# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2023

####################################################################### 
# 
# 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_pic2_bibri_0025
_database_code_depnum_ccdc_archive 'CCDC 2205385'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br4.389 I0.611, C14 H18 N2'
_chemical_formula_sum            'C14 H18 Bi Br4.39 I0.61 N2'
_chemical_formula_weight         851.61
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.0767(8)
_cell_length_b                   11.5480(9)
_cell_length_c                   14.9324(10)
_cell_angle_alpha                90
_cell_angle_beta                 92.349(3)
_cell_angle_gamma                90
_cell_volume                     2080.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4808
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.922
_cell_measurement_theta_min      2.444
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.470
_exptl_absorpt_coefficient_mu    17.805
_exptl_absorpt_correction_T_max  0.0955
_exptl_absorpt_correction_T_min  0.0575
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1011 before and 0.0577 after correction.
The Ratio of minimum to maximum transmission is 0.6021.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.719
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1540
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.002
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0590
_diffrn_reflns_av_unetI/netI     0.0611
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            14073
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.012
_diffrn_reflns_theta_min         2.127
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Quest'
_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                3331
_reflns_number_total             4091
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.174
_refine_diff_density_min         -1.205
_refine_diff_density_rms         0.222
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4091
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.093
_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)+(0.0068P)²+3.4272P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0573
_refine_ls_wR_factor_ref         0.0609
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 I2-Bi1
 2.95 with sigma of 0.02
 Bi1-I1
 2.85 with sigma of 0.02
 I3-Bi1
 2.9 with sigma of 0.02
 Br4-Bi1
 3.08 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Br4) = Uanis(I4)
Uanis(I1) = Uanis(Br1)
Uanis(I3) = Uanis(Br3)
Uanis(Br2) = Uanis(I2)
4. Others
 Fixed Sof: I1(0.10696) I2(0.04503) I3(0.05277) I4(0.40663) Br1(0.89304)
 Br2(0.95497) Br3(0.94723) Br4(0.59337)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_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 0.50212(3) 0.53096(2) 0.65461(2) 0.01539(8) Uani 1 1 d D . . . .
I1 I 0.628(3) 0.458(2) 0.8093(13) 0.0207(5) Uani 0.107 1 d D . P A 2
I2 I 0.363(4) 0.662(4) 0.776(3) 0.0219(3) Uani 0.045 1 d D . P A 2
I3 I 0.658(4) 0.722(4) 0.655(3) 0.0212(5) Uani 0.0528 1 d D . P A 2
I4 I 0.640(2) 0.370(2) 0.5126(15) 0.0178(12) Uani 0.4066 1 d . . P A 1
Br1 Br 0.6300(4) 0.4461(4) 0.7965(2) 0.0207(5) Uani 0.893 1 d . . P A 1
Br2 Br 0.3760(2) 0.6597(2) 0.76116(15) 0.0219(3) Uani 0.955 1 d . . P A 1
Br3 Br 0.6556(3) 0.7177(3) 0.64020(19) 0.0212(5) Uani 0.9472 1 d . . P A 1
Br4 Br 0.629(2) 0.376(2) 0.5228(15) 0.0178(12) Uani 0.5934 1 d D . P A 2
Br5 Br 0.35330(7) 0.34734(6) 0.68073(6) 0.02105(19) Uani 1 1 d . . . . .
N1 N 0.4724(5) 0.0362(5) 0.6073(4) 0.0189(15) Uani 1 1 d . . . . .
N2 N 0.5458(6) 0.0657(5) 0.7940(4) 0.0190(16) Uani 1 1 d . . . . .
C1 C 0.4326(7) -0.0680(6) 0.6351(5) 0.0196(19) Uani 1 1 d . . . . .
H1 H 0.4802 -0.1208 0.6667 0.024 Uiso 1 1 calc R U . . .
C2 C 0.3228(7) -0.0963(7) 0.6169(6) 0.0214(19) Uani 1 1 d . . . . .
H2 H 0.2942 -0.1667 0.6394 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2543(7) -0.0242(7) 0.5667(5) 0.0208(18) Uani 1 1 d . . . . .
C4 C 0.2988(7) 0.0792(7) 0.5368(6) 0.024(2) Uani 1 1 d . . . . .
H4 H 0.2538 0.1300 0.5009 0.029 Uiso 1 1 calc R U . . .
C5 C 0.4062(7) 0.1091(6) 0.5580(5) 0.021(2) Uani 1 1 d . . . . .
H5 H 0.4346 0.1810 0.5383 0.026 Uiso 1 1 calc R U . . .
C6 C 0.1370(7) -0.0575(7) 0.5450(6) 0.031(2) Uani 1 1 d . . . . .
H6A H 0.1324 -0.1416 0.5363 0.046 Uiso 1 1 calc R U . . .
H6B H 0.1109 -0.0182 0.4899 0.046 Uiso 1 1 calc R U . . .
H6C H 0.0907 -0.0348 0.5944 0.046 Uiso 1 1 calc R U . . .
C7 C 0.5861(6) 0.0703(7) 0.6335(5) 0.0215(19) Uani 1 1 d . . . . .
H7A H 0.6162 0.1192 0.5858 0.026 Uiso 1 1 calc R U . . .
H7B H 0.6329 0.0002 0.6397 0.026 Uiso 1 1 calc R U . . .
C8 C 0.5911(7) 0.1363(6) 0.7207(5) 0.0196(19) Uani 1 1 d . . . . .
H8A H 0.6690 0.1572 0.7365 0.023 Uiso 1 1 calc R U . . .
H8B H 0.5479 0.2088 0.7136 0.023 Uiso 1 1 calc R U . . .
C9 C 0.6039(7) -0.0223(7) 0.8303(5) 0.0206(18) Uani 1 1 d . . . . .
H9 H 0.6788 -0.0322 0.8146 0.025 Uiso 1 1 calc R U . . .
C10 C 0.5600(7) -0.0981(7) 0.8886(6) 0.024(2) Uani 1 1 d . . . . .
H10 H 0.6030 -0.1609 0.9118 0.029 Uiso 1 1 calc R U . . .
C11 C 0.4514(7) -0.0829(7) 0.9142(5) 0.026(2) Uani 1 1 d . . . . .
C12 C 0.3935(7) 0.0123(7) 0.8780(6) 0.025(2) Uani 1 1 d . . . . .
H12 H 0.3201 0.0273 0.8955 0.030 Uiso 1 1 calc R U . . .
C13 C 0.4417(7) 0.0845(7) 0.8173(6) 0.025(2) Uani 1 1 d . . . . .
H13 H 0.4008 0.1477 0.7921 0.030 Uiso 1 1 calc R U . . .
C14 C 0.3981(7) -0.1664(7) 0.9757(6) 0.026(2) Uani 1 1 d . . . . .
H14A H 0.3406 -0.1264 1.0083 0.040 Uiso 1 1 calc R U . . .
H14B H 0.4542 -0.1974 1.0185 0.040 Uiso 1 1 calc R U . . .
H14C H 0.3647 -0.2300 0.9406 0.040 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 I1 2.840(17) . ?
Bi1 I2 2.943(18) . ?
Bi1 I3 2.90(2) . ?
Bi1 I4 3.318(14) . ?
Bi1 I4 3.18(3) 3_666 ?
Bi1 Br1 2.751(3) . ?
Bi1 Br2 2.6946(12) . ?
Bi1 Br3 2.8581(18) . ?
Bi1 Br4 3.22(3) 3_666 ?
Bi1 Br4 3.113(15) . ?
Bi1 Br5 2.8170(8) . ?
I4 Bi1 3.18(3) 3_666 ?
Br4 Bi1 3.22(3) 3_666 ?
N1 C1 1.366(9) . ?
N1 C5 1.357(10) . ?
N1 C7 1.466(9) . ?
N2 C8 1.487(10) . ?
N2 C9 1.338(9) . ?
N2 C13 1.336(10) . ?
C1 H1 0.9500 . ?
C1 C2 1.382(11) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(11) . ?
C3 C4 1.391(11) . ?
C3 C6 1.490(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.367(11) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.507(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.358(11) . ?
C10 H10 0.9500 . ?
C10 C11 1.392(11) . ?
C11 C12 1.400(11) . ?
C11 C14 1.494(11) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(11) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
I1 Bi1 I2 87.2(11) . . ?
I1 Bi1 I3 84.2(13) . . ?
I1 Bi1 Br4 94.7(7) . . ?
I1 Bi1 Br4 176.8(9) . 3_666 ?
I2 Bi1 Br4 93.5(10) . 3_666 ?
I2 Bi1 Br4 174.4(11) . . ?
I3 Bi1 I2 89.7(16) . . ?
I3 Bi1 Br4 95.8(13) . . ?
I3 Bi1 Br4 92.7(11) . 3_666 ?
I4 Bi1 I4 88.2(5) 3_666 . ?
Br1 Bi1 I4 90.7(5) . . ?
Br1 Bi1 I4 178.4(4) . 3_666 ?
Br1 Bi1 Br3 88.94(15) . . ?
Br1 Bi1 Br5 88.07(13) . . ?
Br2 Bi1 I4 175.4(5) . . ?
Br2 Bi1 I4 88.0(3) . 3_666 ?
Br2 Bi1 Br1 93.13(10) . . ?
Br2 Bi1 Br3 90.70(11) . . ?
Br2 Bi1 Br5 87.37(7) . . ?
Br3 Bi1 I4 91.8(5) . . ?
Br3 Bi1 I4 90.0(5) . 3_666 ?
Br4 Bi1 Br4 84.9(6) . 3_666 ?
Br5 Bi1 I1 89.2(7) . . ?
Br5 Bi1 I2 85.4(10) . . ?
Br5 Bi1 I3 171.9(9) . . ?
Br5 Bi1 I4 90.3(5) . . ?
Br5 Bi1 I4 93.1(5) . 3_666 ?
Br5 Bi1 Br3 176.35(6) . . ?
Br5 Bi1 Br4 89.4(5) . . ?
Br5 Bi1 Br4 94.0(5) . 3_666 ?
Bi1 I4 Bi1 91.8(5) 3_666 . ?
Bi1 Br4 Bi1 95.1(6) . 3_666 ?
C1 N1 C7 119.6(7) . . ?
C5 N1 C1 120.3(7) . . ?
C5 N1 C7 120.1(7) . . ?
C9 N2 C8 120.8(7) . . ?
C13 N2 C8 118.8(7) . . ?
C13 N2 C9 120.1(7) . . ?
N1 C1 H1 120.2 . . ?
N1 C1 C2 119.7(7) . . ?
C2 C1 H1 120.2 . . ?
C1 C2 H2 119.5 . . ?
C3 C2 C1 121.0(7) . . ?
C3 C2 H2 119.5 . . ?
C2 C3 C4 117.6(8) . . ?
C2 C3 C6 120.5(7) . . ?
C4 C3 C6 121.9(8) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.2(8) . . ?
C5 C4 H4 119.4 . . ?
N1 C5 C4 120.1(7) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
N1 C7 C8 111.8(7) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.3 . . ?
C8 C7 H7B 109.3 . . ?
N2 C8 C7 110.8(6) . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 H9 118.8 . . ?
N2 C9 C10 122.5(8) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.5(8) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 C12 117.0(8) . . ?
C10 C11 C14 121.5(8) . . ?
C12 C11 C14 121.5(8) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 C11 120.8(8) . . ?
C13 C12 H12 119.6 . . ?
N2 C13 C12 120.0(8) . . ?
N2 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 3.8(12) . . . . ?
N1 C7 C8 N2 58.6(9) . . . . ?
N2 C9 C10 C11 -1.8(13) . . . . ?
C1 N1 C5 C4 0.8(11) . . . . ?
C1 N1 C7 C8 -90.2(9) . . . . ?
C1 C2 C3 C4 -1.4(12) . . . . ?
C1 C2 C3 C6 177.9(8) . . . . ?
C2 C3 C4 C5 -1.3(12) . . . . ?
C3 C4 C5 N1 1.6(12) . . . . ?
C5 N1 C1 C2 -3.5(12) . . . . ?
C5 N1 C7 C8 87.9(9) . . . . ?
C6 C3 C4 C5 179.4(8) . . . . ?
C7 N1 C1 C2 174.6(7) . . . . ?
C7 N1 C5 C4 -177.3(7) . . . . ?
C8 N2 C9 C10 -171.1(8) . . . . ?
C8 N2 C13 C12 172.9(7) . . . . ?
C9 N2 C8 C7 74.5(9) . . . . ?
C9 N2 C13 C12 -0.9(12) . . . . ?
C9 C10 C11 C12 -0.6(12) . . . . ?
C9 C10 C11 C14 177.8(8) . . . . ?
C10 C11 C12 C13 2.3(12) . . . . ?
C11 C12 C13 N2 -1.6(12) . . . . ?
C13 N2 C8 C7 -99.2(8) . . . . ?
C13 N2 C9 C10 2.6(12) . . . . ?
C14 C11 C12 C13 -176.1(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_pic2_bibri_005
_database_code_depnum_ccdc_archive 'CCDC 2205386'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br4.057 I0.943, C14 H18 N2'
_chemical_formula_sum            'C14 H18 Bi Br4.06 I0.94 N2'
_chemical_formula_weight         867.12
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.1086(4)
_cell_length_b                   11.5295(4)
_cell_length_c                   15.0033(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.440(2)
_cell_angle_gamma                90
_cell_volume                     2092.65(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4350
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.921
_cell_measurement_theta_min      2.228
_shelx_estimated_absorpt_T_max   0.933
_shelx_estimated_absorpt_T_min   0.301
_exptl_absorpt_coefficient_mu    17.561
_exptl_absorpt_correction_T_max  0.0473
_exptl_absorpt_correction_T_min  0.0196
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1224 before and 0.0587 after correction.
The Ratio of minimum to maximum transmission is 0.4144.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.752
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1564
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.004
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0588
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            16052
_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         27.102
_diffrn_reflns_theta_min         2.118
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest'
_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                3559
_reflns_number_total             4621
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         1.757
_refine_diff_density_min         -1.176
_refine_diff_density_rms         0.222
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4621
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.025
_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)+(0.0340P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0852
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 I1-Bi1
 2.85 with sigma of 0.02
 Bi1-I2
 2.85 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(Br4) = Uanis(I4)
Uanis(I1) = Uanis(Br1)
Uanis(I3) = Uanis(Br3)
Uanis(Br2) = Uanis(I2)
4. Others
 Fixed Sof: I1(0.12508) I2(0.04183) I3(0.04706) I4(0.72933) Br1(0.87492)
 Br2(0.95817) Br3(0.95294) Br4(0.27067)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_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 0.50256(3) 0.53179(3) 0.65665(2) 0.02295(9) Uani 1 1 d D . . . .
I1 I 0.635(6) 0.446(7) 0.805(4) 0.0312(4) Uani 0.1251 1 d D . P A 1
I2 I 0.368(3) 0.684(2) 0.753(2) 0.0304(3) Uani 0.0418 1 d D . P A 1
I3 I 0.670(4) 0.725(5) 0.654(3) 0.0285(4) Uani 0.0471 1 d . . P A 2
I4 I 0.3638(4) 0.6319(2) 0.4811(3) 0.0254(4) Uani 0.7293 1 d . . P A 1
Br1 Br 0.6291(13) 0.4483(15) 0.7982(8) 0.0312(4) Uani 0.8749 1 d . . P A 2
Br2 Br 0.37561(18) 0.65980(11) 0.76338(11) 0.0304(3) Uani 0.9582 1 d . . P A 2
Br3 Br 0.6546(3) 0.7187(3) 0.64164(19) 0.0285(4) Uani 0.9529 1 d . . P A 1
Br4 Br 0.3579(18) 0.6135(12) 0.4843(14) 0.0254(4) Uani 0.2707 1 d . . P A 2
Br5 Br 0.35459(7) 0.34752(7) 0.68132(6) 0.0296(2) Uani 1 1 d . . . . .
N1 N 0.4705(6) 0.0330(6) 0.6070(5) 0.0264(16) Uani 1 1 d . . . . .
N2 N 0.5450(6) 0.0641(6) 0.7939(5) 0.0296(17) Uani 1 1 d . . . . .
C1 C 0.4294(8) -0.0682(7) 0.6354(6) 0.029(2) Uani 1 1 d . . . . .
H1 H 0.4760 -0.1209 0.6679 0.035 Uiso 1 1 calc R U . . .
C2 C 0.3211(8) -0.0952(8) 0.6177(6) 0.034(2) Uani 1 1 d . . . . .
H2 H 0.2922 -0.1653 0.6405 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2530(7) -0.0228(8) 0.5676(6) 0.031(2) Uani 1 1 d . . . . .
C4 C 0.2988(7) 0.0802(7) 0.5378(5) 0.0281(19) Uani 1 1 d . . . . .
H4 H 0.2549 0.1321 0.5021 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4074(7) 0.1073(8) 0.5599(5) 0.030(2) Uani 1 1 d . . . . .
H5 H 0.4373 0.1792 0.5415 0.036 Uiso 1 1 calc R U . . .
C6 C 0.1368(7) -0.0551(8) 0.5460(6) 0.032(2) Uani 1 1 d . . . . .
H6A H 0.0953 -0.0549 0.6006 0.048 Uiso 1 1 calc R U . . .
H6B H 0.1341 -0.1328 0.5194 0.048 Uiso 1 1 calc R U . . .
H6C H 0.1039 0.0010 0.5035 0.048 Uiso 1 1 calc R U . . .
C7 C 0.5853(7) 0.0669(8) 0.6339(6) 0.031(2) Uani 1 1 d . . . . .
H7A H 0.6155 0.1154 0.5863 0.037 Uiso 1 1 calc R U . . .
H7B H 0.6313 -0.0039 0.6396 0.037 Uiso 1 1 calc R U . . .
C8 C 0.5942(7) 0.1331(7) 0.7209(6) 0.0288(19) Uani 1 1 d . . . . .
H8A H 0.6728 0.1495 0.7367 0.035 Uiso 1 1 calc R U . . .
H8B H 0.5549 0.2081 0.7141 0.035 Uiso 1 1 calc R U . . .
C9 C 0.6024(8) -0.0263(8) 0.8297(6) 0.035(2) Uani 1 1 d . . . . .
H9 H 0.6764 -0.0387 0.8134 0.042 Uiso 1 1 calc R U . . .
C10 C 0.5570(7) -0.0992(8) 0.8883(6) 0.031(2) Uani 1 1 d . . . . .
H10 H 0.5989 -0.1623 0.9124 0.037 Uiso 1 1 calc R U . . .
C11 C 0.4508(8) -0.0824(8) 0.9128(6) 0.032(2) Uani 1 1 d . . . . .
C12 C 0.3926(8) 0.0122(8) 0.8762(6) 0.035(2) Uani 1 1 d . . . . .
H12 H 0.3188 0.0260 0.8925 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4409(8) 0.0862(8) 0.8163(6) 0.031(2) Uani 1 1 d . . . . .
H13 H 0.4015 0.1507 0.7919 0.038 Uiso 1 1 calc R U . . .
C14 C 0.3962(8) -0.1646(8) 0.9746(6) 0.037(2) Uani 1 1 d . . . . .
H14A H 0.3645 -0.2298 0.9404 0.056 Uiso 1 1 calc R U . . .
H14B H 0.3374 -0.1241 1.0049 0.056 Uiso 1 1 calc R U . . .
H14C H 0.4511 -0.1937 1.0190 0.056 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 I1 2.86(2) . ?
Bi1 I2 2.838(18) . ?
Bi1 I3 3.01(5) . ?
Bi1 I4 3.273(5) . ?
Bi1 I4 3.277(4) 3_666 ?
Bi1 Br1 2.740(4) . ?
Bi1 Br2 2.7046(13) . ?
Bi1 Br3 2.849(3) . ?
Bi1 Br4 3.20(2) . ?
Bi1 Br4 3.23(2) 3_666 ?
Bi1 Br5 2.8138(9) . ?
I4 Bi1 3.277(4) 3_666 ?
Br4 Bi1 3.23(2) 3_666 ?
N1 C1 1.345(11) . ?
N1 C5 1.330(11) . ?
N1 C7 1.484(11) . ?
N2 C8 1.498(10) . ?
N2 C9 1.351(11) . ?
N2 C13 1.342(11) . ?
C1 H1 0.9500 . ?
C1 C2 1.363(12) . ?
C2 H2 0.9500 . ?
C2 C3 1.374(13) . ?
C3 C4 1.392(12) . ?
C3 C6 1.479(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.379(12) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.512(12) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.349(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.367(12) . ?
C11 C12 1.398(13) . ?
C11 C14 1.500(12) . ?
C12 H12 0.9500 . ?
C12 C13 1.385(12) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
I1 Bi1 I4 90.9(17) . 3_666 ?
I1 Bi1 I4 176.9(17) . . ?
I2 Bi1 I1 97.6(18) . . ?
I2 Bi1 I4 171.5(7) . 3_666 ?
I2 Bi1 I4 84.6(7) . . ?
I2 Bi1 Br3 87.8(8) . . ?
I3 Bi1 Br4 96.6(10) . . ?
I3 Bi1 Br4 90.3(11) . 3_666 ?
I4 Bi1 I4 86.89(11) . 3_666 ?
Br1 Bi1 I3 85.3(10) . . ?
Br1 Bi1 Br4 176.2(5) . . ?
Br1 Bi1 Br4 92.0(5) . 3_666 ?
Br1 Bi1 Br5 88.3(4) . . ?
Br2 Bi1 I3 90.2(11) . . ?
Br2 Bi1 Br1 92.6(4) . . ?
Br2 Bi1 Br4 90.7(4) . . ?
Br2 Bi1 Br4 175.4(4) . 3_666 ?
Br2 Bi1 Br5 87.31(5) . . ?
Br3 Bi1 I1 89.0(18) . . ?
Br3 Bi1 I4 92.74(9) . 3_666 ?
Br3 Bi1 I4 88.90(8) . . ?
Br4 Bi1 Br4 84.7(6) . 3_666 ?
Br5 Bi1 I1 88.5(18) . . ?
Br5 Bi1 I2 90.9(8) . . ?
Br5 Bi1 I3 173.0(9) . . ?
Br5 Bi1 I4 93.68(6) . . ?
Br5 Bi1 I4 88.99(6) . 3_666 ?
Br5 Bi1 Br3 176.97(6) . . ?
Br5 Bi1 Br4 89.9(3) . . ?
Br5 Bi1 Br4 92.8(3) . 3_666 ?
Bi1 I4 Bi1 93.11(11) . 3_666 ?
Bi1 Br4 Bi1 95.3(5) . 3_666 ?
C1 N1 C7 119.8(7) . . ?
C5 N1 C1 121.1(8) . . ?
C5 N1 C7 119.0(7) . . ?
C9 N2 C8 119.1(7) . . ?
C13 N2 C8 119.3(7) . . ?
C13 N2 C9 121.2(8) . . ?
N1 C1 H1 119.9 . . ?
N1 C1 C2 120.1(9) . . ?
C2 C1 H1 119.9 . . ?
C1 C2 H2 119.4 . . ?
C1 C2 C3 121.2(9) . . ?
C3 C2 H2 119.4 . . ?
C2 C3 C4 117.2(9) . . ?
C2 C3 C6 120.7(8) . . ?
C4 C3 C6 122.2(8) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(9) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 120.1(8) . . ?
N1 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
N1 C7 C8 113.6(7) . . ?
H7A C7 H7B 107.7 . . ?
C8 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
N2 C8 C7 110.3(7) . . ?
N2 C8 H8A 109.6 . . ?
N2 C8 H8B 109.6 . . ?
C7 C8 H8A 109.6 . . ?
C7 C8 H8B 109.6 . . ?
H8A C8 H8B 108.1 . . ?
N2 C9 H9 119.2 . . ?
C10 C9 N2 121.5(8) . . ?
C10 C9 H9 119.2 . . ?
C9 C10 H10 120.0 . . ?
C9 C10 C11 120.0(9) . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C12 118.0(8) . . ?
C10 C11 C14 121.4(9) . . ?
C12 C11 C14 120.6(8) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.0(8) . . ?
C13 C12 H12 119.5 . . ?
N2 C13 C12 118.2(9) . . ?
N2 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 2.9(13) . . . . ?
N1 C7 C8 N2 56.3(10) . . . . ?
N2 C9 C10 C11 -0.2(14) . . . . ?
C1 N1 C5 C4 -1.4(12) . . . . ?
C1 N1 C7 C8 -88.5(9) . . . . ?
C1 C2 C3 C4 -1.7(13) . . . . ?
C1 C2 C3 C6 177.7(8) . . . . ?
C2 C3 C4 C5 -1.0(12) . . . . ?
C3 C4 C5 N1 2.6(12) . . . . ?
C5 N1 C1 C2 -1.3(12) . . . . ?
C5 N1 C7 C8 86.9(9) . . . . ?
C6 C3 C4 C5 179.6(8) . . . . ?
C7 N1 C1 C2 174.0(7) . . . . ?
C7 N1 C5 C4 -176.8(7) . . . . ?
C8 N2 C9 C10 -172.4(8) . . . . ?
C8 N2 C13 C12 172.3(8) . . . . ?
C9 N2 C8 C7 76.0(10) . . . . ?
C9 N2 C13 C12 -1.3(13) . . . . ?
C9 C10 C11 C12 -0.6(14) . . . . ?
C9 C10 C11 C14 177.4(9) . . . . ?
C10 C11 C12 C13 0.4(14) . . . . ?
C11 C12 C13 N2 0.5(14) . . . . ?
C13 N2 C8 C7 -97.7(9) . . . . ?
C13 N2 C9 C10 1.2(14) . . . . ?
C14 C11 C12 C13 -177.5(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_pic2_bibri_010
_database_code_depnum_ccdc_archive 'CCDC 2205388'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-27 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br3.413 I1.587, C14 H18 N2'
_chemical_formula_sum            'C14 H18 Bi Br3.41 I1.59 N2'
_chemical_formula_weight         897.43
_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'
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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.1996(7)
_cell_length_b                   11.5845(8)
_cell_length_c                   15.0730(11)
_cell_angle_alpha                90
_cell_angle_beta                 92.533(5)
_cell_angle_gamma                90
_cell_volume                     2128.1(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3189
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.508
_cell_measurement_theta_min      2.196
_shelx_estimated_absorpt_T_max   0.935
_shelx_estimated_absorpt_T_min   0.281
_exptl_absorpt_coefficient_mu    16.993
_exptl_absorpt_correction_T_max  0.0210
_exptl_absorpt_correction_T_min  0.0043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1182 before and 0.0569 after correction.
The Ratio of minimum to maximum transmission is 0.2048.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.801
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1610
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.015
_exptl_crystal_size_min          0.004
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0733
_diffrn_reflns_av_unetI/netI     0.0750
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15210
_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         26.022
_diffrn_reflns_theta_min         2.103
_diffrn_ambient_temperature      100.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker Quest'
_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                2989
_reflns_number_total             4193
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'XT  (Sheldrick, 2015)'
_refine_diff_density_max         2.436
_refine_diff_density_min         -1.643
_refine_diff_density_rms         0.297
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4193
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.006
_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)+(0.0807P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1335
_refine_ls_wR_factor_ref         0.1489
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 I2-Bi1
 2.9 with sigma of 0.01
 I3-Bi1
 2.95 with sigma of 0.02
 I1-Bi1
 2.9 with sigma of 0.02
 Br4-Bi1
 3.15 with sigma of 0.02
 Br4_$1-Bi1
 3.15 with sigma of 0.02
2. Uiso/Uaniso restraints and constraints
Uanis(Br3) = Uanis(I3)
Uanis(Br2) = Uanis(I2)
Uanis(Br1) = Uanis(I1)
Uanis(I4) = Uanis(Br4)
3. Others
 Fixed Sof: I1(0.3426) I2(0.1406) I3(0.18) I4(0.9241) Br1(0.6574) Br2(0.8594)
 Br3(0.82) Br4(0.0759)
4.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
4.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
4.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_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 0.50206(4) 0.46846(5) 0.65681(4) 0.03563(17) Uani 1 1 d D . . . .
I1 I 0.637(4) 0.552(5) 0.806(3) 0.0431(19) Uani 0.3426 1 d D . P A 2
I2 I 0.371(4) 0.334(4) 0.774(3) 0.0431(8) Uani 0.1406 1 d D . P A 2
I3 I 0.666(2) 0.282(3) 0.651(3) 0.0398(11) Uani 0.18 1 d D . P A 2
I4 I 0.3614(3) 0.3698(3) 0.48104(10) 0.0390(3) Uani 0.9241 1 d . . P A 1
Br1 Br 0.625(3) 0.554(4) 0.798(2) 0.0431(19) Uani 0.6574 1 d . . P A 1
Br2 Br 0.3752(10) 0.3395(10) 0.7612(6) 0.0431(8) Uani 0.8594 1 d . . P A 1
Br3 Br 0.6529(7) 0.2807(9) 0.6396(8) 0.0398(11) Uani 0.82 1 d . . P A 1
Br4 Br 0.371(6) 0.386(7) 0.4831(14) 0.0390(3) Uani 0.0759 1 d D . P A 2
Br5 Br 0.35455(12) 0.65298(13) 0.68089(11) 0.0417(4) Uani 1 1 d . . . . .
N1 N 0.4688(9) 0.9665(10) 0.6074(9) 0.038(3) Uani 1 1 d . . . . .
N2 N 0.5436(10) 0.9361(11) 0.7921(9) 0.041(3) Uani 1 1 d . . . . .
C1 C 0.4272(13) 1.0685(12) 0.6360(11) 0.041(4) Uani 1 1 d . . . . .
H1 H 0.4728 1.1211 0.6689 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3193(12) 1.0944(13) 0.6172(10) 0.040(3) Uani 1 1 d . . . . .
H2 H 0.2904 1.1642 0.6396 0.048 Uiso 1 1 calc R U . . .
C3 C 0.2542(12) 1.0264(14) 0.5693(11) 0.043(4) Uani 1 1 d . . . . .
C4 C 0.2990(13) 0.9171(13) 0.5380(11) 0.043(4) Uani 1 1 d . . . . .
H4 H 0.2548 0.8642 0.5041 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4063(11) 0.8944(13) 0.5593(10) 0.035(3) Uani 1 1 d . . . . .
H5 H 0.4375 0.8245 0.5391 0.042 Uiso 1 1 calc R U . . .
C6 C 0.1360(11) 1.0532(14) 0.5458(11) 0.043(4) Uani 1 1 d . . . . .
H6A H 0.1017 1.0866 0.5974 0.064 Uiso 1 1 calc R U . . .
H6B H 0.0976 0.9820 0.5280 0.064 Uiso 1 1 calc R U . . .
H6C H 0.1317 1.1085 0.4965 0.064 Uiso 1 1 calc R U . . .
C7 C 0.5849(11) 0.9363(14) 0.6346(11) 0.042(4) Uani 1 1 d . . . . .
H7A H 0.6279 1.0082 0.6432 0.051 Uiso 1 1 calc R U . . .
H7B H 0.6176 0.8917 0.5864 0.051 Uiso 1 1 calc R U . . .
C8 C 0.5919(12) 0.8668(12) 0.7186(11) 0.041(4) Uani 1 1 d . . . . .
H8A H 0.6695 0.8480 0.7344 0.049 Uiso 1 1 calc R U . . .
H8B H 0.5510 0.7936 0.7101 0.049 Uiso 1 1 calc R U . . .
C9 C 0.6003(13) 1.0268(14) 0.8300(11) 0.045(4) Uani 1 1 d . . . . .
H9 H 0.6744 1.0384 0.8151 0.054 Uiso 1 1 calc R U . . .
C10 C 0.5561(12) 1.1000(15) 0.8871(12) 0.047(4) Uani 1 1 d . . . . .
H10 H 0.5973 1.1637 0.9100 0.056 Uiso 1 1 calc R U . . .
C11 C 0.4485(12) 1.0818(16) 0.9127(11) 0.047(4) Uani 1 1 d . . . . .
C12 C 0.3930(13) 0.9875(14) 0.8763(11) 0.043(4) Uani 1 1 d . . . . .
H12 H 0.3205 0.9714 0.8934 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4410(13) 0.9171(15) 0.8159(12) 0.049(4) Uani 1 1 d . . . . .
H13 H 0.4007 0.8540 0.7908 0.059 Uiso 1 1 calc R U . . .
C14 C 0.3986(15) 1.1658(15) 0.9766(12) 0.054(4) Uani 1 1 d . . . . .
H14A H 0.3912 1.2418 0.9485 0.081 Uiso 1 1 calc R U . . .
H14B H 0.4462 1.1719 1.0305 0.081 Uiso 1 1 calc R U . . .
H14C H 0.3261 1.1379 0.9922 0.081 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 I1 2.899(19) . ?
Bi1 I2 2.894(10) . ?
Bi1 I3 2.949(18) . ?
Bi1 I4 3.2965(16) . ?
Bi1 I4 3.3027(14) 3_666 ?
Bi1 Br1 2.733(15) . ?
Bi1 Br2 2.705(3) . ?
Bi1 Br3 2.868(6) . ?
Bi1 Br4 3.16(2) 3_666 ?
Bi1 Br4 3.15(2) . ?
Bi1 Br5 2.8279(15) . ?
I4 Bi1 3.3026(14) 3_666 ?
Br4 Bi1 3.16(2) 3_666 ?
N1 C1 1.363(19) . ?
N1 C5 1.325(19) . ?
N1 C7 1.497(18) . ?
N2 C8 1.508(19) . ?
N2 C9 1.37(2) . ?
N2 C13 1.34(2) . ?
C1 H1 0.9500 . ?
C1 C2 1.37(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.31(2) . ?
C3 C4 1.47(2) . ?
C3 C6 1.502(19) . ?
C4 H4 0.9500 . ?
C4 C5 1.36(2) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.50(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.34(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.40(2) . ?
C11 C12 1.38(2) . ?
C11 C14 1.52(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.37(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
I1 Bi1 I3 84.5(13) . . ?
I1 Bi1 Br4 93.6(13) . 3_666 ?
I1 Bi1 Br4 174.8(14) . . ?
I2 Bi1 I1 90.9(17) . . ?
I2 Bi1 I3 91.1(15) . . ?
I2 Bi1 Br4 175.2(15) . 3_666 ?
I2 Bi1 Br4 94.2(12) . . ?
I3 Bi1 Br4 91(2) . 3_666 ?
I3 Bi1 Br4 94(2) . . ?
I4 Bi1 I4 87.14(4) . 3_666 ?
Br1 Bi1 I4 90.5(10) . 3_666 ?
Br1 Bi1 I4 177.5(10) . . ?
Br1 Bi1 Br3 90.8(9) . . ?
Br1 Bi1 Br5 87.4(9) . . ?
Br2 Bi1 I4 175.3(3) . 3_666 ?
Br2 Bi1 I4 89.2(3) . . ?
Br2 Bi1 Br1 93.3(11) . . ?
Br2 Bi1 Br3 91.1(4) . . ?
Br2 Bi1 Br5 87.6(3) . . ?
Br3 Bi1 I4 91.7(3) . 3_666 ?
Br3 Bi1 I4 88.71(19) . . ?
Br4 Bi1 Br4 81.4(6) . 3_666 ?
Br5 Bi1 I1 89.4(11) . . ?
Br5 Bi1 I2 87.4(12) . . ?
Br5 Bi1 I3 173.7(6) . . ?
Br5 Bi1 I4 93.08(10) . . ?
Br5 Bi1 I4 89.62(9) . 3_666 ?
Br5 Bi1 Br3 177.8(2) . . ?
Br5 Bi1 Br4 92.0(19) . . ?
Br5 Bi1 Br4 90.8(19) . 3_666 ?
Bi1 I4 Bi1 92.86(4) . 3_666 ?
Bi1 Br4 Bi1 98.6(6) . 3_666 ?
C1 N1 C7 118.5(13) . . ?
C5 N1 C1 120.4(13) . . ?
C5 N1 C7 121.1(13) . . ?
C9 N2 C8 120.5(12) . . ?
C13 N2 C8 120.7(13) . . ?
C13 N2 C9 118.5(14) . . ?
N1 C1 H1 120.2 . . ?
N1 C1 C2 119.5(15) . . ?
C2 C1 H1 120.2 . . ?
C1 C2 H2 118.8 . . ?
C3 C2 C1 122.4(15) . . ?
C3 C2 H2 118.8 . . ?
C2 C3 C4 118.1(14) . . ?
C2 C3 C6 123.8(15) . . ?
C4 C3 C6 118.0(15) . . ?
C3 C4 H4 121.3 . . ?
C5 C4 C3 117.3(15) . . ?
C5 C4 H4 121.3 . . ?
N1 C5 C4 122.2(14) . . ?
N1 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.2 . . ?
N1 C7 H7B 109.2 . . ?
N1 C7 C8 112.0(12) . . ?
H7A C7 H7B 107.9 . . ?
C8 C7 H7A 109.2 . . ?
C8 C7 H7B 109.2 . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
C7 C8 N2 109.0(11) . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 H9 118.5 . . ?
C10 C9 N2 122.9(15) . . ?
C10 C9 H9 118.5 . . ?
C9 C10 H10 120.3 . . ?
C9 C10 C11 119.4(17) . . ?
C11 C10 H10 120.3 . . ?
C10 C11 C14 119.1(16) . . ?
C12 C11 C10 117.2(15) . . ?
C12 C11 C14 123.7(14) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 C11 121.1(14) . . ?
C13 C12 H12 119.5 . . ?
N2 C13 C12 120.8(16) . . ?
N2 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -3(2) . . . . ?
N1 C7 C8 N2 -59.9(17) . . . . ?
N2 C9 C10 C11 3(3) . . . . ?
C1 N1 C5 C4 -1(2) . . . . ?
C1 N1 C7 C8 91.9(16) . . . . ?
C1 C2 C3 C4 2(2) . . . . ?
C1 C2 C3 C6 -178.7(15) . . . . ?
C2 C3 C4 C5 -1(2) . . . . ?
C3 C4 C5 N1 1(2) . . . . ?
C5 N1 C1 C2 2(2) . . . . ?
C5 N1 C7 C8 -85.7(18) . . . . ?
C6 C3 C4 C5 179.6(14) . . . . ?
C7 N1 C1 C2 -175.6(14) . . . . ?
C7 N1 C5 C4 176.3(14) . . . . ?
C8 N2 C9 C10 171.2(16) . . . . ?
C8 N2 C13 C12 -173.3(15) . . . . ?
C9 N2 C8 C7 -74.6(18) . . . . ?
C9 N2 C13 C12 1(2) . . . . ?
C9 C10 C11 C12 0(3) . . . . ?
C9 C10 C11 C14 -179.4(16) . . . . ?
C10 C11 C12 C13 -2(3) . . . . ?
C11 C12 C13 N2 1(3) . . . . ?
C13 N2 C8 C7 99.2(16) . . . . ?
C13 N2 C9 C10 -3(2) . . . . ?
C14 C11 C12 C13 177.3(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_vrf_PLAT971_pic2_bibri_010      
;
PROBLEM: Large positive calculated residual density near bismuth 
atoms. 
RESPONSE: The error is related to the strong absorption of the 
crystalline samples.
;
####################################################################### 
# 
# 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_pic2_bibri_0075
_database_code_depnum_ccdc_archive 'CCDC 2205387'
loop_
_audit_author_name
_audit_author_address
'Petr Buikin'
;N S Kurnakov Institute of General and Inorganic Chemistry Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2022-12-21 deposited with the CCDC.	2023-01-02 downloaded from the CCDC.
;
_audit_creation_date             2022-12-21
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br3.783 I1.217, C14 H18 N2'
_chemical_formula_sum            'C14 H18 Bi Br3.78 I1.22 N2'
_chemical_formula_weight         880.04
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   12.168(3)
_cell_length_b                   11.602(3)
_cell_length_c                   15.055(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.439(6)
_cell_angle_gamma                90
_cell_volume                     2123.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1148
_cell_measurement_temperature    140
_cell_measurement_theta_max      21.064
_cell_measurement_theta_min      2.217
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.232
_exptl_absorpt_coefficient_mu    17.188
_exptl_absorpt_correction_T_max  0.0192
_exptl_absorpt_correction_T_min  0.0037
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1117 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.1927.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.753
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0962
_diffrn_reflns_av_unetI/netI     0.1188
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            12550
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.068
_diffrn_reflns_theta_min         2.109
_diffrn_ambient_temperature      140.00
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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                2404
_reflns_number_total             4189
_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 V8.40B (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         1.129
_refine_diff_density_min         -1.288
_refine_diff_density_rms         0.218
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.913
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     213
_refine_ls_number_reflns         4189
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1076
_refine_ls_R_factor_gt           0.0472
_refine_ls_restrained_S_all      0.913
_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)+(0.0271P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0891
_refine_ls_wR_factor_ref         0.1060
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 I2-Bi1
 2.9 with sigma of 0.05
3. Uiso/Uaniso restraints and constraints
Uanis(Br4) = Uanis(I4)
Uanis(I1) = Uanis(Br1)
Uanis(I3) = Uanis(Br3)
Uanis(Br2) = Uanis(I2)
4. Others
 Fixed Sof: I1(0.25154) I2(0.15426) I3(0.13395) I4(0.67765) Br1(0.74846)
 Br2(0.84574) Br3(0.86605) Br4(0.32235)
5.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B)
5.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C9(H9), C10(H10), C12(H12), C13(H13)
5.c Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C14(H14A,H14B,H14C)
;
_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 0.50203(4) 0.53114(4) 0.65577(4) 0.04067(15) Uani 1 1 d D . . . .
I1 I 0.629(4) 0.444(4) 0.811(3) 0.047(2) Uani 0.2515 1 d . . P A 2
I2 I 0.373(5) 0.673(3) 0.767(4) 0.0505(10) Uani 0.1543 1 d D . P A 2
I3 I 0.668(4) 0.713(4) 0.632(4) 0.0467(12) Uani 0.134 1 d . . P A 2
I4 I 0.3611(9) 0.6314(7) 0.4828(9) 0.0443(9) Uani 0.6776 1 d . . P A 1
Br1 Br 0.630(2) 0.448(2) 0.7954(12) 0.047(2) Uani 0.7485 1 d . . P A 1
Br2 Br 0.3751(12) 0.6573(8) 0.7618(10) 0.0505(10) Uani 0.8457 1 d . . P A 1
Br3 Br 0.6538(7) 0.7191(9) 0.6435(8) 0.0467(12) Uani 0.866 1 d . . P A 1
Br4 Br 0.372(3) 0.617(3) 0.478(3) 0.0443(9) Uani 0.3224 1 d . . P A 2
Br5 Br 0.35423(11) 0.34743(10) 0.68107(10) 0.0473(4) Uani 1 1 d . . . . .
N1 N 0.4702(10) 0.0348(9) 0.6072(8) 0.048(3) Uani 1 1 d . . . . .
N2 N 0.5446(9) 0.0640(8) 0.7927(8) 0.048(3) Uani 1 1 d . . . . .
C1 C 0.4281(11) -0.0682(10) 0.6352(9) 0.044(4) Uani 1 1 d . . . . .
H1 H 0.4739 -0.1212 0.6675 0.053 Uiso 1 1 calc R U . . .
C2 C 0.3213(12) -0.0939(11) 0.6167(9) 0.050(4) Uani 1 1 d . . . . .
H2 H 0.2925 -0.1635 0.6395 0.060 Uiso 1 1 calc R U . . .
C3 C 0.2543(12) -0.0251(11) 0.5672(10) 0.051(4) Uani 1 1 d . . . . .
C4 C 0.2991(12) 0.0801(11) 0.5358(10) 0.050(4) Uani 1 1 d . . . . .
H4 H 0.2558 0.1299 0.4985 0.060 Uiso 1 1 calc R U . . .
C5 C 0.4038(11) 0.1080(10) 0.5596(9) 0.044(4) Uani 1 1 d . . . . .
H5 H 0.4318 0.1808 0.5427 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1332(13) -0.0580(12) 0.5469(11) 0.067(5) Uani 1 1 d . . . . .
H6A H 0.1239 -0.0830 0.4849 0.100 Uiso 1 1 calc R U . . .
H6B H 0.0862 0.0090 0.5567 0.100 Uiso 1 1 calc R U . . .
H6C H 0.1125 -0.1210 0.5862 0.100 Uiso 1 1 calc R U . . .
C7 C 0.5858(11) 0.0676(11) 0.6348(10) 0.050(4) Uani 1 1 d . . . . .
H7A H 0.6175 0.1141 0.5871 0.060 Uiso 1 1 calc R U . . .
H7B H 0.6306 -0.0032 0.6424 0.060 Uiso 1 1 calc R U . . .
C8 C 0.5921(12) 0.1354(10) 0.7203(9) 0.046(4) Uani 1 1 d . . . . .
H8A H 0.6696 0.1549 0.7363 0.055 Uiso 1 1 calc R U . . .
H8B H 0.5502 0.2082 0.7127 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6035(11) -0.0249(10) 0.8283(10) 0.048(4) Uani 1 1 d . . . . .
H9 H 0.6769 -0.0370 0.8113 0.058 Uiso 1 1 calc R U . . .
C10 C 0.5586(11) -0.0973(11) 0.8883(10) 0.049(4) Uani 1 1 d . . . . .
H10 H 0.6013 -0.1585 0.9136 0.059 Uiso 1 1 calc R U . . .
C11 C 0.4490(11) -0.0818(12) 0.9128(10) 0.048(4) Uani 1 1 d . . . . .
C12 C 0.3930(12) 0.0130(10) 0.8748(10) 0.051(4) Uani 1 1 d . . . . .
H12 H 0.3195 0.0279 0.8905 0.061 Uiso 1 1 calc R U . . .
C13 C 0.4412(13) 0.0846(12) 0.8157(10) 0.051(4) Uani 1 1 d . . . . .
H13 H 0.4017 0.1485 0.7912 0.061 Uiso 1 1 calc R U . . .
C14 C 0.4012(13) -0.1667(11) 0.9737(10) 0.060(4) Uani 1 1 d . . . . .
H14A H 0.3998 -0.2429 0.9456 0.089 Uiso 1 1 calc R U . . .
H14B H 0.3261 -0.1434 0.9865 0.089 Uiso 1 1 calc R U . . .
H14C H 0.4461 -0.1698 1.0292 0.089 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 I1 2.92(4) . ?
Bi1 I2 2.86(4) . ?
Bi1 I3 2.96(5) . ?
Bi1 I4 3.271(12) . ?
Bi1 I4 3.313(9) 3_666 ?
Bi1 Br1 2.739(18) . ?
Bi1 Br2 2.699(10) . ?
Bi1 Br3 2.868(11) . ?
Bi1 Br4 3.11(3) 3_666 ?
Bi1 Br4 3.21(4) . ?
Bi1 Br5 2.8251(15) . ?
I4 Bi1 3.313(9) 3_666 ?
Br4 Bi1 3.11(3) 3_666 ?
N1 C1 1.374(15) . ?
N1 C5 1.355(15) . ?
N1 C7 1.499(17) . ?
N2 C8 1.505(17) . ?
N2 C9 1.353(14) . ?
N2 C13 1.340(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.350(18) . ?
C2 H2 0.9500 . ?
C2 C3 1.344(18) . ?
C3 C4 1.425(18) . ?
C3 C6 1.54(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.348(18) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.507(18) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.365(19) . ?
C10 H10 0.9500 . ?
C10 C11 1.410(19) . ?
C11 C12 1.403(18) . ?
C11 C14 1.480(19) . ?
C12 H12 0.9500 . ?
C12 C13 1.37(2) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?

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
I1 Bi1 I3 90.1(15) . . ?
I1 Bi1 Br4 176.4(11) . . ?
I1 Bi1 Br4 93.7(13) . 3_666 ?
I2 Bi1 I1 91.1(16) . . ?
I2 Bi1 I3 93.1(13) . . ?
I2 Bi1 Br4 175.2(15) . 3_666 ?
I2 Bi1 Br4 92.5(14) . . ?
I3 Bi1 Br4 89.7(13) . . ?
I3 Bi1 Br4 87.6(11) . 3_666 ?
I4 Bi1 I4 87.8(2) . 3_666 ?
Br1 Bi1 I4 176.8(5) . . ?
Br1 Bi1 I4 89.9(6) . 3_666 ?
Br1 Bi1 Br3 88.2(6) . . ?
Br1 Bi1 Br5 88.7(5) . . ?
Br2 Bi1 I4 175.3(4) . 3_666 ?
Br2 Bi1 I4 89.1(4) . . ?
Br2 Bi1 Br1 93.3(6) . . ?
Br2 Bi1 Br3 90.7(3) . . ?
Br2 Bi1 Br5 86.9(3) . . ?
Br3 Bi1 I4 89.8(3) . . ?
Br3 Bi1 I4 92.9(3) . 3_666 ?
Br4 Bi1 Br4 82.7(8) 3_666 . ?
Br5 Bi1 I1 87.1(10) . . ?
Br5 Bi1 I2 89.3(11) . . ?
Br5 Bi1 I3 176.3(9) . . ?
Br5 Bi1 I4 93.5(2) . . ?
Br5 Bi1 I4 89.7(2) . 3_666 ?
Br5 Bi1 Br3 175.9(2) . . ?
Br5 Bi1 Br4 90.2(7) . 3_666 ?
Br5 Bi1 Br4 93.0(7) . . ?
Bi1 I4 Bi1 92.2(2) . 3_666 ?
Bi1 Br4 Bi1 97.3(8) 3_666 . ?
C1 N1 C7 119.6(11) . . ?
C5 N1 C1 119.1(12) . . ?
C5 N1 C7 121.2(11) . . ?
C9 N2 C8 119.5(12) . . ?
C13 N2 C8 118.9(12) . . ?
C13 N2 C9 121.4(13) . . ?
N1 C1 H1 120.1 . . ?
C2 C1 N1 119.8(13) . . ?
C2 C1 H1 120.1 . . ?
C1 C2 H2 118.7 . . ?
C3 C2 C1 122.6(13) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 C4 117.5(13) . . ?
C2 C3 C6 121.0(13) . . ?
C4 C3 C6 121.5(13) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.2(13) . . ?
C5 C4 H4 120.4 . . ?
N1 C5 H5 119.2 . . ?
C4 C5 N1 121.7(12) . . ?
C4 C5 H5 119.2 . . ?
C3 C6 H6A 109.5 . . ?
C3 C6 H6B 109.5 . . ?
C3 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
N1 C7 C8 112.5(12) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 109.1 . . ?
C8 C7 H7B 109.1 . . ?
N2 C8 C7 108.9(10) . . ?
N2 C8 H8A 109.9 . . ?
N2 C8 H8B 109.9 . . ?
C7 C8 H8A 109.9 . . ?
C7 C8 H8B 109.9 . . ?
H8A C8 H8B 108.3 . . ?
N2 C9 H9 119.6 . . ?
N2 C9 C10 120.7(13) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.3(13) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C14 118.6(14) . . ?
C12 C11 C10 116.2(14) . . ?
C12 C11 C14 125.2(14) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 C11 121.8(15) . . ?
C13 C12 H12 119.1 . . ?
N2 C13 C12 119.6(14) . . ?
N2 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 4(2) . . . . ?
N1 C7 C8 N2 59.2(14) . . . . ?
N2 C9 C10 C11 1(2) . . . . ?
C1 N1 C5 C4 -3(2) . . . . ?
C1 N1 C7 C8 -90.7(14) . . . . ?
C1 C2 C3 C4 -2(2) . . . . ?
C1 C2 C3 C6 179.5(14) . . . . ?
C2 C3 C4 C5 -3(2) . . . . ?
C3 C4 C5 N1 5(2) . . . . ?
C5 N1 C1 C2 -1(2) . . . . ?
C5 N1 C7 C8 85.1(15) . . . . ?
C6 C3 C4 C5 176.2(14) . . . . ?
C7 N1 C1 C2 174.6(13) . . . . ?
C7 N1 C5 C4 -178.8(13) . . . . ?
C8 N2 C9 C10 -174.0(12) . . . . ?
C8 N2 C13 C12 173.3(12) . . . . ?
C9 N2 C8 C7 74.9(14) . . . . ?
C9 N2 C13 C12 -1(2) . . . . ?
C9 C10 C11 C12 -2(2) . . . . ?
C9 C10 C11 C14 176.2(13) . . . . ?
C10 C11 C12 C13 1(2) . . . . ?
C11 C12 C13 N2 0(2) . . . . ?
C13 N2 C8 C7 -99.9(14) . . . . ?
C13 N2 C9 C10 1(2) . . . . ?
C14 C11 C12 C13 -176.8(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
