# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2022

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

data_1-Cl
_database_code_depnum_ccdc_archive 'CCDC 2190606'
loop_
_audit_author_name
_audit_author_address
'Andreas Stoy'
;University of Marburg
Germany
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C57 H37 B Bi Cl2 F24 N5'
_chemical_formula_sum            'C57 H37 B Bi Cl2 F24 N5'
_chemical_formula_weight         1538.60

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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 '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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   12.1154(11)
_cell_length_b                   34.301(3)
_cell_length_c                   14.2847(14)
_cell_angle_alpha                90
_cell_angle_beta                 92.730(4)
_cell_angle_gamma                90
_cell_volume                     5929.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6272
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      25.43


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_F_000             3008
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.098
_exptl_crystal_size_min          0.065
_exptl_absorpt_coefficient_mu    3.182
_shelx_estimated_absorpt_T_min   0.701
_shelx_estimated_absorpt_T_max   0.820
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2641
_exptl_absorpt_correction_T_max  0.3361
_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon II)'
_diffrn_detector_area_resol_mean 7.5
_diffrn_reflns_number            51721
_diffrn_reflns_av_unetI/netI     0.1525
_diffrn_reflns_av_R_equivalents  0.1638
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.235
_diffrn_reflns_theta_max         26.071
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11673
_reflns_number_gt                6886
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.37A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.37A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger. The atomic displacement parameters of 
atoms C24, F13, F14, F15 were restraint with RIGU keyword in ShelXL input ('enhanced rigid 
bond' restraint for all bonds in the connectivity list. Standard values of 
0.004 for both parameters s1 and s2 were used).
The displacement parameters of atoms C24, F13, F14, F15 were 
restrained to the same value with similarity restraint SIMU.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0313P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11673
_refine_ls_number_parameters     811
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0594
_refine_ls_wR_factor_ref         0.1167
_refine_ls_wR_factor_gt          0.0938
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.44505(3) 0.13209(2) 0.38020(2) 0.01794(9) Uani 1 1 d . . . . .
F1 F 0.8083(4) 0.37184(16) 0.3992(3) 0.0413(14) Uani 1 1 d . . . . .
N1 N 0.3373(6) 0.06871(19) 0.3669(5) 0.0224(17) Uani 1 1 d . . . . .
C1 C 0.4618(6) 0.3821(2) 0.4078(5) 0.0153(18) Uani 1 1 d . . . . .
Cl1 Cl 0.58197(18) 0.10158(7) 0.51227(16) 0.0317(5) Uani 1 1 d . . . . .
B1 B 0.3719(8) 0.3919(3) 0.3204(7) 0.018(2) Uani 1 1 d . . . . .
Cl2 Cl 0.30233(17) 0.16643(6) 0.26315(14) 0.0235(5) Uani 1 1 d . . . . .
F2 F 0.8180(4) 0.33608(15) 0.5211(3) 0.0356(13) Uani 1 1 d . . . . .
N2 N 0.2907(5) 0.1367(2) 0.5007(4) 0.0216(16) Uani 1 1 d . . . . .
C2 C 0.5693(6) 0.3699(2) 0.3954(5) 0.0187(17) Uani 1 1 d . . . . .
H2 H 0.5955 0.3702 0.3338 0.022 Uiso 1 1 calc R U . . .
N4 N 0.6054(6) 0.1740(2) 0.3152(5) 0.0248(17) Uani 1 1 d . . . . .
F4 F 0.5261(4) 0.35386(17) 0.7347(3) 0.0475(16) Uani 1 1 d . . . . .
C4 C 0.6072(7) 0.3582(2) 0.5591(5) 0.022(2) Uani 1 1 d . . . . .
H4 H 0.6558 0.3502 0.6097 0.026 Uiso 1 1 calc R U . . .
C3 C 0.6404(6) 0.3574(2) 0.4681(5) 0.0146(18) Uani 1 1 d . . . . .
F3 F 0.7525(4) 0.31323(16) 0.3910(4) 0.0513(17) Uani 1 1 d . . . . .
N3 N 0.4582(5) 0.19863(19) 0.4687(4) 0.0202(16) Uani 1 1 d . . . . .
N5 N 0.5220(6) 0.09715(18) 0.2401(5) 0.0223(17) Uani 1 1 d . . . . .
F5 F 0.3598(4) 0.35934(15) 0.6799(3) 0.0366(14) Uani 1 1 d . . . . .
C5 C 0.5003(6) 0.3711(2) 0.5752(5) 0.0163(17) Uani 1 1 d . . . . .
C6 C 0.4307(7) 0.3823(2) 0.5018(6) 0.021(2) Uani 1 1 d . . . . .
H6 H 0.3582 0.3907 0.5148 0.025 Uiso 1 1 calc R U . . .
F6 F 0.4583(5) 0.41031(15) 0.7027(3) 0.0410(14) Uani 1 1 d . . . . .
C7 C 0.7525(7) 0.3449(3) 0.4455(6) 0.024(2) Uani 1 1 d . . . . .
F7 F 0.3384(5) 0.28604(15) 0.0622(3) 0.0504(17) Uani 1 1 d . . . . .
F8 F 0.4164(4) 0.24553(15) 0.1563(4) 0.0411(14) Uani 1 1 d . . . . .
C8 C 0.4627(7) 0.3737(3) 0.6725(6) 0.030(2) Uani 1 1 d . . . . .
F9 F 0.2464(4) 0.23720(15) 0.1120(4) 0.0422(15) Uani 1 1 d . . . . .
C9 C 0.3068(6) 0.3507(2) 0.3000(5) 0.0155(18) Uani 1 1 d . . . . .
C10 C 0.3396(7) 0.3241(2) 0.2343(6) 0.0200(19) Uani 1 1 d . . . . .
H10 H 0.4013 0.3303 0.1984 0.024 Uiso 1 1 calc R U . . .
F10 F 0.1047(6) 0.25567(17) 0.4497(5) 0.081(2) Uani 1 1 d . . . . .
C11 C 0.2869(7) 0.2889(2) 0.2184(5) 0.0189(19) Uani 1 1 d . . . . .
F11 F -0.0135(5) 0.2841(2) 0.3598(4) 0.086(3) Uani 1 1 d . . . . .
C12 C 0.2039(7) 0.2764(2) 0.2741(6) 0.026(2) Uani 1 1 d . . . . .
H12 H 0.1697 0.2517 0.2647 0.031 Uiso 1 1 calc R U . . .
F12 F 0.0611(5) 0.31373(17) 0.4737(4) 0.0557(17) Uani 1 1 d . . . . .
C13 C 0.1726(7) 0.3014(2) 0.3447(6) 0.0192(19) Uani 1 1 d . . . . .
F13 F -0.0387(5) 0.43108(18) 0.2531(5) 0.0744(19) Uani 1 1 d . U . . .
C14 C 0.2215(6) 0.3382(2) 0.3564(5) 0.0146(18) Uani 1 1 d . . . . .
H14 H 0.1965 0.3552 0.4036 0.018 Uiso 1 1 calc R U . . .
F14 F -0.0736(5) 0.4651(2) 0.3691(4) 0.0669(17) Uani 1 1 d . U . . .
C17 C 0.2896(6) 0.4272(2) 0.3471(5) 0.0149(18) Uani 1 1 d . . . . .
F17 F 0.2477(5) 0.55718(15) 0.4692(5) 0.066(2) Uani 1 1 d . . . . .
C16 C 0.0823(8) 0.2891(3) 0.4064(7) 0.032(2) Uani 1 1 d . . . . .
F16 F 0.3397(6) 0.51711(17) 0.5553(4) 0.066(2) Uani 1 1 d . . . . .
C15 C 0.3205(8) 0.2644(3) 0.1380(7) 0.030(2) Uani 1 1 d . . . . .
F15 F -0.0335(4) 0.49246(17) 0.2464(4) 0.0597(17) Uani 1 1 d . U . . .
C18 C 0.1779(6) 0.4294(2) 0.3145(5) 0.0178(19) Uani 1 1 d . . . . .
H18 H 0.1468 0.4081 0.2799 0.021 Uiso 1 1 calc R U . . .
F18 F 0.4078(4) 0.53826(15) 0.4335(4) 0.0502(17) Uani 1 1 d . . . . .
C19 C 0.1115(6) 0.4615(2) 0.3312(5) 0.0177(19) Uani 1 1 d . . . . .
F19 F 0.7357(4) 0.46773(15) 0.2512(4) 0.0433(15) Uani 1 1 d . . . . .
C20 C 0.1538(7) 0.4939(2) 0.3802(6) 0.021(2) Uani 1 1 d . . . . .
H20 H 0.1089 0.5160 0.3907 0.025 Uiso 1 1 calc R U . . .
F20 F 0.7255(5) 0.48601(18) 0.1085(4) 0.0587(19) Uani 1 1 d . . . . .
C21 C 0.2634(7) 0.4928(2) 0.4128(6) 0.0189(19) Uani 1 1 d . . . . .
F21 F 0.6281(4) 0.51394(15) 0.2113(4) 0.0503(17) Uani 1 1 d . . . . .
C22 C 0.3285(7) 0.4599(2) 0.3975(5) 0.0181(19) Uani 1 1 d . . . . .
H22 H 0.4026 0.4597 0.4224 0.022 Uiso 1 1 calc R U . . .
F22 F 0.4934(5) 0.40892(19) -0.0986(3) 0.0590(19) Uani 1 1 d . . . . .
C23 C 0.3121(7) 0.5263(3) 0.4665(7) 0.029(2) Uani 1 1 d . . . . .
F23 F 0.3856(5) 0.36625(17) -0.0429(3) 0.0568(17) Uani 1 1 d . . . . .
C24 C -0.0056(7) 0.4624(3) 0.2988(8) 0.0415(17) Uani 1 1 d . U . . .
F24 F 0.3279(5) 0.42398(18) -0.0704(4) 0.0565(17) Uani 1 1 d . . . . .
C26 C 0.5226(6) 0.4347(2) 0.2399(5) 0.0185(19) Uani 1 1 d . . . . .
H26 H 0.5487 0.4418 0.3013 0.022 Uiso 1 1 calc R U . . .
C25 C 0.4342(6) 0.4086(2) 0.2294(5) 0.0150(18) Uani 1 1 d . . . . .
C28 C 0.5405(7) 0.4410(2) 0.0737(5) 0.019(2) Uani 1 1 d . . . . .
H28 H 0.5773 0.4516 0.0222 0.023 Uiso 1 1 calc R U . . .
C27 C 0.5737(7) 0.4506(2) 0.1641(6) 0.021(2) Uani 1 1 d . . . . .
C29 C 0.4530(6) 0.4158(2) 0.0592(5) 0.0156(18) Uani 1 1 d . . . . .
C30 C 0.4003(6) 0.4006(2) 0.1359(5) 0.0160(18) Uani 1 1 d . . . . .
H30 H 0.3382 0.3841 0.1243 0.019 Uiso 1 1 calc R U . . .
C31 C 0.6655(7) 0.4795(3) 0.1826(6) 0.029(2) Uani 1 1 d . . . . .
C32 C 0.4158(8) 0.4036(3) -0.0369(6) 0.027(2) Uani 1 1 d . . . . .
C33 C 0.3771(7) 0.0353(2) 0.4034(6) 0.025(2) Uani 1 1 d . . . . .
H33 H 0.4487 0.0355 0.4336 0.030 Uiso 1 1 calc R U . . .
C34 C 0.3196(8) 0.0008(2) 0.3996(6) 0.030(2) Uani 1 1 d . . . . .
H34 H 0.3500 -0.0222 0.4278 0.036 Uiso 1 1 calc R U . . .
C35 C 0.2171(8) 0.0001(3) 0.3540(6) 0.029(2) Uani 1 1 d . . . . .
H35 H 0.1761 -0.0234 0.3492 0.035 Uiso 1 1 calc R U . . .
C36 C 0.1746(7) 0.0338(3) 0.3158(6) 0.029(2) Uani 1 1 d . . . . .
H36 H 0.1038 0.0338 0.2842 0.035 Uiso 1 1 calc R U . . .
C37 C 0.2366(7) 0.0681(2) 0.3237(6) 0.023(2) Uani 1 1 d . . . . .
H37 H 0.2066 0.0915 0.2978 0.028 Uiso 1 1 calc R U . . .
C38 C 0.3069(7) 0.1210(2) 0.5854(6) 0.025(2) Uani 1 1 d . . . . .
H38 H 0.3636 0.1021 0.5945 0.030 Uiso 1 1 calc R U . . .
C39 C 0.2454(7) 0.1311(3) 0.6609(5) 0.028(2) Uani 1 1 d . . . . .
H39 H 0.2603 0.1196 0.7207 0.033 Uiso 1 1 calc R U . . .
C40 C 0.1628(7) 0.1578(2) 0.6475(6) 0.029(2) Uani 1 1 d . . . . .
H40 H 0.1201 0.1657 0.6982 0.035 Uiso 1 1 calc R U . . .
C41 C 0.1421(7) 0.1731(2) 0.5594(6) 0.028(2) Uani 1 1 d . . . . .
H41 H 0.0827 0.1908 0.5480 0.033 Uiso 1 1 calc R U . . .
C42 C 0.2082(7) 0.1625(2) 0.4879(6) 0.028(2) Uani 1 1 d . . . . .
H42 H 0.1950 0.1738 0.4277 0.033 Uiso 1 1 calc R U . . .
C43 C 0.4798(6) 0.1992(2) 0.5617(5) 0.0195(19) Uani 1 1 d . . . . .
H43 H 0.5002 0.1756 0.5928 0.023 Uiso 1 1 calc R U . . .
C44 C 0.4734(7) 0.2330(3) 0.6134(6) 0.029(2) Uani 1 1 d . . . . .
H44 H 0.4883 0.2327 0.6793 0.035 Uiso 1 1 calc R U . . .
C45 C 0.4449(7) 0.2673(2) 0.5676(6) 0.030(2) Uani 1 1 d . . . . .
H45 H 0.4377 0.2909 0.6019 0.036 Uiso 1 1 calc R U . . .
C46 C 0.4271(7) 0.2670(2) 0.4718(7) 0.030(2) Uani 1 1 d . . . . .
H46 H 0.4101 0.2904 0.4385 0.036 Uiso 1 1 calc R U . . .
C47 C 0.4346(7) 0.2320(2) 0.4251(6) 0.023(2) Uani 1 1 d . . . . .
H47 H 0.4224 0.2318 0.3589 0.028 Uiso 1 1 calc R U . . .
C48 C 0.6892(7) 0.1858(2) 0.3716(6) 0.028(2) Uani 1 1 d . . . . .
H48 H 0.6993 0.1741 0.4316 0.033 Uiso 1 1 calc R U . . .
C49 C 0.7619(7) 0.2143(3) 0.3468(6) 0.038(3) Uani 1 1 d . . . . .
H49 H 0.8206 0.2222 0.3890 0.045 Uiso 1 1 calc R U . . .
C50 C 0.7480(7) 0.2309(3) 0.2602(6) 0.033(2) Uani 1 1 d . . . . .
H50 H 0.7966 0.2510 0.2424 0.040 Uiso 1 1 calc R U . . .
C51 C 0.6649(8) 0.2189(3) 0.1989(6) 0.034(2) Uani 1 1 d . . . . .
H51 H 0.6559 0.2298 0.1379 0.041 Uiso 1 1 calc R U . . .
C52 C 0.5939(7) 0.1901(2) 0.2290(6) 0.024(2) Uani 1 1 d . . . . .
H52 H 0.5353 0.1816 0.1875 0.029 Uiso 1 1 calc R U . . .
C53 C 0.4709(7) 0.0991(2) 0.1550(6) 0.024(2) Uani 1 1 d . . . . .
H53 H 0.3984 0.1096 0.1493 0.028 Uiso 1 1 calc R U . . .
C54 C 0.5195(7) 0.0863(2) 0.0753(6) 0.025(2) Uani 1 1 d . . . . .
H54 H 0.4807 0.0880 0.0161 0.030 Uiso 1 1 calc R U . . .
C55 C 0.6250(7) 0.0710(2) 0.0821(6) 0.024(2) Uani 1 1 d . . . . .
H55 H 0.6605 0.0624 0.0279 0.029 Uiso 1 1 calc R U . . .
C56 C 0.6773(7) 0.0686(2) 0.1696(6) 0.027(2) Uani 1 1 d . . . . .
H56 H 0.7499 0.0582 0.1769 0.032 Uiso 1 1 calc R U . . .
C57 C 0.6234(7) 0.0814(2) 0.2461(6) 0.022(2) Uani 1 1 d . . . . .
H57 H 0.6596 0.0790 0.3062 0.027 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N1 2.539(7) . ?
Bi1 N5 2.547(7) . ?
Bi1 N2 2.606(6) . ?
Bi1 N3 2.611(6) . ?
Bi1 N4 2.621(7) . ?
Bi1 Cl2 2.626(2) . ?
Bi1 Cl1 2.666(2) . ?
F1 C7 1.340(9) . ?
N1 C33 1.339(10) . ?
N1 C37 1.341(10) . ?
C1 C2 1.388(10) . ?
C1 C6 1.412(10) . ?
C1 B1 1.652(12) . ?
B1 C17 1.625(11) . ?
B1 C25 1.636(12) . ?
B1 C9 1.639(12) . ?
F2 C7 1.343(9) . ?
N2 C38 1.330(10) . ?
N2 C42 1.340(10) . ?
C2 C3 1.387(10) . ?
C2 H2 0.9500 . ?
N4 C48 1.330(10) . ?
N4 C52 1.352(10) . ?
F4 C8 1.333(9) . ?
C4 C3 1.379(10) . ?
C4 C5 1.398(11) . ?
C4 H4 0.9500 . ?
C3 C7 1.475(11) . ?
F3 C7 1.336(9) . ?
N3 C47 1.329(9) . ?
N3 C43 1.341(9) . ?
N5 C53 1.340(10) . ?
N5 C57 1.341(10) . ?
F5 C8 1.350(10) . ?
C5 C6 1.368(10) . ?
C5 C8 1.487(11) . ?
C6 H6 0.9500 . ?
F6 C8 1.328(10) . ?
F7 C15 1.338(10) . ?
F8 C15 1.345(10) . ?
F9 C15 1.334(10) . ?
C9 C10 1.381(10) . ?
C9 C14 1.407(10) . ?
C10 C11 1.380(10) . ?
C10 H10 0.9500 . ?
F10 C16 1.325(10) . ?
C11 C12 1.379(11) . ?
C11 C15 1.496(11) . ?
F11 C16 1.322(10) . ?
C12 C13 1.392(11) . ?
C12 H12 0.9500 . ?
F12 C16 1.315(10) . ?
C13 C14 1.401(10) . ?
C13 C16 1.498(11) . ?
F13 C24 1.309(11) . ?
C14 H14 0.9500 . ?
F14 C24 1.332(11) . ?
C17 C22 1.402(10) . ?
C17 C18 1.412(10) . ?
F17 C23 1.318(10) . ?
F16 C23 1.334(10) . ?
F15 C24 1.310(11) . ?
C18 C19 1.390(10) . ?
C18 H18 0.9500 . ?
F18 C23 1.337(10) . ?
C19 C20 1.400(11) . ?
C19 C24 1.471(11) . ?
F19 C31 1.329(9) . ?
C20 C21 1.387(11) . ?
C20 H20 0.9500 . ?
F20 C31 1.331(10) . ?
C21 C22 1.400(10) . ?
C21 C23 1.487(11) . ?
F21 C31 1.337(10) . ?
C22 H22 0.9500 . ?
F22 C32 1.331(9) . ?
F23 C32 1.335(9) . ?
F24 C32 1.343(10) . ?
C26 C27 1.384(11) . ?
C26 C25 1.399(10) . ?
C26 H26 0.9500 . ?
C25 C30 1.405(10) . ?
C28 C27 1.374(10) . ?
C28 C29 1.376(11) . ?
C28 H28 0.9500 . ?
C27 C31 1.503(11) . ?
C29 C30 1.395(10) . ?
C29 C32 1.484(11) . ?
C30 H30 0.9500 . ?
C33 C34 1.375(11) . ?
C33 H33 0.9500 . ?
C34 C35 1.375(12) . ?
C34 H34 0.9500 . ?
C35 C36 1.366(12) . ?
C35 H35 0.9500 . ?
C36 C37 1.397(11) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C38 C39 1.384(11) . ?
C38 H38 0.9500 . ?
C39 C40 1.364(11) . ?
C39 H39 0.9500 . ?
C40 C41 1.375(11) . ?
C40 H40 0.9500 . ?
C41 C42 1.377(11) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C44 1.379(11) . ?
C43 H43 0.9500 . ?
C44 C45 1.384(12) . ?
C44 H44 0.9500 . ?
C45 C46 1.376(12) . ?
C45 H45 0.9500 . ?
C46 C47 1.377(11) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
C48 C49 1.372(12) . ?
C48 H48 0.9500 . ?
C49 C50 1.366(12) . ?
C49 H49 0.9500 . ?
C50 C51 1.366(11) . ?
C50 H50 0.9500 . ?
C51 C52 1.390(12) . ?
C51 H51 0.9500 . ?
C52 H52 0.9500 . ?
C53 C54 1.377(11) . ?
C53 H53 0.9500 . ?
C54 C55 1.381(11) . ?
C54 H54 0.9500 . ?
C55 C56 1.377(11) . ?
C55 H55 0.9500 . ?
C56 C57 1.371(11) . ?
C56 H56 0.9500 . ?
C57 H57 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
N1 Bi1 N5 75.2(2) . . ?
N1 Bi1 N2 73.7(2) . . ?
N5 Bi1 N2 148.0(2) . . ?
N1 Bi1 N3 143.6(2) . . ?
N5 Bi1 N3 140.9(2) . . ?
N2 Bi1 N3 69.9(2) . . ?
N1 Bi1 N4 146.1(2) . . ?
N5 Bi1 N4 71.0(2) . . ?
N2 Bi1 N4 140.2(2) . . ?
N3 Bi1 N4 70.3(2) . . ?
N1 Bi1 Cl2 90.90(16) . . ?
N5 Bi1 Cl2 88.01(16) . . ?
N2 Bi1 Cl2 85.51(15) . . ?
N3 Bi1 Cl2 86.53(15) . . ?
N4 Bi1 Cl2 90.30(16) . . ?
N1 Bi1 Cl1 91.00(16) . . ?
N5 Bi1 Cl1 97.62(16) . . ?
N2 Bi1 Cl1 89.92(15) . . ?
N3 Bi1 Cl1 88.78(15) . . ?
N4 Bi1 Cl1 91.09(16) . . ?
Cl2 Bi1 Cl1 174.35(7) . . ?
C33 N1 C37 118.0(7) . . ?
C33 N1 Bi1 121.9(6) . . ?
C37 N1 Bi1 120.1(5) . . ?
C2 C1 C6 114.7(7) . . ?
C2 C1 B1 123.6(7) . . ?
C6 C1 B1 121.5(7) . . ?
C17 B1 C25 103.7(6) . . ?
C17 B1 C9 112.9(7) . . ?
C25 B1 C9 113.4(7) . . ?
C17 B1 C1 111.3(6) . . ?
C25 B1 C1 111.0(7) . . ?
C9 B1 C1 104.6(6) . . ?
C38 N2 C42 117.9(7) . . ?
C38 N2 Bi1 119.8(5) . . ?
C42 N2 Bi1 120.3(5) . . ?
C3 C2 C1 123.5(7) . . ?
C3 C2 H2 118.3 . . ?
C1 C2 H2 118.3 . . ?
C48 N4 C52 117.9(7) . . ?
C48 N4 Bi1 120.7(5) . . ?
C52 N4 Bi1 120.1(5) . . ?
C3 C4 C5 118.4(7) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C3 C2 120.1(7) . . ?
C4 C3 C7 121.7(7) . . ?
C2 C3 C7 118.2(7) . . ?
C47 N3 C43 118.6(7) . . ?
C47 N3 Bi1 121.3(5) . . ?
C43 N3 Bi1 119.8(5) . . ?
C53 N5 C57 117.4(7) . . ?
C53 N5 Bi1 121.3(5) . . ?
C57 N5 Bi1 120.5(5) . . ?
C6 C5 C4 120.3(7) . . ?
C6 C5 C8 119.7(7) . . ?
C4 C5 C8 120.0(7) . . ?
C5 C6 C1 123.0(8) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
F3 C7 F1 105.0(7) . . ?
F3 C7 F2 105.7(7) . . ?
F1 C7 F2 105.1(6) . . ?
F3 C7 C3 112.9(7) . . ?
F1 C7 C3 113.5(7) . . ?
F2 C7 C3 113.8(7) . . ?
F6 C8 F4 107.3(7) . . ?
F6 C8 F5 105.6(7) . . ?
F4 C8 F5 105.4(7) . . ?
F6 C8 C5 112.2(7) . . ?
F4 C8 C5 113.6(7) . . ?
F5 C8 C5 112.1(7) . . ?
C10 C9 C14 115.6(7) . . ?
C10 C9 B1 122.6(7) . . ?
C14 C9 B1 121.4(7) . . ?
C11 C10 C9 122.9(8) . . ?
C11 C10 H10 118.5 . . ?
C9 C10 H10 118.5 . . ?
C12 C11 C10 121.5(8) . . ?
C12 C11 C15 120.1(8) . . ?
C10 C11 C15 118.5(8) . . ?
C11 C12 C13 117.2(7) . . ?
C11 C12 H12 121.4 . . ?
C13 C12 H12 121.4 . . ?
C12 C13 C14 121.0(8) . . ?
C12 C13 C16 119.0(7) . . ?
C14 C13 C16 120.0(7) . . ?
C13 C14 C9 121.5(7) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C22 C17 C18 114.9(7) . . ?
C22 C17 B1 121.4(7) . . ?
C18 C17 B1 123.4(7) . . ?
F12 C16 F11 104.7(8) . . ?
F12 C16 F10 105.0(8) . . ?
F11 C16 F10 106.1(8) . . ?
F12 C16 C13 115.0(7) . . ?
F11 C16 C13 112.9(8) . . ?
F10 C16 C13 112.3(8) . . ?
F9 C15 F7 107.2(8) . . ?
F9 C15 F8 106.3(7) . . ?
F7 C15 F8 104.6(7) . . ?
F9 C15 C11 113.7(8) . . ?
F7 C15 C11 111.7(7) . . ?
F8 C15 C11 112.7(8) . . ?
C19 C18 C17 122.6(8) . . ?
C19 C18 H18 118.7 . . ?
C17 C18 H18 118.7 . . ?
C18 C19 C20 121.0(7) . . ?
C18 C19 C24 121.3(8) . . ?
C20 C19 C24 117.7(8) . . ?
C21 C20 C19 117.9(7) . . ?
C21 C20 H20 121.1 . . ?
C19 C20 H20 121.1 . . ?
C20 C21 C22 120.5(7) . . ?
C20 C21 C23 120.1(7) . . ?
C22 C21 C23 119.4(7) . . ?
C21 C22 C17 123.1(8) . . ?
C21 C22 H22 118.4 . . ?
C17 C22 H22 118.4 . . ?
F17 C23 F16 106.4(8) . . ?
F17 C23 F18 106.7(7) . . ?
F16 C23 F18 103.0(8) . . ?
F17 C23 C21 114.6(8) . . ?
F16 C23 C21 112.5(7) . . ?
F18 C23 C21 112.7(7) . . ?
F13 C24 F15 107.2(8) . . ?
F13 C24 F14 104.3(8) . . ?
F15 C24 F14 102.9(8) . . ?
F13 C24 C19 114.1(8) . . ?
F15 C24 C19 114.5(8) . . ?
F14 C24 C19 112.8(8) . . ?
C27 C26 C25 122.5(7) . . ?
C27 C26 H26 118.7 . . ?
C25 C26 H26 118.7 . . ?
C26 C25 C30 114.4(7) . . ?
C26 C25 B1 121.3(7) . . ?
C30 C25 B1 124.2(7) . . ?
C27 C28 C29 118.7(7) . . ?
C27 C28 H28 120.6 . . ?
C29 C28 H28 120.6 . . ?
C28 C27 C26 121.2(7) . . ?
C28 C27 C31 120.3(7) . . ?
C26 C27 C31 118.5(7) . . ?
C28 C29 C30 119.6(7) . . ?
C28 C29 C32 120.9(7) . . ?
C30 C29 C32 119.4(7) . . ?
C29 C30 C25 123.4(7) . . ?
C29 C30 H30 118.3 . . ?
C25 C30 H30 118.3 . . ?
F19 C31 F20 106.4(7) . . ?
F19 C31 F21 104.9(7) . . ?
F20 C31 F21 107.4(7) . . ?
F19 C31 C27 111.8(7) . . ?
F20 C31 C27 113.5(7) . . ?
F21 C31 C27 112.2(7) . . ?
F22 C32 F23 106.8(7) . . ?
F22 C32 F24 105.4(7) . . ?
F23 C32 F24 105.4(7) . . ?
F22 C32 C29 112.4(7) . . ?
F23 C32 C29 113.6(7) . . ?
F24 C32 C29 112.6(7) . . ?
N1 C33 C34 123.3(8) . . ?
N1 C33 H33 118.3 . . ?
C34 C33 H33 118.3 . . ?
C33 C34 C35 118.5(8) . . ?
C33 C34 H34 120.8 . . ?
C35 C34 H34 120.8 . . ?
C36 C35 C34 119.4(8) . . ?
C36 C35 H35 120.3 . . ?
C34 C35 H35 120.3 . . ?
C35 C36 C37 119.2(8) . . ?
C35 C36 H36 120.4 . . ?
C37 C36 H36 120.4 . . ?
N1 C37 C36 121.6(8) . . ?
N1 C37 H37 119.2 . . ?
C36 C37 H37 119.2 . . ?
N2 C38 C39 123.2(8) . . ?
N2 C38 H38 118.4 . . ?
C39 C38 H38 118.4 . . ?
C40 C39 C38 118.5(8) . . ?
C40 C39 H39 120.8 . . ?
C38 C39 H39 120.8 . . ?
C39 C40 C41 119.1(8) . . ?
C39 C40 H40 120.5 . . ?
C41 C40 H40 120.5 . . ?
C40 C41 C42 119.4(8) . . ?
C40 C41 H41 120.3 . . ?
C42 C41 H41 120.3 . . ?
N2 C42 C41 122.0(8) . . ?
N2 C42 H42 119.0 . . ?
C41 C42 H42 119.0 . . ?
N3 C43 C44 122.0(8) . . ?
N3 C43 H43 119.0 . . ?
C44 C43 H43 119.0 . . ?
C43 C44 C45 118.8(8) . . ?
C43 C44 H44 120.6 . . ?
C45 C44 H44 120.6 . . ?
C46 C45 C44 119.2(8) . . ?
C46 C45 H45 120.4 . . ?
C44 C45 H45 120.4 . . ?
C45 C46 C47 118.6(8) . . ?
C45 C46 H46 120.7 . . ?
C47 C46 H46 120.7 . . ?
N3 C47 C46 122.8(8) . . ?
N3 C47 H47 118.6 . . ?
C46 C47 H47 118.6 . . ?
N4 C48 C49 122.9(8) . . ?
N4 C48 H48 118.6 . . ?
C49 C48 H48 118.6 . . ?
C50 C49 C48 118.6(9) . . ?
C50 C49 H49 120.7 . . ?
C48 C49 H49 120.7 . . ?
C51 C50 C49 120.7(9) . . ?
C51 C50 H50 119.7 . . ?
C49 C50 H50 119.7 . . ?
C50 C51 C52 117.6(8) . . ?
C50 C51 H51 121.2 . . ?
C52 C51 H51 121.2 . . ?
N4 C52 C51 122.3(8) . . ?
N4 C52 H52 118.8 . . ?
C51 C52 H52 118.8 . . ?
N5 C53 C54 122.4(8) . . ?
N5 C53 H53 118.8 . . ?
C54 C53 H53 118.8 . . ?
C53 C54 C55 119.6(8) . . ?
C53 C54 H54 120.2 . . ?
C55 C54 H54 120.2 . . ?
C56 C55 C54 118.1(8) . . ?
C56 C55 H55 121.0 . . ?
C54 C55 H55 121.0 . . ?
C57 C56 C55 119.2(8) . . ?
C57 C56 H56 120.4 . . ?
C55 C56 H56 120.4 . . ?
N5 C57 C56 123.3(8) . . ?
N5 C57 H57 118.4 . . ?
C56 C57 H57 118.4 . . ?

_refine_diff_density_max         1.206
_refine_diff_density_min         -1.380
_refine_diff_density_rms         0.180


####################################################################### 
# 
# 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_2-I
_database_code_depnum_ccdc_archive 'CCDC 2190609'
loop_
_audit_author_name
_audit_author_address
'Andreas Stoy'
;University of Marburg
Germany
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Bi2 I6 N4'
_chemical_formula_sum            'C20 H20 Bi2 I6 N4'
_chemical_formula_weight         1495.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

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

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

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

_cell_length_a                   8.9149(13)
_cell_length_b                   9.1675(16)
_cell_length_c                   11.3283(18)
_cell_angle_alpha                106.444(8)
_cell_angle_beta                 90.005(7)
_cell_angle_gamma                117.801(7)
_cell_volume                     775.9(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9891
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.39

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.201
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.054
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.039
_exptl_absorpt_coefficient_mu    17.309
_shelx_estimated_absorpt_T_min   0.455
_shelx_estimated_absorpt_T_max   0.552
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.538389
_exptl_absorpt_correction_T_max  0.745490
_exptl_absorpt_process_details   'TWINABS 2012/1 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube micro focus'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3048
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3048
_reflns_number_gt                2855
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+11.8962P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3048
_refine_ls_number_parameters     145
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0650
_refine_ls_wR_factor_gt          0.0631
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1_1 N 0.7455(8) 0.9226(9) 0.7172(7) 0.0179(15) Uani 1 1 d . . . . .
C2_1 C 0.7933(10) 0.9531(11) 0.6120(8) 0.0200(18) Uani 1 1 d . . . . .
H2_1 H 0.766403 0.857031 0.539365 0.024 Uiso 1 1 calc R U . . .
C3_1 C 0.8808(11) 1.1193(12) 0.6039(8) 0.0225(19) Uani 1 1 d . . . . .
H3_1 H 0.915093 1.137036 0.527463 0.027 Uiso 1 1 calc R U . . .
C4_1 C 0.9177(10) 1.2598(11) 0.7091(8) 0.0191(18) Uani 1 1 d . . . . .
H4_1 H 0.976333 1.375213 0.705582 0.023 Uiso 1 1 calc R U . . .
C5_1 C 0.8683(11) 1.2296(11) 0.8182(8) 0.0204(18) Uani 1 1 d . . . . .
H5_1 H 0.892199 1.324070 0.891237 0.024 Uiso 1 1 calc R U . . .
C6_1 C 0.7826(10) 1.0590(11) 0.8209(8) 0.0183(17) Uani 1 1 d . . . . .
H6_1 H 0.749586 1.038048 0.896773 0.022 Uiso 1 1 calc R U . . .
N1_2 N 0.4296(8) 0.3029(9) 0.7342(6) 0.0159(14) Uani 1 1 d . . . . .
C2_2 C 0.2914(10) 0.2441(11) 0.7901(8) 0.0205(18) Uani 1 1 d . . . . .
H2_2 H 0.249612 0.320877 0.830014 0.025 Uiso 1 1 calc R U . . .
C3_2 C 0.2070(11) 0.0726(12) 0.7912(9) 0.0237(19) Uani 1 1 d . . . . .
H3_2 H 0.110092 0.033468 0.832677 0.028 Uiso 1 1 calc R U . . .
C4_2 C 0.2659(11) -0.0396(12) 0.7313(8) 0.0205(18) Uani 1 1 d . . . . .
H4_2 H 0.208767 -0.157716 0.729096 0.025 Uiso 1 1 calc R U . . .
C5_2 C 0.4092(11) 0.0230(12) 0.6746(9) 0.0228(19) Uani 1 1 d . . . . .
H5_2 H 0.453819 -0.050877 0.634174 0.027 Uiso 1 1 calc R U . . .
C6_2 C 0.4869(10) 0.1933(11) 0.6773(8) 0.0201(18) Uani 1 1 d . . . . .
H6_2 H 0.584993 0.235128 0.637393 0.024 Uiso 1 1 calc R U . . .
Bi1_3 Bi 0.57729(4) 0.60838(4) 0.72272(3) 0.01297(9) Uani 1 1 d . . . . .
I2_3 I 0.87213(6) 0.67881(7) 0.88366(5) 0.01800(12) Uani 1 1 d . . . . .
I3_3 I 0.40929(7) 0.71643(7) 0.92083(5) 0.01936(13) Uani 1 1 d . . . . .
I4_3 I 0.25960(6) 0.51534(7) 0.52035(5) 0.01621(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1_1 C2_1 1.326(11) . ?
N1_1 C6_1 1.355(11) . ?
N1_1 Bi1_3 2.573(7) . ?
C2_1 C3_1 1.381(12) . ?
C3_1 C4_1 1.387(12) . ?
C4_1 C5_1 1.370(12) . ?
C5_1 C6_1 1.394(12) . ?
N1_2 C2_2 1.335(10) . ?
N1_2 C6_2 1.341(11) . ?
N1_2 Bi1_3 2.522(7) . ?
C2_2 C3_2 1.396(12) . ?
C3_2 C4_2 1.379(12) . ?
C4_2 C5_2 1.378(12) . ?
C5_2 C6_2 1.371(12) . ?
Bi1_3 I3_3 2.8959(7) . ?
Bi1_3 I2_3 2.8982(7) . ?
Bi1_3 I4_3 3.2623(7) . ?
Bi1_3 I4_3 3.2794(7) 2_666 ?

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
C2_1 N1_1 C6_1 119.0(7) . . ?
C2_1 N1_1 Bi1_3 120.4(6) . . ?
C6_1 N1_1 Bi1_3 120.5(5) . . ?
N1_1 C2_1 C3_1 122.5(8) . . ?
C2_1 C3_1 C4_1 118.9(8) . . ?
C5_1 C4_1 C3_1 119.0(8) . . ?
C4_1 C5_1 C6_1 119.4(8) . . ?
N1_1 C6_1 C5_1 121.1(8) . . ?
C2_2 N1_2 C6_2 118.8(7) . . ?
C2_2 N1_2 Bi1_3 122.2(5) . . ?
C6_2 N1_2 Bi1_3 118.9(5) . . ?
N1_2 C2_2 C3_2 121.5(8) . . ?
C4_2 C3_2 C2_2 119.2(8) . . ?
C5_2 C4_2 C3_2 118.7(8) . . ?
C6_2 C5_2 C4_2 119.3(8) . . ?
N1_2 C6_2 C5_2 122.5(8) . . ?
N1_2 Bi1_3 N1_1 176.4(2) . . ?
N1_2 Bi1_3 I3_3 90.90(15) . . ?
N1_1 Bi1_3 I3_3 90.21(15) . . ?
N1_2 Bi1_3 I2_3 88.28(15) . . ?
N1_1 Bi1_3 I2_3 88.24(15) . . ?
I3_3 Bi1_3 I2_3 96.09(2) . . ?
N1_2 Bi1_3 I4_3 91.32(15) . . ?
N1_1 Bi1_3 I4_3 92.08(15) . . ?
I3_3 Bi1_3 I4_3 89.09(2) . . ?
I2_3 Bi1_3 I4_3 174.805(18) . . ?
N1_2 Bi1_3 I4_3 90.25(16) . 2_666 ?
N1_1 Bi1_3 I4_3 88.97(15) . 2_666 ?
I3_3 Bi1_3 I4_3 174.490(18) . 2_666 ?
I2_3 Bi1_3 I4_3 89.33(2) . 2_666 ?
I4_3 Bi1_3 I4_3 85.492(19) . 2_666 ?
Bi1_3 I4_3 Bi1_3 94.508(19) . 2_666 ?

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
C6_1 N1_1 C2_1 C3_1 0.4(12) . . . . ?
Bi1_3 N1_1 C2_1 C3_1 178.7(6) . . . . ?
N1_1 C2_1 C3_1 C4_1 -1.1(13) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.8(12) . . . . ?
C3_1 C4_1 C5_1 C6_1 0.1(12) . . . . ?
C2_1 N1_1 C6_1 C5_1 0.6(12) . . . . ?
Bi1_3 N1_1 C6_1 C5_1 -177.7(6) . . . . ?
C4_1 C5_1 C6_1 N1_1 -0.8(12) . . . . ?
C6_2 N1_2 C2_2 C3_2 0.5(13) . . . . ?
Bi1_3 N1_2 C2_2 C3_2 177.3(6) . . . . ?
N1_2 C2_2 C3_2 C4_2 -1.2(14) . . . . ?
C2_2 C3_2 C4_2 C5_2 1.5(13) . . . . ?
C3_2 C4_2 C5_2 C6_2 -1.3(13) . . . . ?
C2_2 N1_2 C6_2 C5_2 -0.2(13) . . . . ?
Bi1_3 N1_2 C6_2 C5_2 -177.1(7) . . . . ?
C4_2 C5_2 C6_2 N1_2 0.6(14) . . . . ?

_refine_diff_density_max         1.240
_refine_diff_density_min         -1.462
_refine_diff_density_rms         0.274



####################################################################### 
# 
# 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_2-Br
_database_code_depnum_ccdc_archive 'CCDC 2190608'
loop_
_audit_author_name
_audit_author_address
'Andreas Stoy'
;University of Marburg
Germany
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Bi Br3 N2'
_chemical_formula_weight         606.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'I 2/m'
_space_group_name_Hall           '-I 2y'

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

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

_cell_length_a                   7.5209(13)
_cell_length_b                   16.657(2)
_cell_length_c                   13.686(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.262(10)
_cell_angle_gamma                90
_cell_volume                     1711.7(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9972
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      28.33

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.355
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.076
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_max          0.395
_exptl_absorpt_coefficient_mu    17.283
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.5633
_exptl_absorpt_correction_T_min  0.2463
_exptl_special_details           
;
 The following wavelength and cell were deduced by SADABS from the
 direction cosines etc. They are given here for emergency use only:
 CELL 0.71070   15.250   16.667    7.521   89.985  116.264   89.979
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube micro focus'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17238
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.446
_diffrn_reflns_theta_max         26.003
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             1743
_reflns_number_gt                1720
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0190P)²+6.0260P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1743
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0137
_refine_ls_R_factor_gt           0.0135
_refine_ls_wR_factor_ref         0.0379
_refine_ls_wR_factor_gt          0.0378
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1_1 N 0.3430(3) 0.63632(14) 0.65679(18) 0.0155(5) Uani 1 1 d . . . . .
C2_1 C 0.4239(4) 0.66023(19) 0.7419(2) 0.0188(6) Uani 1 1 d . . . . .
H2_1 H 0.546218 0.674586 0.743130 0.023 Uiso 1 1 calc R U . . .
C3_1 C 0.3365(4) 0.66478(19) 0.8275(2) 0.0205(6) Uani 1 1 d . . . . .
H3_1 H 0.397534 0.682149 0.886424 0.025 Uiso 1 1 calc R U . . .
C4_1 C 0.1582(4) 0.64364(19) 0.8264(2) 0.0205(6) Uani 1 1 d . . . . .
H4_1 H 0.094969 0.646274 0.884432 0.025 Uiso 1 1 calc R U . . .
C5_1 C 0.0741(4) 0.61861(19) 0.7391(2) 0.0209(6) Uani 1 1 d . . . . .
H5_1 H -0.047896 0.603441 0.736291 0.025 Uiso 1 1 calc R U . . .
C6_1 C 0.1705(4) 0.61604(19) 0.6560(2) 0.0182(6) Uani 1 1 d . . . . .
H6_1 H 0.112195 0.599257 0.596035 0.022 Uiso 1 1 calc R U . . .
Bi1_2 Bi 0.500000 0.63216(2) 0.500000 0.01087(6) Uani 1 2 d S T P . .
Br2_2 Br 0.73660(3) 0.74160(2) 0.57308(2) 0.01736(8) Uani 1 1 d . . . . .
Br3_2 Br 0.26090(5) 0.500000 0.41872(3) 0.01806(10) Uani 1 2 d S T P . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1_1 0.0165(12) 0.0164(12) 0.0136(12) -0.0010(9) 0.0021(10) -0.0033(9)
C2_1 0.0141(13) 0.0225(16) 0.0197(14) 0.0004(12) -0.0005(11) -0.0031(12)
C3_1 0.0213(15) 0.0251(16) 0.0150(13) -0.0032(12) -0.0013(11) -0.0048(13)
C4_1 0.0220(15) 0.0216(15) 0.0186(15) -0.0031(12) 0.0061(12) -0.0030(13)
C5_1 0.0153(14) 0.0256(16) 0.0220(15) -0.0018(12) 0.0044(12) -0.0046(12)
C6_1 0.0170(14) 0.0215(15) 0.0159(14) -0.0037(12) -0.0006(11) -0.0042(12)
Bi1_2 0.01095(8) 0.01090(8) 0.01072(8) 0.000 0.00027(5) 0.000
Br2_2 0.01620(14) 0.01820(15) 0.01756(14) -0.00101(10) -0.00020(11)
-0.00571(10)
Br3_2 0.0172(2) 0.0136(2) 0.0224(2) 0.000 -0.00771(16) 0.000

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1_1 C6_1 1.340(4) . ?
N1_1 C2_1 1.344(4) . ?
N1_1 Bi1_2 2.508(2) . ?
C2_1 C3_1 1.377(4) . ?
C3_1 C4_1 1.385(4) . ?
C4_1 C5_1 1.384(4) . ?
C5_1 C6_1 1.385(4) . ?
Bi1_2 Br2_2 2.6994(4) 2_656 ?
Bi1_2 Br2_2 2.6994(4) . ?
Bi1_2 Br3_2 3.0149(4) 5_666 ?
Bi1_2 Br3_2 3.0149(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6_1 N1_1 C2_1 118.2(3) . . ?
C6_1 N1_1 Bi1_2 119.24(19) . . ?
C2_1 N1_1 Bi1_2 122.55(19) . . ?
N1_1 C2_1 C3_1 122.6(3) . . ?
C2_1 C3_1 C4_1 119.0(3) . . ?
C5_1 C4_1 C3_1 118.8(3) . . ?
C4_1 C5_1 C6_1 118.9(3) . . ?
N1_1 C6_1 C5_1 122.5(3) . . ?
N1_1 Bi1_2 N1_1 176.84(11) . 2_656 ?
N1_1 Bi1_2 Br2_2 88.04(6) . 2_656 ?
N1_1 Bi1_2 Br2_2 89.82(6) 2_656 2_656 ?
N1_1 Bi1_2 Br2_2 89.82(6) . . ?
N1_1 Bi1_2 Br2_2 88.04(6) 2_656 . ?
Br2_2 Bi1_2 Br2_2 95.050(17) 2_656 . ?
N1_1 Bi1_2 Br3_2 90.26(6) . 5_666 ?
N1_1 Bi1_2 Br3_2 92.05(6) 2_656 5_666 ?
Br2_2 Bi1_2 Br3_2 175.225(9) 2_656 5_666 ?
Br2_2 Bi1_2 Br3_2 89.405(14) . 5_666 ?
N1_1 Bi1_2 Br3_2 92.05(6) . . ?
N1_1 Bi1_2 Br3_2 90.25(6) 2_656 . ?
Br2_2 Bi1_2 Br3_2 89.404(14) 2_656 . ?
Br2_2 Bi1_2 Br3_2 175.225(9) . . ?
Br3_2 Bi1_2 Br3_2 86.197(15) 5_666 . ?
Bi1_2 Br3_2 Bi1_2 93.802(15) 5_666 . ?

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
C6_1 N1_1 C2_1 C3_1 -0.2(5) . . . . ?
Bi1_2 N1_1 C2_1 C3_1 178.1(2) . . . . ?
N1_1 C2_1 C3_1 C4_1 0.3(5) . . . . ?
C2_1 C3_1 C4_1 C5_1 0.0(5) . . . . ?
C3_1 C4_1 C5_1 C6_1 -0.4(5) . . . . ?
C2_1 N1_1 C6_1 C5_1 -0.2(5) . . . . ?
Bi1_2 N1_1 C6_1 C5_1 -178.5(2) . . . . ?
C4_1 C5_1 C6_1 N1_1 0.5(5) . . . . ?

_refine_diff_density_max         0.568
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.112



####################################################################### 
# 
# 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_2-Cl
_database_code_depnum_ccdc_archive 'CCDC 2190607'
loop_
_audit_author_name
_audit_author_address
'Andreas Stoy'
;University of Marburg
Germany
;
_audit_update_record             
;
2022-07-15 deposited with the CCDC.	2022-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H20 Bi2 Cl6 N4'
_chemical_formula_sum            'C20 H20 Bi2 Cl6 N4'
_chemical_formula_weight         947.06

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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'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                   14.610(5)
_cell_length_b                   16.550(6)
_cell_length_c                   7.346(3)
_cell_angle_alpha                90
_cell_angle_beta                 114.522(7)
_cell_angle_gamma                90
_cell_volume                     1616.1(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1401
_cell_measurement_theta_min      3.05
_cell_measurement_theta_max      20.83


_exptl_special_details           
;
The crystal was immersed in a film of perfluoropolyether oil, mounted on a 
polyimide microloop (MicroMounts of MiTeGen) and transferred to stream of cold 
nitrogen (Bruker Kryoflex2).
;
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.946
_exptl_crystal_F_000             872
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.154
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    11.384
_shelx_estimated_absorpt_T_min   0.273
_shelx_estimated_absorpt_T_max   0.548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2683
_exptl_absorpt_correction_T_max  0.7454
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2.00 0.00 -1.00 0.0160
-1.00 1.00 2.00 0.0230
1.00 -1.00 -2.00 0.0510
0.00 1.00 2.00 0.0410
0.00 -1.00 -2.00 0.0220
-2.00 -1.00 -2.00 0.0190
2.00 1.00 2.00 0.0620
-2.00 1.00 1.00 0.0150
2.00 -1.00 -1.00 0.0690
1.00 -1.00 -1.00 0.0670
-1.00 1.00 1.00 0.0130
-1.00 -2.00 -2.00 0.0260
-1.00 -2.00 -1.00 0.0290
0.00 2.00 1.00 0.0310
-2.00 2.00 1.00 0.0110
2.00 -2.00 -1.00 0.0740
1.00 -2.00 0.00 0.0740
-1.00 2.00 0.00 0.0070
-1.00 -2.00 1.00 0.0330
0.00 -2.00 1.00 0.0450
0.00 2.00 -1.00 0.0090
1.00 -2.00 1.00 0.0660
1.00 2.00 -2.00 0.0250
0.00 -1.00 2.00 0.0470
0.00 1.00 -2.00 0.0090

_exptl_absorpt_process_details   'SadAbs 2016/2 (Bruker AXS)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'multi-layer mirror'
_diffrn_source                   'microfocus sealed tube (Incoatec ImS)'
_diffrn_measurement_device_type  'Bruker D8 Quest'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector                 'CMOS area detector (Photon 100)'
_diffrn_detector_area_resol_mean 10.24
_diffrn_reflns_number            11470
_diffrn_reflns_av_unetI/netI     0.1124
_diffrn_reflns_av_R_equivalents  0.1715
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.461
_diffrn_reflns_theta_max         26.689
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1771
_reflns_number_gt                1384
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 ver. 2014.9 (Bruker AXS)'
_computing_cell_refinement       'Saint+ ver. V8.40A (Bruker AXS)'
_computing_data_reduction        'Saint+ ver. V8.40A (Bruker AXS)'
_computing_structure_solution    'SHELXT (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'ShelXLe (Huebschle et all, 2011)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_refine_special_details          
;

 Refinement of F² against ALL reflections. The weighted R-factor wR and 
goodness of fit S are based on F², conventional R-factors R are based on F, 
with F set to zero for negative F². The threshold expression of F² > 
2sigma(F²) is used only for calculating R-factors(gt) etc. and is not 
relevant to the choice of reflections for refinement. R-factors based on F² 
are statistically about twice as large as those based on F, and R-factors 
based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1771
_refine_ls_number_parameters     75
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0662
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0940
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.500000 0.37101(3) 1.000000 0.01845(17) Uani 1 2 d S T P . .
C1 C 0.2535(7) 0.3371(6) 0.6824(15) 0.029(2) Uani 1 1 d . . . . .
H1 H 0.251302 0.321877 0.805264 0.035 Uiso 1 1 calc R U . . .
N1 N 0.3383(6) 0.3646(4) 0.6854(11) 0.0231(17) Uani 1 1 d . . . . .
Cl1 Cl 0.5770(3) 0.500000 0.8363(5) 0.0245(7) Uani 1 2 d S T P . .
Cl2 Cl 0.4270(2) 0.26492(14) 1.1560(4) 0.0277(6) Uani 1 1 d . . . . .
C2 C 0.1687(8) 0.3295(6) 0.5110(16) 0.033(3) Uani 1 1 d . . . . .
H2 H 0.109430 0.307451 0.514427 0.040 Uiso 1 1 calc R U . . .
C5 C 0.3414(8) 0.3875(5) 0.5105(15) 0.027(2) Uani 1 1 d . . . . .
H5 H 0.402754 0.407175 0.511865 0.033 Uiso 1 1 calc R U . . .
C4 C 0.2580(8) 0.3829(5) 0.3318(15) 0.029(2) Uani 1 1 d . . . . .
H4 H 0.262035 0.399371 0.211488 0.034 Uiso 1 1 calc R U . . .
C3 C 0.1690(8) 0.3545(5) 0.3274(16) 0.030(2) Uani 1 1 d . . . . .
H3 H 0.109973 0.351754 0.206019 0.036 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 N1 2.530(8) 2_657 ?
Bi1 N1 2.530(8) . ?
Bi1 Cl2 2.559(2) 2_657 ?
Bi1 Cl2 2.559(2) . ?
Bi1 Cl1 2.897(2) 5_667 ?
Bi1 Cl1 2.897(2) . ?
C1 N1 1.312(11) . ?
C1 C2 1.357(14) . ?
C1 H1 0.9500 . ?
N1 C5 1.358(12) . ?
C2 C3 1.412(13) . ?
C2 H2 0.9500 . ?
C5 C4 1.373(14) . ?
C5 H5 0.9500 . ?
C4 C3 1.371(13) . ?
C4 H4 0.9500 . ?
C3 H3 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
N1 Bi1 N1 175.2(3) 2_657 . ?
N1 Bi1 Cl2 88.59(18) 2_657 2_657 ?
N1 Bi1 Cl2 88.11(18) . 2_657 ?
N1 Bi1 Cl2 88.11(18) 2_657 . ?
N1 Bi1 Cl2 88.58(18) . . ?
Cl2 Bi1 Cl2 93.35(12) 2_657 . ?
N1 Bi1 Cl1 91.62(18) 2_657 5_667 ?
N1 Bi1 Cl1 91.93(18) . 5_667 ?
Cl2 Bi1 Cl1 175.86(7) 2_657 5_667 ?
Cl2 Bi1 Cl1 90.79(7) . 5_667 ?
N1 Bi1 Cl1 91.93(18) 2_657 . ?
N1 Bi1 Cl1 91.62(18) . . ?
Cl2 Bi1 Cl1 90.79(7) 2_657 . ?
Cl2 Bi1 Cl1 175.86(7) . . ?
Cl1 Bi1 Cl1 85.08(9) 5_667 . ?
N1 C1 C2 122.7(10) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C1 N1 C5 118.9(9) . . ?
C1 N1 Bi1 123.2(6) . . ?
C5 N1 Bi1 117.8(6) . . ?
Bi1 Cl1 Bi1 94.92(9) . 5_667 ?
C1 C2 C3 119.7(10) . . ?
C1 C2 H2 120.1 . . ?
C3 C2 H2 120.1 . . ?
N1 C5 C4 121.6(9) . . ?
N1 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C3 C4 C5 119.9(10) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C3 C2 117.2(10) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?

_refine_diff_density_max         2.060
_refine_diff_density_min         -1.577
_refine_diff_density_rms         0.261



