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

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

data_IG137
_database_code_depnum_ccdc_archive 'CCDC 1588907'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H30 Bi Br8 N3'
_chemical_formula_weight         1172.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.2266(2)
_cell_length_b                   17.8388(4)
_cell_length_c                   17.6539(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.857(2)
_cell_angle_gamma                90
_cell_volume                     3220.24(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5767
_cell_measurement_theta_min      3.81
_cell_measurement_theta_max      29.22

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.419
_exptl_crystal_F_000             2160
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_absorpt_coefficient_mu    15.417
_shelx_estimated_absorpt_T_min   0.077
_shelx_estimated_absorpt_T_max   0.221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40281
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            17474
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.616
_diffrn_reflns_theta_max         29.545
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             7605
_reflns_number_gt                6054
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0235P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7605
_refine_ls_number_parameters     304
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0546
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.75187(2) 0.74870(2) 0.39114(2) 0.01324(4) Uani 1 1 d . . . . .
Br1 Br 0.74988(4) 0.86210(2) 0.26837(2) 0.01866(9) Uani 1 1 d . . . . .
Br2 Br 0.74283(3) 0.86640(2) 0.50584(2) 0.01719(9) Uani 1 1 d . . . . .
Br3 Br 1.01509(4) 0.74973(2) 0.39792(2) 0.02344(10) Uani 1 1 d . . . . .
Br4 Br 0.74270(3) 0.63772(2) 0.50148(2) 0.01792(9) Uani 1 1 d . . . . .
Br5 Br 0.73802(4) 0.63719(2) 0.27674(2) 0.02162(9) Uani 1 1 d . . . . .
Br6 Br 0.45576(4) 0.76546(2) 0.41098(2) 0.02198(10) Uani 1 1 d . . . . .
Br7 Br 0.33877(3) 0.66302(2) 0.32588(2) 0.01742(9) Uani 1 1 d . . . . .
Br8 Br 0.22777(4) 0.57280(3) 0.24421(3) 0.03006(11) Uani 1 1 d . . . . .
N1 N 0.7612(3) 1.00914(19) 0.38063(17) 0.0174(7) Uani 1 1 d . . . . .
H1 H 0.758879 0.974494 0.345151 0.021 Uiso 1 1 calc R U . . .
C11 C 0.9971(4) 0.9981(3) 0.3685(2) 0.0319(11) Uani 1 1 d . . . . .
H11A H 1.077210 1.018288 0.391865 0.048 Uiso 1 1 calc R U . . .
H11B H 0.996177 1.009239 0.314150 0.048 Uiso 1 1 calc R U . . .
H11C H 0.994094 0.943751 0.376075 0.048 Uiso 1 1 calc R U . . .
C12 C 0.8797(4) 1.0338(2) 0.4047(2) 0.0212(9) Uani 1 1 d . . . . .
C13 C 0.8841(4) 1.0877(2) 0.4593(2) 0.0254(10) Uani 1 1 d . . . . .
H13 H 0.965934 1.105825 0.477693 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7695(4) 1.1156(3) 0.4876(2) 0.0298(10) Uani 1 1 d . . . . .
H14 H 0.772068 1.153736 0.525214 0.036 Uiso 1 1 calc R U . . .
C15 C 0.6496(4) 1.0882(2) 0.4613(2) 0.0251(10) Uani 1 1 d . . . . .
H15 H 0.570332 1.107304 0.481015 0.030 Uiso 1 1 calc R U . . .
C16 C 0.6467(4) 1.0339(2) 0.4072(2) 0.0186(9) Uani 1 1 d . . . . .
C17 C 0.5259(4) 0.9987(3) 0.3747(2) 0.0263(10) Uani 1 1 d . . . . .
H17A H 0.448968 1.019737 0.399412 0.040 Uiso 1 1 calc R U . . .
H17B H 0.528818 0.944427 0.383153 0.040 Uiso 1 1 calc R U . . .
H17C H 0.520527 1.008839 0.320168 0.040 Uiso 1 1 calc R U . . .
N2 N 0.7476(3) 0.75044(18) 0.65609(18) 0.0179(7) Uani 1 1 d . . . . .
H2 H 0.745749 0.788715 0.624642 0.021 Uiso 1 1 calc R U . . .
C21 C 0.5120(4) 0.7641(3) 0.6542(3) 0.0307(11) Uani 1 1 d . . . . .
H21A H 0.434932 0.735104 0.668563 0.046 Uiso 1 1 calc R U . . .
H21B H 0.513808 0.769198 0.598938 0.046 Uiso 1 1 calc R U . . .
H21C H 0.508085 0.813999 0.677356 0.046 Uiso 1 1 calc R U . . .
C22 C 0.6330(4) 0.7246(2) 0.6812(2) 0.0206(9) Uani 1 1 d . . . . .
C23 C 0.6361(4) 0.6652(2) 0.7304(2) 0.0281(10) Uani 1 1 d . . . . .
H23 H 0.556925 0.645766 0.749882 0.034 Uiso 1 1 calc R U . . .
C24 C 0.7539(4) 0.6338(2) 0.7516(2) 0.0303(11) Uani 1 1 d . . . . .
H24 H 0.755778 0.592225 0.785240 0.036 Uiso 1 1 calc R U . . .
C25 C 0.8689(4) 0.6622(2) 0.7242(2) 0.0242(9) Uani 1 1 d . . . . .
H25 H 0.950164 0.640388 0.738978 0.029 Uiso 1 1 calc R U . . .
C26 C 0.8659(4) 0.7218(2) 0.6757(2) 0.0177(8) Uani 1 1 d . . . . .
C27 C 0.9830(4) 0.7591(2) 0.6431(2) 0.0265(10) Uani 1 1 d . . . . .
H27A H 1.062456 0.733654 0.661140 0.040 Uiso 1 1 calc R U . . .
H27B H 0.985411 0.811728 0.659029 0.040 Uiso 1 1 calc R U . . .
H27C H 0.978015 0.756497 0.587659 0.040 Uiso 1 1 calc R U . . .
N3 N 0.7501(3) 0.48547(19) 0.38912(17) 0.0176(7) Uani 1 1 d . . . . .
H3 H 0.745726 0.525792 0.360482 0.021 Uiso 1 1 calc R U . . .
C31 C 0.5141(4) 0.4917(3) 0.3843(2) 0.0278(10) Uani 1 1 d . . . . .
H31A H 0.438689 0.463793 0.402985 0.042 Uiso 1 1 calc R U . . .
H31B H 0.510883 0.492910 0.328756 0.042 Uiso 1 1 calc R U . . .
H31C H 0.511915 0.543078 0.403913 0.042 Uiso 1 1 calc R U . . .
C32 C 0.6375(4) 0.4542(2) 0.4103(2) 0.0189(9) Uani 1 1 d . . . . .
C33 C 0.6437(4) 0.3917(2) 0.4554(2) 0.0238(9) Uani 1 1 d . . . . .
H33 H 0.565641 0.368582 0.472363 0.029 Uiso 1 1 calc R U . . .
C34 C 0.7642(4) 0.3625(3) 0.4761(2) 0.0271(10) Uani 1 1 d . . . . .
H34 H 0.769315 0.318369 0.506139 0.032 Uiso 1 1 calc R U . . .
C35 C 0.8763(4) 0.3973(2) 0.4533(2) 0.0244(10) Uani 1 1 d . . . . .
H35 H 0.959134 0.378081 0.468616 0.029 Uiso 1 1 calc R U . . .
C36 C 0.8693(4) 0.4595(2) 0.4085(2) 0.0214(9) Uani 1 1 d . . . . .
C37 C 0.9866(4) 0.5028(3) 0.3800(2) 0.0302(11) Uani 1 1 d . . . . .
H37A H 1.066895 0.481717 0.402176 0.045 Uiso 1 1 calc R U . . .
H37B H 0.978845 0.555578 0.394619 0.045 Uiso 1 1 calc R U . . .
H37C H 0.989642 0.499014 0.324631 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 Br1 2.9646(4) . yes
Bi1 Br2 2.9194(4) . yes
Bi1 Br3 2.6928(4) . yes
Bi1 Br4 2.7799(4) . yes
Bi1 Br5 2.8367(4) . yes
Bi1 Br6 3.0682(4) . yes
Br6 Br7 2.6408(6) . yes
Br7 Br8 2.4308(6) . yes
N1 H1 0.8800 . ?
N1 C12 1.352(5) . ?
N1 C16 1.341(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C12 1.508(5) . ?
C12 C13 1.362(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(6) . ?
C14 H14 0.9500 . ?
C14 C15 1.394(5) . ?
C15 H15 0.9500 . ?
C15 C16 1.361(6) . ?
C16 C17 1.493(5) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
N2 H2 0.8800 . ?
N2 C22 1.340(5) . ?
N2 C26 1.354(5) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 C22 1.496(6) . ?
C22 C23 1.370(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.376(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.375(6) . ?
C25 H25 0.9500 . ?
C25 C26 1.366(6) . ?
C26 C27 1.493(5) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
N3 H3 0.8800 . ?
N3 C32 1.338(5) . ?
N3 C36 1.344(5) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
C31 C32 1.495(5) . ?
C32 C33 1.371(6) . ?
C33 H33 0.9500 . ?
C33 C34 1.382(5) . ?
C34 H34 0.9500 . ?
C34 C35 1.370(6) . ?
C35 H35 0.9500 . ?
C35 C36 1.363(6) . ?
C36 C37 1.518(5) . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Bi1 Br6 91.204(11) . . yes
Br2 Bi1 Br1 90.937(12) . . yes
Br2 Bi1 Br6 78.998(11) . . yes
Br3 Bi1 Br1 91.360(12) . . yes
Br3 Bi1 Br2 90.357(12) . . yes
Br3 Bi1 Br4 91.024(12) . . yes
Br3 Bi1 Br5 94.341(13) . . yes
Br3 Bi1 Br6 169.089(13) . . yes
Br4 Bi1 Br1 176.654(12) . . yes
Br4 Bi1 Br2 91.396(12) . . yes
Br4 Bi1 Br5 89.867(12) . . yes
Br4 Bi1 Br6 86.887(12) . . yes
Br5 Bi1 Br1 87.612(12) . . yes
Br5 Bi1 Br2 175.113(11) . . yes
Br5 Bi1 Br6 96.360(12) . . yes
Br7 Br6 Bi1 107.885(15) . . yes
Br8 Br7 Br6 177.66(2) . . yes
C12 N1 H1 117.7 . . ?
C16 N1 H1 117.7 . . ?
C16 N1 C12 124.5(4) . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
N1 C12 C11 116.5(4) . . ?
N1 C12 C13 118.1(3) . . ?
C13 C12 C11 125.4(4) . . ?
C12 C13 H13 120.2 . . ?
C12 C13 C14 119.6(4) . . ?
C14 C13 H13 120.2 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C15 120.1(4) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 120.2 . . ?
C16 C15 C14 119.6(4) . . ?
C16 C15 H15 120.2 . . ?
N1 C16 C15 118.0(4) . . ?
N1 C16 C17 116.7(4) . . ?
C15 C16 C17 125.3(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C22 N2 H2 117.7 . . ?
C22 N2 C26 124.6(4) . . ?
C26 N2 H2 117.7 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
N2 C22 C21 117.1(4) . . ?
N2 C22 C23 117.6(4) . . ?
C23 C22 C21 125.3(4) . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(4) . . ?
C24 C23 H23 120.0 . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.3(4) . . ?
C25 C24 H24 119.8 . . ?
C24 C25 H25 120.1 . . ?
C26 C25 C24 119.7(4) . . ?
C26 C25 H25 120.1 . . ?
N2 C26 C25 117.8(4) . . ?
N2 C26 C27 116.9(4) . . ?
C25 C26 C27 125.4(4) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C32 N3 H3 117.7 . . ?
C32 N3 C36 124.5(4) . . ?
C36 N3 H3 117.7 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C32 C31 H31A 109.5 . . ?
C32 C31 H31B 109.5 . . ?
C32 C31 H31C 109.5 . . ?
N3 C32 C31 116.9(4) . . ?
N3 C32 C33 118.0(3) . . ?
C33 C32 C31 125.0(4) . . ?
C32 C33 H33 120.2 . . ?
C32 C33 C34 119.5(4) . . ?
C34 C33 H33 120.2 . . ?
C33 C34 H34 120.1 . . ?
C35 C34 C33 119.9(4) . . ?
C35 C34 H34 120.1 . . ?
C34 C35 H35 119.9 . . ?
C36 C35 C34 120.2(4) . . ?
C36 C35 H35 119.9 . . ?
N3 C36 C35 117.8(4) . . ?
N3 C36 C37 117.3(4) . . ?
C35 C36 C37 124.9(4) . . ?
C36 C37 H37A 109.5 . . ?
C36 C37 H37B 109.5 . . ?
C36 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?

_refine_diff_density_max         1.118
_refine_diff_density_min         -1.357
_refine_diff_density_rms         0.156

####################################################################### 
# 
# 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_sa1186
_database_code_depnum_ccdc_archive 'CCDC 1588909'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H16 Bi Br7 N2'
_chemical_formula_weight         968.63

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

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

_cell_length_a                   8.3504(3)
_cell_length_b                   14.0462(8)
_cell_length_c                   19.2571(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2258.69(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2871
_cell_measurement_theta_min      4.24
_cell_measurement_theta_max      28.47

_exptl_crystal_description       stick
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.848
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    20.188
_shelx_estimated_absorpt_T_min   0.101
_shelx_estimated_absorpt_T_max   0.432
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52978
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            7022
_diffrn_reflns_av_unetI/netI     0.0283
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.490
_diffrn_reflns_theta_max         28.869
_diffrn_reflns_theta_full        25.500
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2660
_reflns_number_gt                2243
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0204P)²+0.2405P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2660
_refine_ls_number_parameters     112
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0369
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0517
_refine_ls_wR_factor_gt          0.0488
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.81697(3) 0.750000 0.36388(2) 0.01249(7) Uani 1 2 d S T P . .
Br1 Br 0.57538(7) 0.750000 0.46512(3) 0.01627(14) Uani 1 2 d S T P . .
Br2 Br 1.06024(7) 0.750000 0.25237(3) 0.02081(14) Uani 1 2 d S T P . .
Br3 Br 1.05201(7) 0.750000 0.45942(3) 0.02085(15) Uani 1 2 d S T P . .
Br4 Br 0.78176(5) 0.54835(3) 0.36702(2) 0.02399(12) Uani 1 1 d . . . . .
Br5 Br 0.61730(7) 0.33254(4) 0.36095(2) 0.03553(14) Uani 1 1 d . . . . .
N1 N 0.3564(4) 0.5780(3) 0.3922(2) 0.0287(9) Uani 1 1 d . . . . .
H1N H 0.420383 0.626659 0.399751 0.034 Uiso 1 1 calc R U . . .
C1 C 0.3269(6) 0.5527(4) 0.3273(3) 0.0311(12) Uani 1 1 d . . . . .
H1 H 0.373394 0.586959 0.289810 0.037 Uiso 1 1 calc R U . . .
C2 C 0.2285(5) 0.4766(3) 0.3146(2) 0.0249(11) Uani 1 1 d . . . . .
H2 H 0.206922 0.458052 0.268082 0.030 Uiso 1 1 calc R U . . .
C3 C 0.1603(5) 0.4264(3) 0.3690(2) 0.0178(9) Uani 1 1 d . . . . .
C4 C 0.1950(5) 0.4558(3) 0.4362(2) 0.0224(10) Uani 1 1 d . . . . .
H4 H 0.150753 0.422578 0.474633 0.027 Uiso 1 1 calc R U . . .
C5 C 0.2932(5) 0.5328(3) 0.4471(2) 0.0273(11) Uani 1 1 d . . . . .
H5 H 0.316027 0.553823 0.492984 0.033 Uiso 1 1 calc R U . . .
C6 C 0.0595(5) 0.3403(3) 0.3564(2) 0.0208(10) Uani 1 1 d . . . . .
H6A H 0.008775 0.344796 0.310061 0.025 Uiso 1 1 calc R U . . .
H6B H -0.026585 0.337039 0.391692 0.025 Uiso 1 1 calc R U . . .
C7 C 0.1624(7) 0.250000 0.3602(3) 0.0185(14) Uani 1 2 d S T P . .
H7A H 0.239998 0.250000 0.321377 0.022 Uiso 1 2 calc R U P . .
H7B H 0.223657 0.249999 0.404235 0.022 Uiso 1 2 calc R U P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br1 2.8055(6) . yes
Bi1 Br2 2.9560(6) . yes
Bi1 Br2 3.0995(6) 6_556 yes
Bi1 Br3 2.6903(6) . yes
Bi1 Br4 2.8482(5) . yes
Bi1 Br4 2.8482(5) 7_575 yes
Br5 Br5 2.3188(11) 7_565 yes
N1 H1N 0.8800 . ?
N1 C1 1.324(6) . ?
N1 C5 1.341(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.370(6) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(6) . ?
C3 C4 1.389(6) . ?
C3 C6 1.494(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.374(6) . ?
C5 H5 0.9500 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C6 C7 1.534(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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 Br2 90.259(17) . 6_556 yes
Br1 Bi1 Br2 177.432(18) . . yes
Br1 Bi1 Br4 84.894(10) . . yes
Br1 Bi1 Br4 84.894(10) . 7_575 ?
Br2 Bi1 Br2 87.173(6) . 6_556 yes
Br3 Bi1 Br1 92.827(18) . . yes
Br3 Bi1 Br2 89.741(19) . . yes
Br3 Bi1 Br2 176.914(19) . 6_556 yes
Br3 Bi1 Br4 93.483(10) . . yes
Br3 Bi1 Br4 93.484(10) . 7_575 ?
Br4 Bi1 Br2 86.787(10) 7_575 6_556 ?
Br4 Bi1 Br2 86.788(10) . 6_556 yes
Br4 Bi1 Br2 94.955(10) . . yes
Br4 Bi1 Br2 94.955(10) 7_575 . ?
Br4 Bi1 Br4 167.90(2) 7_575 . yes
Bi1 Br2 Bi1 179.65(2) . 6_656 yes
C1 N1 H1N 118.5 . . ?
C1 N1 C5 123.0(4) . . ?
C5 N1 H1N 118.5 . . ?
N1 C1 H1 120.4 . . ?
N1 C1 C2 119.3(4) . . ?
C2 C1 H1 120.4 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.6(4) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C4 117.9(4) . . ?
C2 C3 C6 121.4(4) . . ?
C4 C3 C6 120.6(4) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4 119.9 . . ?
N1 C5 C4 119.1(4) . . ?
N1 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C3 C6 H6A 109.6 . . ?
C3 C6 H6B 109.6 . . ?
C3 C6 C7 110.3(4) . . ?
H6A C6 H6B 108.1 . . ?
C7 C6 H6A 109.6 . . ?
C7 C6 H6B 109.6 . . ?
C6 C7 C6 111.6(5) 7_565 . ?
C6 C7 H7A 109.3 . . ?
C6 C7 H7A 109.3 7_565 . ?
C6 C7 H7B 109.3 . . ?
C6 C7 H7B 109.3 7_565 . ?
H7A C7 H7B 108.0 . . ?

_refine_diff_density_max         0.900
_refine_diff_density_min         -1.016
_refine_diff_density_rms         0.152

####################################################################### 
# 
# 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_ig345
_database_code_depnum_ccdc_archive 'CCDC 1588908'
_audit_update_record             
;
2017-12-04 deposited with the CCDC.
2018-01-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 Bi Br7 Cl2 N2'
_chemical_formula_weight         997.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   20.2722(7)
_cell_length_b                   7.6512(3)
_cell_length_c                   28.2787(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4386.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    2918
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      28.40

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    3.021
_exptl_crystal_F_000             3568
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.54
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    21.033
_shelx_estimated_absorpt_T_min   0.031
_shelx_estimated_absorpt_T_max   0.206
_exptl_absorpt_correction_T_min  0.922
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_special_details   ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 11 -5 0.2493
-1 10 -16 0.2536
-28 -1 -1 0.0380
2 0 -40 0.1292
28 1 4 0.0649
-18 0 -31 0.0929
20 0 28 0.0654
-2 0 40 0.1150
6 -9 22 0.1834
13 -8 19 0.1739
-2 -9 -19 0.2760

_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            12407
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.341
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3971
_reflns_number_gt                2787
_reflns_threshold_expression     >2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017 (Sheldrick, 2015)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2015)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3971
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0786
_refine_ls_R_factor_gt           0.0498
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1165
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.35874(2) 0.75638(4) 0.62306(2) 0.01053(16) Uani 1 1 d . . . . .
Br1 Br 0.46320(5) 0.53622(13) 0.62213(3) 0.0150(3) Uani 1 1 d . . . . .
Br2 Br 0.28141(5) 0.41442(13) 0.62259(3) 0.0182(3) Uani 1 1 d . . . . .
Br3 Br 0.36019(5) 0.75324(12) 0.72206(4) 0.0207(3) Uani 1 1 d . . . . .
Br4 Br 0.43976(5) 1.03603(13) 0.62374(4) 0.0221(3) Uani 1 1 d . . . . .
Br5 Br 0.35520(6) 0.75119(13) 0.52151(4) 0.0236(3) Uani 1 1 d . . . . .
Br6 Br 0.38910(6) 0.73034(14) 0.41523(4) 0.0267(3) Uani 1 1 d . . . . .
Br7 Br 0.39541(6) 0.76162(14) 0.33347(4) 0.0273(3) Uani 1 1 d . . . . .
Cl1 Cl 0.73136(15) 0.5795(4) 0.68692(12) 0.0430(8) Uani 1 1 d . . . . .
N1 N 0.6226(5) 0.7900(11) 0.7848(3) 0.029(2) Uani 1 1 d . . . . .
H1 H 0.627784 0.824207 0.814251 0.034 Uiso 1 1 calc R U . . .
C11 C 0.6744(6) 0.7209(13) 0.7627(4) 0.027(3) Uani 1 1 d . . . . .
H11 H 0.715717 0.706475 0.778063 0.032 Uiso 1 1 calc R U . . .
C12 C 0.6647(5) 0.6708(13) 0.7159(4) 0.026(3) Uani 1 1 d . . . . .
C13 C 0.6054(6) 0.6921(14) 0.6946(4) 0.025(3) Uani 1 1 d . . . . .
H13 H 0.599483 0.657923 0.662573 0.030 Uiso 1 1 calc R U . . .
C14 C 0.5538(6) 0.7637(13) 0.7197(4) 0.030(3) Uani 1 1 d . . . . .
H14 H 0.511793 0.779841 0.705406 0.036 Uiso 1 1 calc R U . . .
C15 C 0.5644(6) 0.8105(15) 0.7654(4) 0.032(3) Uani 1 1 d . . . . .
H15 H 0.529329 0.858441 0.783552 0.038 Uiso 1 1 calc R U . . .
Cl2 Cl 0.28371(18) 0.1350(5) 0.41651(14) 0.0593(11) Uani 1 1 d . . . . .
N2 N 0.3786(5) 0.2851(12) 0.5288(3) 0.031(2) Uani 1 1 d . . . . .
H2 H 0.368222 0.325628 0.556936 0.037 Uiso 1 1 calc R U . . .
C21 C 0.3297(6) 0.2455(12) 0.5001(4) 0.027(3) Uani 1 1 d . . . . .
H21 H 0.285096 0.259008 0.509615 0.032 Uiso 1 1 calc R U . . .
C22 C 0.3458(6) 0.1825(15) 0.4549(4) 0.028(3) Uani 1 1 d . . . . .
C23 C 0.4118(6) 0.1685(13) 0.4428(4) 0.025(3) Uani 1 1 d . . . . .
H23 H 0.424115 0.128634 0.412220 0.029 Uiso 1 1 calc R U . . .
C24 C 0.4587(6) 0.2120(14) 0.4749(4) 0.027(3) Uani 1 1 d . . . . .
H24 H 0.504020 0.202536 0.466735 0.033 Uiso 1 1 calc R U . . .
C25 C 0.4416(7) 0.2690(14) 0.5188(5) 0.034(3) Uani 1 1 d . . . . .
H25 H 0.474322 0.296528 0.541588 0.041 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 2.7060(11) . yes
Bi1 Br2 3.0502(11) . yes
Bi1 Br2 3.0877(11) 8_665 yes
Bi1 Br3 2.8000(12) . yes
Bi1 Br4 2.6975(11) . yes
Bi1 Br5 2.8729(12) . yes
Br6 Br7 2.3278(18) . yes
Cl1 C12 1.728(11) . ?
N1 H1 0.8800 . ?
N1 C11 1.331(15) . ?
N1 C15 1.309(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(16) . ?
C12 C13 1.355(16) . ?
C13 H13 0.9500 . ?
C13 C14 1.379(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.360(16) . ?
C15 H15 0.9500 . ?
Cl2 C22 1.701(11) . ?
N2 H2 0.8800 . ?
N2 C21 1.316(16) . ?
N2 C25 1.314(16) . ?
C21 H21 0.9500 . ?
C21 C22 1.404(16) . ?
C22 C23 1.386(15) . ?
C23 H23 0.9500 . ?
C23 C24 1.358(16) . ?
C24 H24 0.9500 . ?
C24 C25 1.358(16) . ?
C25 H25 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 Br2 82.43(3) . . yes
Br1 Bi1 Br2 164.53(3) . 8_665 yes
Br1 Bi1 Br3 89.78(3) . . yes
Br1 Bi1 Br5 90.07(3) . . yes
Br2 Bi1 Br2 82.125(15) . 8_665 yes
Br3 Bi1 Br2 90.14(3) . . yes
Br3 Bi1 Br2 90.99(3) . 8_665 yes
Br3 Bi1 Br5 178.47(3) . . yes
Br4 Bi1 Br1 90.99(3) . . yes
Br4 Bi1 Br2 104.46(3) . 8_665 yes
Br4 Bi1 Br2 173.41(3) . . yes
Br4 Bi1 Br3 89.61(3) . . yes
Br4 Bi1 Br5 91.91(3) . . yes
Br5 Bi1 Br2 88.34(3) . . yes
Br5 Bi1 Br2 88.75(3) . 8_665 yes
Bi1 Br2 Bi1 143.98(4) . 8_655 yes
C11 N1 H1 117.9 . . ?
C15 N1 H1 117.9 . . ?
C15 N1 C11 124.2(11) . . ?
N1 C11 H11 121.8 . . ?
N1 C11 C12 116.3(11) . . ?
C12 C11 H11 121.8 . . ?
C11 C12 Cl1 116.9(9) . . ?
C13 C12 Cl1 122.1(9) . . ?
C13 C12 C11 121.0(11) . . ?
C12 C13 H13 120.3 . . ?
C12 C13 C14 119.5(10) . . ?
C14 C13 H13 120.3 . . ?
C13 C14 H14 120.9 . . ?
C15 C14 C13 118.3(11) . . ?
C15 C14 H14 120.9 . . ?
N1 C15 C14 120.6(12) . . ?
N1 C15 H15 119.7 . . ?
C14 C15 H15 119.7 . . ?
C21 N2 H2 117.4 . . ?
C25 N2 H2 117.4 . . ?
C25 N2 C21 125.2(11) . . ?
N2 C21 H21 121.1 . . ?
N2 C21 C22 117.8(11) . . ?
C22 C21 H21 121.1 . . ?
C21 C22 Cl2 118.9(10) . . ?
C23 C22 Cl2 122.7(9) . . ?
C23 C22 C21 118.4(11) . . ?
C22 C23 H23 120.2 . . ?
C24 C23 C22 119.5(10) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.7 . . ?
C23 C24 C25 120.7(11) . . ?
C25 C24 H24 119.7 . . ?
N2 C25 C24 118.4(13) . . ?
N2 C25 H25 120.8 . . ?
C24 C25 H25 120.8 . . ?

_refine_diff_density_max         3.232
_refine_diff_density_min         -2.868
_refine_diff_density_rms         0.332

