uani 1 1 d . . . . .
H5 H 0.3589 0.1827 0.2433 0.016 Uiso 1 1 calc R . . . .
C1 C 0.42832(12) 0.50109(14) 0.26952(14) 0.0118(3) Uani 1 1 d . . . . .
H1 H 0.3765 0.5399 0.2827 0.014 Uiso 1 1 calc R . . . .
C6 C 0.42006(12) 0.03267(15) 0.24506(14) 0.0144(4) Uani 1 1 d . . . . .
H6 H 0.3624 -0.0061 0.2409 0.017 Uiso 1 1 calc R . . . .
C11 C 0.66837(14) 0.40570(15) 0.51201(15) 0.0172(4) Uani 1 1 d . . . . .
H11 H 0.6208 0.3630 0.5296 0.021 Uiso 1 1 calc R . . . .
C10 C 0.65927(15) 0.51806(16) 0.50749(15) 0.0193(4) Uani 1 1 d . . . . .
H10 H 0.6057 0.5526 0.5211 0.023 Uiso 1 1 calc R . . . .
C7 C 0.81084(14) 0.41453(16) 0.46700(15) 0.0185(4) Uani 1 1 d . . . . .
H7 H 0.8633 0.3780 0.4527 0.022 Uiso 1 1 calc R . . . .
C9 C 0.72947(15) 0.57959(16) 0.48277(14) 0.0204(4) Uani 1 1 d . . . . .
H9 H 0.7252 0.6571 0.4804 0.024 Uiso 1 1 calc R . . . .
C8 C 0.80603(15) 0.52708(16) 0.46154(15) 0.0214(4) Uani 1 1 d . . . . .
H8 H 0.8545 0.5679 0.4435 0.026 Uiso 1 1 calc R . . . .


_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
Tb1 Cl1 2.6268(4) . ?
Tb1 Cl1 2.6267(4) 2_655 ?
Tb1 Cl2 2.6224(4) 2_655 ?
Tb1 Cl2 2.6225(4) . ?
Tb1 N1 2.537(2) . ?
Tb1 N2 2.542(2) 1_565 ?
N1 C1 1.349(2) . ?
N1 C1 1.349(2) 2_655 ?
N3 H3 0.8800 . ?
N3 C11 1.337(2) . ?
N3 C7 1.340(2) . ?
N2 Tb1 2.542(2) 1_545 ?
N2 C6 1.348(2) . ?
N2 C6 1.348(2) 2_655 ?
C4 C3 1.490(3) . ?
C4 C5 1.398(2) 2_655 ?
C4 C5 1.398(2) . ?
C3 C2 1.396(2) 2_655 ?
C3 C2 1.396(2) . ?
C2 H2 0.9500 . ?
C2 C1 1.390(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.387(3) . ?
C1 H1 0.9500 . ?
C6 H6 0.9500 . ?
C11 H11 0.9500 . ?
C11 C10 1.380(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.384(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.379(3) . ?
C9 H9 0.9500 . ?
C9 C8 1.385(3) . ?
C8 H8 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
Cl1 Tb1 Cl1 179.936(18) 2_655 . ?
Cl2 Tb1 Cl1 86.786(14) 2_655 . ?
Cl2 Tb1 Cl1 93.213(14) 2_655 2_655 ?
Cl2 Tb1 Cl1 86.786(14) . 2_655 ?
Cl2 Tb1 Cl1 93.213(14) . . ?
Cl2 Tb1 Cl2 177.394(19) 2_655 . ?
N1 Tb1 Cl1 89.967(9) . 2_655 ?
N1 Tb1 Cl1 89.968(9) . . ?
N1 Tb1 Cl2 88.697(9) . . ?
N1 Tb1 Cl2 88.698(9) . 2_655 ?
N1 Tb1 N2 180.0 . 1_565 ?
N2 Tb1 Cl1 90.033(9) 1_565 2_655 ?
N2 Tb1 Cl1 90.032(9) 1_565 . ?
N2 Tb1 Cl2 91.302(9) 1_565 2_655 ?
N2 Tb1 Cl2 91.303(9) 1_565 . ?
C1 N1 Tb1 121.81(10) . . ?
C1 N1 Tb1 121.81(10) 2_655 . ?
C1 N1 C1 116.4(2) 2_655 . ?
C11 N3 H3 119.8 . . ?
C11 N3 C7 120.35(17) . . ?
C7 N3 H3 119.8 . . ?
C6 N2 Tb1 121.90(11) . 1_545 ?
C6 N2 Tb1 121.90(11) 2_655 1_545 ?
C6 N2 C6 116.2(2) 2_655 . ?
C5 C4 C3 121.71(11) 2_655 . ?
C5 C4 C3 121.71(11) . . ?
C5 C4 C5 116.6(2) . 2_655 ?
C2 C3 C4 121.52(11) 2_655 . ?
C2 C3 C4 121.52(11) . . ?
C2 C3 C2 117.0(2) . 2_655 ?
C3 C2 H2 120.2 . . ?
C1 C2 C3 119.70(16) . . ?
C1 C2 H2 120.2 . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.84(17) . . ?
C6 C5 H5 120.1 . . ?
N1 C1 C2 123.62(16) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
N2 C6 C5 123.76(17) . . ?
N2 C6 H6 118.1 . . ?
C5 C6 H6 118.1 . . ?
N3 C11 H11 119.4 . . ?
N3 C11 C10 121.23(18) . . ?
C10 C11 H11 119.4 . . ?
C11 C10 H10 120.5 . . ?
C11 C10 C9 118.94(18) . . ?
C9 C10 H10 120.5 . . ?
N3 C7 H7 119.4 . . ?
N3 C7 C8 121.19(18) . . ?
C8 C7 H7 119.4 . . ?
C10 C9 H9 120.3 . . ?
C10 C9 C8 119.34(18) . . ?
C8 C9 H9 120.3 . . ?
C7 C8 C9 118.93(18) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 120.5 . . ?

_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_compound5
_database_code_depnum_ccdc_archive 'CCDC 1554514'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2018/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C15 H12.5 Bi Cl4 N3, C10 H8.5 N2'
_chemical_formula_sum            'C25 H21 Bi Cl4 N5'
_chemical_formula_weight         742.25
_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'
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'
N N 0.0061 0.0033 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.7574(7)
_cell_length_b                   11.1147(9)
_cell_length_c                   14.6158(12)
_cell_angle_alpha                82.7440(10)
_cell_angle_beta                 78.5740(10)
_cell_angle_gamma                70.6280(10)
_cell_volume                     1312.67(18)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9933
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.070
_cell_measurement_theta_min      2.486
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    7.147
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0773 before and 0.0387 after correction.
The Ratio of minimum to maximum transmission is 0.7788.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             714
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0747
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            19881
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.120
_diffrn_reflns_theta_min         1.424
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω 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                6915
_reflns_number_total             7664
_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+ ver. 7.68S (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68S (Bruker AXS)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.860
_refine_diff_density_min         -1.366
_refine_diff_density_rms         0.185
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.768
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     352
_refine_ls_number_reflns         7664
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      0.766
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1057
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C21B \\sim C22B \\sim C25 \\sim C24B \\sim C23B \\sim N1: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
C21A \\sim C22A \\sim C25 \\sim C24A \\sim C23A \\sim N1: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
3. Others
 Fixed Sof: H3(0.5) H5(0.5) C24A(0.5) H24A(0.5) C22B(0.5) H22B(0.5) C21B(0.5)
 H21B(0.5) C22A(0.5) H22A(0.5) C21A(0.5) H21A(0.5) C23A(0.5) H23A(0.5)
 C23B(0.5) H23B(0.5) C24B(0.5) H24B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N5(H5), C1(H1), C6(H6), C8(H8), C3(H3A), C9(H9), C2(H2), C7(H7),
 C17(H17), C4(H4), C19(H19), C12(H12), C14(H14), C20(H20), C11(H11), C18(H18),
 C13(H13), C24A(H24A), C22B(H22B), C21B(H21B), C22A(H22A), C21A(H21A),
 C23A(H23A), C23B(H23B), C24B(H24B)
;
_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
Bi1 Bi 0.51222(2) 0.76368(2) 0.25374(2) 0.01627(6) Uani 1 1 d . . . . .
Cl2 Cl 0.74178(16) 0.70865(13) 0.10130(9) 0.0306(2) Uani 1 1 d . . . . .
Cl1 Cl 0.59075(17) 0.97606(13) 0.25072(10) 0.0341(3) Uani 1 1 d . . . . .
Cl3 Cl 0.42872(18) 0.55340(14) 0.24786(11) 0.0383(3) Uani 1 1 d . . . . .
Cl4 Cl 0.29936(18) 0.82431(15) 0.41164(10) 0.0390(3) Uani 1 1 d . . . . .
N3 N 1.3831(5) 0.1060(4) 0.4850(3) 0.0241(8) Uani 1 1 d . . . . .
H3 H 1.462332 0.039543 0.497922 0.029 Uiso 0.5 1 calc R . P . .
N1 N 0.2953(5) 0.8683(4) 0.1503(3) 0.0235(7) Uani 1 1 d . U . . .
C25 C 0.0620(5) 0.9733(4) 0.0312(3) 0.0219(7) Uani 1 1 d . U . . .
N2 N 0.7323(5) 0.6224(4) 0.3433(3) 0.0230(8) Uani 1 1 d . . . . .
N5 N 1.3924(6) 0.4453(5) 0.0481(3) 0.0357(10) Uani 1 1 d . . . . .
H5 H 1.461167 0.481219 0.016340 0.043 Uiso 0.5 1 calc R . P . .
N4 N 0.8243(6) 0.1545(5) 0.3173(4) 0.0381(11) Uani 1 1 d . . . . .
C10 C 1.1269(5) 0.3169(4) 0.4393(3) 0.0188(8) Uani 1 1 d . . . . .
C5 C 0.9898(5) 0.4261(4) 0.4093(3) 0.0163(7) Uani 1 1 d . . . . .
C1 C 0.8874(6) 0.6227(5) 0.3172(3) 0.0258(9) Uani 1 1 d . . . . .
H1 H 0.908558 0.688889 0.276571 0.031 Uiso 1 1 calc R . . . .
C6 C 1.2906(5) 0.3063(5) 0.4016(3) 0.0250(9) Uani 1 1 d . . . . .
H6 H 1.315576 0.370627 0.360290 0.030 Uiso 1 1 calc R . . . .
C8 C 1.0984(5) 0.2196(5) 0.5028(3) 0.0268(9) Uani 1 1 d . . . . .
H8 H 0.991776 0.224490 0.530979 0.032 Uiso 1 1 calc R . . . .
C15 C 1.1699(6) 0.3296(5) 0.1507(3) 0.0285(10) Uani 1 1 d . . . . .
C3 C 0.7042(5) 0.5284(5) 0.4026(3) 0.0254(9) Uani 1 1 d . . . . .
H3A H 0.596047 0.529278 0.421732 0.031 Uiso 1 1 calc R . . . .
C9 C 1.2290(6) 0.1153(4) 0.5241(4) 0.0272(10) Uani 1 1 d . . . . .
H9 H 1.208641 0.050359 0.566458 0.033 Uiso 1 1 calc R . . . .
C2 C 1.0188(5) 0.5265(4) 0.3490(3) 0.0242(9) Uani 1 1 d . . . . .
H2 H 1.125299 0.529572 0.329959 0.029 Uiso 1 1 calc R . . . .
C16 C 1.0509(6) 0.2668(5) 0.2060(3) 0.0273(9) Uani 1 1 d . . . . .
C7 C 1.4143(6) 0.1997(5) 0.4262(4) 0.0289(10) Uani 1 1 d . . . . .
H7 H 1.522730 0.193119 0.400861 0.035 Uiso 1 1 calc R . . . .
C17 C 1.1023(7) 0.1597(5) 0.2677(4) 0.0313(11) Uani 1 1 d . . . . .
H17 H 1.212664 0.122931 0.272615 0.038 Uiso 1 1 calc R . . . .
C4 C 0.8261(5) 0.4294(5) 0.4377(3) 0.0266(9) Uani 1 1 d . . . . .
H4 H 0.799913 0.366002 0.479412 0.032 Uiso 1 1 calc R . . . .
C19 C 0.8837(7) 0.3146(7) 0.2016(4) 0.0388(13) Uani 1 1 d . . . . .
H19 H 0.843578 0.385296 0.161606 0.047 Uiso 1 1 calc R . . . .
C12 C 1.3399(7) 0.2662(5) 0.1381(4) 0.0342(11) Uani 1 1 d . . . . .
H12 H 1.380754 0.183705 0.164483 0.041 Uiso 1 1 calc R . . . .
C14 C 1.1177(7) 0.4523(5) 0.1106(4) 0.0346(11) Uani 1 1 d . . . . .
H14 H 1.006341 0.498126 0.117694 0.042 Uiso 1 1 calc R . . . .
C20 C 0.7790(7) 0.2562(6) 0.2568(4) 0.0397(13) Uani 1 1 d . . . . .
H20 H 0.668206 0.289580 0.252059 0.048 Uiso 1 1 calc R . . . .
C11 C 1.4442(7) 0.3266(6) 0.0869(4) 0.0390(13) Uani 1 1 d . . . . .
H11 H 1.556384 0.283401 0.078654 0.047 Uiso 1 1 calc R . . . .
C18 C 0.9848(7) 0.1098(6) 0.3213(4) 0.0377(12) Uani 1 1 d . . . . .
H18 H 1.020486 0.040217 0.363097 0.045 Uiso 1 1 calc R . . . .
C13 C 1.2317(8) 0.5068(6) 0.0598(4) 0.0384(12) Uani 1 1 d . . . . .
H13 H 1.194916 0.589385 0.032781 0.046 Uiso 1 1 calc R . . . .
C24A C 0.0404(13) 0.8845(10) 0.1063(8) 0.0233(15) Uani 0.5 1 d . U P A 1
H24A H -0.052799 0.858898 0.116458 0.028 Uiso 0.5 1 calc R . P A 1
C22B C 0.2234(15) 0.9679(11) 0.0009(8) 0.0246(17) Uani 0.5 1 d . U P A 2
H22B H 0.256888 0.999065 -0.059175 0.029 Uiso 0.5 1 calc R . P A 2
C21B C 0.3356(16) 0.9146(11) 0.0623(8) 0.0236(17) Uani 0.5 1 d . U P A 2
H21B H 0.444372 0.910825 0.041198 0.028 Uiso 0.5 1 calc R . P A 2
C22A C 0.2090(14) 1.0041(10) 0.0172(8) 0.0207(15) Uani 0.5 1 d . U P A 1
H22A H 0.231139 1.060581 -0.032245 0.025 Uiso 0.5 1 calc R . P A 1
C21A C 0.3220(15) 0.9481(11) 0.0790(8) 0.0206(15) Uani 0.5 1 d . U P A 1
H21A H 0.419163 0.968258 0.069129 0.025 Uiso 0.5 1 calc R . P A 1
C23A C 0.1566(14) 0.8342(12) 0.1658(9) 0.0279(16) Uani 0.5 1 d . U P A 1
H23A H 0.138950 0.777321 0.216014 0.033 Uiso 0.5 1 calc R . P A 1
C23B C 0.1370(13) 0.8760(10) 0.1794(8) 0.0195(14) Uani 0.5 1 d . U P A 2
H23B H 0.106385 0.845189 0.240010 0.023 Uiso 0.5 1 calc R . P A 2
C24B C 0.0176(12) 0.9276(9) 0.1237(7) 0.0168(14) Uani 0.5 1 d . U P A 2
H24B H -0.090892 0.932055 0.146889 0.020 Uiso 0.5 1 calc R . P A 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
Bi1 Cl2 2.6709(12) . ?
Bi1 Cl1 2.6619(13) . ?
Bi1 Cl3 2.6860(14) . ?
Bi1 Cl4 2.6665(13) . ?
Bi1 N1 2.545(4) . ?
Bi1 N2 2.523(4) . ?
N3 H3 0.8600 . ?
N3 C9 1.332(6) . ?
N3 C7 1.330(6) . ?
N1 C21B 1.348(13) . ?
N1 C21A 1.316(13) . ?
N1 C23A 1.358(13) . ?
N1 C23B 1.344(11) . ?
C25 C25 1.481(8) 2_575 ?
C25 C24A 1.408(11) . ?
C25 C22B 1.378(13) . ?
C25 C22A 1.408(13) . ?
C25 C24B 1.409(10) . ?
N2 C1 1.337(6) . ?
N2 C3 1.327(6) . ?
N5 H5 0.8600 . ?
N5 C11 1.336(8) . ?
N5 C13 1.331(8) . ?
N4 C20 1.344(8) . ?
N4 C18 1.337(7) . ?
C10 C5 1.489(5) . ?
C10 C6 1.402(6) . ?
C10 C8 1.387(6) . ?
C5 C2 1.392(6) . ?
C5 C4 1.400(6) . ?
C1 H1 0.9300 . ?
C1 C2 1.398(6) . ?
C6 H6 0.9300 . ?
C6 C7 1.379(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.386(6) . ?
C15 C16 1.494(7) . ?
C15 C12 1.405(7) . ?
C15 C14 1.380(8) . ?
C3 H3A 0.9300 . ?
C3 C4 1.381(6) . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C16 C17 1.402(7) . ?
C16 C19 1.394(7) . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.389(8) . ?
C4 H4 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.372(9) . ?
C12 H12 0.9300 . ?
C12 C11 1.362(8) . ?
C14 H14 0.9300 . ?
C14 C13 1.382(8) . ?
C20 H20 0.9300 . ?
C11 H11 0.9300 . ?
C18 H18 0.9300 . ?
C13 H13 0.9300 . ?
C24A H24A 0.9300 . ?
C24A C23A 1.399(15) . ?
C22B H22B 0.9300 . ?
C22B C21B 1.396(15) . ?
C21B H21B 0.9300 . ?
C22A H22A 0.9300 . ?
C22A C21A 1.410(15) . ?
C21A H21A 0.9300 . ?
C23A H23A 0.9300 . ?
C23B H23B 0.9300 . ?
C23B C24B 1.381(13) . ?
C24B H24B 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
Cl2 Bi1 Cl3 92.45(5) . . ?
Cl1 Bi1 Cl2 86.05(4) . . ?
Cl1 Bi1 Cl3 177.00(4) . . ?
Cl1 Bi1 Cl4 90.68(4) . . ?
Cl4 Bi1 Cl2 175.52(4) . . ?
Cl4 Bi1 Cl3 90.96(5) . . ?
N1 Bi1 Cl2 89.78(10) . . ?
N1 Bi1 Cl1 93.08(10) . . ?
N1 Bi1 Cl3 84.31(10) . . ?
N1 Bi1 Cl4 93.46(10) . . ?
N2 Bi1 Cl2 85.81(10) . . ?
N2 Bi1 Cl1 96.23(10) . . ?
N2 Bi1 Cl3 86.25(10) . . ?
N2 Bi1 Cl4 91.52(10) . . ?
N2 Bi1 N1 169.40(13) . . ?
C9 N3 H3 120.0 . . ?
C7 N3 H3 120.0 . . ?
C7 N3 C9 120.0(4) . . ?
C21B N1 Bi1 121.2(6) . . ?
C21A N1 Bi1 120.4(6) . . ?
C21A N1 C23A 120.5(8) . . ?
C23A N1 Bi1 119.0(6) . . ?
C23B N1 Bi1 121.8(5) . . ?
C23B N1 C21B 116.9(8) . . ?
C24A C25 C25 120.8(6) . 2_575 ?
C24A C25 C22A 116.6(7) . . ?
C22B C25 C25 121.1(7) . 2_575 ?
C22B C25 C24B 118.2(7) . . ?
C22A C25 C25 122.5(7) . 2_575 ?
C24B C25 C25 120.7(6) . 2_575 ?
C1 N2 Bi1 120.1(3) . . ?
C3 N2 Bi1 120.2(3) . . ?
C3 N2 C1 118.1(4) . . ?
C11 N5 H5 120.8 . . ?
C13 N5 H5 120.8 . . ?
C13 N5 C11 118.5(5) . . ?
C18 N4 C20 115.2(5) . . ?
C6 C10 C5 120.8(4) . . ?
C8 C10 C5 121.7(4) . . ?
C8 C10 C6 117.4(4) . . ?
C2 C5 C10 121.6(4) . . ?
C2 C5 C4 117.2(4) . . ?
C4 C5 C10 121.2(4) . . ?
N2 C1 H1 119.0 . . ?
N2 C1 C2 122.1(4) . . ?
C2 C1 H1 119.0 . . ?
C10 C6 H6 120.3 . . ?
C7 C6 C10 119.4(4) . . ?
C7 C6 H6 120.3 . . ?
C10 C8 H8 120.0 . . ?
C9 C8 C10 119.9(4) . . ?
C9 C8 H8 120.0 . . ?
C12 C15 C16 121.2(5) . . ?
C14 C15 C16 121.5(5) . . ?
C14 C15 C12 117.3(5) . . ?
N2 C3 H3A 118.1 . . ?
N2 C3 C4 123.9(4) . . ?
C4 C3 H3A 118.1 . . ?
N3 C9 C8 121.3(4) . . ?
N3 C9 H9 119.3 . . ?
C8 C9 H9 119.3 . . ?
C5 C2 C1 119.8(4) . . ?
C5 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C17 C16 C15 121.1(5) . . ?
C19 C16 C15 121.8(5) . . ?
C19 C16 C17 117.1(5) . . ?
N3 C7 C6 121.9(4) . . ?
N3 C7 H7 119.0 . . ?
C6 C7 H7 119.0 . . ?
C16 C17 H17 120.7 . . ?
C18 C17 C16 118.6(5) . . ?
C18 C17 H17 120.7 . . ?
C5 C4 H4 120.5 . . ?
C3 C4 C5 118.9(4) . . ?
C3 C4 H4 120.5 . . ?
C16 C19 H19 120.3 . . ?
C20 C19 C16 119.3(6) . . ?
C20 C19 H19 120.3 . . ?
C15 C12 H12 120.3 . . ?
C11 C12 C15 119.4(5) . . ?
C11 C12 H12 120.3 . . ?
C15 C14 H14 120.2 . . ?
C15 C14 C13 119.7(5) . . ?
C13 C14 H14 120.2 . . ?
N4 C20 C19 125.0(6) . . ?
N4 C20 H20 117.5 . . ?
C19 C20 H20 117.5 . . ?
N5 C11 C12 122.8(5) . . ?
N5 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
N4 C18 C17 124.8(6) . . ?
N4 C18 H18 117.6 . . ?
C17 C18 H18 117.6 . . ?
N5 C13 C14 122.4(5) . . ?
N5 C13 H13 118.8 . . ?
C14 C13 H13 118.8 . . ?
C25 C24A H24A 119.4 . . ?
C23A C24A C25 121.1(9) . . ?
C23A C24A H24A 119.4 . . ?
C25 C22B H22B 120.7 . . ?
C25 C22B C21B 118.6(10) . . ?
C21B C22B H22B 120.7 . . ?
N1 C21B C22B 123.8(10) . . ?
N1 C21B H21B 118.1 . . ?
C22B C21B H21B 118.1 . . ?
C25 C22A H22A 120.4 . . ?
C25 C22A C21A 119.2(9) . . ?
C21A C22A H22A 120.4 . . ?
N1 C21A C22A 122.5(10) . . ?
N1 C21A H21A 118.7 . . ?
C22A C21A H21A 118.7 . . ?
N1 C23A C24A 120.0(10) . . ?
N1 C23A H23A 120.0 . . ?
C24A C23A H23A 120.0 . . ?
N1 C23B H23B 118.4 . . ?
N1 C23B C24B 123.2(9) . . ?
C24B C23B H23B 118.4 . . ?
C25 C24B H24B 120.4 . . ?
C23B C24B C25 119.2(8) . . ?
C23B C24B H24B 120.4 . . ?

_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_compound4
_database_code_depnum_ccdc_archive 'CCDC 1554520'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2016-10-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Bi Cl4 N2, C10 H11 N2'
_chemical_formula_sum            'C20 H19 Bi Cl4 N4'
_chemical_formula_weight         666.17
_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'
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'
N N 0.0061 0.0033 '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           12
_space_group_name_H-M_alt        'C 1 2/m 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'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'

_cell_length_a                   13.062(3)
_cell_length_b                   12.287(2)
_cell_length_c                   8.1125(15)
_cell_angle_alpha                90
_cell_angle_beta                 121.421(5)
_cell_angle_gamma                90
_cell_volume                     1111.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6224
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.47
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.430
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5223
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0787 before and 0.0547 after correction.
The Ratio of minimum to maximum transmission is 0.7004.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.301
_exptl_crystal_size_mid          0.214
_exptl_crystal_size_min          0.205
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_unetI/netI     0.0262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            8185
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.346
_diffrn_reflns_theta_min         2.467
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1439
_reflns_number_total             1446
_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+ ver. 7.68A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         1.786
_refine_diff_density_min         -1.708
_refine_diff_density_rms         0.151
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.173
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     73
_refine_ls_number_reflns         1446
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0225
_refine_ls_R_factor_gt           0.0223
_refine_ls_restrained_S_all      1.173
_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)+(0.0264P)²+2.4370P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0554
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H2(0.25)
3.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C11(H11), N2(H2), C4(H4), C6(H6), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
Bi1 Bi 0.5000 0.0000 0.5000 0.02452(9) Uani 1 4 d S T P . .
Cl2 Cl 0.31712(9) 0.0000 0.56130(14) 0.0250(2) Uani 1 2 d S T P . .
Cl3 Cl 0.33157(10) 0.0000 0.12326(14) 0.0309(2) Uani 1 2 d S T P . .
N4 N 0.5000 0.2095(4) 0.5000 0.0321(9) Uani 1 2 d S T P . .
C5 C 0.5000 0.4391(4) 0.5000 0.0290(9) Uani 1 2 d S T P . .
C8 C 0.4116(3) 0.3783(4) 0.3450(5) 0.0421(10) Uani 1 1 d . . . . .
H8 H 0.3481 0.4145 0.2360 0.051 Uiso 1 1 calc R . . . .
C11 C 0.4161(3) 0.2668(4) 0.3496(5) 0.0415(9) Uani 1 1 d . . . . .
H11 H 0.3564 0.2281 0.2400 0.050 Uiso 1 1 calc R . . . .
N2 N 0.0000 0.1059(3) 0.0000 0.0257(7) Uani 1 2 d S T P . .
H2 H 0.0000 0.0343 0.0000 0.031 Uiso 0.5 2 calc RS T P . .
C4 C 0.0932(3) 0.1598(3) 0.1422(5) 0.0327(7) Uani 1 1 d . . . . .
H4 H 0.1587 0.1202 0.2420 0.039 Uiso 1 1 calc R . . . .
C6 C 0.0954(4) 0.2717(3) 0.1461(8) 0.0491(11) Uani 1 1 d . . . . .
H6 H 0.1618 0.3095 0.2480 0.059 Uiso 1 1 calc R . . . .
C14 C 0.0000 0.3284(4) 0.0000 0.057(2) Uani 1 2 d S T P . .
H14 H 0.0000 0.4058 0.0000 0.068 Uiso 1 2 calc RS T P . .


_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 Cl2 2.6818(12) 5_656 ?
Bi1 Cl2 2.6818(12) . ?
Bi1 Cl3 2.6778(11) 5_656 ?
Bi1 Cl3 2.6778(11) . ?
Bi1 N4 2.575(5) . ?
Bi1 N4 2.575(5) 5_656 ?
N4 C11 1.338(4) . ?
N4 C11 1.338(4) 2_656 ?
C5 C5 1.497(11) 5_666 ?
C5 C8 1.400(5) . ?
C5 C8 1.400(5) 2_656 ?
C8 H8 0.9500 . ?
C8 C11 1.371(6) . ?
C11 H11 0.9500 . ?
N2 H2 0.8800 . ?
N2 C4 1.336(4) 2 ?
N2 C4 1.336(4) . ?
C4 H4 0.9500 . ?
C4 C6 1.376(5) . ?
C6 H6 0.9500 . ?
C6 C14 1.380(5) . ?
C14 C6 1.380(5) 2 ?
C14 H14 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
Cl2 Bi1 Cl2 180.0 5_656 . ?
Cl3 Bi1 Cl2 86.01(4) . . ?
Cl3 Bi1 Cl2 86.01(4) 5_656 5_656 ?
Cl3 Bi1 Cl2 93.99(4) 5_656 . ?
Cl3 Bi1 Cl2 93.99(4) . 5_656 ?
Cl3 Bi1 Cl3 180.0 5_656 . ?
N4 Bi1 Cl2 90.0 . 5_656 ?
N4 Bi1 Cl2 90.0 5_656 . ?
N4 Bi1 Cl2 90.0 5_656 5_656 ?
N4 Bi1 Cl2 90.0 . . ?
N4 Bi1 Cl3 90.0 . . ?
N4 Bi1 Cl3 90.0 . 5_656 ?
N4 Bi1 Cl3 90.0 5_656 5_656 ?
N4 Bi1 Cl3 90.0 5_656 . ?
N4 Bi1 N4 180.0 5_656 . ?
C11 N4 Bi1 121.7(2) . . ?
C11 N4 Bi1 121.7(2) 2_656 . ?
C11 N4 C11 116.6(5) 2_656 . ?
C8 C5 C5 122.3(2) 2_656 5_666 ?
C8 C5 C5 122.3(2) . 5_666 ?
C8 C5 C8 115.5(5) . 2_656 ?
C5 C8 H8 119.8 . . ?
C11 C8 C5 120.3(3) . . ?
C11 C8 H8 119.8 . . ?
N4 C11 C8 123.6(3) . . ?
N4 C11 H11 118.2 . . ?
C8 C11 H11 118.2 . . ?
C4 N2 H2 119.7 2 . ?
C4 N2 H2 119.7 . . ?
C4 N2 C4 120.6(4) 2 . ?
N2 C4 H4 119.5 . . ?
N2 C4 C6 120.9(3) . . ?
C6 C4 H4 119.5 . . ?
C4 C6 H6 120.5 . . ?
C4 C6 C14 119.1(4) . . ?
C14 C6 H6 120.5 . . ?
C6 C14 C6 119.3(5) . 2 ?
C6 C14 H14 120.3 . . ?
C6 C14 H14 120.3 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
Bi1 N4 C11 C8 178.8(3) . . . . ?
C5 C5 C8 C11 178.9(3) 5_666 . . . ?
C5 C8 C11 N4 2.3(6) . . . . ?
C8 C5 C8 C11 -1.1(3) 2_656 . . . ?
C11 N4 C11 C8 -1.2(3) 2_656 . . . ?
N2 C4 C6 C14 -0.3(6) . . . . ?
C4 N2 C4 C6 0.2(3) 2 . . . ?
C4 C6 C14 C6 0.2(3) . . . 2 ?

_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_compound10
_database_code_depnum_ccdc_archive 'CCDC 1554518'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2018/1

_chemical_name_systematic        
; 
Bis(pyridinium)-catena-[tris(μ-(4,4'-bipyridyl-N,N')tetrachloropraseodymate 4,4'-bipyridine solvate]
;
_chemical_name_common            ?
_chemical_formula_moiety         'C15 H12 Cl4 N3 Pr, C5 H6 N, C10 H8 N2'
_chemical_formula_sum            'C30 H26 Cl4 N6 Pr'
_chemical_formula_weight         753.28
_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'
Pr Pr -0.2180 2.8214 '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                   8.8374(18)
_cell_length_b                   20.136(4)
_cell_length_c                   17.364(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.75(3)
_cell_angle_gamma                90
_cell_volume                     3086.4(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    999
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      23.01
_cell_measurement_theta_min      2.31
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.956
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6119
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(Bruker SADABS, 2011)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1500
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0988
_diffrn_reflns_av_unetI/netI     0.0723
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            37589
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.158
_diffrn_reflns_theta_min         1.550
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_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                4813
_reflns_number_total             6808
_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+ ver. 7.68 (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'SAINT+ ver. 7.68 (Bruker AXS)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.935
_refine_diff_density_min         -0.495
_refine_diff_density_rms         0.127
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     554
_refine_ls_number_reflns         6808
_refine_ls_number_restraints     396
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0443
_refine_ls_restrained_S_all      0.994
_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)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0740
_refine_ls_wR_factor_ref         0.0823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
N1 \\sim C1A \\sim C2A \\sim C3 \\sim C4A \\sim C5A: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008
N1 \\sim C1B \\sim C2B \\sim C3 \\sim C4B \\sim C5B: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008
N3 \\sim C11A \\sim C12A \\sim C13 \\sim C14A \\sim C15A: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
N3 \\sim C11B \\sim C12B \\sim C13 \\sim C14B \\sim C15B: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
N2 \\sim C6A \\sim C7A \\sim C8 \\sim C9A \\sim C10A: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008
N2 \\sim C6B \\sim C7B \\sim C8 \\sim C9B \\sim C10B: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008
N5 \\sim C21A \\sim C22A \\sim C23 \\sim C24A \\sim C25A: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
N5 \\sim C21B \\sim C22B \\sim C23 \\sim C24B \\sim C25B: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
N6 \\sim C26A \\sim C27A \\sim C28 \\sim C29A \\sim C30A: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
N6 \\sim C26B \\sim C27B \\sim C28 \\sim C29B \\sim C30B: within 2A with sigma
of 0.004 and sigma for terminal atoms of 0.008
N4 \\sim C16 \\sim C17 \\sim C18 \\sim C19 \\sim C20: within 2A with sigma of
0.004 and sigma for terminal atoms of 0.008
3. Others
 Sof(C21B)=Sof(H21B)=Sof(C22B)=Sof(H22B)=Sof(C24B)=Sof(H24B)=Sof(C25B)=
 Sof(H25B)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=Sof(C29B)=Sof(H29B)=
 Sof(C30B)=Sof(H30B)=1-FVAR(1)
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=Sof(C24A)=Sof(H24A)=Sof(C25A)=
 Sof(H25A)=Sof(C26A)=Sof(H26A)=Sof(C27A)=Sof(H27A)=Sof(C29A)=Sof(H29A)=
 Sof(C30A)=Sof(H30A)=FVAR(1)
 Sof(C2A)=Sof(C1B)=Sof(H1B)=Sof(H2B)=Sof(C4B)=Sof(H4B)=Sof(C5B)=Sof(H5B)=1-
 FVAR(2)
 Sof(C1A)=Sof(H1A)=Sof(H2A)=Sof(C4A)=Sof(H4A)=Sof(C5A)=Sof(H5A)=Sof(C2B)=FVAR(2)
 Sof(C10A)=Sof(C6B)=Sof(H6B)=Sof(C7B)=Sof(H7B)=Sof(C9B)=Sof(H9B)=Sof(H10B)=1-
 FVAR(3)
 Sof(C6A)=Sof(H6A)=Sof(C7A)=Sof(H7A)=Sof(C9A)=Sof(H9A)=Sof(H10A)=Sof(C10B)=
 FVAR(3)
 Sof(C11B)=Sof(H11B)=Sof(C12B)=Sof(H12B)=Sof(C14B)=Sof(H14B)=Sof(C15B)=
 Sof(H15B)=1-FVAR(4)
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15A)=FVAR(4)
4.a Aromatic/amide H refined with riding coordinates:
 N4(H4), C20(H20), C16(H16), C17(H17), C19(H19), C18(H18), C21A(H21A),
 C22A(H22A), C24A(H24A), C25A(H25A), C26A(H26A), C27A(H27A), C29A(H29A),
 C30A(H30A), C21B(H21B), C22B(H22B), C24B(H24B), C25B(H25B), C26B(H26B),
 C27B(H27B), C29B(H29B), C30B(H30B), C1A(H1A), C2A(H2A), C4A(H4A), C5A(H5A),
 C1B(H1B), C2B(H2B), C4B(H4B), C5B(H5B), C6A(H6A), C7A(H7A), C9A(H9A),
 C10A(H10A), C6B(H6B), C7B(H7B), C9B(H9B), C10B(H10B), C11A(H11A), C12A(H12A),
 C14A(H14A), C15A(H15A), C11B(H11B), C12B(H12B), C14B(H14B), C15B(H15B)
;
_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
Pr1 Pr 0.51875(3) 0.80253(2) 0.85004(2) 0.01714(7) Uani 1 1 d . . . . .
Cl3 Cl 0.34417(12) 0.70792(6) 0.92038(6) 0.0248(3) Uani 1 1 d . . . . .
Cl1 Cl 0.59695(14) 0.87957(6) 0.72788(7) 0.0308(3) Uani 1 1 d . . . . .
Cl2 Cl 0.33251(14) 0.89102(6) 0.91685(7) 0.0342(3) Uani 1 1 d . . . . .
Cl4 Cl 0.65325(12) 0.70376(6) 0.77025(6) 0.0253(2) Uani 1 1 d . . . . .
N2 N 0.7067(4) 0.74965(18) 0.9562(2) 0.0230(8) Uani 1 1 d . U . . .
N3 N 0.2905(4) 0.78468(18) 0.7486(2) 0.0219(8) Uani 1 1 d . U . . .
N1 N 0.7256(4) 0.88999(18) 0.9127(2) 0.0274(8) Uani 1 1 d . U . . .
C13 C 0.0566(5) 0.7708(2) 0.6345(2) 0.0203(8) Uani 1 1 d . U . . .
C3 C 0.9435(5) 0.9762(2) 0.9822(3) 0.0272(9) Uani 1 1 d . U . . .
C8 C 0.9357(5) 0.7357(2) 1.0726(2) 0.0213(9) Uani 1 1 d . U . . .
N4 N 0.5268(5) 1.0492(2) 0.7385(2) 0.0416(10) Uani 1 1 d . U . . .
H4 H 0.478248 1.037621 0.695186 0.050 Uiso 1 1 calc R . . . .
C20 C 0.6431(7) 1.0905(3) 0.7356(3) 0.0450(11) Uani 1 1 d . U . . .
H20 H 0.671809 1.107267 0.687320 0.054 Uiso 1 1 calc R . . . .
C23 C 0.9019(6) 1.0072(3) 0.6056(3) 0.0364(10) Uani 1 1 d . U . . .
N5 N 1.1090(5) 1.0227(2) 0.7337(3) 0.0459(10) Uani 1 1 d . U . . .
C16 C 0.4808(7) 1.0248(3) 0.8043(3) 0.0459(12) Uani 1 1 d . U . . .
H16 H 0.396758 0.995374 0.804190 0.055 Uiso 1 1 calc R . . . .
C17 C 0.5539(7) 1.0420(3) 0.8719(3) 0.0499(12) Uani 1 1 d . U . . .
H17 H 0.521312 1.024531 0.919139 0.060 Uiso 1 1 calc R . . . .
C19 C 0.7221(7) 1.1090(3) 0.8017(3) 0.0529(12) Uani 1 1 d . U . . .
H19 H 0.806987 1.137775 0.800063 0.063 Uiso 1 1 calc R . . . .
N6 N 0.6118(5) 0.9798(2) 0.4032(3) 0.0389(9) Uani 1 1 d . U . . .
C28 C 0.7973(6) 0.9987(2) 0.5370(3) 0.0344(10) Uani 1 1 d . U . . .
C18 C 0.6746(7) 1.0844(3) 0.8717(3) 0.0519(12) Uani 1 1 d . U . . .
H18 H 0.725705 1.097104 0.918767 0.062 Uiso 1 1 calc R . . . .
C21A C 1.0243(15) 0.9621(8) 0.7129(9) 0.0400(18) Uani 0.483(9) 1 d . U P A 1
H21A H 1.041570 0.924663 0.745524 0.048 Uiso 0.483(9) 1 calc R . P A 1
C22A C 0.9221(14) 0.9537(7) 0.6511(9) 0.0368(18) Uani 0.483(9) 1 d . U P A 1
H22A H 0.869836 0.913086 0.641393 0.044 Uiso 0.483(9) 1 calc R . P A 1
C24A C 0.9698(15) 1.0636(7) 0.6132(8) 0.0366(18) Uani 0.483(9) 1 d . U P A 1
H24A H 0.951782 1.099048 0.577881 0.044 Uiso 0.483(9) 1 calc R . P A 1
C25A C 1.0713(15) 1.0690(7) 0.6765(8) 0.0396(18) Uani 0.483(9) 1 d . U P A 1
H25A H 1.122380 1.110368 0.681526 0.048 Uiso 0.483(9) 1 calc R . P A 1
C26A C 0.6198(15) 1.0373(6) 0.4290(7) 0.0353(17) Uani 0.483(9) 1 d . U P A 1
H26A H 0.565204 1.072770 0.404578 0.042 Uiso 0.483(9) 1 calc R . P A 1
C27A C 0.7110(15) 1.0475(6) 0.4944(7) 0.0346(17) Uani 0.483(9) 1 d . U P A 1
H27A H 0.717297 1.091801 0.513193 0.041 Uiso 0.483(9) 1 calc R . P A 1
C29A C 0.7664(13) 0.9334(6) 0.4965(7) 0.0353(17) Uani 0.483(9) 1 d . U P A 1
H29A H 0.811710 0.894467 0.518151 0.042 Uiso 0.483(9) 1 calc R . P A 1
C30A C 0.6764(13) 0.9273(6) 0.4300(7) 0.0360(17) Uani 0.483(9) 1 d . U P A 1
H30A H 0.662753 0.885584 0.404948 0.043 Uiso 0.483(9) 1 calc R . P A 1
C21B C 1.0802(14) 0.9666(8) 0.7096(8) 0.0416(18) Uani 0.517(9) 1 d . U P A 2
H21B H 1.129224 0.929733 0.734107 0.050 Uiso 0.517(9) 1 calc R . P A 2
C22B C 0.9797(14) 0.9554(7) 0.6485(9) 0.0379(17) Uani 0.517(9) 1 d . U P A 2
H22B H 0.960307 0.910658 0.633561 0.045 Uiso 0.517(9) 1 calc R . P A 2
C24B C 0.9498(14) 1.0724(7) 0.6421(7) 0.0372(17) Uani 0.517(9) 1 d . U P A 2
H24B H 0.909335 1.112203 0.620207 0.045 Uiso 0.517(9) 1 calc R . P A 2
C25B C 1.0491(14) 1.0771(7) 0.7054(7) 0.0410(17) Uani 0.517(9) 1 d . U P A 2
H25B H 1.073425 1.118963 0.727918 0.049 Uiso 0.517(9) 1 calc R . P A 2
C26B C 0.6900(14) 1.0387(6) 0.4231(7) 0.0364(17) Uani 0.517(9) 1 d . U P A 2
H26B H 0.677968 1.074456 0.387647 0.044 Uiso 0.517(9) 1 calc R . P A 2
C27B C 0.7820(14) 1.0505(6) 0.4880(7) 0.0343(16) Uani 0.517(9) 1 d . U P A 2
H27B H 0.830926 1.091949 0.497523 0.041 Uiso 0.517(9) 1 calc R . P A 2
C29B C 0.7256(12) 0.9431(5) 0.5307(7) 0.0336(16) Uani 0.517(9) 1 d . U P A 2
H29B H 0.733908 0.909892 0.569557 0.040 Uiso 0.517(9) 1 calc R . P A 2
C30B C 0.6363(13) 0.9348(5) 0.4643(7) 0.0352(16) Uani 0.517(9) 1 d . U P A 2
H30B H 0.584910 0.893436 0.459140 0.042 Uiso 0.517(9) 1 calc R . P A 2
C1A C 0.728(2) 0.9048(10) 0.9914(11) 0.0284(17) Uani 0.55(5) 1 d . U P B 3
H1A H 0.652446 0.885983 1.021818 0.034 Uiso 0.55(5) 1 calc R . P B 3
C2A C 0.835(2) 0.9453(11) 1.0265(14) 0.0279(18) Uani 0.45(5) 1 d . U P B 3
H2A H 0.835484 0.952508 1.080617 0.034 Uiso 0.55(5) 1 calc R . P B 3
C4A C 0.942(2) 0.9623(9) 0.9023(11) 0.0273(17) Uani 0.55(5) 1 d . U P B 3
H4A H 1.014568 0.981911 0.870792 0.033 Uiso 0.55(5) 1 calc R . P B 3
C5A C 0.835(2) 0.9205(9) 0.8711(12) 0.0273(17) Uani 0.55(5) 1 d . U P B 3
H5A H 0.834938 0.911863 0.817288 0.033 Uiso 0.55(5) 1 calc R . P B 3
C1B C 0.711(3) 0.9127(11) 0.9798(13) 0.0271(18) Uani 0.45(5) 1 d . U P B 4
H1B H 0.623433 0.899918 1.005832 0.033 Uiso 0.45(5) 1 calc R . P B 4
C2B C 0.815(2) 0.9557(8) 1.0192(12) 0.0263(18) Uani 0.55(5) 1 d . U P B 4
H2B H 0.797988 0.970250 1.070038 0.032 Uiso 0.45(5) 1 calc R . P B 4
C4B C 0.959(3) 0.9508(11) 0.9103(13) 0.0276(18) Uani 0.45(5) 1 d . U P B 4
H4B H 1.045096 0.961906 0.882345 0.033 Uiso 0.45(5) 1 calc R . P B 4
C5B C 0.846(3) 0.9073(11) 0.8765(14) 0.0280(18) Uani 0.45(5) 1 d . U P B 4
H5B H 0.858468 0.890553 0.826042 0.034 Uiso 0.45(5) 1 calc R . P B 4
C6A C 0.677(3) 0.7399(9) 1.0294(14) 0.0228(18) Uani 0.51(4) 1 d . U P C 5
H6A H 0.573575 0.738148 1.042069 0.027 Uiso 0.51(4) 1 calc R . P C 5
C7A C 0.785(3) 0.7320(10) 1.0881(13) 0.0218(18) Uani 0.51(4) 1 d . U P C 5
H7A H 0.755262 0.724071 1.139241 0.026 Uiso 0.51(4) 1 calc R . P C 5
C9A C 0.971(2) 0.7454(10) 0.9966(11) 0.0220(17) Uani 0.51(4) 1 d . U P C 5
H9A H 1.073684 0.746832 0.983449 0.026 Uiso 0.51(4) 1 calc R . P C 5
C10A C 0.857(2) 0.7529(9) 0.9397(12) 0.0230(18) Uani 0.49(4) 1 d . U P C 5
H10A H 0.883681 0.760448 0.888042 0.028 Uiso 0.51(4) 1 calc R . P C 5
C6B C 0.674(3) 0.7518(9) 1.0307(15) 0.0215(18) Uani 0.49(4) 1 d . U P C 6
H6B H 0.571235 0.758189 1.043048 0.026 Uiso 0.49(4) 1 calc R . P C 6
C7B C 0.782(3) 0.7453(10) 1.0908(14) 0.0209(17) Uani 0.49(4) 1 d . U P C 6
H7B H 0.754303 0.747274 1.142882 0.025 Uiso 0.49(4) 1 calc R . P C 6
C9B C 0.966(2) 0.7300(10) 0.9946(11) 0.0208(17) Uani 0.49(4) 1 d . U P C 6
H9B H 1.065320 0.720963 0.979252 0.025 Uiso 0.49(4) 1 calc R . P C 6
C10B C 0.849(2) 0.7375(9) 0.9405(12) 0.0215(17) Uani 0.51(4) 1 d . U P C 6
H10B H 0.871806 0.733795 0.887752 0.026 Uiso 0.49(4) 1 calc R . P C 6
C11A C 0.318(3) 0.7709(13) 0.6779(13) 0.0213(18) Uani 0.48(7) 1 d . U P D 7
H11A H 0.420596 0.765611 0.665156 0.026 Uiso 0.48(7) 1 calc R . P D 7
C12A C 0.203(3) 0.7633(13) 0.6181(12) 0.0207(18) Uani 0.48(7) 1 d . U P D 7
H12A H 0.229713 0.752958 0.567092 0.025 Uiso 0.48(7) 1 calc R . P D 7
C14A C 0.026(3) 0.7692(14) 0.7128(12) 0.0212(18) Uani 0.48(7) 1 d . U P D 7
H14A H -0.074100 0.761266 0.727931 0.025 Uiso 0.48(7) 1 calc R . P D 7
C15A C 0.139(3) 0.7788(13) 0.7672(17) 0.0218(18) Uani 0.48(7) 1 d . U P D 7
H15A H 0.114410 0.781744 0.819750 0.026 Uiso 0.48(7) 1 calc R . P D 7
C11B C 0.320(2) 0.7839(12) 0.6719(11) 0.0213(17) Uani 0.52(7) 1 d . U P D 8
H11B H 0.422463 0.788508 0.658429 0.026 Uiso 0.52(7) 1 calc R . P D 8
C12B C 0.213(2) 0.7770(12) 0.6143(12) 0.0210(17) Uani 0.52(7) 1 d . U P D 8
H12B H 0.239974 0.776294 0.561965 0.025 Uiso 0.52(7) 1 calc R . P D 8
C14B C 0.028(2) 0.7839(12) 0.7108(11) 0.0199(17) Uani 0.52(7) 1 d . U P D 8
H14B H -0.073334 0.789328 0.726132 0.024 Uiso 0.52(7) 1 calc R . P D 8
C15B C 0.150(3) 0.7891(11) 0.7652(14) 0.0208(17) Uani 0.52(7) 1 d . U P D 8
H15B H 0.128337 0.796278 0.817527 0.025 Uiso 0.52(7) 1 calc R . P D 8


_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
Pr1 Cl3 2.7718(12) . ?
Pr1 Cl1 2.7428(13) . ?
Pr1 Cl2 2.7227(13) . ?
Pr1 Cl4 2.7287(12) . ?
Pr1 N2 2.645(4) . ?
Pr1 N3 2.638(3) . ?
Pr1 N1 2.727(4) . ?
N2 C6A 1.32(3) . ?
N2 C10A 1.38(2) . ?
N2 C6B 1.34(3) . ?
N2 C10B 1.322(19) . ?
N3 C11A 1.29(2) . ?
N3 C15A 1.40(3) . ?
N3 C11B 1.37(2) . ?
N3 C15B 1.29(2) . ?
N1 C1A 1.40(2) . ?
N1 C5A 1.38(2) . ?
N1 C1B 1.26(2) . ?
N1 C5B 1.31(2) . ?
C13 C8 1.484(6) 4_475 ?
C13 C12A 1.35(2) . ?
C13 C14A 1.40(2) . ?
C13 C12B 1.45(2) . ?
C13 C14B 1.39(2) . ?
C3 C3 1.495(9) 3_777 ?
C3 C2A 1.40(2) . ?
C3 C4A 1.416(19) . ?
C3 C2B 1.392(19) . ?
C3 C4B 1.36(2) . ?
C8 C7A 1.38(2) . ?
C8 C9A 1.38(2) . ?
C8 C7B 1.42(2) . ?
C8 C9B 1.40(2) . ?
N4 C20 1.324(7) . ?
N4 C16 1.326(6) . ?
C20 C19 1.366(8) . ?
C23 C28 1.483(7) . ?
C23 C22A 1.341(15) . ?
C23 C24A 1.289(14) . ?
C23 C22B 1.437(14) . ?
C23 C24B 1.509(14) . ?
N5 C21A 1.467(16) . ?
N5 C25A 1.391(14) . ?
N5 C21B 1.227(16) . ?
N5 C25B 1.302(14) . ?
C16 C17 1.356(8) . ?
C17 C18 1.368(8) . ?
C19 C18 1.394(8) . ?
N6 C26A 1.242(12) . ?
N6 C30A 1.279(12) . ?
N6 C26B 1.407(13) . ?
N6 C30B 1.405(12) . ?
C28 C27A 1.428(13) . ?
C28 C29A 1.509(13) . ?
C28 C27B 1.348(12) . ?
C28 C29B 1.289(11) . ?
C21A C22A 1.380(19) . ?
C24A C25A 1.389(18) . ?
C26A C27A 1.376(17) . ?
C29A C30A 1.377(16) . ?
C21B C22B 1.369(18) . ?
C24B C25B 1.377(16) . ?
C26B C27B 1.380(16) . ?
C29B C30B 1.376(14) . ?
C1A C2A 1.37(3) . ?
C4A C5A 1.36(2) . ?
C1B C2B 1.42(3) . ?
C4B C5B 1.43(3) . ?
C6A C7A 1.37(3) . ?
C9A C10A 1.38(2) . ?
C6B C7B 1.39(3) . ?
C9B C10B 1.37(2) . ?
C11A C12A 1.43(3) . ?
C14A C15A 1.35(3) . ?
C11B C12B 1.35(2) . ?
C14B C15B 1.41(3) . ?

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 Pr1 Cl3 153.60(4) . . ?
Cl2 Pr1 Cl3 84.34(4) . . ?
Cl2 Pr1 Cl1 98.01(4) . . ?
Cl2 Pr1 Cl4 168.61(4) . . ?
Cl2 Pr1 N1 79.32(9) . . ?
Cl4 Pr1 Cl3 89.32(4) . . ?
Cl4 Pr1 Cl1 83.54(4) . . ?
N2 Pr1 Cl3 76.13(8) . . ?
N2 Pr1 Cl1 126.41(8) . . ?
N2 Pr1 Cl2 109.79(8) . . ?
N2 Pr1 Cl4 77.66(8) . . ?
N2 Pr1 N1 66.14(11) . . ?
N3 Pr1 Cl3 77.08(8) . . ?
N3 Pr1 Cl1 76.93(8) . . ?
N3 Pr1 Cl2 85.13(8) . . ?
N3 Pr1 Cl4 84.24(8) . . ?
N3 Pr1 N2 147.65(11) . . ?
N3 Pr1 N1 146.19(11) . . ?
N1 Pr1 Cl3 130.14(9) . . ?
N1 Pr1 Cl1 75.78(9) . . ?
N1 Pr1 Cl4 111.92(9) . . ?
C6A N2 Pr1 125.6(11) . . ?
C6A N2 C10A 116.5(14) . . ?
C10A N2 Pr1 114.6(8) . . ?
C6B N2 Pr1 120.1(11) . . ?
C10B N2 Pr1 120.1(9) . . ?
C10B N2 C6B 117.3(14) . . ?
C11A N3 Pr1 119.4(11) . . ?
C11A N3 C15A 115.3(16) . . ?
C15A N3 Pr1 124.6(12) . . ?
C11B N3 Pr1 118.3(9) . . ?
C15B N3 Pr1 123.7(11) . . ?
C15B N3 C11B 116.6(14) . . ?
C1A N1 Pr1 120.4(9) . . ?
C5A N1 Pr1 123.5(8) . . ?
C5A N1 C1A 116.1(12) . . ?
C1B N1 Pr1 120.3(11) . . ?
C1B N1 C5B 117.9(15) . . ?
C5B N1 Pr1 121.7(11) . . ?
C12A C13 C8 120.2(10) . 4_475 ?
C12A C13 C14A 115.7(13) . . ?
C14A C13 C8 122.5(10) . 4_475 ?
C12B C13 C8 119.7(9) . 4_475 ?
C14B C13 C8 123.3(9) . 4_475 ?
C14B C13 C12B 115.8(12) . . ?
C2A C3 C4A 118.3(12) . . ?
C4B C3 C2B 115.4(13) . . ?
C7A C8 C9A 117.2(13) . . ?
C9B C8 C7B 117.0(13) . . ?
C20 N4 C16 122.4(5) . . ?
N4 C20 C19 120.3(5) . . ?
C28 C23 C24B 126.0(6) . . ?
C22A C23 C28 116.2(8) . . ?
C24A C23 C28 116.9(8) . . ?
C24A C23 C22A 126.8(10) . . ?
C22B C23 C28 126.7(8) . . ?
C22B C23 C24B 107.3(9) . . ?
C25A N5 C21A 106.3(10) . . ?
C21B N5 C25B 124.8(11) . . ?
N4 C16 C17 119.9(6) . . ?
C16 C17 C18 119.8(6) . . ?
C20 C19 C18 118.2(6) . . ?
C26A N6 C30A 128.5(10) . . ?
C30B N6 C26B 107.6(8) . . ?
C23 C28 C29A 124.4(6) . . ?
C27A C28 C23 129.4(7) . . ?
C27A C28 C29A 106.1(8) . . ?
C27B C28 C23 117.2(7) . . ?
C29B C28 C23 116.9(7) . . ?
C29B C28 C27B 125.8(9) . . ?
C17 C18 C19 119.4(6) . . ?
C22A C21A N5 126.9(13) . . ?
C23 C22A C21A 115.0(12) . . ?
C23 C24A C25A 115.4(12) . . ?
C24A C25A N5 129.5(12) . . ?
N6 C26A C27A 117.3(11) . . ?
C26A C27A C28 127.0(11) . . ?
C30A C29A C28 123.6(10) . . ?
N6 C30A C29A 117.4(10) . . ?
N5 C21B C22B 122.2(13) . . ?
C21B C22B C23 123.9(12) . . ?
C25B C24B C23 123.3(11) . . ?
N5 C25B C24B 118.4(12) . . ?
C27B C26B N6 127.6(10) . . ?
C28 C27B C26B 114.8(10) . . ?
C28 C29B C30B 115.9(9) . . ?
C29B C30B N6 128.0(9) . . ?
C2A C1A N1 122.7(17) . . ?
C1A C2A C3 119.7(18) . . ?
C5A C4A C3 119.2(15) . . ?
C4A C5A N1 124.0(16) . . ?
N1 C1B C2B 125.0(19) . . ?
C3 C2B C1B 119.0(16) . . ?
C3 C4B C5B 120.5(18) . . ?
N1 C5B C4B 122.2(19) . . ?
N2 C6A C7A 125(2) . . ?
C6A C7A C8 119.6(18) . . ?
C8 C9A C10A 120.7(16) . . ?
N2 C10A C9A 121.4(16) . . ?
N2 C6B C7B 123.3(19) . . ?
C6B C7B C8 118.6(18) . . ?
C10B C9B C8 119.0(15) . . ?
N2 C10B C9B 124.8(16) . . ?
N3 C11A C12A 123.7(18) . . ?
C13 C12A C11A 119.4(17) . . ?
C15A C14A C13 120.4(18) . . ?
C14A C15A N3 122(2) . . ?
C12B C11B N3 124.2(16) . . ?
C11B C12B C13 118.2(15) . . ?
C13 C14B C15B 119.0(17) . . ?
N3 C15B C14B 124.3(19) . . ?

_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_compound1a
_database_code_depnum_ccdc_archive 'CCDC 1554517'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-03-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_chemical_formula_moiety         'C10 H8 Bi Cl3 N2'
_chemical_formula_sum            'C10 H8 Bi Cl3 N2'
_chemical_formula_weight         471.53
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.14873 0.16029 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.98376 10.58997 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   10.0218(9)
_cell_length_b                   24.140(2)
_cell_length_c                   11.8811(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.732(1)
_cell_angle_gamma                90
_cell_volume                     2631.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9960
_cell_measurement_temperature    100
_cell_measurement_theta_max      30.079
_cell_measurement_theta_min      2.375
_exptl_absorpt_coefficient_mu    13.982
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.4146
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1484 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.5558.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.3804
_exptl_crystal_description       block
_exptl_crystal_F_000             1701.8954
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.1574
_diffrn_reflns_av_unetI/netI     0.0584
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            30068
_diffrn_reflns_theta_full        30.1169
_diffrn_reflns_theta_max         30.12
_diffrn_reflns_theta_min         1.69
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -14
_reflns_limit_k_max              34
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3497
_reflns_number_total             3869
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'Saint+ ver. 7.68A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         5.8475
_refine_diff_density_min         -3.6787
_refine_diff_density_rms         0.3866
_refine_ls_d_res_high            0.7082
_refine_ls_d_res_low             12.0701
_refine_ls_goodness_of_fit_ref   1.0620
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     146
_refine_ls_number_reflns         3869
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0431
_refine_ls_R_factor_gt           0.0395
_refine_ls_restrained_S_all      1.0620
_refine_ls_shift/su_max          0.0002
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0608P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1020
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C4(H4), C9(H9), C2(H2), C1(H1), C6(H6), C10(H10)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Bi1 Bi 0.163984(16) 0.121755(6) 0.180370(13) 0.01519(8) Uani 1.000000 1 . . .
Cl3 Cl 0.0 0.03933(8) 0.25 0.0305(4) Uani 1.000000 2 S T P
Cl2 Cl 0.0 0.20318(7) 0.25 0.0232(3) Uani 1.000000 2 S T P
Cl1 Cl 0.28386(14) 0.20450(5) 0.13108(12) 0.0276(3) Uani 1.000000 1 . . .
Cl4 Cl 0.29813(16) 0.05006(6) 0.10818(14) 0.0349(3) Uani 1.000000 1 . . .
C8 C 0.7145(6) 0.12365(17) 0.7480(5) 0.0169(9) Uani 1.000000 1 . . .
C3 C 0.5868(6) 0.12336(17) 0.6302(4) 0.0163(9) Uani 1.000000 1 . . .
C7 C 0.7518(5) 0.1707(2) 0.8244(4) 0.0222(10) Uani 1.000000 1 . . .
H7 H 0.6934(5) 0.2032(2) 0.8013(4) 0.0266(12) Uiso 1.000000 1 R . .
C5 C 0.3859(5) 0.0772(2) 0.4721(4) 0.0210(9) Uani 1.000000 1 . . .
H5 H 0.3279(5) 0.0450(2) 0.4431(4) 0.0252(11) Uiso 1.000000 1 R . .
C4 C 0.5007(5) 0.0762(2) 0.5882(4) 0.0224(9) Uani 1.000000 1 . . .
H4 H 0.5198(5) 0.0439(2) 0.6378(4) 0.0269(11) Uiso 1.000000 1 R . .
C9 C 0.8072(6) 0.0782(2) 0.7858(5) 0.0308(12) Uani 1.000000 1 . . .
H9 H 0.7873(6) 0.0459(2) 0.7359(5) 0.0369(15) Uiso 1.000000 1 R . .
C2 C 0.5486(5) 0.1706(2) 0.5566(4) 0.0207(9) Uani 1.000000 1 . . .
H2 H 0.6010(5) 0.2042(2) 0.5848(4) 0.0249(11) Uiso 1.000000 1 R . .
N1 N 0.3549(5) 0.12267(15) 0.3999(4) 0.0177(9) Uani 1.000000 1 . . .
N2 N 0.9618(6) 0.12457(15) 0.9690(5) 0.0229(10) Uani 1.000000 1 . . .
C1 C 0.4340(5) 0.1684(2) 0.4426(4) 0.0218(10) Uani 1.000000 1 . . .
H1 H 0.4105(5) 0.2006(2) 0.3926(4) 0.0262(12) Uiso 1.000000 1 R . .
C6 C 0.8741(6) 0.1691(2) 0.9329(4) 0.0277(11) Uani 1.000000 1 . . .
H6 H 0.8976(6) 0.2008(2) 0.9846(4) 0.0332(14) Uiso 1.000000 1 R . .
C10 C 0.9283(6) 0.0800(2) 0.8961(5) 0.0299(12) Uani 1.000000 1 . . .
H10 H 0.9898(6) 0.0484(2) 0.9209(5) 0.0359(15) Uiso 1.000000 1 R . .


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 Cl3 2.9050(13) . ?
Bi1 Cl2 2.8885(12) . ?
Bi1 Cl1 2.5184(13) . ?
Bi1 Cl4 2.5429(13) . ?
Bi1 N1 2.539(4) . ?
Bi1 N2 2.514(5) 1_454 ?
C8 C3 1.469(8) . ?
C8 C7 1.408(6) . ?
C8 C9 1.390(6) . ?
C3 C4 1.394(6) . ?
C3 C2 1.394(6) . ?
C7 C6 1.377(6) . ?
C5 C4 1.396(6) . ?
C5 N1 1.350(6) . ?
C9 C10 1.383(6) . ?
C2 C1 1.380(5) . ?
N1 C1 1.334(6) . ?
N2 C6 1.345(6) . ?
N2 C10 1.337(6) . ?

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 Bi1 Cl3 86.12(4) . . ?
Cl1 Bi1 Cl3 170.75(4) . . ?
Cl1 Bi1 Cl2 84.63(4) . . ?
Cl4 Bi1 Cl3 93.80(5) . . ?
Cl4 Bi1 Cl2 177.10(3) . . ?
Cl4 Bi1 Cl1 95.45(5) . . ?
N1 Bi1 Cl3 89.56(10) . . ?
N1 Bi1 Cl2 88.88(10) . . ?
N1 Bi1 Cl1 89.95(10) . . ?
N1 Bi1 Cl4 94.02(11) . . ?
N2 Bi1 Cl3 88.98(12) 1_454 . ?
N2 Bi1 Cl2 86.85(11) 1_454 . ?
N2 Bi1 Cl1 90.82(11) 1_454 . ?
N2 Bi1 Cl4 90.25(11) 1_454 . ?
N2 Bi1 N1 175.57(14) 1_454 . ?
Bi1 Cl3 Bi1 93.53(5) 2 . ?
Bi1 Cl2 Bi1 94.23(5) 2 . ?
C7 C8 C3 121.4(4) . . ?
C9 C8 C3 121.1(4) . . ?
C9 C8 C7 117.4(5) . . ?
C4 C3 C8 121.4(4) . . ?
C2 C3 C8 120.5(4) . . ?
C2 C3 C4 118.0(4) . . ?
C6 C7 C8 119.1(4) . . ?
N1 C5 C4 122.0(4) . . ?
C5 C4 C3 118.9(4) . . ?
C10 C9 C8 119.9(5) . . ?
C1 C2 C3 119.5(4) . . ?
C5 N1 Bi1 122.1(3) . . ?
C1 N1 Bi1 119.0(3) . . ?
C1 N1 C5 118.7(4) . . ?
C6 N2 Bi1 120.0(3) . 1_656 ?
C10 N2 Bi1 121.1(3) . 1_656 ?
C10 N2 C6 118.4(5) . . ?
N1 C1 C2 122.6(4) . . ?
N2 C6 C7 122.8(5) . . ?
N2 C10 C9 122.3(5) . . ?

_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_compound8
_database_code_depnum_ccdc_archive 'CCDC 1554519'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-03-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2018/1





# start Validation Reply Form
_vrf_PLAT094_compound8           
;
PROBLEM: Ratio of Maximum / Minimum Residual Density .... 4.65 Report
RESPONSE: The maximum residual density is located next to the Lu atom.
There are no hints for twinning or any remaining solvent molecules in 
the final structure.
;
# end Validation Reply Form

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Cl4 Lu N2, 2(C5 H5.5 N)'
_chemical_formula_sum            'C20 H19 Cl4 Lu N4'
_chemical_formula_weight         632.16
_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'
Lu Lu -0.4720 5.8584 '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'

_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                   14.516(3)
_cell_length_b                   12.071(2)
_cell_length_c                   13.240(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.64(3)
_cell_angle_gamma                90
_cell_volume                     2234.1(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    923
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.009
_cell_measurement_theta_min      2.504
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.912
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4478
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1319 before and 0.0413 after correction.
The Ratio of minimum to maximum transmission is 0.6007.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.880
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (10 s exposure) covering -0.500° degrees in ω.
 The crystal to detector distance was 5.1 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13338
_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         27.039
_diffrn_reflns_theta_min         2.229
_diffrn_ambient_temperature      100.0
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX2 microsource'
_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                2395
_reflns_number_total             2454
_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 v7.53A (Bruker, 2008)'
_computing_data_collection       'SMART V5.631 (?, 2016)'
_computing_data_reduction        'SAINT v7.53A (Bruker, 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.538
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.101
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.158
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     134
_refine_ls_number_reflns         2454
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0187
_refine_ls_R_factor_gt           0.0177
_refine_ls_restrained_S_all      1.158
_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)+(0.0195P)²+2.2402P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0420
_refine_ls_wR_factor_ref         0.0424
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Others
 Fixed Sof: H3(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C6(H6), C2(H2), C5(H5), N3(H3), C10(H10), C8(H8), C9(H9), C7(H7),
 C11(H11)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
Lu1 Lu 0.000000 0.27378(2) 0.250000 0.01807(5) Uani 1 2 d S T P . .
Cl1 Cl 0.18086(4) 0.27293(5) 0.26964(5) 0.02542(13) Uani 1 1 d . . . . .
Cl2 Cl -0.02531(4) 0.27068(5) 0.05122(5) 0.02727(13) Uani 1 1 d . . . . .
N1 N 0.000000 0.4770(2) 0.250000 0.0210(6) Uani 1 2 d S T P . .
N2 N 0.000000 1.0693(2) 0.250000 0.0199(5) Uani 1 2 d S T P . .
C3 C 0.000000 0.7123(3) 0.250000 0.0191(6) Uani 1 2 d S T P . .
C1 C -0.08073(17) 0.5368(2) 0.2387(2) 0.0288(6) Uani 1 1 d . . . . .
H1 H -0.139157 0.497716 0.230069 0.035 Uiso 1 1 calc R . . . .
C4 C 0.000000 0.8356(3) 0.250000 0.0182(6) Uani 1 2 d S T P . .
C6 C 0.07238(16) 1.01107(19) 0.23120(19) 0.0217(5) Uani 1 1 d . . . . .
H6 H 0.124664 1.050523 0.218237 0.026 Uiso 1 1 calc R . . . .
C2 C -0.08379(16) 0.6513(2) 0.2389(2) 0.0272(6) Uani 1 1 d . . . . .
H2 H -0.142942 0.688421 0.231575 0.033 Uiso 1 1 calc R . . . .
C5 C 0.07478(16) 0.89643(19) 0.22972(19) 0.0226(5) Uani 1 1 d . . . . .
H5 H 0.127309 0.859210 0.214902 0.027 Uiso 1 1 calc R . . . .
N3 N 0.25994(15) 0.35790(18) 0.00984(17) 0.0316(5) Uani 1 1 d . . . . .
H3 H 0.253362 0.285453 0.005406 0.038 Uiso 0.5 1 calc R . . A -1
C10 C 0.3487(2) 0.5187(2) -0.0032(2) 0.0332(6) Uani 1 1 d . . . . .
H10 H 0.403611 0.551694 -0.016571 0.040 Uiso 1 1 calc R . . . .
C8 C 0.2017(2) 0.5329(3) 0.0430(2) 0.0379(6) Uani 1 1 d . . . . .
H8 H 0.154138 0.576025 0.061821 0.045 Uiso 1 1 calc R . . . .
C9 C 0.2802(2) 0.5832(2) 0.0226(2) 0.0330(6) Uani 1 1 d . . . . .
H9 H 0.286939 0.661457 0.026266 0.040 Uiso 1 1 calc R . . . .
C7 C 0.1935(2) 0.4197(2) 0.0357(2) 0.0351(6) Uani 1 1 d . . . . .
H7 H 0.139417 0.384701 0.049269 0.042 Uiso 1 1 calc R . . . .
C11 C 0.3364(2) 0.4059(2) -0.0093(2) 0.0329(6) Uani 1 1 d . . . . .
H11 H 0.383305 0.361092 -0.027488 0.040 Uiso 1 1 calc R . . . .


_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
Lu1 Cl1 2.5675(8) 2 ?
Lu1 Cl1 2.5675(8) . ?
Lu1 Cl2 2.5576(9) 2 ?
Lu1 Cl2 2.5577(9) . ?
Lu1 N1 2.453(3) . ?
Lu1 N2 2.468(3) 1_545 ?
N1 C1 1.350(3) 2 ?
N1 C1 1.350(3) . ?
N2 C6 1.342(3) 2 ?
N2 C6 1.342(3) . ?
C3 C4 1.489(4) . ?
C3 C2 1.395(3) 2 ?
C3 C2 1.395(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.383(3) . ?
C4 C5 1.395(3) . ?
C4 C5 1.395(3) 2 ?
C6 H6 0.9500 . ?
C6 C5 1.384(3) . ?
C2 H2 0.9500 . ?
C5 H5 0.9500 . ?
N3 H3 0.8800 . ?
N3 C7 1.335(3) . ?
N3 C11 1.336(3) . ?
C10 H10 0.9500 . ?
C10 C9 1.375(4) . ?
C10 C11 1.372(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.381(4) . ?
C8 C7 1.373(4) . ?
C9 H9 0.9500 . ?
C7 H7 0.9500 . ?
C11 H11 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
Cl1 Lu1 Cl1 179.55(2) . 2 ?
Cl2 Lu1 Cl1 87.91(4) 2 2 ?
Cl2 Lu1 Cl1 92.09(4) 2 . ?
Cl2 Lu1 Cl1 87.91(4) . . ?
Cl2 Lu1 Cl1 92.09(4) . 2 ?
Cl2 Lu1 Cl2 178.33(3) 2 . ?
N1 Lu1 Cl1 90.227(13) . . ?
N1 Lu1 Cl1 90.226(12) . 2 ?
N1 Lu1 Cl2 90.836(14) . . ?
N1 Lu1 Cl2 90.835(14) . 2 ?
N1 Lu1 N2 180.0 . 1_545 ?
N2 Lu1 Cl1 89.773(13) 1_545 . ?
N2 Lu1 Cl1 89.774(13) 1_545 2 ?
N2 Lu1 Cl2 89.165(14) 1_545 2 ?
N2 Lu1 Cl2 89.164(14) 1_545 . ?
C1 N1 Lu1 122.33(14) . . ?
C1 N1 Lu1 122.33(14) 2 . ?
C1 N1 C1 115.3(3) 2 . ?
C6 N2 Lu1 121.61(14) . 1_565 ?
C6 N2 Lu1 121.61(14) 2 1_565 ?
C6 N2 C6 116.8(3) 2 . ?
C2 C3 C4 121.85(15) . . ?
C2 C3 C4 121.85(15) 2 . ?
C2 C3 C2 116.3(3) 2 . ?
N1 C1 H1 117.9 . . ?
N1 C1 C2 124.2(2) . . ?
C2 C1 H1 117.9 . . ?
C5 C4 C3 121.75(14) 2 . ?
C5 C4 C3 121.75(14) . . ?
C5 C4 C5 116.5(3) . 2 ?
N2 C6 H6 118.3 . . ?
N2 C6 C5 123.4(2) . . ?
C5 C6 H6 118.3 . . ?
C3 C2 H2 120.0 . . ?
C1 C2 C3 120.0(2) . . ?
C1 C2 H2 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0(2) . . ?
C6 C5 H5 120.0 . . ?
C7 N3 H3 120.0 . . ?
C7 N3 C11 120.1(2) . . ?
C11 N3 H3 120.0 . . ?
C9 C10 H10 120.5 . . ?
C11 C10 H10 120.5 . . ?
C11 C10 C9 119.0(3) . . ?
C9 C8 H8 120.5 . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(3) . . ?
C10 C9 C8 119.3(3) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N3 C7 C8 121.3(3) . . ?
N3 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
N3 C11 C10 121.4(3) . . ?
N3 C11 H11 119.3 . . ?
C10 C11 H11 119.3 . . ?

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
Lu1 N1 C1 C2 179.6(2) . . . . ?
Lu1 N2 C6 C5 -179.50(18) 1_565 . . . ?
N1 C1 C2 C3 0.9(4) . . . . ?
N2 C6 C5 C4 -1.0(4) . . . . ?
C3 C4 C5 C6 -179.54(17) . . . . ?
C1 N1 C1 C2 -0.4(2) 2 . . . ?
C4 C3 C2 C1 179.60(18) . . . . ?
C6 N2 C6 C5 0.50(18) 2 . . . ?
C2 C3 C4 C5 19.42(17) . . . 2 ?
C2 C3 C4 C5 -160.58(17) . . . . ?
C2 C3 C4 C5 -160.58(17) 2 . . 2 ?
C2 C3 C4 C5 19.42(17) 2 . . . ?
C2 C3 C2 C1 -0.40(18) 2 . . . ?
C5 C4 C5 C6 0.46(17) 2 . . . ?
C9 C10 C11 N3 -0.4(4) . . . . ?
C9 C8 C7 N3 0.3(4) . . . . ?
C7 N3 C11 C10 -0.1(4) . . . . ?
C7 C8 C9 C10 -0.8(4) . . . . ?
C11 N3 C7 C8 0.1(4) . . . . ?
C11 C10 C9 C8 0.9(4) . . . . ?

_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_compound9
_database_code_depnum_ccdc_archive 'CCDC 1554521'
_audit_update_record             
;
2018-03-28 deposited with the CCDC.
2018-04-25 downloaded from the CCDC.
;
_audit_creation_date             2018-03-26
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2018/1

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'0.5(C60 H48 Cl16 N12 Sm4), 2(C5 H6 N), 2(C10 H8 N2)'
_chemical_formula_sum            'C60 H52 Cl8 N12 Sm2'
_chemical_formula_weight         1525.43
_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'
Sm Sm -0.1638 3.4418 '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                   8.7594(4)
_cell_length_b                   20.0090(9)
_cell_length_c                   17.2945(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.8550(10)
_cell_angle_gamma                90
_cell_volume                     3027.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9919
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.37
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.324
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. 
wR2(int) was 0.0735 before and 0.0541 after correction. 
The Ratio of minimum to maximum transmission is 0.8276. 
The λ/2 correction factor is 0.0015.'
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.673
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1512
_exptl_crystal_size_max          0.433
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.189
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0653
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            48005
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.086
_diffrn_reflns_theta_min         1.557
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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                6477
_reflns_number_total             8676
_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+ ver. 7.68A (Bruker AXS)'
_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. 7.68A (Bruker AXS)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.761
_refine_diff_density_min         -1.748
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     478
_refine_ls_number_reflns         8676
_refine_ls_number_restraints     144
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0334
_refine_ls_restrained_S_all      1.003
_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)+(0.0159P)²+3.9233P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0522
_refine_ls_wR_factor_ref         0.0601
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Uiso/Uaniso restraints and constraints
C23A \\sim C24A \\sim C22A \\sim C26A \\sim C25A \\sim N6A: within 2A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C23B \\sim C24B \\sim C22B \\sim C25B \\sim C26B \\sim N6B: within 2A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C27A \\sim C28A \\sim C21A \\sim C30A \\sim C29A \\sim N5A: within 2A with
sigma of 0.004 and sigma for terminal atoms of 0.008
C27B \\sim C28B \\sim C21B \\sim C30B \\sim C29B \\sim N5B: within 2A with
sigma of 0.004 and sigma for terminal atoms of 0.008
3. Others
 Fixed Sof: C25B(0.5) H25B(0.5) C26A(0.5) H26A(0.5) C26B(0.5) H26B(0.5)
 C25A(0.5) H25A(0.5) C24B(0.5) H24B(0.5) C24A(0.5) H24A(0.5) C23B(0.5)
 H23B(0.5) C23A(0.5) H23A(0.5) C28A(0.5) H28A(0.5) C30B(0.5) H30B(0.5)
 C30A(0.5) H30A(0.5) C29B(0.5) H29B(0.5) C29A(0.5) H29A(0.5) C28B(0.5)
 H28B(0.5) C27B(0.5) H27B(0.5) N6B(0.5) N6A(0.5) N5B(0.5) C27A(0.5) H27A(0.5)
 N5A(0.5) C22A(0.5) C21A(0.5) C22B(0.5) C21B(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5), C15(H15), C1(H1), C11(H11), C10(H10), C12(H12), C14(H14),
 C2(H2), C4(H4), C7(H7), C9(H9), N4(H4A), C16(H16), C17(H17), C18(H18),
 C20(H20), C19(H19), C25B(H25B), C26A(H26A), C26B(H26B), C25A(H25A), C24B(H24B),
  C24A(H24A), C23B(H23B), C23A(H23A), C28A(H28A), C30B(H30B), C30A(H30A),
 C29B(H29B), C29A(H29A), C28B(H28B), C27B(H27B), C27A(H27A)
;
_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
Sm1 Sm 0.51834(2) 0.69702(2) 0.34988(2) 0.00798(4) Uani 1 1 d . . . . .
Cl3 Cl 0.59441(8) 0.62008(4) 0.22923(4) 0.01652(15) Uani 1 1 d . . . . .
Cl4 Cl 0.33416(8) 0.60900(4) 0.41557(4) 0.01778(16) Uani 1 1 d . . . . .
Cl2 Cl 0.34417(8) 0.79077(3) 0.41905(4) 0.01232(15) Uani 1 1 d . . . . .
Cl1 Cl 0.65031(8) 0.79513(4) 0.27062(4) 0.01286(14) Uani 1 1 d . . . . .
N2 N 0.7027(3) 0.74912(12) 0.45471(13) 0.0114(5) Uani 1 1 d . . . . .
N3 N 0.7239(3) 0.61082(12) 0.41130(14) 0.0147(5) Uani 1 1 d . . . . .
N1 N 0.2921(3) 0.71432(12) 0.24948(13) 0.0110(5) Uani 1 1 d . . . . .
C6 C 0.7181(3) 0.59199(16) 0.48524(18) 0.0189(7) Uani 1 1 d . . . . .
H6 H 0.638901 0.608592 0.513552 0.023 Uiso 1 1 calc R . . . .
C5 C 0.8508(3) 0.75532(16) 0.43886(16) 0.0150(6) Uani 1 1 d . . . . .
H5 H 0.876160 0.754566 0.387280 0.018 Uiso 1 1 calc R . . . .
C15 C 0.3215(3) 0.72261(16) 0.17479(16) 0.0159(6) Uani 1 1 d . . . . .
H15 H 0.423063 0.723629 0.161535 0.019 Uiso 1 1 calc R . . . .
C1 C 0.6701(3) 0.75338(16) 0.52905(16) 0.0144(6) Uani 1 1 d . . . . .
H1 H 0.568116 0.750991 0.541351 0.017 Uiso 1 1 calc R . . . .
C11 C 0.1444(3) 0.71416(15) 0.26692(16) 0.0145(6) Uani 1 1 d . . . . .
H11 H 0.121160 0.709208 0.318495 0.017 Uiso 1 1 calc R . . . .
C10 C 0.8408(3) 0.58633(16) 0.37271(18) 0.0183(7) Uani 1 1 d . . . . .
H10 H 0.848500 0.598655 0.321206 0.022 Uiso 1 1 calc R . . . .
C3 C 0.9326(3) 0.76469(14) 0.57246(15) 0.0097(6) Uani 1 1 d . . . . .
C12 C 0.0250(3) 0.72097(16) 0.21209(16) 0.0149(6) Uani 1 1 d . . . . .
H12 H -0.075506 0.720495 0.227038 0.018 Uiso 1 1 calc R . . . .
C13 C 0.0561(3) 0.72857(14) 0.13426(16) 0.0105(6) Uani 1 1 d . . . . .
C14 C 0.2092(3) 0.72973(16) 0.11633(16) 0.0153(6) Uani 1 1 d . . . . .
H14 H 0.235768 0.735272 0.065333 0.018 Uiso 1 1 calc R . . . .
C8 C 0.9431(3) 0.52358(15) 0.48192(18) 0.0146(6) Uani 1 1 d . . . . .
C2 C 0.7795(3) 0.76114(16) 0.58895(17) 0.0152(6) Uani 1 1 d . . . . .
H2 H 0.750482 0.763950 0.639849 0.018 Uiso 1 1 calc R . . . .
C4 C 0.9670(3) 0.76273(16) 0.49481(16) 0.0158(6) Uani 1 1 d . . . . .
H4 H 1.067753 0.766394 0.480794 0.019 Uiso 1 1 calc R . . . .
C7 C 0.8225(4) 0.54931(16) 0.52241(18) 0.0197(7) Uani 1 1 d . . . . .
H7 H 0.812250 0.537900 0.574019 0.024 Uiso 1 1 calc R . . . .
C9 C 0.9504(3) 0.54380(16) 0.40537(18) 0.0197(7) Uani 1 1 d . . . . .
H9 H 1.029331 0.528633 0.375928 0.024 Uiso 1 1 calc R . . . .
N4 N 0.4716(4) 0.54974(14) 0.76032(16) 0.0291(7) Uani 1 1 d . . . . .
H4A H 0.520625 0.538236 0.802544 0.035 Uiso 1 1 calc R . . . .
C16 C 0.5162(5) 0.52488(18) 0.6929(2) 0.0345(10) Uani 1 1 d . . . . .
H16 H 0.598298 0.495444 0.692227 0.041 Uiso 1 1 calc R . . . .
C17 C 0.4402(5) 0.5432(2) 0.6255(2) 0.0440(12) Uani 1 1 d . . . . .
H17 H 0.470918 0.526430 0.578546 0.053 Uiso 1 1 calc R . . . .
C18 C 0.3180(6) 0.5864(2) 0.6268(2) 0.0431(11) Uani 1 1 d . . . . .
H18 H 0.265531 0.599127 0.581062 0.052 Uiso 1 1 calc R . . . .
C20 C 0.3543(5) 0.59143(17) 0.7640(2) 0.0328(9) Uani 1 1 d . . . . .
H20 H 0.326526 0.607521 0.811743 0.039 Uiso 1 1 calc R . . . .
C19 C 0.2742(5) 0.61083(18) 0.6981(2) 0.0401(10) Uani 1 1 d . . . . .
H19 H 0.191733 0.639878 0.700587 0.048 Uiso 1 1 calc R . . . .
C25B C 0.7664(7) 0.5671(3) -0.0058(4) 0.0182(11) Uani 0.5 1 d . U P A 2
H25B H 0.813760 0.604747 0.015870 0.022 Uiso 0.5 1 calc R . P A 2
C26A C 0.7270(7) 0.5559(3) 0.0339(4) 0.0188(11) Uani 0.5 1 d . U P B 1
H26A H 0.733313 0.589462 0.071198 0.023 Uiso 0.5 1 calc R . P B 1
C26B C 0.6743(7) 0.5725(3) -0.0720(4) 0.0183(11) Uani 0.5 1 d . U P A 2
H26B H 0.661547 0.614567 -0.094195 0.022 Uiso 0.5 1 calc R . P A 2
C25A C 0.6376(8) 0.5650(3) -0.0331(4) 0.0195(11) Uani 0.5 1 d . U P B 1
H25A H 0.587195 0.605546 -0.040518 0.023 Uiso 0.5 1 calc R . P B 1
C24B C 0.7088(8) 0.4509(3) -0.0059(4) 0.0164(11) Uani 0.5 1 d . U P A 2
H24B H 0.717462 0.408274 0.015239 0.020 Uiso 0.5 1 calc R . P A 2
C24A C 0.7859(8) 0.4474(4) -0.0098(4) 0.0177(12) Uani 0.5 1 d . U P B 1
H24A H 0.834048 0.406219 -0.003095 0.021 Uiso 0.5 1 calc R . P B 1
C23B C 0.6181(8) 0.4620(4) -0.0715(4) 0.0174(12) Uani 0.5 1 d . U P A 2
H23B H 0.564008 0.425951 -0.092913 0.021 Uiso 0.5 1 calc R . P A 2
C23A C 0.6925(8) 0.4597(4) -0.0750(4) 0.0190(12) Uani 0.5 1 d . U P B 1
H23A H 0.679514 0.425772 -0.111519 0.023 Uiso 0.5 1 calc R . P B 1
C28A C 0.9911(8) 0.5421(4) 0.1493(5) 0.0203(13) Uani 0.5 1 d . U P B 1
H28A H 0.973298 0.585099 0.130596 0.024 Uiso 0.5 1 calc R . P B 1
C30B C 0.9686(8) 0.4363(4) 0.1140(4) 0.0183(13) Uani 0.5 1 d . U P A 2
H30B H 0.951486 0.399770 0.081408 0.022 Uiso 0.5 1 calc R . P A 2
C30A C 0.9494(8) 0.4245(4) 0.1458(4) 0.0196(13) Uani 0.5 1 d . U P B 1
H30A H 0.903276 0.386208 0.124962 0.024 Uiso 0.5 1 calc R . P B 1
C29B C 1.0702(9) 0.4309(4) 0.1774(4) 0.0220(13) Uani 0.5 1 d . U P A 2
H29B H 1.119842 0.390253 0.185954 0.026 Uiso 0.5 1 calc R . P A 2
C29A C 1.0532(9) 0.4202(4) 0.2094(4) 0.0211(13) Uani 0.5 1 d . U P B 1
H29A H 1.073251 0.377965 0.229833 0.025 Uiso 0.5 1 calc R . P B 1
C28B C 0.9238(8) 0.5475(4) 0.1498(4) 0.0173(13) Uani 0.5 1 d . U P A 2
H28B H 0.875223 0.588542 0.142536 0.021 Uiso 0.5 1 calc R . P A 2
C27B C 1.0278(8) 0.5386(4) 0.2119(5) 0.0211(14) Uani 0.5 1 d . U P A 2
H27B H 1.047423 0.574842 0.244507 0.025 Uiso 0.5 1 calc R . P A 2
N6B N 0.6023(14) 0.5213(6) -0.1065(5) 0.0182(14) Uani 0.5 1 d . U P A 2
N6A N 0.6196(13) 0.5178(7) -0.0886(5) 0.0197(15) Uani 0.5 1 d . U P B 1
N5B N 1.1018(12) 0.4817(6) 0.2283(6) 0.0223(15) Uani 0.5 1 d . U P A 2
C27A C 1.0908(9) 0.5313(5) 0.2115(5) 0.0232(14) Uani 0.5 1 d . U P B 1
H27A H 1.138750 0.568486 0.233943 0.028 Uiso 0.5 1 calc R . P B 1
N5A N 1.1251(12) 0.4710(5) 0.2430(6) 0.0235(15) Uani 0.5 1 d . U P B 1
C22A C 0.8073(13) 0.4971(6) 0.0458(5) 0.0156(15) Uani 0.5 1 d . U P B 1
C21A C 0.9159(12) 0.4871(6) 0.1141(6) 0.0175(16) Uani 0.5 1 d . U P B 1
C22B C 0.7883(13) 0.5045(6) 0.0286(5) 0.0161(15) Uani 0.5 1 d . U P A 2
C21B C 0.8921(12) 0.4960(6) 0.0986(6) 0.0161(15) Uani 0.5 1 d . U P A 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
Sm1 Cl3 2.7031(7) . ?
Sm1 Cl4 2.6792(7) . ?
Sm1 Cl2 2.7311(7) . ?
Sm1 Cl1 2.6882(7) . ?
Sm1 N2 2.587(2) . ?
Sm1 N3 2.675(2) . ?
Sm1 N1 2.592(2) . ?
N2 C5 1.345(3) . ?
N2 C1 1.333(3) . ?
N3 C6 1.336(4) . ?
N3 C10 1.342(4) . ?
N1 C15 1.340(3) . ?
N1 C11 1.343(3) . ?
C6 C7 1.386(4) . ?
C5 C4 1.377(4) . ?
C15 C14 1.382(4) . ?
C1 C2 1.384(4) . ?
C11 C12 1.383(4) . ?
C10 C9 1.382(4) . ?
C3 C13 1.489(4) 4_676 ?
C3 C2 1.387(4) . ?
C3 C4 1.392(4) . ?
C12 C13 1.395(4) . ?
C13 C14 1.391(4) . ?
C8 C8 1.488(6) 3_766 ?
C8 C7 1.394(4) . ?
C8 C9 1.389(4) . ?
N4 C16 1.344(4) . ?
N4 C20 1.327(5) . ?
C16 C17 1.364(6) . ?
C17 C18 1.378(6) . ?
C18 C19 1.398(5) . ?
C20 C19 1.364(5) . ?
C25B C26B 1.372(9) . ?
C25B C22B 1.396(12) . ?
C26A C25A 1.379(9) . ?
C26A C22A 1.380(12) . ?
C26B N6B 1.329(13) . ?
C25A N6A 1.350(13) . ?
C24B C23B 1.369(9) . ?
C24B C22B 1.396(14) . ?
C24A C23A 1.383(10) . ?
C24A C22A 1.389(13) . ?
C23B N6B 1.336(13) . ?
C23A N6A 1.341(14) . ?
C28A C27A 1.369(11) . ?
C28A C21A 1.405(13) . ?
C30B C29B 1.382(10) . ?
C30B C21B 1.389(11) . ?
C30A C29A 1.395(10) . ?
C30A C21A 1.393(12) . ?
C29B N5B 1.364(13) . ?
C29A N5A 1.315(13) . ?
C28B C27B 1.385(10) . ?
C28B C21B 1.378(14) . ?
C27B N5B 1.333(11) . ?
C27A N5A 1.351(12) . ?
C22A C21A 1.493(12) . ?
C22B C21B 1.488(12) . ?

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 Sm1 Cl2 153.36(2) . . ?
Cl4 Sm1 Cl3 97.45(2) . . ?
Cl4 Sm1 Cl2 84.52(2) . . ?
Cl4 Sm1 Cl1 168.40(2) . . ?
Cl1 Sm1 Cl3 83.88(2) . . ?
Cl1 Sm1 Cl2 89.18(2) . . ?
N2 Sm1 Cl3 126.96(5) . . ?
N2 Sm1 Cl4 109.62(5) . . ?
N2 Sm1 Cl2 76.06(5) . . ?
N2 Sm1 Cl1 78.10(5) . . ?
N2 Sm1 N3 66.24(8) . . ?
N2 Sm1 N1 147.73(8) . . ?
N3 Sm1 Cl3 75.66(6) . . ?
N3 Sm1 Cl4 79.36(5) . . ?
N3 Sm1 Cl2 130.44(6) . . ?
N3 Sm1 Cl1 112.04(5) . . ?
N1 Sm1 Cl3 76.62(5) . . ?
N1 Sm1 Cl4 85.15(5) . . ?
N1 Sm1 Cl2 77.09(5) . . ?
N1 Sm1 Cl1 83.96(5) . . ?
N1 Sm1 N3 146.01(7) . . ?
C5 N2 Sm1 117.98(18) . . ?
C1 N2 Sm1 123.05(18) . . ?
C1 N2 C5 116.5(2) . . ?
C6 N3 Sm1 120.31(19) . . ?
C6 N3 C10 116.1(3) . . ?
C10 N3 Sm1 123.58(19) . . ?
C15 N1 Sm1 119.02(18) . . ?
C15 N1 C11 116.7(2) . . ?
C11 N1 Sm1 124.21(18) . . ?
N3 C6 C7 124.2(3) . . ?
N2 C5 C4 123.6(3) . . ?
N1 C15 C14 123.6(3) . . ?
N2 C1 C2 123.7(3) . . ?
N1 C11 C12 123.4(3) . . ?
N3 C10 C9 123.6(3) . . ?
C2 C3 C13 122.2(2) . 4_676 ?
C2 C3 C4 117.1(3) . . ?
C4 C3 C13 120.7(2) . 4_676 ?
C11 C12 C13 119.7(3) . . ?
C12 C13 C3 122.2(2) . 4_475 ?
C14 C13 C3 120.8(2) . 4_475 ?
C14 C13 C12 117.0(3) . . ?
C15 C14 C13 119.6(3) . . ?
C7 C8 C8 122.1(3) . 3_766 ?
C9 C8 C8 121.6(3) . 3_766 ?
C9 C8 C7 116.3(3) . . ?
C1 C2 C3 119.5(3) . . ?
C5 C4 C3 119.6(3) . . ?
C6 C7 C8 119.6(3) . . ?
C10 C9 C8 120.3(3) . . ?
C20 N4 C16 122.2(4) . . ?
N4 C16 C17 119.5(4) . . ?
C16 C17 C18 120.1(3) . . ?
C17 C18 C19 118.8(4) . . ?
N4 C20 C19 120.4(3) . . ?
C20 C19 C18 119.0(4) . . ?
C26B C25B C22B 119.3(7) . . ?
C25A C26A C22A 120.0(7) . . ?
N6B C26B C25B 124.1(7) . . ?
N6A C25A C26A 123.2(7) . . ?
C23B C24B C22B 119.1(7) . . ?
C23A C24A C22A 119.4(7) . . ?
N6B C23B C24B 124.2(7) . . ?
N6A C23A C24A 123.7(7) . . ?
C27A C28A C21A 119.0(7) . . ?
C29B C30B C21B 120.3(8) . . ?
C21A C30A C29A 118.8(7) . . ?
N5B C29B C30B 123.8(7) . . ?
N5A C29A C30A 125.5(7) . . ?
C21B C28B C27B 120.3(7) . . ?
N5B C27B C28B 124.7(8) . . ?
C26B N6B C23B 116.4(7) . . ?
C23A N6A C25A 116.3(7) . . ?
C27B N5B C29B 114.7(8) . . ?
N5A C27A C28A 125.3(8) . . ?
C29A N5A C27A 114.8(8) . . ?
C26A C22A C24A 117.2(8) . . ?
C26A C22A C21A 122.2(10) . . ?
C24A C22A C21A 120.6(9) . . ?
C28A C21A C22A 120.2(9) . . ?
C30A C21A C28A 116.7(7) . . ?
C30A C21A C22A 123.1(10) . . ?
C25B C22B C24B 116.9(7) . . ?
C25B C22B C21B 121.0(10) . . ?
C24B C22B C21B 122.1(9) . . ?
C30B C21B C22B 121.6(10) . . ?
C28B C21B C30B 116.2(8) . . ?
C28B C21B C22B 122.1(9) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
