# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 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_220303f_auto
_database_code_depnum_ccdc_archive 'CCDC 2208613'
loop_
_audit_author_name
_audit_author_address
'Zongyi Zhang'
;Shandong University
China
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br5, 2(C8 H12 N)'
_chemical_formula_sum            'C16 H24 Bi Br5 N2'
_chemical_formula_weight         852.90
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         BiBrCN
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.7909(5)
_cell_length_b                   14.4589(6)
_cell_length_c                   12.0013(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.108(3)
_cell_angle_gamma                90
_cell_volume                     2389.55(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7391
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      27.5970
_cell_measurement_theta_min      2.6680
_shelx_estimated_absorpt_T_max   0.572
_shelx_estimated_absorpt_T_min   0.452
_exptl_absorpt_coefficient_mu    15.742
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50338
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0591
_diffrn_reflns_av_unetI/netI     0.0884
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24122
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.940
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.732
_diffrn_reflns_theta_min         2.313
_diffrn_ambient_temperature      173.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -70.00   3.00   1.00    2.73    --   16.30 -19.00  60.00   73
  2  ω    -72.00  -3.00   1.00    2.73    --   16.30 -19.00 150.00   69
  3  ω    -70.00   3.00   1.00    2.73    --   16.30 -19.00 -90.00   73
  4  ω    -69.00   4.00   1.00    2.73    --   16.30 -19.00-150.00   73
  5  ω     45.00 101.00   1.00    2.73    --   16.30 178.00 120.00   56
  6  ω    -71.00 -27.00   1.00    2.73    --  -15.36 113.00-119.00   44
  7  ω     23.00  73.00   1.00    2.73    --   16.30-113.00 147.00   50
  8  ω     39.00 105.00   1.00    2.73    --   16.30-178.00 150.00   66
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0178393000
_diffrn_orient_matrix_UB_12      -0.0467081000
_diffrn_orient_matrix_UB_13      0.0014520000
_diffrn_orient_matrix_UB_21      0.0384128000
_diffrn_orient_matrix_UB_22      -0.0117791000
_diffrn_orient_matrix_UB_23      -0.0353699000
_diffrn_orient_matrix_UB_31      0.0413444000
_diffrn_orient_matrix_UB_32      -0.0092608000
_diffrn_orient_matrix_UB_33      0.0373663000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_full    0.963
_reflns_Friedel_fraction_max     0.920
_reflns_number_gt                7532
_reflns_number_total             9545
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.415
_refine_diff_density_min         -1.647
_refine_diff_density_rms         0.203
_refine_ls_abs_structure_details 
;
 Flack x determined using 2801 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.015(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.995
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         9545
_refine_ls_number_restraints     248
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1024
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C12
 1.4 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C3 \\sim C18 \\sim C22 \\sim C5 \\sim C10 \\sim C23 \\sim C2 \\sim
C12: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N4 \\sim C26 \\sim C4 \\sim C1 \\sim C28 \\sim C19 \\sim C9 \\sim C27 \\sim C7:
within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008 within
1.7A
N3 \\sim C16 \\sim C6 \\sim C30 \\sim C17 \\sim C25 \\sim C13 \\sim C31 \\sim
C8: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N2 \\sim C20 \\sim C24 \\sim C29 \\sim C21 \\sim C11 \\sim C14 \\sim C15:
within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008 within
1.7A
N2 \\sim C20 \\sim C24 \\sim C29 \\sim C32 \\sim C21 \\sim C11 \\sim C14 \\sim
C15: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
Uanis(N4) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.005
Uanis(N3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.005
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.005
Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.005
Uanis(C32) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C20(H20), C25(H25), C7(H7), C12(H12)
4.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C28(H28), C19(H19), C26(H26), C27(H27), C6(H6), C24(H24), C29(H29),
 C30(H30), C17(H17), C21(H21), C14(H14), C2(H2), C3(H3), C22(H22), C18(H18),
 C10(H10), C15(H15), C31(H31), C8(H8)
4.c Fitted hexagon refined as free rotating group:
 C1(C9,C28,C19,C26,C27), C2(C3,C22,C18,C10,C5)
4.d Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N3(H3A,H3B,H3C), N2(H2A,H2B,H2C), N4(H4A,H4B,H4C), C4(H4D,
 H4E,H4F), C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.89446(5) 0.26850(4) 0.60826(6) 0.0226(2) Uani 1 1 d . . . . .
Bi2 Bi 0.40455(5) 0.70467(4) 0.60446(6) 0.0224(2) Uani 1 1 d . . . . .
Br8 Br 0.41809(17) 0.71924(17) 0.79880(17) 0.0388(6) Uani 1 1 d . . . . .
Br5 Br 0.83268(13) 0.27655(18) 0.38628(16) 0.0297(5) Uani 1 1 d . . . . .
Br10 Br 0.97856(16) 0.08757(16) 0.57348(18) 0.0309(5) Uani 1 1 d . . . . .
Br1 Br 0.47722(14) 0.88709(16) 0.56239(17) 0.0275(5) Uani 1 1 d . . . . .
Br7 Br 0.91625(17) 0.2671(2) 0.80343(17) 0.0443(6) Uani 1 1 d . . . . .
Br2 Br 0.81291(14) 0.45171(16) 0.61328(17) 0.0264(5) Uani 1 1 d . . . . .
Br9 Br 0.61734(15) 0.64274(17) 0.59543(19) 0.0353(6) Uani 1 1 d . . . . .
Br3 Br 0.33540(14) 0.68704(16) 0.38236(17) 0.0287(5) Uani 1 1 d . . . . .
Br4 Br 1.10839(15) 0.33618(17) 0.59945(19) 0.0355(6) Uani 1 1 d . . . . .
Br6 Br 0.32501(15) 0.51990(16) 0.62294(17) 0.0264(5) Uani 1 1 d . . . . .
N1 N 0.4423(11) 0.8956(12) 0.3174(11) 0.030(3) Uani 1 1 d D U . . .
H1A H 0.501605 0.923156 0.324063 0.035 Uiso 1 1 calc R U . . .
H1B H 0.446766 0.836896 0.344569 0.035 Uiso 1 1 calc R U . . .
H1C H 0.399338 0.928359 0.356717 0.035 Uiso 1 1 calc R U . . .
N3 N 0.7533(11) 0.5092(13) 0.3832(13) 0.042(4) Uani 1 1 d . U . . .
H3A H 0.770644 0.449887 0.368284 0.050 Uiso 1 1 calc R U . . .
H3B H 0.724556 0.511140 0.449611 0.050 Uiso 1 1 calc R U . . .
H3C H 0.807120 0.545676 0.386742 0.050 Uiso 1 1 calc R U . . .
N2 N 0.2486(11) 0.4433(11) 0.4046(11) 0.030(3) Uani 1 1 d . U . . .
H2A H 0.221871 0.500043 0.391258 0.036 Uiso 1 1 calc R U . . .
H2B H 0.314443 0.448151 0.408897 0.036 Uiso 1 1 calc R U . . .
H2C H 0.228134 0.420767 0.470122 0.036 Uiso 1 1 calc R U . . .
N4 N 0.9430(11) 0.0613(12) 0.3217(12) 0.030(3) Uani 1 1 d . U . . .
H4A H 0.905804 0.113251 0.321822 0.036 Uiso 1 1 calc R U . . .
H4B H 0.999912 0.071638 0.361721 0.036 Uiso 1 1 calc R U . . .
H4C H 0.910721 0.013841 0.353047 0.036 Uiso 1 1 calc R U . . .
C4 C 0.8546(15) 0.0039(14) 0.1686(14) 0.045(4) Uani 1 1 d . U . . .
H4D H 0.809466 0.056280 0.165309 0.067 Uiso 1 1 calc R U . . .
H4E H 0.830830 -0.043567 0.218695 0.067 Uiso 1 1 calc R U . . .
H4F H 0.859232 -0.022225 0.093744 0.067 Uiso 1 1 calc R U . . .
C16 C 0.6513(18) 0.6440(18) 0.3153(18) 0.068(5) Uani 1 1 d . U . . .
H16A H 0.675072 0.663249 0.390190 0.102 Uiso 1 1 calc R U . . .
H16B H 0.580186 0.647117 0.309781 0.102 Uiso 1 1 calc R U . . .
H16C H 0.677706 0.685207 0.259693 0.102 Uiso 1 1 calc R U . . .
C1 C 1.0249(9) 0.1168(8) 0.1723(10) 0.044(3) Uani 1 1 d G U . . .
C9 C 1.1256(9) 0.1235(8) 0.1789(11) 0.046(3) Uani 1 1 d G U . . .
H9 H 1.163556 0.076976 0.216293 0.055 Uiso 1 1 calc R U . . .
C28 C 1.1709(7) 0.1984(10) 0.1308(11) 0.048(3) Uani 1 1 d G U . . .
H28 H 1.239672 0.202979 0.135339 0.058 Uiso 1 1 calc R U . . .
C19 C 1.1154(9) 0.2665(8) 0.0761(10) 0.050(3) Uani 1 1 d G U . . .
H19 H 1.146279 0.317668 0.043264 0.060 Uiso 1 1 calc R U . . .
C26 C 1.0147(9) 0.2598(8) 0.0695(10) 0.048(3) Uani 1 1 d G U . . .
H26 H 0.976768 0.306356 0.032142 0.058 Uiso 1 1 calc R U . . .
C27 C 0.9695(7) 0.1849(9) 0.1176(11) 0.048(3) Uani 1 1 d G U . . .
H27 H 0.900651 0.180354 0.113095 0.058 Uiso 1 1 calc R U . . .
C20 C 0.2195(14) 0.3827(14) 0.3170(14) 0.038(3) Uani 1 1 d . U . . .
H20 H 0.256427 0.323534 0.327152 0.045 Uiso 1 1 calc R U . . .
C6 C 0.7741(17) 0.4332(17) 0.0637(18) 0.057(3) Uani 1 1 d . U . . .
H6 H 0.760704 0.381499 0.016489 0.068 Uiso 1 1 calc R U . . .
C24 C 0.1967(16) 0.5043(15) 0.1849(14) 0.043(3) Uani 1 1 d . U . . .
H24 H 0.139844 0.524302 0.219172 0.052 Uiso 1 1 calc R U . . .
C29 C 0.3483(16) 0.3994(17) 0.1798(16) 0.040(3) Uani 1 1 d . U . . .
H29 H 0.384595 0.351319 0.216183 0.048 Uiso 1 1 calc R U . . .
C30 C 0.7130(18) 0.4508(17) 0.1439(17) 0.056(3) Uani 1 1 d . U . . .
H30 H 0.654869 0.417746 0.155311 0.067 Uiso 1 1 calc R U . . .
C17 C 0.8586(17) 0.4874(16) 0.0448(19) 0.057(3) Uani 1 1 d . U . . .
H17 H 0.894597 0.468824 -0.016675 0.068 Uiso 1 1 calc R U . . .
C32 C 0.1027(14) 0.3595(15) 0.3162(16) 0.046(4) Uani 1 1 d . U . . .
H32A H 0.089768 0.320436 0.380458 0.069 Uiso 1 1 calc R U . . .
H32B H 0.082732 0.326944 0.247148 0.069 Uiso 1 1 calc R U . . .
H32C H 0.066074 0.417358 0.320611 0.069 Uiso 1 1 calc R U . . .
C21 C 0.3172(15) 0.5090(15) 0.0492(16) 0.046(3) Uani 1 1 d . U . . .
H21 H 0.335623 0.538710 -0.016951 0.055 Uiso 1 1 calc R U . . .
C23 C 0.4127(15) 0.9972(13) 0.1681(15) 0.041(4) Uani 1 1 d . U . . .
H23A H 0.366072 1.033062 0.209285 0.061 Uiso 1 1 calc R U . . .
H23B H 0.395093 1.000711 0.087994 0.061 Uiso 1 1 calc R U . . .
H23C H 0.478023 1.022513 0.182808 0.061 Uiso 1 1 calc R U . . .
C11 C 0.2556(15) 0.4312(15) 0.2245(15) 0.039(3) Uani 1 1 d . U . . .
C25 C 0.6844(17) 0.5429(16) 0.2936(16) 0.054(3) Uani 1 1 d . U . . .
H25 H 0.626657 0.501065 0.286175 0.065 Uiso 1 1 calc R U . . .
C13 C 0.7475(17) 0.5248(17) 0.2075(18) 0.052(3) Uani 1 1 d . U . . .
C14 C 0.3786(16) 0.4369(15) 0.0927(16) 0.044(3) Uani 1 1 d . U . . .
H14 H 0.436679 0.418709 0.059747 0.053 Uiso 1 1 calc R U . . .
C2 C 0.4612(7) 0.7539(9) 0.1076(10) 0.042(3) Uani 1 1 d G U . . .
H2 H 0.393584 0.741033 0.104785 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5247(9) 0.6929(7) 0.0596(10) 0.046(3) Uani 1 1 d G U . . .
H3 H 0.500509 0.638282 0.024043 0.055 Uiso 1 1 calc R U . . .
C22 C 0.6237(8) 0.7118(8) 0.0638(10) 0.046(3) Uani 1 1 d G U . . .
H22 H 0.667096 0.670084 0.030991 0.055 Uiso 1 1 calc R U . . .
C18 C 0.6591(7) 0.7917(9) 0.1159(11) 0.048(3) Uani 1 1 d G U . . .
H18 H 0.726758 0.804637 0.118681 0.057 Uiso 1 1 calc R U . . .
C10 C 0.5956(9) 0.8528(7) 0.1638(10) 0.044(3) Uani 1 1 d G U . . .
H10 H 0.619835 0.907389 0.199424 0.052 Uiso 1 1 calc R U . . .
C5 C 0.4967(9) 0.8339(8) 0.1597(10) 0.038(3) Uani 1 1 d G U . . .
C15 C 0.2287(15) 0.5409(16) 0.0973(15) 0.047(3) Uani 1 1 d . U . . .
H15 H 0.193594 0.590545 0.062531 0.056 Uiso 1 1 calc R U . . .
C31 C 0.8933(17) 0.5600(17) 0.1015(18) 0.053(3) Uani 1 1 d . U . . .
H31 H 0.949773 0.593925 0.085118 0.064 Uiso 1 1 calc R U . . .
C7 C 0.9617(15) 0.0391(14) 0.2155(13) 0.038(3) Uani 1 1 d . U . . .
H7 H 1.003803 -0.017209 0.220378 0.046 Uiso 1 1 calc R U . . .
C8 C 0.8375(17) 0.5773(19) 0.1835(19) 0.051(3) Uani 1 1 d . U . . .
H8 H 0.855437 0.627171 0.231813 0.062 Uiso 1 1 calc R U . . .
C12 C 0.4107(14) 0.8931(13) 0.2071(11) 0.035(3) Uani 1 1 d D U . . .
H12 H 0.345588 0.863354 0.194360 0.042 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 Br5 2.755(2) . ?
Bi1 Br10 2.901(2) . ?
Bi1 Br7 2.345(2) . ?
Bi1 Br2 2.880(3) . ?
Bi1 Br4 3.116(2) . ?
Bi2 Br8 2.339(2) . ?
Bi2 Br1 2.876(2) . ?
Bi2 Br9 3.076(2) . ?
Bi2 Br3 2.794(2) . ?
Bi2 Br6 2.901(2) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C12 1.371(11) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C25 1.48(2) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C20 1.41(2) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
N4 C7 1.35(2) . ?
C4 H4D 0.9800 . ?
C4 H4E 0.9800 . ?
C4 H4F 0.9800 . ?
C4 C7 1.63(2) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C16 C25 1.56(3) . ?
C1 C9 1.3900 . ?
C1 C27 1.3900 . ?
C1 C7 1.53(2) . ?
C9 H9 0.9500 . ?
C9 C28 1.3900 . ?
C28 H28 0.9500 . ?
C28 C19 1.3900 . ?
C19 H19 0.9500 . ?
C19 C26 1.3900 . ?
C26 H26 0.9500 . ?
C26 C27 1.3900 . ?
C27 H27 0.9500 . ?
C20 H20 1.0000 . ?
C20 C32 1.64(3) . ?
C20 C11 1.43(3) . ?
C6 H6 0.9500 . ?
C6 C30 1.34(3) . ?
C6 C17 1.43(3) . ?
C24 H24 0.9500 . ?
C24 C11 1.40(3) . ?
C24 C15 1.28(3) . ?
C29 H29 0.9500 . ?
C29 C11 1.49(3) . ?
C29 C14 1.27(3) . ?
C30 H30 0.9500 . ?
C30 C13 1.38(3) . ?
C17 H17 0.9500 . ?
C17 C31 1.33(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C14 1.42(3) . ?
C21 C15 1.45(3) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C23 C12 1.58(3) . ?
C25 H25 1.0000 . ?
C25 C13 1.41(3) . ?
C13 C8 1.49(3) . ?
C14 H14 0.9500 . ?
C2 H2 0.9500 . ?
C2 C3 1.3900 . ?
C2 C5 1.3900 . ?
C3 H3 0.9500 . ?
C3 C22 1.3900 . ?
C22 H22 0.9500 . ?
C22 C18 1.3900 . ?
C18 H18 0.9500 . ?
C18 C10 1.3900 . ?
C10 H10 0.9500 . ?
C10 C5 1.3900 . ?
C5 C12 1.59(2) . ?
C15 H15 0.9500 . ?
C31 H31 0.9500 . ?
C31 C8 1.31(3) . ?
C7 H7 1.0000 . ?
C8 H8 0.9500 . ?
C12 H12 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br5 Bi1 Br10 90.23(7) . . ?
Br5 Bi1 Br2 83.15(7) . . ?
Br5 Bi1 Br4 101.40(6) . . ?
Br10 Bi1 Br4 83.78(7) . . ?
Br7 Bi1 Br5 169.18(8) . . ?
Br7 Bi1 Br10 96.04(8) . . ?
Br7 Bi1 Br2 90.92(8) . . ?
Br7 Bi1 Br4 88.07(8) . . ?
Br2 Bi1 Br10 172.83(7) . . ?
Br2 Bi1 Br4 94.78(7) . . ?
Br8 Bi2 Br1 94.74(8) . . ?
Br8 Bi2 Br9 92.10(7) . . ?
Br8 Bi2 Br3 164.64(8) . . ?
Br8 Bi2 Br6 90.96(8) . . ?
Br1 Bi2 Br9 85.33(7) . . ?
Br1 Bi2 Br6 174.15(7) . . ?
Br3 Bi2 Br1 91.17(7) . . ?
Br3 Bi2 Br9 102.52(7) . . ?
Br3 Bi2 Br6 82.99(7) . . ?
Br6 Bi2 Br9 95.74(7) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C12 N1 H1A 109.5 . . ?
C12 N1 H1B 109.5 . . ?
C12 N1 H1C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C25 N3 H3A 109.5 . . ?
C25 N3 H3B 109.5 . . ?
C25 N3 H3C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C20 N2 H2A 109.5 . . ?
C20 N2 H2B 109.5 . . ?
C20 N2 H2C 109.5 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C7 N4 H4A 109.5 . . ?
C7 N4 H4B 109.5 . . ?
C7 N4 H4C 109.5 . . ?
H4D C4 H4E 109.5 . . ?
H4D C4 H4F 109.5 . . ?
H4E C4 H4F 109.5 . . ?
C7 C4 H4D 109.5 . . ?
C7 C4 H4E 109.5 . . ?
C7 C4 H4F 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C25 C16 H16A 109.5 . . ?
C25 C16 H16B 109.5 . . ?
C25 C16 H16C 109.5 . . ?
C9 C1 C27 120.0 . . ?
C9 C1 C7 128.2(12) . . ?
C27 C1 C7 111.8(12) . . ?
C1 C9 H9 120.0 . . ?
C1 C9 C28 120.0 . . ?
C28 C9 H9 120.0 . . ?
C9 C28 H28 120.0 . . ?
C19 C28 C9 120.0 . . ?
C19 C28 H28 120.0 . . ?
C28 C19 H19 120.0 . . ?
C28 C19 C26 120.0 . . ?
C26 C19 H19 120.0 . . ?
C19 C26 H26 120.0 . . ?
C19 C26 C27 120.0 . . ?
C27 C26 H26 120.0 . . ?
C1 C27 H27 120.0 . . ?
C26 C27 C1 120.0 . . ?
C26 C27 H27 120.0 . . ?
N2 C20 H20 108.6 . . ?
N2 C20 C32 111.7(15) . . ?
N2 C20 C11 100.3(17) . . ?
C32 C20 H20 108.6 . . ?
C11 C20 H20 108.6 . . ?
C11 C20 C32 118.6(16) . . ?
C30 C6 H6 118.0 . . ?
C30 C6 C17 124(2) . . ?
C17 C6 H6 118.0 . . ?
C11 C24 H24 124.1 . . ?
C15 C24 H24 124.1 . . ?
C15 C24 C11 112(2) . . ?
C11 C29 H29 120.2 . . ?
C14 C29 H29 120.2 . . ?
C14 C29 C11 120(2) . . ?
C6 C30 H30 125.3 . . ?
C6 C30 C13 109(2) . . ?
C13 C30 H30 125.3 . . ?
C6 C17 H17 115.6 . . ?
C31 C17 C6 129(3) . . ?
C31 C17 H17 115.6 . . ?
C20 C32 H32A 109.5 . . ?
C20 C32 H32B 109.5 . . ?
C20 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C14 C21 H21 117.2 . . ?
C14 C21 C15 126(2) . . ?
C15 C21 H21 117.2 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C23 H23A 109.5 . . ?
C12 C23 H23B 109.5 . . ?
C12 C23 H23C 109.5 . . ?
C20 C11 C29 118.2(19) . . ?
C24 C11 C20 114(2) . . ?
C24 C11 C29 127(2) . . ?
N3 C25 C16 111.8(18) . . ?
N3 C25 H25 110.1 . . ?
C16 C25 H25 110.1 . . ?
C13 C25 N3 94.2(17) . . ?
C13 C25 C16 120(2) . . ?
C13 C25 H25 110.1 . . ?
C30 C13 C25 110(2) . . ?
C30 C13 C8 123(2) . . ?
C25 C13 C8 127(2) . . ?
C29 C14 C21 114(2) . . ?
C29 C14 H14 123.2 . . ?
C21 C14 H14 123.2 . . ?
C3 C2 H2 120.0 . . ?
C3 C2 C5 120.0 . . ?
C5 C2 H2 120.0 . . ?
C2 C3 H3 120.0 . . ?
C22 C3 C2 120.0 . . ?
C22 C3 H3 120.0 . . ?
C3 C22 H22 120.0 . . ?
C18 C22 C3 120.0 . . ?
C18 C22 H22 120.0 . . ?
C22 C18 H18 120.0 . . ?
C10 C18 C22 120.0 . . ?
C10 C18 H18 120.0 . . ?
C18 C10 H10 120.0 . . ?
C18 C10 C5 120.0 . . ?
C5 C10 H10 120.0 . . ?
C2 C5 C12 110.9(10) . . ?
C10 C5 C2 120.0 . . ?
C10 C5 C12 129.1(10) . . ?
C24 C15 C21 122(2) . . ?
C24 C15 H15 119.0 . . ?
C21 C15 H15 119.0 . . ?
C17 C31 H31 125.5 . . ?
C8 C31 C17 109(2) . . ?
C8 C31 H31 125.5 . . ?
N4 C7 C4 100.6(16) . . ?
N4 C7 C1 106.7(14) . . ?
N4 C7 H7 106.1 . . ?
C4 C7 H7 106.1 . . ?
C1 C7 C4 129.3(15) . . ?
C1 C7 H7 106.1 . . ?
C13 C8 H8 117.4 . . ?
C31 C8 C13 125(2) . . ?
C31 C8 H8 117.4 . . ?
N1 C12 C23 104.6(14) . . ?
N1 C12 C5 99.0(13) . . ?
N1 C12 H12 113.2 . . ?
C23 C12 C5 112.5(15) . . ?
C23 C12 H12 113.2 . . ?
C5 C12 H12 113.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N3 C25 C13 C30 109.3(19) . . . . ?
N3 C25 C13 C8 -72(3) . . . . ?
N2 C20 C11 C24 -80(2) . . . . ?
N2 C20 C11 C29 101(2) . . . . ?
C16 C25 C13 C30 -133(2) . . . . ?
C16 C25 C13 C8 46(3) . . . . ?
C1 C9 C28 C19 0.0 . . . . ?
C9 C1 C27 C26 0.0 . . . . ?
C9 C1 C7 N4 89.5(18) . . . . ?
C9 C1 C7 C4 -151.0(16) . . . . ?
C9 C28 C19 C26 0.0 . . . . ?
C28 C19 C26 C27 0.0 . . . . ?
C19 C26 C27 C1 0.0 . . . . ?
C27 C1 C9 C28 0.0 . . . . ?
C27 C1 C7 N4 -92.7(15) . . . . ?
C27 C1 C7 C4 27(2) . . . . ?
C6 C30 C13 C25 -178.9(19) . . . . ?
C6 C30 C13 C8 3(3) . . . . ?
C6 C17 C31 C8 0(3) . . . . ?
C30 C6 C17 C31 2(4) . . . . ?
C30 C13 C8 C31 0(4) . . . . ?
C17 C6 C30 C13 -3(3) . . . . ?
C17 C31 C8 C13 -1(3) . . . . ?
C32 C20 C11 C24 42(2) . . . . ?
C32 C20 C11 C29 -137.4(18) . . . . ?
C11 C24 C15 C21 -1(3) . . . . ?
C11 C29 C14 C21 1(3) . . . . ?
C25 C13 C8 C31 -178(2) . . . . ?
C14 C29 C11 C20 175(2) . . . . ?
C14 C29 C11 C24 -4(3) . . . . ?
C14 C21 C15 C24 -1(3) . . . . ?
C2 C3 C22 C18 0.0 . . . . ?
C2 C5 C12 N1 121.8(12) . . . . ?
C2 C5 C12 C23 -128.3(11) . . . . ?
C3 C2 C5 C10 0.0 . . . . ?
C3 C2 C5 C12 179.5(11) . . . . ?
C3 C22 C18 C10 0.0 . . . . ?
C22 C18 C10 C5 0.0 . . . . ?
C18 C10 C5 C2 0.0 . . . . ?
C18 C10 C5 C12 -179.4(13) . . . . ?
C10 C5 C12 N1 -58.8(16) . . . . ?
C10 C5 C12 C23 51.1(15) . . . . ?
C5 C2 C3 C22 0.0 . . . . ?
C15 C24 C11 C20 -175.2(18) . . . . ?
C15 C24 C11 C29 4(3) . . . . ?
C15 C21 C14 C29 1(3) . . . . ?
C7 C1 C9 C28 177.6(14) . . . . ?
C7 C1 C27 C26 -178.0(12) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.623
_oxdiff_exptl_absorpt_empirical_full_min 0.753
####################################################################### 
# 
# 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_mo_211218j_0m
_database_code_depnum_ccdc_archive 'CCDC 2208615'
loop_
_audit_author_name
_audit_author_address
'Zongyi Zhang'
;Shandong University
China
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-12-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Br10, 4(C8 H12 N)'
_chemical_formula_sum            'C32 H48 Bi2 Br10 N4'
_chemical_formula_weight         1705.80
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.7062(7)
_cell_length_b                   14.5646(7)
_cell_length_c                   11.9207(6)
_cell_angle_alpha                90
_cell_angle_beta                 93.110(2)
_cell_angle_gamma                90
_cell_volume                     2376.2(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7026
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.38
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   0.364
_shelx_estimated_absorpt_T_min   0.300
_exptl_absorpt_coefficient_mu    15.830
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1272 before and 0.0634 after correction.
The Ratio of minimum to maximum transmission is 0.5105.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.384
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0422
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            32491
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.520
_diffrn_reflns_theta_min         2.042
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4519
_reflns_number_total             5364
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.870
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       0.00115(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5364
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0253
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0219P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0535
_refine_ls_wR_factor_ref         0.0565
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
C11 \\sim C3 \\sim C7 \\sim C12 \\sim C1 \\sim C9 \\sim C14 \\sim C15 \\sim N2:
within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008 within
1.7A
C2 \\sim C10 \\sim C6 \\sim C16 \\sim C8 \\sim C4 \\sim C5 \\sim C13 \\sim N1:
within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008 within
1.7A
3.a Ternary CH refined with riding coordinates:
 C5(H5), C14(H14)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12),
 C16(H16)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.10744(2) 0.46896(2) 0.65041(2) 0.02308(6) Uani 1 1 d . . . . .
Br1 Br 0.06793(3) 0.65000(3) 0.72381(4) 0.03005(10) Uani 1 1 d . . . . .
Br2 Br 0.09909(3) 0.40776(3) 0.86756(4) 0.03811(11) Uani 1 1 d . . . . .
Br3 Br 0.30337(3) 0.48115(3) 0.66444(4) 0.03692(12) Uani 1 1 d . . . . .
Br4 Br 0.11483(3) 0.54624(3) 0.41637(4) 0.02878(10) Uani 1 1 d . . . . .
Br5 Br 0.12349(3) 0.28321(3) 0.57418(4) 0.02780(10) Uani 1 1 d . . . . .
N1 N 0.1814(2) 0.3356(2) 0.3151(3) 0.0315(8) Uani 1 1 d . U . . .
H1A H 0.170363 0.312047 0.244806 0.038 Uiso 1 1 calc R U . . .
H1B H 0.155287 0.392917 0.317876 0.038 Uiso 1 1 calc R U . . .
H1C H 0.153057 0.298771 0.365718 0.038 Uiso 1 1 calc R U . . .
N2 N 0.1013(3) 0.7895(3) 0.4983(3) 0.0394(9) Uani 1 1 d . U . . .
H2A H 0.094259 0.784984 0.422149 0.047 Uiso 1 1 calc R U . . .
H2B H 0.046438 0.814856 0.524966 0.047 Uiso 1 1 calc R U . . .
H2C H 0.110663 0.732590 0.528469 0.047 Uiso 1 1 calc R U . . .
C1 C 0.2804(3) 0.8040(3) 0.4942(5) 0.0424(9) Uani 1 1 d . U . . .
C2 C 0.4301(3) 0.5251(3) 0.1236(5) 0.0397(9) Uani 1 1 d . U . . .
H2 H 0.462182 0.566015 0.075690 0.048 Uiso 1 1 calc R U . . .
C3 C 0.4553(4) 0.7334(4) 0.4280(5) 0.0568(12) Uani 1 1 d . U . . .
H3 H 0.516026 0.709665 0.406274 0.068 Uiso 1 1 calc R U . . .
C4 C 0.3374(3) 0.4051(3) 0.2640(4) 0.0328(8) Uani 1 1 d . U . . .
C5 C 0.2900(3) 0.3405(3) 0.3429(4) 0.0332(9) Uani 1 1 d . U . . .
H5 H 0.300288 0.365436 0.420847 0.040 Uiso 1 1 calc R U . . .
C6 C 0.3923(3) 0.4792(3) 0.3065(5) 0.0385(9) Uani 1 1 d . U . . .
H6 H 0.397410 0.489451 0.385296 0.046 Uiso 1 1 calc R U . . .
C7 C 0.4111(4) 0.8070(4) 0.3701(5) 0.0549(12) Uani 1 1 d . U . . .
H7 H 0.441560 0.833536 0.308064 0.066 Uiso 1 1 calc R U . . .
C8 C 0.3299(3) 0.3931(3) 0.1482(4) 0.0372(9) Uani 1 1 d . U . . .
H8 H 0.293320 0.342856 0.117226 0.045 Uiso 1 1 calc R U . . .
C9 C 0.3232(4) 0.7299(3) 0.5507(5) 0.0502(11) Uani 1 1 d . U . . .
H9 H 0.292839 0.702840 0.612349 0.060 Uiso 1 1 calc R U . . .
C10 C 0.4389(3) 0.5374(3) 0.2371(5) 0.0402(10) Uani 1 1 d . U . . .
H10 H 0.477344 0.586455 0.267890 0.048 Uiso 1 1 calc R U . . .
C11 C 0.4102(4) 0.6963(4) 0.5160(6) 0.0562(12) Uani 1 1 d . U . . .
H11 H 0.439687 0.645608 0.554730 0.067 Uiso 1 1 calc R U . . .
C12 C 0.3237(4) 0.8411(4) 0.4027(5) 0.0461(10) Uani 1 1 d . U . . .
H12 H 0.292882 0.890273 0.362157 0.055 Uiso 1 1 calc R U . . .
C13 C 0.3309(4) 0.2447(3) 0.3420(5) 0.0461(12) Uani 1 1 d . U . . .
H13A H 0.294775 0.205637 0.392297 0.069 Uiso 1 1 calc R U . . .
H13B H 0.400015 0.246074 0.367507 0.069 Uiso 1 1 calc R U . . .
H13C H 0.324410 0.219979 0.265468 0.069 Uiso 1 1 calc R U . . .
C14 C 0.1879(4) 0.8491(4) 0.5302(5) 0.0541(12) Uani 1 1 d . U . . .
H14 H 0.179590 0.905027 0.481939 0.065 Uiso 1 1 calc R U . . .
C15 C 0.1855(4) 0.8819(5) 0.6431(6) 0.0752(19) Uani 1 1 d . U . . .
H15A H 0.125651 0.917559 0.651334 0.113 Uiso 1 1 calc R U . . .
H15B H 0.242516 0.920963 0.660431 0.113 Uiso 1 1 calc R U . . .
H15C H 0.186584 0.829612 0.694915 0.113 Uiso 1 1 calc R U . . .
C16 C 0.3747(4) 0.4531(3) 0.0775(5) 0.0414(10) Uani 1 1 d . U . . .
H16 H 0.367749 0.445267 -0.001634 0.050 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 Br1 2.8395(4) . ?
Bi1 Br2 2.7460(5) . ?
Bi1 Br3 2.6874(5) . ?
Bi1 Br4 3.0152(5) . ?
Bi1 Br4 3.1146(4) 3_566 ?
Bi1 Br5 2.8663(4) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C5 1.509(5) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C14 1.503(6) . ?
C1 C9 1.385(7) . ?
C1 C12 1.380(8) . ?
C1 C14 1.511(7) . ?
C2 H2 0.9500 . ?
C2 C10 1.363(7) . ?
C2 C16 1.391(7) . ?
C3 H3 0.9500 . ?
C3 C7 1.395(8) . ?
C3 C11 1.359(9) . ?
C4 C5 1.504(6) . ?
C4 C6 1.395(6) . ?
C4 C8 1.389(7) . ?
C5 H5 1.0000 . ?
C5 C13 1.504(6) . ?
C6 H6 0.9500 . ?
C6 C10 1.367(7) . ?
C7 H7 0.9500 . ?
C7 C12 1.373(8) . ?
C8 H8 0.9500 . ?
C8 C16 1.381(7) . ?
C9 H9 0.9500 . ?
C9 C11 1.373(8) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 H14 1.0000 . ?
C14 C15 1.430(8) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16 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
Br1 Bi1 Br4 86.820(12) . 3_566 ?
Br1 Bi1 Br4 87.421(13) . . ?
Br1 Bi1 Br5 173.413(13) . . ?
Br2 Bi1 Br1 89.574(14) . . ?
Br2 Bi1 Br4 97.332(14) . 3_566 ?
Br2 Bi1 Br4 176.993(14) . . ?
Br2 Bi1 Br5 90.018(14) . . ?
Br3 Bi1 Br1 97.245(14) . . ?
Br3 Bi1 Br2 93.177(15) . . ?
Br3 Bi1 Br4 87.096(14) . . ?
Br3 Bi1 Br4 168.769(15) . 3_566 ?
Br3 Bi1 Br5 89.342(13) . . ?
Br4 Bi1 Br4 82.618(13) . 3_566 ?
Br5 Bi1 Br4 86.712(12) . 3_566 ?
Br5 Bi1 Br4 92.979(13) . . ?
Bi1 Br4 Bi1 97.383(13) . 3_566 ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C5 N1 H1A 109.5 . . ?
C5 N1 H1B 109.5 . . ?
C5 N1 H1C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C14 N2 H2A 109.5 . . ?
C14 N2 H2B 109.5 . . ?
C14 N2 H2C 109.5 . . ?
C9 C1 C14 122.7(5) . . ?
C12 C1 C9 120.0(5) . . ?
C12 C1 C14 117.3(5) . . ?
C10 C2 H2 119.7 . . ?
C10 C2 C16 120.6(5) . . ?
C16 C2 H2 119.7 . . ?
C7 C3 H3 120.5 . . ?
C11 C3 H3 120.5 . . ?
C11 C3 C7 118.9(6) . . ?
C6 C4 C5 120.0(4) . . ?
C8 C4 C5 122.1(4) . . ?
C8 C4 C6 117.9(4) . . ?
N1 C5 H5 108.1 . . ?
C4 C5 N1 110.3(3) . . ?
C4 C5 H5 108.1 . . ?
C4 C5 C13 113.7(4) . . ?
C13 C5 N1 108.5(3) . . ?
C13 C5 H5 108.1 . . ?
C4 C6 H6 119.3 . . ?
C10 C6 C4 121.3(5) . . ?
C10 C6 H6 119.3 . . ?
C3 C7 H7 120.0 . . ?
C12 C7 C3 120.0(6) . . ?
C12 C7 H7 120.0 . . ?
C4 C8 H8 119.5 . . ?
C16 C8 C4 121.0(4) . . ?
C16 C8 H8 119.5 . . ?
C1 C9 H9 120.6 . . ?
C11 C9 C1 118.9(6) . . ?
C11 C9 H9 120.6 . . ?
C2 C10 C6 120.0(4) . . ?
C2 C10 H10 120.0 . . ?
C6 C10 H10 120.0 . . ?
C3 C11 C9 122.0(6) . . ?
C3 C11 H11 119.0 . . ?
C9 C11 H11 119.0 . . ?
C1 C12 H12 119.9 . . ?
C7 C12 C1 120.1(5) . . ?
C7 C12 H12 119.9 . . ?
C5 C13 H13A 109.5 . . ?
C5 C13 H13B 109.5 . . ?
C5 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N2 C14 C1 109.9(4) . . ?
N2 C14 H14 105.2 . . ?
C1 C14 H14 105.2 . . ?
C15 C14 N2 111.9(5) . . ?
C15 C14 C1 118.4(5) . . ?
C15 C14 H14 105.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C2 C16 H16 120.4 . . ?
C8 C16 C2 119.2(5) . . ?
C8 C16 H16 120.4 . . ?

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
C1 C9 C11 C3 -0.1(8) . . . . ?
C3 C7 C12 C1 1.4(8) . . . . ?
C4 C6 C10 C2 1.7(7) . . . . ?
C4 C8 C16 C2 1.6(7) . . . . ?
C5 C4 C6 C10 177.9(4) . . . . ?
C5 C4 C8 C16 -179.6(4) . . . . ?
C6 C4 C5 N1 123.6(4) . . . . ?
C6 C4 C5 C13 -114.3(5) . . . . ?
C6 C4 C8 C16 -0.5(7) . . . . ?
C7 C3 C11 C9 -1.0(8) . . . . ?
C8 C4 C5 N1 -57.3(5) . . . . ?
C8 C4 C5 C13 64.8(5) . . . . ?
C8 C4 C6 C10 -1.2(7) . . . . ?
C9 C1 C12 C7 -2.6(7) . . . . ?
C9 C1 C14 N2 -75.1(6) . . . . ?
C9 C1 C14 C15 55.1(7) . . . . ?
C10 C2 C16 C8 -1.1(7) . . . . ?
C11 C3 C7 C12 0.4(8) . . . . ?
C12 C1 C9 C11 1.9(7) . . . . ?
C12 C1 C14 N2 106.5(5) . . . . ?
C12 C1 C14 C15 -123.2(6) . . . . ?
C14 C1 C9 C11 -176.4(5) . . . . ?
C14 C1 C12 C7 175.9(4) . . . . ?
C16 C2 C10 C6 -0.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_220303e_auto
_database_code_depnum_ccdc_archive 'CCDC 2208617'
loop_
_audit_author_name
_audit_author_address
'Zongyi Zhang'
;Shandong University
China
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2022-09-21
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi Br5, 2(C8 H12 N)'
_chemical_formula_sum            'C16 H24 Bi Br5 N2'
_chemical_formula_weight         852.90
_chemical_absolute_configuration syn
_chemical_melting_point          ?
_chemical_oxdiff_formula         BiBrCN
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   12.0027(7)
_cell_length_b                   14.4943(8)
_cell_length_c                   13.8026(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.175(5)
_cell_angle_gamma                90
_cell_volume                     2397.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7795
_cell_measurement_temperature    173.00
_cell_measurement_theta_max      28.9970
_cell_measurement_theta_min      2.8470
_shelx_estimated_absorpt_T_max   0.573
_shelx_estimated_absorpt_T_min   0.453
_exptl_absorpt_coefficient_mu    15.689
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09069
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.112a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.363
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0827
_diffrn_reflns_av_unetI/netI     0.0976
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26684
_diffrn_reflns_point_group_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.733
_diffrn_reflns_theta_min         2.811
_diffrn_ambient_temperature      173.00
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  37.00   1.00    5.22    --    4.80 -99.00  30.00   43
  2  ω    -60.00  11.00   1.00    5.22    --    4.80 -56.00 -89.00   71
  3  ω      3.00  73.00   1.00    5.22    --    4.80  56.00  52.00   70
  4  ω    -23.00  28.00   1.00    5.22    --   -3.63 -99.00  90.00   51
  5  ω    -23.00  27.00   1.00    5.22    --   -3.63 -99.00-120.00   50
  6  ω     -9.00  62.00   1.00    5.22    --   -3.63  38.00-180.00   71
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0426271000
_diffrn_orient_matrix_UB_12      -0.0314114000
_diffrn_orient_matrix_UB_13      0.0155706000
_diffrn_orient_matrix_UB_21      0.0294181000
_diffrn_orient_matrix_UB_22      0.0103878000
_diffrn_orient_matrix_UB_23      -0.0418665000
_diffrn_orient_matrix_UB_31      0.0286265000
_diffrn_orient_matrix_UB_32      0.0360632000
_diffrn_orient_matrix_UB_33      0.0255654000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.893
_reflns_Friedel_fraction_full    0.965
_reflns_Friedel_fraction_max     0.928
_reflns_number_gt                7664
_reflns_number_total             9609
_reflns_odcompleteness_completeness 99.75
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.112a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.691
_refine_diff_density_min         -2.078
_refine_diff_density_rms         0.241
_refine_ls_abs_structure_details 
;
 Flack x determined using 2739 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.024(15)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     417
_refine_ls_number_reflns         9609
_refine_ls_number_restraints     243
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.020
_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)+(0.0465P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1153
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-C3 = N3-C15
 1.45 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N1 \\sim C3 \\sim C22 \\sim C5 \\sim C24 \\sim C30 \\sim C2 \\sim C27 \\sim
C11: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N3 \\sim C18 \\sim C16 \\sim C6 \\sim C7 \\sim C29 \\sim C10 \\sim C1 \\sim
C15: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N4 \\sim C4 \\sim C28 \\sim C17 \\sim C19 \\sim C23 \\sim C13 \\sim C14 \\sim
C9: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N2 \\sim C26 \\sim C20 \\sim C32 \\sim C21 \\sim C12 \\sim C25 \\sim C31 \\sim
C8: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
Uanis(N3) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N1) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N4) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(N2) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Ternary CH refined with riding coordinates:
 C3(H3), C20(H20), C19(H19), C15(H15)
4.b Aromatic/amide H refined with riding coordinates:
 C26(H26), C4(H4), C22(H22), C30(H30), C27(H27), C2(H2), C11(H11), C17(H17),
 C32(H32), C23(H23), C12(H12), C25(H25), C13(H13), C1(H1), C16(H16), C18(H18),
 C29(H29), C6(H6), C31(H31), C9(H9)
4.c Fitted hexagon refined as free rotating group:
 C22(C30,C27,C5,C2,C11), C1(C7,C16,C18,C29,C6)
4.d Idealised Me refined as rotating group:
 N2(H2A,H2B,H2C), N1(H1A,H1B,H1C), N3(H3A,H3B,H3C), N4(H4A,H4B,H4C), C24(H24A,
 H24B,H24C), C10(H10A,H10B,H10C), C21(H21A,H21B,H21C), C14(H14A,H14B,H14C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.39554(7) 0.57841(5) 0.59508(7) 0.0167(2) Uani 1 1 d . . . . .
Bi2 Bi 0.39177(6) 0.14228(5) 0.10577(7) 0.0175(2) Uani 1 1 d . . . . .
Br7 Br 0.61386(18) 0.1504(2) 0.16738(19) 0.0241(6) Uani 1 1 d . . . . .
Br5 Br 0.3772(2) 0.39423(19) 0.6747(2) 0.0228(6) Uani 1 1 d . . . . .
Br9 Br 0.1965(2) 0.1408(2) 0.0836(2) 0.0393(7) Uani 1 1 d . . . . .
Br1 Br 0.4373(2) 0.76125(19) 0.5229(2) 0.0235(6) Uani 1 1 d . . . . .
Br10 Br 0.4269(2) -0.03812(19) 0.0211(2) 0.0255(6) Uani 1 1 d . . . . .
Br2 Br 0.6176(2) 0.56074(19) 0.6645(2) 0.0249(6) Uani 1 1 d . . . . .
Br8 Br 0.4012(2) 0.2103(2) -0.1083(2) 0.0318(7) Uani 1 1 d . . . . .
Br3 Br 0.4042(2) 0.5166(2) 0.3825(2) 0.0300(7) Uani 1 1 d . . . . .
Br4 Br 0.38644(19) 0.32598(19) 0.1869(2) 0.0215(6) Uani 1 1 d . . . . .
Br6 Br 0.2010(2) 0.5930(2) 0.5817(3) 0.0346(7) Uani 1 1 d . . . . .
N2 N 0.6152(17) 0.3829(15) 0.2449(17) 0.043(5) Uani 1 1 d . U . . .
H2A H 0.596217 0.427546 0.200718 0.052 Uiso 1 1 calc R U . . .
H2B H 0.553715 0.365653 0.276164 0.052 Uiso 1 1 calc R U . . .
H2C H 0.643054 0.333203 0.214036 0.052 Uiso 1 1 calc R U . . .
N1 N 0.6814(13) 0.7717(14) 0.5558(16) 0.027(4) Uani 1 1 d D U . . .
H1A H 0.677241 0.787489 0.491865 0.032 Uiso 1 1 calc R U . . .
H1B H 0.644871 0.814618 0.590254 0.032 Uiso 1 1 calc R U . . .
H1C H 0.649340 0.715494 0.563244 0.032 Uiso 1 1 calc R U . . .
N3 N 0.3234(13) 0.4373(13) -0.0588(15) 0.025(4) Uani 1 1 d D U . . .
H3A H 0.349672 0.396984 -0.102722 0.029 Uiso 1 1 calc R U . . .
H3B H 0.369587 0.437229 -0.004263 0.029 Uiso 1 1 calc R U . . .
H3C H 0.320727 0.494967 -0.084816 0.029 Uiso 1 1 calc R U . . .
N4 N 0.5946(14) 0.3168(12) 0.7521(14) 0.022(4) Uani 1 1 d . U . . .
H4A H 0.594215 0.328160 0.687282 0.027 Uiso 1 1 calc R U . . .
H4B H 0.604963 0.370608 0.785356 0.027 Uiso 1 1 calc R U . . .
H4C H 0.528273 0.291319 0.766668 0.027 Uiso 1 1 calc R U . . .
C3 C 0.7949(13) 0.7681(15) 0.5901(19) 0.034(3) Uani 1 1 d D U . . .
H3 H 0.807405 0.739031 0.655494 0.040 Uiso 1 1 calc R U . . .
C26 C 0.956(2) 0.3616(19) 0.143(3) 0.053(4) Uani 1 1 d . U . . .
H26 H 1.019917 0.344959 0.108807 0.063 Uiso 1 1 calc R U . . .
C4 C 0.820(2) 0.270(2) 0.651(2) 0.034(3) Uani 1 1 d . U . . .
H4 H 0.784808 0.219997 0.616997 0.041 Uiso 1 1 calc R U . . .
C22 C 0.9377(12) 0.5849(10) 0.3781(12) 0.042(3) Uani 1 1 d G U . . .
H22 H 0.971481 0.543088 0.335627 0.051 Uiso 1 1 calc R U . . .
C30 C 0.8854(13) 0.6640(12) 0.3412(10) 0.044(3) Uani 1 1 d G U . . .
H30 H 0.883562 0.676303 0.273560 0.053 Uiso 1 1 calc R U . . .
C27 C 0.8360(12) 0.7252(9) 0.4034(12) 0.040(3) Uani 1 1 d G U . . .
H27 H 0.800277 0.779330 0.378209 0.048 Uiso 1 1 calc R U . . .
C5 C 0.8387(12) 0.7073(9) 0.5024(11) 0.035(3) Uani 1 1 d G U . . .
C2 C 0.8909(12) 0.6282(11) 0.5393(10) 0.041(3) Uani 1 1 d G U . . .
H2 H 0.892829 0.615927 0.606995 0.049 Uiso 1 1 calc R U . . .
C11 C 0.9404(12) 0.5670(9) 0.4771(13) 0.042(3) Uani 1 1 d G U . . .
H11 H 0.976115 0.512900 0.502347 0.051 Uiso 1 1 calc R U . . .
C20 C 0.702(2) 0.4197(19) 0.317(2) 0.051(4) Uani 1 1 d . U . . .
H20 H 0.708409 0.379087 0.376128 0.061 Uiso 1 1 calc R U . . .
C24 C 0.8321(17) 0.8653(16) 0.585(2) 0.036(5) Uani 1 1 d . U . . .
H24A H 0.807758 0.891552 0.522251 0.054 Uiso 1 1 calc R U . . .
H24B H 0.913652 0.867912 0.593481 0.054 Uiso 1 1 calc R U . . .
H24C H 0.799429 0.900738 0.637165 0.054 Uiso 1 1 calc R U . . .
C28 C 0.7754(18) 0.3048(17) 0.744(2) 0.032(3) Uani 1 1 d . U . . .
C17 C 0.9074(18) 0.3106(18) 0.620(2) 0.036(3) Uani 1 1 d . U . . .
H17 H 0.939682 0.294850 0.560713 0.044 Uiso 1 1 calc R U . . .
C32 C 0.816(2) 0.448(2) 0.161(3) 0.049(4) Uani 1 1 d . U . . .
H32 H 0.765180 0.496400 0.141679 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6832(16) 0.2543(16) 0.7790(19) 0.031(3) Uani 1 1 d . U . . .
H19 H 0.672979 0.194988 0.742656 0.037 Uiso 1 1 calc R U . . .
C10 C 0.1694(17) 0.375(2) -0.150(2) 0.048(7) Uani 1 1 d . . . . .
H10A H 0.180162 0.425216 -0.195959 0.072 Uiso 1 1 calc R U . . .
H10B H 0.089991 0.359046 -0.150450 0.072 Uiso 1 1 calc R U . . .
H10C H 0.212281 0.320948 -0.168399 0.072 Uiso 1 1 calc R U . . .
C21 C 0.685(2) 0.517(2) 0.346(3) 0.058(5) Uani 1 1 d . U . . .
H21A H 0.641374 0.548661 0.294456 0.087 Uiso 1 1 calc R U . . .
H21B H 0.757820 0.546953 0.356788 0.087 Uiso 1 1 calc R U . . .
H21C H 0.645273 0.518420 0.406102 0.087 Uiso 1 1 calc R U . . .
C23 C 0.9504(18) 0.3824(18) 0.685(2) 0.038(3) Uani 1 1 d . U . . .
H23 H 1.017623 0.411322 0.667623 0.046 Uiso 1 1 calc R U . . .
C12 C 0.856(2) 0.327(2) 0.286(3) 0.053(4) Uani 1 1 d . U . . .
H12 H 0.845342 0.294764 0.345419 0.063 Uiso 1 1 calc R U . . .
C25 C 0.936(2) 0.307(2) 0.225(3) 0.053(4) Uani 1 1 d . U . . .
H25 H 0.980717 0.254143 0.238078 0.064 Uiso 1 1 calc R U . . .
C13 C 0.8143(17) 0.3774(17) 0.803(2) 0.036(3) Uani 1 1 d . U . . .
H13 H 0.779341 0.396719 0.860017 0.043 Uiso 1 1 calc R U . . .
C14 C 0.6874(17) 0.2349(17) 0.898(2) 0.037(5) Uani 1 1 d . U . . .
H14A H 0.758268 0.205134 0.918479 0.056 Uiso 1 1 calc R U . . .
H14B H 0.625365 0.194513 0.913743 0.056 Uiso 1 1 calc R U . . .
H14C H 0.681137 0.293618 0.932773 0.056 Uiso 1 1 calc R U . . .
C1 C 0.1774(12) 0.4968(10) 0.1282(12) 0.040(3) Uani 1 1 d G U . . .
H1 H 0.213982 0.450760 0.167240 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1729(12) 0.4891(9) 0.0277(12) 0.040(3) Uani 1 1 d G U . . .
C16 C 0.1194(13) 0.5565(11) -0.0293(10) 0.042(3) Uani 1 1 d G U . . .
H16 H 0.116350 0.551254 -0.098042 0.051 Uiso 1 1 calc R U . . .
C18 C 0.0704(12) 0.6317(10) 0.0141(12) 0.042(3) Uani 1 1 d G U . . .
H18 H 0.033840 0.677806 -0.024891 0.050 Uiso 1 1 calc R U . . .
C29 C 0.0749(12) 0.6395(9) 0.1146(13) 0.041(3) Uani 1 1 d G U . . .
H29 H 0.041400 0.690836 0.144325 0.049 Uiso 1 1 calc R U . . .
C6 C 0.1284(13) 0.5720(12) 0.1717(10) 0.041(3) Uani 1 1 d G U . . .
H6 H 0.131470 0.577315 0.240392 0.050 Uiso 1 1 calc R U . . .
C15 C 0.2145(14) 0.4100(16) -0.035(2) 0.035(3) Uani 1 1 d D U . . .
H15 H 0.222000 0.353810 0.006913 0.042 Uiso 1 1 calc R U . . .
C31 C 0.897(2) 0.434(2) 0.106(3) 0.051(4) Uani 1 1 d . U . . .
H31 H 0.912199 0.468339 0.049806 0.061 Uiso 1 1 calc R U . . .
C8 C 0.791(2) 0.399(2) 0.253(3) 0.050(3) Uani 1 1 d . U . . .
C9 C 0.9025(18) 0.4151(18) 0.773(2) 0.038(3) Uani 1 1 d . U . . .
H9 H 0.936710 0.464906 0.807802 0.045 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 Br5 2.900(3) . ?
Bi1 Br1 2.885(3) . ?
Bi1 Br2 2.793(3) . ?
Bi1 Br3 3.076(3) . ?
Bi1 Br6 2.341(3) . ?
Bi2 Br7 2.755(3) . ?
Bi2 Br9 2.346(3) . ?
Bi2 Br10 2.905(3) . ?
Bi2 Br8 3.123(3) . ?
Bi2 Br4 2.891(3) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C20 1.50(3) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C3 1.418(13) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C15 1.422(12) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
N4 C19 1.43(3) . ?
C3 H3 1.0000 . ?
C3 C5 1.61(3) . ?
C3 C24 1.48(3) . ?
C26 H26 0.9500 . ?
C26 C25 1.42(4) . ?
C26 C31 1.35(4) . ?
C4 H4 0.9500 . ?
C4 C28 1.50(4) . ?
C4 C17 1.30(3) . ?
C22 H22 0.9500 . ?
C22 C30 1.3900 . ?
C22 C11 1.3900 . ?
C30 H30 0.9500 . ?
C30 C27 1.3900 . ?
C27 H27 0.9500 . ?
C27 C5 1.3900 . ?
C5 C2 1.3900 . ?
C2 H2 0.9500 . ?
C2 C11 1.3900 . ?
C11 H11 0.9500 . ?
C20 H20 1.0000 . ?
C20 C21 1.48(4) . ?
C20 C8 1.46(4) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C28 C19 1.43(3) . ?
C28 C13 1.40(3) . ?
C17 H17 0.9500 . ?
C17 C23 1.45(4) . ?
C32 H32 0.9500 . ?
C32 C31 1.29(4) . ?
C32 C8 1.50(4) . ?
C19 H19 1.0000 . ?
C19 C14 1.67(4) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C10 C15 1.72(4) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C23 H23 0.9500 . ?
C23 C9 1.45(4) . ?
C12 H12 0.9500 . ?
C12 C25 1.34(4) . ?
C12 C8 1.37(4) . ?
C25 H25 0.9500 . ?
C13 H13 0.9500 . ?
C13 C9 1.28(3) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C1 H1 0.9500 . ?
C1 C7 1.3900 . ?
C1 C6 1.3900 . ?
C7 C16 1.3900 . ?
C7 C15 1.54(2) . ?
C16 H16 0.9500 . ?
C16 C18 1.3900 . ?
C18 H18 0.9500 . ?
C18 C29 1.3900 . ?
C29 H29 0.9500 . ?
C29 C6 1.3900 . ?
C6 H6 0.9500 . ?
C15 H15 1.0000 . ?
C31 H31 0.9500 . ?
C9 H9 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
Br5 Bi1 Br3 95.78(9) . . ?
Br1 Bi1 Br5 174.18(8) . . ?
Br1 Bi1 Br3 85.55(9) . . ?
Br2 Bi1 Br5 82.91(8) . . ?
Br2 Bi1 Br1 91.26(8) . . ?
Br2 Bi1 Br3 102.65(8) . . ?
Br6 Bi1 Br5 90.94(9) . . ?
Br6 Bi1 Br1 94.68(10) . . ?
Br6 Bi1 Br2 164.46(11) . . ?
Br6 Bi1 Br3 92.13(10) . . ?
Br7 Bi2 Br10 90.17(9) . . ?
Br7 Bi2 Br8 101.16(8) . . ?
Br7 Bi2 Br4 83.29(9) . . ?
Br9 Bi2 Br7 169.36(12) . . ?
Br9 Bi2 Br10 96.04(10) . . ?
Br9 Bi2 Br8 88.14(10) . . ?
Br9 Bi2 Br4 90.90(10) . . ?
Br10 Bi2 Br8 83.66(9) . . ?
Br4 Bi2 Br10 172.75(7) . . ?
Br4 Bi2 Br8 94.52(9) . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C20 N2 H2A 109.5 . . ?
C20 N2 H2B 109.5 . . ?
C20 N2 H2C 109.5 . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 N1 H1A 109.5 . . ?
C3 N1 H1B 109.5 . . ?
C3 N1 H1C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C15 N3 H3A 109.5 . . ?
C15 N3 H3B 109.5 . . ?
C15 N3 H3C 109.5 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C19 N4 H4A 109.5 . . ?
C19 N4 H4B 109.5 . . ?
C19 N4 H4C 109.5 . . ?
N1 C3 H3 114.2 . . ?
N1 C3 C5 96.8(17) . . ?
N1 C3 C24 103.6(17) . . ?
C5 C3 H3 114.2 . . ?
C24 C3 H3 114.2 . . ?
C24 C3 C5 112.1(19) . . ?
C25 C26 H26 115.8 . . ?
C31 C26 H26 115.8 . . ?
C31 C26 C25 128(3) . . ?
C28 C4 H4 121.2 . . ?
C17 C4 H4 121.2 . . ?
C17 C4 C28 118(3) . . ?
C30 C22 H22 120.0 . . ?
C30 C22 C11 120.0 . . ?
C11 C22 H22 120.0 . . ?
C22 C30 H30 120.0 . . ?
C27 C30 C22 120.0 . . ?
C27 C30 H30 120.0 . . ?
C30 C27 H27 120.0 . . ?
C30 C27 C5 120.0 . . ?
C5 C27 H27 120.0 . . ?
C27 C5 C3 130.3(12) . . ?
C27 C5 C2 120.0 . . ?
C2 C5 C3 109.6(12) . . ?
C5 C2 H2 120.0 . . ?
C5 C2 C11 120.0 . . ?
C11 C2 H2 120.0 . . ?
C22 C11 H11 120.0 . . ?
C2 C11 C22 120.0 . . ?
C2 C11 H11 120.0 . . ?
N2 C20 H20 110.4 . . ?
C21 C20 N2 115(2) . . ?
C21 C20 H20 110.4 . . ?
C8 C20 N2 91(2) . . ?
C8 C20 H20 110.4 . . ?
C8 C20 C21 119(2) . . ?
C3 C24 H24A 109.5 . . ?
C3 C24 H24B 109.5 . . ?
C3 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C19 C28 C4 116(2) . . ?
C13 C28 C4 129(2) . . ?
C13 C28 C19 115(2) . . ?
C4 C17 H17 123.7 . . ?
C4 C17 C23 113(3) . . ?
C23 C17 H17 123.7 . . ?
C31 C32 H32 116.2 . . ?
C31 C32 C8 128(3) . . ?
C8 C32 H32 116.2 . . ?
N4 C19 C28 99.6(19) . . ?
N4 C19 H19 110.2 . . ?
N4 C19 C14 110.2(17) . . ?
C28 C19 H19 110.2 . . ?
C28 C19 C14 116(2) . . ?
C14 C19 H19 110.2 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C15 C10 H10A 109.5 . . ?
C15 C10 H10B 109.5 . . ?
C15 C10 H10C 109.5 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C17 C23 H23 116.3 . . ?
C17 C23 C9 127(2) . . ?
C9 C23 H23 116.3 . . ?
C25 C12 H12 124.5 . . ?
C25 C12 C8 111(3) . . ?
C8 C12 H12 124.5 . . ?
C26 C25 H25 118.4 . . ?
C12 C25 C26 123(3) . . ?
C12 C25 H25 118.4 . . ?
C28 C13 H13 123.8 . . ?
C9 C13 C28 112(3) . . ?
C9 C13 H13 123.8 . . ?
C19 C14 H14A 109.5 . . ?
C19 C14 H14B 109.5 . . ?
C19 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C1 H1 120.0 . . ?
C7 C1 C6 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C7 C16 120.0 . . ?
C1 C7 C15 128.8(15) . . ?
C16 C7 C15 111.1(15) . . ?
C7 C16 H16 120.0 . . ?
C18 C16 C7 120.0 . . ?
C18 C16 H16 120.0 . . ?
C16 C18 H18 120.0 . . ?
C16 C18 C29 120.0 . . ?
C29 C18 H18 120.0 . . ?
C18 C29 H29 120.0 . . ?
C6 C29 C18 120.0 . . ?
C6 C29 H29 120.0 . . ?
C1 C6 H6 120.0 . . ?
C29 C6 C1 120.0 . . ?
C29 C6 H6 120.0 . . ?
N3 C15 C10 96.5(18) . . ?
N3 C15 C7 104.8(15) . . ?
N3 C15 H15 107.8 . . ?
C10 C15 H15 107.8 . . ?
C7 C15 C10 130.0(19) . . ?
C7 C15 H15 107.8 . . ?
C26 C31 H31 126.1 . . ?
C32 C31 C26 108(3) . . ?
C32 C31 H31 126.1 . . ?
C20 C8 C32 127(3) . . ?
C12 C8 C20 112(3) . . ?
C12 C8 C32 121(3) . . ?
C23 C9 H9 119.7 . . ?
C13 C9 C23 121(2) . . ?
C13 C9 H9 119.7 . . ?

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
N2 C20 C8 C32 73(3) . . . . ?
N2 C20 C8 C12 -109(3) . . . . ?
N1 C3 C5 C27 59.8(19) . . . . ?
N1 C3 C5 C2 -123.7(14) . . . . ?
C3 C5 C2 C11 -176.9(12) . . . . ?
C4 C28 C19 N4 -104(2) . . . . ?
C4 C28 C19 C14 138(2) . . . . ?
C4 C28 C13 C9 -3(4) . . . . ?
C4 C17 C23 C9 -4(4) . . . . ?
C22 C30 C27 C5 0.0 . . . . ?
C30 C22 C11 C2 0.0 . . . . ?
C30 C27 C5 C3 176.2(15) . . . . ?
C30 C27 C5 C2 0.0 . . . . ?
C27 C5 C2 C11 0.0 . . . . ?
C5 C2 C11 C22 0.0 . . . . ?
C11 C22 C30 C27 0.0 . . . . ?
C24 C3 C5 C27 -47.9(19) . . . . ?
C24 C3 C5 C2 128.6(15) . . . . ?
C28 C4 C17 C23 2(4) . . . . ?
C28 C13 C9 C23 1(3) . . . . ?
C17 C4 C28 C19 -176(2) . . . . ?
C17 C4 C28 C13 1(4) . . . . ?
C17 C23 C9 C13 3(4) . . . . ?
C19 C28 C13 C9 175(2) . . . . ?
C21 C20 C8 C32 -46(4) . . . . ?
C21 C20 C8 C12 132(3) . . . . ?
C25 C26 C31 C32 1(4) . . . . ?
C25 C12 C8 C20 179(3) . . . . ?
C25 C12 C8 C32 -3(4) . . . . ?
C13 C28 C19 N4 79(3) . . . . ?
C13 C28 C19 C14 -39(3) . . . . ?
C1 C7 C16 C18 0.0 . . . . ?
C1 C7 C15 N3 -95(2) . . . . ?
C1 C7 C15 C10 153.1(18) . . . . ?
C7 C1 C6 C29 0.0 . . . . ?
C7 C16 C18 C29 0.0 . . . . ?
C16 C7 C15 N3 89.0(18) . . . . ?
C16 C7 C15 C10 -23(2) . . . . ?
C16 C18 C29 C6 0.0 . . . . ?
C18 C29 C6 C1 0.0 . . . . ?
C6 C1 C7 C16 0.0 . . . . ?
C6 C1 C7 C15 -175.9(15) . . . . ?
C15 C7 C16 C18 176.6(12) . . . . ?
C31 C26 C25 C12 -7(5) . . . . ?
C31 C32 C8 C20 176(3) . . . . ?
C31 C32 C8 C12 -2(5) . . . . ?
C8 C32 C31 C26 3(5) . . . . ?
C8 C12 C25 C26 6(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 8.653
_oxdiff_exptl_absorpt_empirical_full_min 0.523
####################################################################### 
# 
# 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_mo_211218g_0m
_database_code_depnum_ccdc_archive 'CCDC 2208616'
loop_
_audit_author_name
_audit_author_address
'Zongyi Zhang'
;Shandong University
China
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-12-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Br10, 4(C8 H12 N)'
_chemical_formula_sum            'C32 H48 Bi2 Br10 N4'
_chemical_formula_weight         1705.80
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.9715(10)
_cell_length_b                   14.5680(11)
_cell_length_c                   13.7897(13)
_cell_angle_alpha                90
_cell_angle_beta                 93.389(3)
_cell_angle_gamma                90
_cell_volume                     2400.7(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6688
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.31
_cell_measurement_theta_min      2.96
_shelx_estimated_absorpt_T_max   0.367
_shelx_estimated_absorpt_T_min   0.303
_exptl_absorpt_coefficient_mu    15.668
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.4334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1018 before and 0.0712 after correction.
The Ratio of minimum to maximum transmission is 0.5812.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear greenish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.360
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0685
_diffrn_reflns_av_unetI/netI     0.0746
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            37239
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.333
_diffrn_reflns_theta_min         1.704
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.973
_reflns_number_gt                9446
_reflns_number_total             11740
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.026
_refine_diff_density_min         -0.637
_refine_diff_density_rms         0.139
_refine_ls_abs_structure_details 
;
 Flack x determined using 3700 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.026(9)
_refine_ls_extinction_coef       0.00064(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         11740
_refine_ls_number_restraints     163
_refine_ls_R_factor_all          0.0522
_refine_ls_R_factor_gt           0.0364
_refine_ls_restrained_S_all      0.967
_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)] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0660
_refine_ls_wR_factor_ref         0.0714
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N2 \\sim C8 \\sim C9 \\sim C13 \\sim C19 \\sim C22 \\sim C27 \\sim C30 \\sim
C31: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N4 \\sim C5 \\sim C10 \\sim C11 \\sim C12 \\sim C21 \\sim C24 \\sim C25 \\sim
C32: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N3 \\sim C1 \\sim C3 \\sim C14 \\sim C17 \\sim C18 \\sim C23 \\sim C26 \\sim
C28: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
3.a Ternary CH refined with riding coordinates:
 C3(H3), C19(H19), C29(H29), C32(H32)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C9(H9), C10(H10),
 C11(H11), C13(H13), C14(H14), C18(H18), C20(H20), C21(H21), C23(H23), C24(H24),
  C27(H27), C28(H28), C30(H30)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C), N3(H3A,H3B,H3C), N4(H4A,H4B,H4C), C15(H15A,
 H15B,H15C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C31(H31A,H31B,H31C)
;
_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 0.90427(3) 0.51792(3) 0.60494(4) 0.02692(14) Uani 1 1 d . . . . .
Bi2 Bi 0.60565(3) 0.45381(3) 0.39203(4) 0.02681(13) Uani 1 1 d . . . . .
Br1 Br 0.83577(10) 0.53431(10) 0.38251(12) 0.0331(3) Uani 1 1 d . . . . .
Br2 Br 0.58149(12) 0.45613(13) 0.19699(12) 0.0454(4) Uani 1 1 d . . . . .
Br3 Br 0.92006(13) 0.50414(11) 0.79949(12) 0.0409(4) Uani 1 1 d . . . . .
Br4 Br 0.82310(10) 0.70071(10) 0.62131(12) 0.0325(3) Uani 1 1 d . . . . .
Br5 Br 0.39215(11) 0.38485(12) 0.40376(14) 0.0426(4) Uani 1 1 d . . . . .
Br6 Br 0.97904(10) 0.33694(10) 0.56458(12) 0.0336(3) Uani 1 1 d . . . . .
Br7 Br 0.66786(10) 0.44582(12) 0.61437(11) 0.0349(3) Uani 1 1 d . . . . .
Br8 Br 0.68816(10) 0.27197(11) 0.38574(12) 0.0331(3) Uani 1 1 d . . . . .
Br9 Br 1.11653(11) 0.58170(12) 0.59514(14) 0.0452(4) Uani 1 1 d . . . . .
Br10 Br 0.52102(11) 0.63359(11) 0.42661(12) 0.0358(4) Uani 1 1 d . . . . .
N1 N 0.9432(9) 0.3244(8) 0.3192(9) 0.037(3) Uani 1 1 d . . . . .
H1A H 1.010118 0.295336 0.329401 0.045 Uiso 1 1 calc R U . . .
H1B H 0.889753 0.293387 0.350200 0.045 Uiso 1 1 calc R U . . .
H1C H 0.948758 0.382645 0.342910 0.045 Uiso 1 1 calc R U . . .
N2 N 0.7476(10) 0.2139(10) 0.6161(10) 0.062(3) Uani 1 1 d . U . . .
H2A H 0.786129 0.204842 0.561905 0.075 Uiso 1 1 calc R U . . .
H2B H 0.734181 0.274869 0.623373 0.075 Uiso 1 1 calc R U . . .
H2C H 0.681444 0.183051 0.609939 0.075 Uiso 1 1 calc R U . . .
N3 N 0.5535(9) 0.6573(8) 0.6777(8) 0.037(3) Uani 1 1 d . U . . .
H3A H 0.486274 0.647830 0.644974 0.045 Uiso 1 1 calc R U . . .
H3B H 0.595051 0.605040 0.676688 0.045 Uiso 1 1 calc R U . . .
H3C H 0.590422 0.703542 0.648737 0.045 Uiso 1 1 calc R U . . .
N4 N 0.7478(9) 0.7750(8) 0.4012(8) 0.038(2) Uani 1 1 d . U . . .
H4A H 0.703380 0.724316 0.398221 0.046 Uiso 1 1 calc R U . . .
H4B H 0.736118 0.806931 0.456386 0.046 Uiso 1 1 calc R U . . .
H4C H 0.820843 0.757681 0.401449 0.046 Uiso 1 1 calc R U . . .
C1 C 0.3155(13) 0.5261(11) 0.8682(12) 0.050(2) Uani 1 1 d . U . . .
H1 H 0.236188 0.521945 0.861580 0.060 Uiso 1 1 calc R U . . .
C2 C 1.0179(13) 0.5247(10) 0.0625(12) 0.056(4) Uani 1 1 d . . . . .
H2 H 0.988233 0.576615 0.028094 0.067 Uiso 1 1 calc R U . . .
C3 C 0.5351(11) 0.6832(9) 0.7815(9) 0.044(2) Uani 1 1 d . U . . .
H3 H 0.478924 0.733993 0.779997 0.052 Uiso 1 1 calc R U . . .
C4 C 0.9479(11) 0.4664(8) 0.1089(10) 0.044(3) Uani 1 1 d . . . . .
H4 H 0.869625 0.477762 0.104934 0.052 Uiso 1 1 calc R U . . .
C5 C 0.8173(11) 0.7112(10) 0.0505(11) 0.052(2) Uani 1 1 d . U . . .
H5 H 0.836146 0.686686 -0.010207 0.063 Uiso 1 1 calc R U . . .
C6 C 1.1738(12) 0.4349(12) 0.1170(13) 0.056(5) Uani 1 1 d . . . . .
H6 H 1.252122 0.423887 0.121047 0.067 Uiso 1 1 calc R U . . .
C7 C 1.1030(11) 0.3767(11) 0.1632(12) 0.053(4) Uani 1 1 d . . . . .
H7 H 1.133909 0.325095 0.197308 0.063 Uiso 1 1 calc R U . . .
C8 C 0.6635(13) 0.1463(12) 0.8159(13) 0.055(3) Uani 1 1 d . U . . .
H8 H 0.637276 0.098080 0.774149 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7323(14) 0.2895(12) 0.9355(13) 0.069(3) Uani 1 1 d . U . . .
H9 H 0.754415 0.339148 0.977022 0.083 Uiso 1 1 calc R U . . .
C10 C 0.8466(11) 0.8229(11) 0.1778(11) 0.041(2) Uani 1 1 d . U . . .
H10 H 0.886913 0.873634 0.205444 0.049 Uiso 1 1 calc R U . . .
C11 C 0.7305(11) 0.6755(10) 0.0970(11) 0.052(2) Uani 1 1 d . U . . .
H11 H 0.691644 0.623230 0.071265 0.062 Uiso 1 1 calc R U . . .
C12 C 0.7557(10) 0.7888(9) 0.2238(10) 0.0388(19) Uani 1 1 d . U . . .
C13 C 0.6440(13) 0.2354(11) 0.9576(13) 0.064(3) Uani 1 1 d . U . . .
H13 H 0.605418 0.248527 1.014234 0.076 Uiso 1 1 calc R U . . .
C14 C 0.5476(13) 0.5393(10) 0.8826(11) 0.051(2) Uani 1 1 d . U . . .
H14 H 0.626972 0.542924 0.885473 0.061 Uiso 1 1 calc R U . . .
C15 C 0.9133(10) 0.2305(8) 0.1698(10) 0.043(3) Uani 1 1 d . . . . .
H15A H 0.890555 0.231651 0.100407 0.064 Uiso 1 1 calc R U . . .
H15B H 0.861528 0.191772 0.204086 0.064 Uiso 1 1 calc R U . . .
H15C H 0.989238 0.205607 0.178938 0.064 Uiso 1 1 calc R U . . .
C16 C 0.9898(10) 0.3908(8) 0.1616(9) 0.032(3) Uani 1 1 d . . . . .
C17 C 0.4851(12) 0.6027(10) 0.8318(11) 0.045(2) Uani 1 1 d . U . . .
C18 C 0.3698(12) 0.5948(11) 0.8251(12) 0.047(2) Uani 1 1 d . U . . .
H18 H 0.327140 0.639385 0.788754 0.057 Uiso 1 1 calc R U . . .
C19 C 0.8155(12) 0.1788(11) 0.7036(12) 0.065(3) Uani 1 1 d . U . . .
H19 H 0.887825 0.213330 0.709076 0.077 Uiso 1 1 calc R U . . .
C20 C 1.1315(13) 0.5073(11) 0.0662(12) 0.046(4) Uani 1 1 d . . . . .
H20 H 1.179942 0.546346 0.032907 0.056 Uiso 1 1 calc R U . . .
C21 C 0.8796(11) 0.7850(10) 0.0928(11) 0.048(2) Uani 1 1 d . U . . .
H21 H 0.943325 0.808055 0.062870 0.057 Uiso 1 1 calc R U . . .
C22 C 0.7532(13) 0.1981(12) 0.7922(12) 0.059(2) Uani 1 1 d . U . . .
C23 C 0.4926(14) 0.4659(12) 0.9323(12) 0.056(3) Uani 1 1 d . U . . .
H23 H 0.534130 0.422111 0.970555 0.067 Uiso 1 1 calc R U . . .
C24 C 0.6982(11) 0.7166(9) 0.1840(10) 0.046(2) Uani 1 1 d . U . . .
H24 H 0.635377 0.693193 0.215027 0.055 Uiso 1 1 calc R U . . .
C25 C 0.5962(10) 0.8566(10) 0.3108(10) 0.055(3) Uani 1 1 d . U . . .
H25A H 0.575304 0.892619 0.252475 0.083 Uiso 1 1 calc R U . . .
H25B H 0.579586 0.891924 0.368686 0.083 Uiso 1 1 calc R U . . .
H25C H 0.553578 0.799173 0.309395 0.083 Uiso 1 1 calc R U . . .
C26 C 0.6419(12) 0.7200(10) 0.8276(11) 0.054(3) Uani 1 1 d . U . . .
H26A H 0.631500 0.734921 0.895764 0.081 Uiso 1 1 calc R U . . .
H26B H 0.663454 0.775530 0.793188 0.081 Uiso 1 1 calc R U . . .
H26C H 0.700968 0.673705 0.824086 0.081 Uiso 1 1 calc R U . . .
C27 C 0.7871(14) 0.2734(12) 0.8567(13) 0.066(3) Uani 1 1 d . U . . .
H27 H 0.848781 0.310987 0.842287 0.079 Uiso 1 1 calc R U . . .
C28 C 0.3771(13) 0.4623(12) 0.9218(12) 0.053(2) Uani 1 1 d . U . . .
H28 H 0.339145 0.414119 0.952580 0.064 Uiso 1 1 calc R U . . .
C29 C 0.9111(9) 0.3276(8) 0.2103(8) 0.035(2) Uani 1 1 d . . . . .
H29 H 0.833343 0.352329 0.200536 0.042 Uiso 1 1 calc R U . . .
C30 C 0.6104(13) 0.1642(11) 0.9014(12) 0.057(3) Uani 1 1 d . U . . .
H30 H 0.550815 0.126070 0.919650 0.068 Uiso 1 1 calc R U . . .
C31 C 0.8415(15) 0.0766(13) 0.6828(13) 0.084(4) Uani 1 1 d . U . . .
H31A H 0.891276 0.051987 0.735485 0.126 Uiso 1 1 calc R U . . .
H31B H 0.878073 0.071759 0.621225 0.126 Uiso 1 1 calc R U . . .
H31C H 0.771626 0.041391 0.678444 0.126 Uiso 1 1 calc R U . . .
C32 C 0.7196(10) 0.8353(9) 0.3136(9) 0.040(2) Uani 1 1 d . U . . .
H32 H 0.762016 0.894216 0.322049 0.048 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 Br1 3.1369(17) . ?
Bi1 Br3 2.6859(18) . ?
Bi1 Br4 2.8482(16) . ?
Bi1 Br6 2.8498(16) . ?
Bi1 Br7 3.0288(13) . ?
Bi1 Br9 2.7165(14) . ?
Bi2 Br1 3.0040(14) . ?
Bi2 Br2 2.6882(18) . ?
Bi2 Br5 2.7599(14) . ?
Bi2 Br7 3.1141(17) . ?
Bi2 Br8 2.8304(16) . ?
Bi2 Br10 2.8583(16) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C29 1.528(16) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C19 1.504(19) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C3 1.509(16) . ?
N4 H4A 0.9100 . ?
N4 H4B 0.9100 . ?
N4 H4C 0.9100 . ?
N4 C32 1.515(16) . ?
C1 H1 0.9500 . ?
C1 C18 1.35(2) . ?
C1 C28 1.38(2) . ?
C2 H2 0.9500 . ?
C2 C4 1.378(17) . ?
C2 C20 1.38(2) . ?
C3 H3 1.0000 . ?
C3 C17 1.504(18) . ?
C3 C26 1.494(19) . ?
C4 H4 0.9500 . ?
C4 C16 1.396(16) . ?
C5 H5 0.9500 . ?
C5 C11 1.355(18) . ?
C5 C21 1.41(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.38(2) . ?
C6 C20 1.35(2) . ?
C7 H7 0.9500 . ?
C7 C16 1.369(16) . ?
C8 H8 0.9500 . ?
C8 C22 1.368(19) . ?
C8 C30 1.40(2) . ?
C9 H9 0.9500 . ?
C9 C13 1.367(19) . ?
C9 C27 1.32(2) . ?
C10 H10 0.9500 . ?
C10 C12 1.384(16) . ?
C10 C21 1.374(19) . ?
C11 H11 0.9500 . ?
C11 C24 1.416(18) . ?
C12 C24 1.355(18) . ?
C12 C32 1.497(17) . ?
C13 H13 0.9500 . ?
C13 C30 1.34(2) . ?
C14 H14 0.9500 . ?
C14 C17 1.36(2) . ?
C14 C23 1.45(2) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C15 C29 1.521(16) . ?
C16 C29 1.504(15) . ?
C17 C18 1.384(19) . ?
C18 H18 0.9500 . ?
C19 H19 1.0000 . ?
C19 C22 1.50(2) . ?
C19 C31 1.55(2) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 C27 1.46(2) . ?
C23 H23 0.9500 . ?
C23 C28 1.38(2) . ?
C24 H24 0.9500 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C25 C32 1.508(16) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C29 H29 1.0000 . ?
C30 H30 0.9500 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C32 H32 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br3 Bi1 Br1 168.90(4) . . ?
Br3 Bi1 Br4 89.71(5) . . ?
Br3 Bi1 Br6 96.98(5) . . ?
Br3 Bi1 Br7 86.67(4) . . ?
Br3 Bi1 Br9 93.69(5) . . ?
Br4 Bi1 Br1 86.31(5) . . ?
Br4 Bi1 Br6 173.24(6) . . ?
Br4 Bi1 Br7 89.82(5) . . ?
Br6 Bi1 Br1 86.93(5) . . ?
Br6 Bi1 Br7 89.58(4) . . ?
Br7 Bi1 Br1 82.96(4) . . ?
Br9 Bi1 Br1 96.69(5) . . ?
Br9 Bi1 Br4 90.50(5) . . ?
Br9 Bi1 Br6 90.07(5) . . ?
Br9 Bi1 Br7 179.52(6) . . ?
Br1 Bi2 Br7 83.75(4) . . ?
Br2 Bi2 Br1 89.77(4) . . ?
Br2 Bi2 Br5 91.03(5) . . ?
Br2 Bi2 Br7 172.22(4) . . ?
Br2 Bi2 Br8 89.89(5) . . ?
Br2 Bi2 Br10 97.88(5) . . ?
Br5 Bi2 Br1 178.18(5) . . ?
Br5 Bi2 Br7 95.57(5) . . ?
Br5 Bi2 Br8 89.27(5) . . ?
Br5 Bi2 Br10 89.15(5) . . ?
Br8 Bi2 Br1 92.37(4) . . ?
Br8 Bi2 Br7 86.08(5) . . ?
Br8 Bi2 Br10 172.09(5) . . ?
Br10 Bi2 Br1 89.12(4) . . ?
Br10 Bi2 Br7 86.36(5) . . ?
Bi2 Br1 Bi1 96.60(4) . . ?
Bi1 Br7 Bi2 96.57(4) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C29 N1 H1A 109.5 . . ?
C29 N1 H1B 109.5 . . ?
C29 N1 H1C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C19 N2 H2A 109.5 . . ?
C19 N2 H2B 109.5 . . ?
C19 N2 H2C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C3 N3 H3A 109.5 . . ?
C3 N3 H3B 109.5 . . ?
C3 N3 H3C 109.5 . . ?
H4A N4 H4B 109.5 . . ?
H4A N4 H4C 109.5 . . ?
H4B N4 H4C 109.5 . . ?
C32 N4 H4A 109.5 . . ?
C32 N4 H4B 109.5 . . ?
C32 N4 H4C 109.5 . . ?
C18 C1 H1 120.6 . . ?
C18 C1 C28 118.7(15) . . ?
C28 C1 H1 120.6 . . ?
C4 C2 H2 120.2 . . ?
C4 C2 C20 119.6(14) . . ?
C20 C2 H2 120.2 . . ?
N3 C3 H3 107.5 . . ?
C17 C3 N3 109.1(11) . . ?
C17 C3 H3 107.5 . . ?
C26 C3 N3 108.9(10) . . ?
C26 C3 H3 107.5 . . ?
C26 C3 C17 116.0(13) . . ?
C2 C4 H4 119.4 . . ?
C2 C4 C16 121.2(12) . . ?
C16 C4 H4 119.4 . . ?
C11 C5 H5 120.1 . . ?
C11 C5 C21 119.8(14) . . ?
C21 C5 H5 120.1 . . ?
C7 C6 H6 120.0 . . ?
C20 C6 H6 120.0 . . ?
C20 C6 C7 119.9(14) . . ?
C6 C7 H7 118.9 . . ?
C16 C7 C6 122.3(14) . . ?
C16 C7 H7 118.9 . . ?
C22 C8 H8 119.9 . . ?
C22 C8 C30 120.2(17) . . ?
C30 C8 H8 119.9 . . ?
C13 C9 H9 119.7 . . ?
C27 C9 H9 119.7 . . ?
C27 C9 C13 120.5(18) . . ?
C12 C10 H10 119.3 . . ?
C21 C10 H10 119.3 . . ?
C21 C10 C12 121.3(14) . . ?
C5 C11 H11 120.2 . . ?
C5 C11 C24 119.6(14) . . ?
C24 C11 H11 120.2 . . ?
C10 C12 C32 119.3(13) . . ?
C24 C12 C10 119.2(13) . . ?
C24 C12 C32 121.4(11) . . ?
C9 C13 H13 119.1 . . ?
C30 C13 C9 121.7(17) . . ?
C30 C13 H13 119.1 . . ?
C17 C14 H14 120.2 . . ?
C17 C14 C23 119.6(14) . . ?
C23 C14 H14 120.2 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C29 C15 H15A 109.5 . . ?
C29 C15 H15B 109.5 . . ?
C29 C15 H15C 109.5 . . ?
C4 C16 C29 120.0(11) . . ?
C7 C16 C4 116.9(12) . . ?
C7 C16 C29 123.1(12) . . ?
C14 C17 C3 123.1(13) . . ?
C14 C17 C18 119.7(14) . . ?
C18 C17 C3 117.2(14) . . ?
C1 C18 C17 122.5(17) . . ?
C1 C18 H18 118.8 . . ?
C17 C18 H18 118.8 . . ?
N2 C19 H19 108.3 . . ?
N2 C19 C31 106.4(14) . . ?
C22 C19 N2 108.7(13) . . ?
C22 C19 H19 108.3 . . ?
C22 C19 C31 116.5(12) . . ?
C31 C19 H19 108.3 . . ?
C2 C20 H20 119.9 . . ?
C6 C20 C2 120.1(13) . . ?
C6 C20 H20 119.9 . . ?
C5 C21 H21 120.5 . . ?
C10 C21 C5 119.0(12) . . ?
C10 C21 H21 120.5 . . ?
C8 C22 C19 121.9(16) . . ?
C8 C22 C27 117.6(16) . . ?
C27 C22 C19 120.5(14) . . ?
C14 C23 H23 121.4 . . ?
C28 C23 C14 117.3(16) . . ?
C28 C23 H23 121.4 . . ?
C11 C24 H24 119.5 . . ?
C12 C24 C11 120.9(12) . . ?
C12 C24 H24 119.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C32 C25 H25A 109.5 . . ?
C32 C25 H25B 109.5 . . ?
C32 C25 H25C 109.5 . . ?
C3 C26 H26A 109.5 . . ?
C3 C26 H26B 109.5 . . ?
C3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C9 C27 C22 120.2(15) . . ?
C9 C27 H27 119.9 . . ?
C22 C27 H27 119.9 . . ?
C1 C28 C23 122.1(15) . . ?
C1 C28 H28 118.9 . . ?
C23 C28 H28 118.9 . . ?
N1 C29 H29 108.8 . . ?
C15 C29 N1 108.9(10) . . ?
C15 C29 H29 108.8 . . ?
C16 C29 N1 109.3(9) . . ?
C16 C29 C15 112.3(9) . . ?
C16 C29 H29 108.8 . . ?
C8 C30 H30 120.1 . . ?
C13 C30 C8 119.7(15) . . ?
C13 C30 H30 120.1 . . ?
C19 C31 H31A 109.5 . . ?
C19 C31 H31B 109.5 . . ?
C19 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
N4 C32 H32 108.4 . . ?
C12 C32 N4 109.6(10) . . ?
C12 C32 C25 113.7(12) . . ?
C12 C32 H32 108.4 . . ?
C25 C32 N4 108.1(9) . . ?
C25 C32 H32 108.4 . . ?

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
N2 C19 C22 C8 76.7(19) . . . . ?
N2 C19 C22 C27 -103.5(17) . . . . ?
N3 C3 C17 C14 92.4(17) . . . . ?
N3 C3 C17 C18 -87.8(15) . . . . ?
C2 C4 C16 C7 -1(2) . . . . ?
C2 C4 C16 C29 -179.2(13) . . . . ?
C3 C17 C18 C1 -179.2(14) . . . . ?
C4 C2 C20 C6 -2(2) . . . . ?
C4 C16 C29 N1 -121.9(12) . . . . ?
C4 C16 C29 C15 117.1(13) . . . . ?
C5 C11 C24 C12 -3(2) . . . . ?
C6 C7 C16 C4 1(2) . . . . ?
C6 C7 C16 C29 179.2(14) . . . . ?
C7 C6 C20 C2 2(2) . . . . ?
C7 C16 C29 N1 60.3(16) . . . . ?
C7 C16 C29 C15 -60.7(17) . . . . ?
C8 C22 C27 C9 0(2) . . . . ?
C9 C13 C30 C8 -3(2) . . . . ?
C10 C12 C24 C11 1(2) . . . . ?
C10 C12 C32 N4 -108.9(14) . . . . ?
C10 C12 C32 C25 130.0(13) . . . . ?
C11 C5 C21 C10 -4(2) . . . . ?
C12 C10 C21 C5 2(2) . . . . ?
C13 C9 C27 C22 1(2) . . . . ?
C14 C17 C18 C1 1(2) . . . . ?
C14 C23 C28 C1 -1(2) . . . . ?
C17 C14 C23 C28 3(2) . . . . ?
C18 C1 C28 C23 0(2) . . . . ?
C19 C22 C27 C9 -179.4(15) . . . . ?
C20 C2 C4 C16 1(2) . . . . ?
C20 C6 C7 C16 -2(3) . . . . ?
C21 C5 C11 C24 4(2) . . . . ?
C21 C10 C12 C24 0(2) . . . . ?
C21 C10 C12 C32 -177.0(13) . . . . ?
C22 C8 C30 C13 4(3) . . . . ?
C23 C14 C17 C3 177.4(13) . . . . ?
C23 C14 C17 C18 -2(2) . . . . ?
C24 C12 C32 N4 74.3(16) . . . . ?
C24 C12 C32 C25 -46.9(17) . . . . ?
C26 C3 C17 C14 -31(2) . . . . ?
C26 C3 C17 C18 148.9(14) . . . . ?
C27 C9 C13 C30 1(2) . . . . ?
C28 C1 C18 C17 1(2) . . . . ?
C30 C8 C22 C19 177.4(15) . . . . ?
C30 C8 C22 C27 -2(2) . . . . ?
C31 C19 C22 C8 -43(2) . . . . ?
C31 C19 C22 C27 136.4(16) . . . . ?
C32 C12 C24 C11 177.4(12) . . . . ?

_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_mo_211218i_0m
_database_code_depnum_ccdc_archive 'CCDC 2208614'
loop_
_audit_author_name
_audit_author_address
'Zongyi Zhang'
;Shandong University
China
;
_audit_update_record             
;
2022-09-21 deposited with the CCDC.	2023-01-06 downloaded from the CCDC.
;
_audit_creation_date             2021-12-20
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'Bi2 Br10, 4(C8 H12 N)'
_chemical_formula_sum            'C32 H48 Bi2 Br10 N4'
_chemical_formula_weight         1705.80
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.9892(15)
_cell_length_b                   14.601(2)
_cell_length_c                   13.821(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.225(4)
_cell_angle_gamma                90
_cell_volume                     2415.5(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    173.0
_cell_measurement_theta_max      27.94
_cell_measurement_theta_min      3.27
_shelx_estimated_absorpt_T_max   0.369
_shelx_estimated_absorpt_T_min   0.305
_exptl_absorpt_coefficient_mu    15.572
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3224
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1328 before and 0.0833 after correction.
The Ratio of minimum to maximum transmission is 0.4324.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellowish yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   yellowish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.345
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0855
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            70209
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.921
_diffrn_reflns_theta_min         1.701
_diffrn_ambient_temperature      173.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.920
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                9901
_reflns_number_total             11393
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.098
_refine_diff_density_min         -1.172
_refine_diff_density_rms         0.153
_refine_ls_abs_structure_details 
;
 Flack x determined using 4229 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.011(7)
_refine_ls_extinction_coef       0.0018(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     442
_refine_ls_number_reflns         11393
_refine_ls_number_restraints     217
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0321
_refine_ls_restrained_S_all      1.016
_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)+(0.0273P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0697
_refine_ls_wR_factor_ref         0.0734
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
N3 \\sim C1 \\sim C5 \\sim C14 \\sim C17 \\sim C19 \\sim C24 \\sim C26 \\sim
C28: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N4 \\sim C2 \\sim C7 \\sim C10 \\sim C12 \\sim C18 \\sim C20 \\sim C29 \\sim
C31: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N2 \\sim C3 \\sim C11 \\sim C13 \\sim C15 \\sim C21 \\sim C23 \\sim C25 \\sim
C27: within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008
within 1.7A
N1 \\sim C4 \\sim C6 \\sim C8 \\sim C9 \\sim C16 \\sim C22 \\sim C30 \\sim C32:
within 1.7A with sigma of 0.004 and sigma for terminal atoms of 0.008 within
1.7A
3.a Ternary CH refined with riding coordinates:
 C2(H2), C9(H9), C23(H23), C26(H26)
3.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13),
 C14(H14), C15(H15), C16(H16), C17(H17), C20(H20), C22(H22), C25(H25), C28(H28),
  C29(H29), C30(H30), C31(H31), C32(H32)
3.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), N2(H2A,H2B,H2C), N3(H3A,H3B,H3C), N4(H4D,H4E,H4F), C4(H4A,
 H4B,H4C), C7(H7A,H7B,H7C), C19(H19A,H19B,H19C), C27(H27A,H27B,H27C)
;
_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 0.09577(3) 0.49825(2) 0.39515(3) 0.02669(11) Uani 1 1 d . . . . .
Bi2 Bi 0.39414(3) 0.56236(2) 0.60799(3) 0.02692(11) Uani 1 1 d . . . . .
Br1 Br 0.17668(8) 0.31532(9) 0.37852(9) 0.0323(3) Uani 1 1 d . . . . .
Br2 Br 0.08004(10) 0.51198(10) 0.20078(10) 0.0411(3) Uani 1 1 d . . . . .
Br3 Br 0.16433(8) 0.48173(9) 0.61774(9) 0.0333(3) Uani 1 1 d . . . . .
Br4 Br 0.33228(7) 0.57002(10) 0.38577(9) 0.0349(3) Uani 1 1 d . . . . .
Br5 Br 0.41804(10) 0.56031(12) 0.80314(9) 0.0449(3) Uani 1 1 d . . . . .
Br6 Br 0.47914(9) 0.38260(9) 0.57366(10) 0.0359(3) Uani 1 1 d . . . . .
Br7 Br 0.31141(8) 0.74407(9) 0.61369(9) 0.0327(3) Uani 1 1 d . . . . .
Br8 Br 0.02093(8) 0.67954(9) 0.43575(10) 0.0334(3) Uani 1 1 d . . . . .
Br9 Br 0.60764(8) 0.63156(10) 0.59661(11) 0.0431(3) Uani 1 1 d . . . . .
Br10 Br -0.11633(9) 0.43449(10) 0.40507(11) 0.0448(3) Uani 1 1 d . . . . .
N1 N 0.0567(7) 0.6907(7) 0.6811(7) 0.036(2) Uani 1 1 d . U . . .
H1A H 0.108990 0.723268 0.650453 0.043 Uiso 1 1 calc R U . . .
H1B H -0.011330 0.717520 0.670352 0.043 Uiso 1 1 calc R U . . .
H1C H 0.054251 0.632409 0.657750 0.043 Uiso 1 1 calc R U . . .
N2 N 0.2536(8) 0.8021(9) 0.3828(8) 0.060(3) Uani 1 1 d . U . . .
H2A H 0.256689 0.739838 0.380387 0.072 Uiso 1 1 calc R U . . .
H2B H 0.221032 0.819737 0.437656 0.072 Uiso 1 1 calc R U . . .
H2C H 0.324085 0.825307 0.383022 0.072 Uiso 1 1 calc R U . . .
N3 N 0.2526(7) 0.2410(8) 0.5985(7) 0.039(2) Uani 1 1 d . U . . .
H3A H 0.274005 0.212738 0.543807 0.047 Uiso 1 1 calc R U . . .
H3B H 0.289942 0.294995 0.606380 0.047 Uiso 1 1 calc R U . . .
H3C H 0.177827 0.251931 0.593034 0.047 Uiso 1 1 calc R U . . .
N4 N 0.4474(7) 0.3578(7) 0.3224(7) 0.037(2) Uani 1 1 d . U . . .
H4D H 0.407810 0.410958 0.323872 0.045 Uiso 1 1 calc R U . . .
H4E H 0.514663 0.365466 0.355282 0.045 Uiso 1 1 calc R U . . .
H4F H 0.408731 0.312402 0.350739 0.045 Uiso 1 1 calc R U . . .
C1 C 0.1522(8) 0.1935(10) 0.8223(9) 0.0414(19) Uani 1 1 d . U . . .
H1 H 0.110394 0.144366 0.793388 0.050 Uiso 1 1 calc R U . . .
C2 C 0.4654(8) 0.3325(8) 0.2191(7) 0.0370(18) Uani 1 1 d . U . . .
H2 H 0.521108 0.281508 0.219799 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2683(12) 0.7262(11) 0.0631(12) 0.072(3) Uani 1 1 d . U . . .
H3 H 0.245517 0.677073 0.021520 0.086 Uiso 1 1 calc R U . . .
C4 C 0.0856(9) 0.7860(8) 0.8289(8) 0.043(2) Uani 1 1 d . U . . .
H4A H 0.008947 0.809475 0.823664 0.064 Uiso 1 1 calc R U . . .
H4B H 0.133510 0.825004 0.791020 0.064 Uiso 1 1 calc R U . . .
H4C H 0.113243 0.786378 0.896963 0.064 Uiso 1 1 calc R U . . .
C5 C 0.2692(10) 0.3390(10) 0.9013(9) 0.054(2) Uani 1 1 d . U . . .
H5 H 0.309140 0.390240 0.927604 0.064 Uiso 1 1 calc R U . . .
C6 C -0.1043(9) 0.6409(9) 0.8383(9) 0.044(2) Uani 1 1 d . U . . .
H6 H -0.134469 0.693222 0.805482 0.052 Uiso 1 1 calc R U . . .
C7 C 0.3550(9) 0.2963(9) 0.1707(9) 0.048(3) Uani 1 1 d . U . . .
H7A H 0.299193 0.345394 0.167791 0.072 Uiso 1 1 calc R U . . .
H7B H 0.327756 0.245028 0.208597 0.072 Uiso 1 1 calc R U . . .
H7C H 0.367835 0.275345 0.104832 0.072 Uiso 1 1 calc R U . . .
C8 C 0.0102(9) 0.6240(8) 0.8390(9) 0.0387(17) Uani 1 1 d . U . . .
C9 C 0.0875(8) 0.6888(7) 0.7900(7) 0.0371(18) Uani 1 1 d . U . . .
H9 H 0.165484 0.664779 0.799839 0.045 Uiso 1 1 calc R U . . .
C10 C 0.6233(10) 0.5537(10) 0.0775(10) 0.052(2) Uani 1 1 d . U . . .
H10 H 0.660586 0.600574 0.044316 0.063 Uiso 1 1 calc R U . . .
C11 C 0.3363(10) 0.8701(11) 0.1846(11) 0.054(2) Uani 1 1 d . U . . .
H11 H 0.361259 0.918923 0.225839 0.065 Uiso 1 1 calc R U . . .
C12 C 0.6867(10) 0.4916(9) 0.1333(10) 0.050(2) Uani 1 1 d . U . . .
H12 H 0.765573 0.497593 0.140948 0.060 Uiso 1 1 calc R U . . .
C13 C 0.3579(12) 0.7802(10) 0.0416(12) 0.067(2) Uani 1 1 d . U . . .
H13 H 0.397559 0.767838 -0.014518 0.080 Uiso 1 1 calc R U . . .
C14 C 0.2997(10) 0.2998(9) 0.8160(9) 0.048(2) Uani 1 1 d . U . . .
H14 H 0.361020 0.324556 0.783990 0.058 Uiso 1 1 calc R U . . .
C15 C 0.3897(11) 0.8513(11) 0.1010(11) 0.058(2) Uani 1 1 d . U . . .
H15 H 0.450362 0.888961 0.084336 0.070 Uiso 1 1 calc R U . . .
C16 C -0.1737(9) 0.5830(9) 0.8845(9) 0.046(2) Uani 1 1 d . U . . .
H16 H -0.251716 0.594660 0.882270 0.056 Uiso 1 1 calc R U . . .
C17 C 0.1204(9) 0.2297(10) 0.9078(9) 0.048(2) Uani 1 1 d . U . . .
H17 H 0.058445 0.205136 0.939051 0.058 Uiso 1 1 calc R U . . .
C18 C 0.5157(9) 0.4139(8) 0.1685(9) 0.0406(18) Uani 1 1 d . U . . .
C19 C 0.4020(9) 0.1577(10) 0.6877(10) 0.059(3) Uani 1 1 d . U . . .
H19A H 0.418276 0.121831 0.630243 0.088 Uiso 1 1 calc R U . . .
H19B H 0.421935 0.121992 0.746170 0.088 Uiso 1 1 calc R U . . .
H19C H 0.445598 0.214500 0.688702 0.088 Uiso 1 1 calc R U . . .
C20 C 0.5072(11) 0.5498(9) 0.0682(10) 0.053(2) Uani 1 1 d . U . . .
H20 H 0.465395 0.593605 0.030561 0.064 Uiso 1 1 calc R U . . .
C21 C 0.2462(10) 0.8171(11) 0.2076(11) 0.058(2) Uani 1 1 d . U . . .
C22 C 0.0519(9) 0.5496(8) 0.8915(9) 0.045(2) Uani 1 1 d . U . . .
H22 H 0.130029 0.538256 0.896223 0.054 Uiso 1 1 calc R U . . .
C23 C 0.1856(11) 0.8376(11) 0.2950(10) 0.065(2) Uani 1 1 d . U . . .
H23 H 0.113472 0.802996 0.290045 0.078 Uiso 1 1 calc R U . . .
C24 C 0.2442(8) 0.2269(8) 0.7769(9) 0.0400(18) Uani 1 1 d . U . . .
C25 C 0.2122(12) 0.7439(11) 0.1450(11) 0.068(2) Uani 1 1 d . U . . .
H25 H 0.150249 0.706977 0.159809 0.081 Uiso 1 1 calc R U . . .
C26 C 0.2793(8) 0.1804(8) 0.6846(8) 0.0423(19) Uani 1 1 d . U . . .
H26 H 0.235983 0.122230 0.675628 0.051 Uiso 1 1 calc R U . . .
C27 C 0.1587(13) 0.9384(13) 0.3157(12) 0.087(4) Uani 1 1 d . U . . .
H27A H 0.172208 0.975577 0.258483 0.130 Uiso 1 1 calc R U . . .
H27B H 0.206499 0.960033 0.370864 0.130 Uiso 1 1 calc R U . . .
H27C H 0.080105 0.943967 0.330990 0.130 Uiso 1 1 calc R U . . .
C28 C 0.1809(10) 0.3037(9) 0.9482(10) 0.052(2) Uani 1 1 d . U . . .
H28 H 0.160946 0.329378 1.007924 0.063 Uiso 1 1 calc R U . . .
C29 C 0.6325(9) 0.4215(9) 0.1773(10) 0.046(2) Uani 1 1 d . U . . .
H29 H 0.674711 0.377372 0.214253 0.055 Uiso 1 1 calc R U . . .
C30 C -0.0194(10) 0.4920(9) 0.9366(10) 0.048(2) Uani 1 1 d . U . . .
H30 H 0.010158 0.439976 0.970393 0.057 Uiso 1 1 calc R U . . .
C31 C 0.4528(10) 0.4773(8) 0.1175(9) 0.049(2) Uani 1 1 d . U . . .
H31 H 0.373568 0.473476 0.114702 0.059 Uiso 1 1 calc R U . . .
C32 C -0.1309(10) 0.5079(10) 0.9341(9) 0.046(2) Uani 1 1 d . U . . .
H32 H -0.178925 0.467624 0.966216 0.055 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 Br1 2.8554(14) . ?
Bi1 Br2 2.6898(15) . ?
Bi1 Br3 3.1486(14) . ?
Bi1 Br4 3.0325(11) . ?
Bi1 Br8 2.8606(14) . ?
Bi1 Br10 2.7187(11) . ?
Bi2 Br3 3.0061(11) . ?
Bi2 Br4 3.1206(14) . ?
Bi2 Br5 2.6964(14) . ?
Bi2 Br6 2.8647(14) . ?
Bi2 Br7 2.8351(14) . ?
Bi2 Br9 2.7646(12) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N1 C9 1.530(14) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N2 C23 1.515(16) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
N3 C26 1.503(13) . ?
N4 H4D 0.9100 . ?
N4 H4E 0.9100 . ?
N4 H4F 0.9100 . ?
N4 C2 1.503(14) . ?
C1 H1 0.9500 . ?
C1 C17 1.368(17) . ?
C1 C24 1.389(15) . ?
C2 H2 1.0000 . ?
C2 C7 1.543(14) . ?
C2 C18 1.520(15) . ?
C3 H3 0.9500 . ?
C3 C13 1.377(18) . ?
C3 C25 1.37(2) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C4 C9 1.519(15) . ?
C5 H5 0.9500 . ?
C5 C14 1.379(17) . ?
C5 C28 1.372(17) . ?
C6 H6 0.9500 . ?
C6 C8 1.394(14) . ?
C6 C16 1.369(16) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.512(14) . ?
C8 C22 1.384(15) . ?
C9 H9 1.0000 . ?
C10 H10 0.9500 . ?
C10 C12 1.39(2) . ?
C10 C20 1.391(17) . ?
C11 H11 0.9500 . ?
C11 C15 1.379(19) . ?
C11 C21 1.381(17) . ?
C12 H12 0.9500 . ?
C12 C29 1.373(17) . ?
C13 H13 0.9500 . ?
C13 C15 1.37(2) . ?
C14 H14 0.9500 . ?
C14 C24 1.351(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C16 C32 1.378(18) . ?
C17 H17 0.9500 . ?
C17 C28 1.400(18) . ?
C18 C29 1.403(15) . ?
C18 C31 1.364(16) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C19 C26 1.506(14) . ?
C20 H20 0.9500 . ?
C20 C31 1.435(17) . ?
C21 C23 1.47(2) . ?
C21 C25 1.42(2) . ?
C22 H22 0.9500 . ?
C22 C30 1.373(16) . ?
C23 H23 1.0000 . ?
C23 C27 1.54(2) . ?
C24 C26 1.525(16) . ?
C25 H25 0.9500 . ?
C26 H26 1.0000 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 H30 0.9500 . ?
C30 C32 1.355(16) . ?
C31 H31 0.9500 . ?
C32 H32 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
Br1 Bi1 Br3 86.32(4) . . ?
Br1 Bi1 Br4 89.83(4) . . ?
Br1 Bi1 Br8 173.26(4) . . ?
Br2 Bi1 Br1 89.68(4) . . ?
Br2 Bi1 Br3 168.90(3) . . ?
Br2 Bi1 Br4 86.83(4) . . ?
Br2 Bi1 Br8 97.00(4) . . ?
Br2 Bi1 Br10 93.59(4) . . ?
Br4 Bi1 Br3 82.81(3) . . ?
Br8 Bi1 Br3 86.95(4) . . ?
Br8 Bi1 Br4 89.60(4) . . ?
Br10 Bi1 Br1 90.38(4) . . ?
Br10 Bi1 Br3 96.78(4) . . ?
Br10 Bi1 Br4 179.52(5) . . ?
Br10 Bi1 Br8 90.14(4) . . ?
Br3 Bi2 Br4 83.71(3) . . ?
Br5 Bi2 Br3 89.82(4) . . ?
Br5 Bi2 Br4 172.23(3) . . ?
Br5 Bi2 Br6 97.86(5) . . ?
Br5 Bi2 Br7 90.02(4) . . ?
Br5 Bi2 Br9 90.82(4) . . ?
Br6 Bi2 Br3 89.09(4) . . ?
Br6 Bi2 Br4 86.38(4) . . ?
Br7 Bi2 Br3 92.42(3) . . ?
Br7 Bi2 Br4 85.97(4) . . ?
Br7 Bi2 Br6 171.99(4) . . ?
Br9 Bi2 Br3 178.25(4) . . ?
Br9 Bi2 Br4 95.77(4) . . ?
Br9 Bi2 Br6 89.21(4) . . ?
Br9 Bi2 Br7 89.20(4) . . ?
Bi2 Br3 Bi1 96.65(3) . . ?
Bi1 Br4 Bi2 96.70(3) . . ?
H1A N1 H1B 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C9 N1 H1A 109.5 . . ?
C9 N1 H1B 109.5 . . ?
C9 N1 H1C 109.5 . . ?
H2A N2 H2B 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C23 N2 H2A 109.5 . . ?
C23 N2 H2B 109.5 . . ?
C23 N2 H2C 109.5 . . ?
H3A N3 H3B 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C26 N3 H3A 109.5 . . ?
C26 N3 H3B 109.5 . . ?
C26 N3 H3C 109.5 . . ?
H4D N4 H4E 109.5 . . ?
H4D N4 H4F 109.5 . . ?
H4E N4 H4F 109.5 . . ?
C2 N4 H4D 109.5 . . ?
C2 N4 H4E 109.5 . . ?
C2 N4 H4F 109.5 . . ?
C17 C1 H1 119.3 . . ?
C17 C1 C24 121.5(13) . . ?
C24 C1 H1 119.3 . . ?
N4 C2 H2 107.8 . . ?
N4 C2 C7 109.3(8) . . ?
N4 C2 C18 109.1(9) . . ?
C7 C2 H2 107.8 . . ?
C18 C2 H2 107.8 . . ?
C18 C2 C7 114.9(9) . . ?
C13 C3 H3 120.2 . . ?
C25 C3 H3 120.2 . . ?
C25 C3 C13 119.6(16) . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C9 C4 H4A 109.5 . . ?
C9 C4 H4B 109.5 . . ?
C9 C4 H4C 109.5 . . ?
C14 C5 H5 120.1 . . ?
C28 C5 H5 120.1 . . ?
C28 C5 C14 119.8(13) . . ?
C8 C6 H6 119.6 . . ?
C16 C6 H6 119.6 . . ?
C16 C6 C8 120.7(12) . . ?
C2 C7 H7A 109.5 . . ?
C2 C7 H7B 109.5 . . ?
C2 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C6 C8 C9 121.0(10) . . ?
C22 C8 C6 118.0(10) . . ?
C22 C8 C9 120.9(9) . . ?
N1 C9 H9 108.2 . . ?
C4 C9 N1 108.9(9) . . ?
C4 C9 H9 108.2 . . ?
C8 C9 N1 109.4(8) . . ?
C8 C9 C4 113.9(9) . . ?
C8 C9 H9 108.2 . . ?
C12 C10 H10 118.7 . . ?
C12 C10 C20 122.5(13) . . ?
C20 C10 H10 118.7 . . ?
C15 C11 H11 120.4 . . ?
C15 C11 C21 119.2(15) . . ?
C21 C11 H11 120.4 . . ?
C10 C12 H12 120.8 . . ?
C29 C12 C10 118.4(11) . . ?
C29 C12 H12 120.8 . . ?
C3 C13 H13 120.0 . . ?
C15 C13 C3 120.0(16) . . ?
C15 C13 H13 120.0 . . ?
C5 C14 H14 119.3 . . ?
C24 C14 C5 121.3(11) . . ?
C24 C14 H14 119.3 . . ?
C11 C15 H15 119.1 . . ?
C13 C15 C11 121.9(14) . . ?
C13 C15 H15 119.1 . . ?
C6 C16 H16 119.8 . . ?
C6 C16 C32 120.3(11) . . ?
C32 C16 H16 119.8 . . ?
C1 C17 H17 120.7 . . ?
C1 C17 C28 118.6(12) . . ?
C28 C17 H17 120.7 . . ?
C29 C18 C2 116.2(10) . . ?
C31 C18 C2 123.1(10) . . ?
C31 C18 C29 120.8(11) . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C26 C19 H19A 109.5 . . ?
C26 C19 H19B 109.5 . . ?
C26 C19 H19C 109.5 . . ?
C10 C20 H20 121.1 . . ?
C10 C20 C31 117.7(13) . . ?
C31 C20 H20 121.1 . . ?
C11 C21 C23 120.2(15) . . ?
C11 C21 C25 118.9(14) . . ?
C25 C21 C23 120.9(12) . . ?
C8 C22 H22 119.9 . . ?
C30 C22 C8 120.2(11) . . ?
C30 C22 H22 119.9 . . ?
N2 C23 H23 107.8 . . ?
N2 C23 C27 106.7(13) . . ?
C21 C23 N2 108.6(11) . . ?
C21 C23 H23 107.8 . . ?
C21 C23 C27 117.7(12) . . ?
C27 C23 H23 107.8 . . ?
C1 C24 C26 119.0(11) . . ?
C14 C24 C1 118.8(12) . . ?
C14 C24 C26 122.2(10) . . ?
C3 C25 C21 120.5(14) . . ?
C3 C25 H25 119.8 . . ?
C21 C25 H25 119.8 . . ?
N3 C26 C19 108.4(9) . . ?
N3 C26 C24 110.1(9) . . ?
N3 C26 H26 108.4 . . ?
C19 C26 C24 112.9(10) . . ?
C19 C26 H26 108.4 . . ?
C24 C26 H26 108.4 . . ?
C23 C27 H27A 109.5 . . ?
C23 C27 H27B 109.5 . . ?
C23 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C5 C28 C17 119.9(13) . . ?
C5 C28 H28 120.1 . . ?
C17 C28 H28 120.1 . . ?
C12 C29 C18 121.0(13) . . ?
C12 C29 H29 119.5 . . ?
C18 C29 H29 119.5 . . ?
C22 C30 H30 119.3 . . ?
C32 C30 C22 121.5(12) . . ?
C32 C30 H30 119.3 . . ?
C18 C31 C20 119.5(11) . . ?
C18 C31 H31 120.3 . . ?
C20 C31 H31 120.3 . . ?
C16 C32 H32 120.4 . . ?
C30 C32 C16 119.2(12) . . ?
C30 C32 H32 120.4 . . ?

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
N4 C2 C18 C29 86.6(12) . . . . ?
N4 C2 C18 C31 -92.9(13) . . . . ?
C1 C17 C28 C5 0.8(18) . . . . ?
C1 C24 C26 N3 108.4(12) . . . . ?
C1 C24 C26 C19 -130.2(11) . . . . ?
C2 C18 C29 C12 179.1(11) . . . . ?
C2 C18 C31 C20 -177.2(11) . . . . ?
C3 C13 C15 C11 2(2) . . . . ?
C5 C14 C24 C1 2.4(18) . . . . ?
C5 C14 C24 C26 -177.7(11) . . . . ?
C6 C8 C9 N1 -63.3(14) . . . . ?
C6 C8 C9 C4 58.8(14) . . . . ?
C6 C8 C22 C30 3.5(18) . . . . ?
C6 C16 C32 C30 0(2) . . . . ?
C7 C2 C18 C29 -150.3(11) . . . . ?
C7 C2 C18 C31 30.2(16) . . . . ?
C8 C6 C16 C32 1.3(19) . . . . ?
C8 C22 C30 C32 -2(2) . . . . ?
C9 C8 C22 C30 179.1(11) . . . . ?
C10 C12 C29 C18 -1.8(18) . . . . ?
C10 C20 C31 C18 -2.1(18) . . . . ?
C11 C21 C23 N2 -77.5(17) . . . . ?
C11 C21 C23 C27 43.8(19) . . . . ?
C11 C21 C25 C3 0(2) . . . . ?
C12 C10 C20 C31 -1(2) . . . . ?
C13 C3 C25 C21 0(2) . . . . ?
C14 C5 C28 C17 -1.8(18) . . . . ?
C14 C24 C26 N3 -71.5(13) . . . . ?
C14 C24 C26 C19 49.8(15) . . . . ?
C15 C11 C21 C23 -178.1(13) . . . . ?
C15 C11 C21 C25 1(2) . . . . ?
C16 C6 C8 C9 -178.7(11) . . . . ?
C16 C6 C8 C22 -3.0(18) . . . . ?
C17 C1 C24 C14 -3.3(18) . . . . ?
C17 C1 C24 C26 176.7(11) . . . . ?
C20 C10 C12 C29 3.1(19) . . . . ?
C21 C11 C15 C13 -2(2) . . . . ?
C22 C8 C9 N1 121.2(11) . . . . ?
C22 C8 C9 C4 -116.7(12) . . . . ?
C22 C30 C32 C16 1(2) . . . . ?
C23 C21 C25 C3 179.1(13) . . . . ?
C24 C1 C17 C28 1.7(19) . . . . ?
C25 C3 C13 C15 -1(2) . . . . ?
C25 C21 C23 N2 103.5(15) . . . . ?
C25 C21 C23 C27 -135.2(15) . . . . ?
C28 C5 C14 C24 0.1(19) . . . . ?
C29 C18 C31 C20 3.3(18) . . . . ?
C31 C18 C29 C12 -1.4(18) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
