# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2016

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1450024'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H30 Bi2 Br13 N3'
_chemical_formula_weight         1781.27

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   11.91371(17)
_cell_length_b                   15.9042(2)
_cell_length_c                   21.6218(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.0689(14)
_cell_angle_gamma                90
_cell_volume                     4096.14(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    17556
_cell_measurement_theta_min      3.57
_cell_measurement_theta_max      29.36

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.888
_exptl_crystal_F_000             3192
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.460
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    21.280
_shelx_estimated_absorpt_T_min   0.037
_shelx_estimated_absorpt_T_max   0.568
_exptl_absorpt_correction_T_min  0.929
_exptl_absorpt_correction_T_max  0.994
_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)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_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
0 0 -30 0.0303
0 0 30 0.0010
-13 -14 -2 0.1696
14 -13 0 0.1786
13 14 2 0.1651
-14 13 0 0.2005
1 -22 -1 0.2176
-2 22 1 0.2763

_diffrn_ambient_temperature      130(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            29030
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0554
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.421
_diffrn_reflns_theta_max         25.680
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3878
_reflns_number_gt                3434
_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    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'

_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)+(0.1240P)²+159.8000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         3878
_refine_ls_number_parameters     211
_refine_ls_number_restraints     62
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1822
_refine_ls_wR_factor_gt          0.1707
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.46120(3) 0.14878(3) 0.34016(2) 0.0191(2) Uani 1 1 d . . . . .
Br1 Br 0.44985(12) 0.29684(8) 0.40159(8) 0.0336(4) Uani 1 1 d . . . . .
Br2 Br 0.25666(11) 0.08652(9) 0.38016(7) 0.0320(4) Uani 1 1 d . . . . .
Br3 Br 0.58939(11) 0.07677(8) 0.43016(7) 0.0296(3) Uani 1 1 d . . . . .
Br4 Br 0.5000 0.00208(11) 0.2500 0.0297(5) Uani 1 2 d S T P . .
Br5 Br 0.65489(11) 0.21862(10) 0.27597(7) 0.0354(4) Uani 1 1 d . . . . .
Br7 Br 0.59729(11) 0.74124(10) 0.24414(7) 0.0332(4) Uani 1 1 d . . . . .
Br6 Br 0.57625(10) 0.51967(8) 0.47015(7) 0.0273(3) Uani 1 1 d . . . . .
N1 N 0.5020(9) 0.1872(7) 0.5926(5) 0.024(2) Uani 1 1 d . . . . .
C11 C 0.3305(13) 0.1436(9) 0.5365(8) 0.035(4) Uani 1 1 d . . . . .
H11A H 0.2515 0.1279 0.5406 0.053 Uiso 1 1 calc R U . . .
H11B H 0.3717 0.0970 0.5178 0.053 Uiso 1 1 calc R U . . .
H11C H 0.3360 0.1934 0.5100 0.053 Uiso 1 1 calc R U . . .
C12 C 0.3807(13) 0.1630(10) 0.5997(9) 0.040(4) Uani 1 1 d . . . . .
H12A H 0.3390 0.2098 0.6190 0.049 Uiso 1 1 calc R U . . .
H12B H 0.3750 0.1131 0.6268 0.049 Uiso 1 1 calc R U . . .
C13 C 0.5268(13) 0.2659(9) 0.5767(9) 0.042(4) Uani 1 1 d . . . . .
H13 H 0.4681 0.3058 0.5713 0.050 Uiso 1 1 calc R U . . .
C14 C 0.6365(14) 0.2900(10) 0.5679(10) 0.048(5) Uani 1 1 d . . . . .
H14 H 0.6529 0.3460 0.5558 0.057 Uiso 1 1 calc R U . . .
C15 C 0.7222(13) 0.2332(10) 0.5766(7) 0.033(3) Uani 1 1 d . . . . .
H15 H 0.7983 0.2488 0.5711 0.039 Uiso 1 1 calc R U . . .
C16 C 0.6931(12) 0.1515(9) 0.5937(7) 0.028(3) Uani 1 1 d . . . . .
H16 H 0.7502 0.1108 0.6007 0.033 Uiso 1 1 calc R U . . .
C17 C 0.5838(12) 0.1298(9) 0.6004(8) 0.033(3) Uani 1 1 d . . . . .
H17 H 0.5650 0.0736 0.6108 0.040 Uiso 1 1 calc R U . . .
N2 N 0.5000 0.4710(11) 0.2500 0.047(4) Uani 1 2 d DS TU P . .
C21 C 0.651(3) 0.510(2) 0.1749(15) 0.041(7) Uani 0.5 1 d D U P . .
H21A H 0.7290 0.4990 0.1640 0.061 Uiso 0.5 1 calc R U P . .
H21B H 0.6404 0.5696 0.1829 0.061 Uiso 0.5 1 calc R U P . .
H21C H 0.6011 0.4920 0.1407 0.061 Uiso 0.5 1 calc R U P . .
C22 C 0.6227(12) 0.4598(19) 0.2327(15) 0.046(5) Uani 0.5 1 d D U P . .
H22A H 0.6717 0.4787 0.2675 0.056 Uiso 0.5 1 calc R U P . .
H22B H 0.6379 0.3994 0.2254 0.056 Uiso 0.5 1 calc R U P . .
C23 C 0.4203(13) 0.4228(12) 0.2276(9) 0.045(4) Uani 0.5 1 d D U P . .
H23 H 0.4347 0.3831 0.1959 0.054 Uiso 0.5 1 calc R U P . .
C24 C 0.3165(14) 0.4315(14) 0.2513(12) 0.040(5) Uani 0.5 1 d D U P . .
H24 H 0.2567 0.3963 0.2375 0.048 Uiso 0.5 1 calc R U P . .
C25 C 0.2989(19) 0.4915(15) 0.2951(13) 0.035(4) Uani 0.5 1 d D U P . .
H25 H 0.2249 0.5018 0.3088 0.042 Uiso 0.5 1 calc R U P . .
C26 C 0.3863(18) 0.5368(18) 0.3196(13) 0.040(5) Uani 0.5 1 d D U P . .
H26 H 0.3737 0.5783 0.3503 0.048 Uiso 0.5 1 calc R U P . .
C27 C 0.4919(16) 0.5215(16) 0.2991(10) 0.045(4) Uani 0.5 1 d D U P . .
H27 H 0.5563 0.5454 0.3187 0.054 Uiso 0.5 1 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 2.7080(14) . yes
Bi1 Br2 2.7831(13) . yes
Bi1 Br3 2.7057(15) . yes
Bi1 Br4 3.0808(14) . yes
Bi1 Br5 2.9332(13) . yes
Bi1 Br5 3.0531(15) 2_655 yes
Br4 Bi1 3.0808(14) 2_655 yes
Br5 Bi1 3.0533(15) 2_655 yes
Br7 Br7 2.337(3) 2_655 yes
Br6 Br6 2.334(3) 5_666 yes
N1 C12 1.507(18) . ?
N1 C13 1.333(19) . ?
N1 C17 1.343(18) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C11 C12 1.51(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13 0.9500 . ?
C13 C14 1.38(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.37(2) . ?
C15 H15 0.9500 . ?
C15 C16 1.40(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.36(2) . ?
C17 H17 0.9500 . ?
N2 C22 1.527(10) . ?
N2 C23 1.306(9) . ?
N2 C23 1.306(9) 2_655 ?
N2 C27 1.335(9) . ?
N2 C27 1.335(9) 2_655 ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C21 C22 1.520(10) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 H23 0.9500 . ?
C23 C24 1.355(10) . ?
C23 C27 1.98(3) 2_655 ?
C24 H24 0.9500 . ?
C24 C25 1.363(10) . ?
C25 H25 0.9500 . ?
C25 C26 1.365(10) . ?
C26 H26 0.9500 . ?
C26 C27 1.364(10) . ?
C27 C23 1.98(3) 2_655 ?
C27 H27 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 96.02(4) . . yes
Br1 Bi1 Br4 168.04(4) . . yes
Br1 Bi1 Br5 87.12(4) . . yes
Br1 Bi1 Br5 93.50(5) . 2_655 yes
Br2 Bi1 Br4 94.00(4) . . yes
Br2 Bi1 Br5 89.96(4) . 2_655 yes
Br2 Bi1 Br5 169.38(5) . . yes
Br3 Bi1 Br1 92.75(5) . . yes
Br3 Bi1 Br2 96.41(5) . . yes
Br3 Bi1 Br4 92.59(4) . . yes
Br3 Bi1 Br5 93.56(5) . . yes
Br3 Bi1 Br5 170.57(4) . 2_655 yes
Br5 Bi1 Br4 79.99(4) 2_655 . yes
Br5 Bi1 Br4 81.88(3) . . yes
Br5 Bi1 Br5 79.71(5) . 2_655 yes
Bi1 Br4 Bi1 81.54(5) . 2_655 yes
Bi1 Br5 Bi1 84.44(4) . 2_655 yes
C13 N1 C12 118.9(12) . . ?
C13 N1 C17 120.5(12) . . ?
C17 N1 C12 120.6(12) . . ?
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 108.8(14) . . ?
N1 C12 H12A 109.9 . . ?
N1 C12 H12B 109.9 . . ?
C11 C12 H12A 109.9 . . ?
C11 C12 H12B 109.9 . . ?
H12A C12 H12B 108.3 . . ?
N1 C13 H13 119.6 . . ?
N1 C13 C14 120.8(13) . . ?
C14 C13 H13 119.6 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(14) . . ?
C15 C14 H14 119.9 . . ?
C14 C15 H15 121.3 . . ?
C14 C15 C16 117.4(14) . . ?
C16 C15 H15 121.3 . . ?
C15 C16 H16 119.7 . . ?
C17 C16 C15 120.6(14) . . ?
C17 C16 H16 119.7 . . ?
N1 C17 C16 120.6(14) . . ?
N1 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C23 N2 C22 47.9(13) 2_655 . ?
C23 N2 C22 122.2(17) . . ?
C23 N2 C23 108(2) . 2_655 ?
C23 N2 C27 97.0(17) . 2_655 ?
C23 N2 C27 97.0(17) 2_655 . ?
C23 N2 C27 125.8(11) . . ?
C23 N2 C27 125.8(11) 2_655 2_655 ?
C27 N2 C22 77.9(12) 2_655 . ?
C27 N2 C22 110.4(16) . . ?
C27 N2 C27 106(3) . 2_655 ?
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 H22A 109.3 . . ?
N2 C22 H22B 109.3 . . ?
C21 C22 N2 112(2) . . ?
C21 C22 H22A 109.3 . . ?
C21 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
N2 C23 H23 121.2 . . ?
N2 C23 C24 117.6(10) . . ?
N2 C23 C27 42.1(9) . 2_655 ?
C24 C23 H23 121.2 . . ?
C24 C23 C27 121.4(14) . 2_655 ?
C27 C23 H23 102.3 2_655 . ?
C23 C24 H24 120.4 . . ?
C23 C24 C25 119.1(14) . . ?
C25 C24 H24 120.4 . . ?
C24 C25 H25 119.6 . . ?
C24 C25 C26 120.9(17) . . ?
C26 C25 H25 119.6 . . ?
C25 C26 H26 120.6 . . ?
C27 C26 C25 118.7(13) . . ?
C27 C26 H26 120.6 . . ?
N2 C27 C23 40.9(9) . 2_655 ?
N2 C27 C26 116.5(10) . . ?
N2 C27 H27 121.7 . . ?
C23 C27 H27 91.2 2_655 . ?
C26 C27 C23 137.1(19) . 2_655 ?
C26 C27 H27 121.7 . . ?

_refine_diff_density_max         4.071
_refine_diff_density_min         -3.245
_refine_diff_density_rms         0.438

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1450025'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H24 Bi2 Br11 N3'
_chemical_formula_weight         1579.37

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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.5341(3)
_cell_length_b                   21.4727(6)
_cell_length_c                   35.0550(10)
_cell_angle_alpha                90
_cell_angle_beta                 97.093(3)
_cell_angle_gamma                90
_cell_volume                     7121.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    8559
_cell_measurement_theta_min      3.56
_cell_measurement_theta_max      28.40

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.946
_exptl_crystal_F_000             5632
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    22.229
_shelx_estimated_absorpt_T_min   0.095
_shelx_estimated_absorpt_T_max   0.215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.41417
_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_ambient_temperature      130(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            30674
_diffrn_reflns_av_unetI/netI     0.0581
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         3.345
_diffrn_reflns_theta_max         25.681
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             13202
_reflns_number_gt                9787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       '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    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'

_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)+(0.0373P)²+94.2001P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         13202
_refine_ls_number_parameters     624
_refine_ls_number_restraints     140
_refine_ls_R_factor_all          0.0761
_refine_ls_R_factor_gt           0.0496
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.038
_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 0.09984(5) 0.15164(2) 0.59729(2) 0.03028(12) Uani 1 1 d . . . . .
Bi2 Bi 0.03105(7) 0.33357(2) 0.59084(2) 0.04435(15) Uani 1 1 d . . . . .
Br11 Br 0.30356(14) 0.08815(6) 0.56796(4) 0.0400(3) Uani 1 1 d . . . . .
Br12 Br -0.11918(13) 0.07787(6) 0.56326(4) 0.0397(3) Uani 1 1 d . . . . .
Br13 Br 0.13252(14) 0.08179(7) 0.66228(4) 0.0483(4) Uani 1 1 d . . . . .
Br14 Br 0.04939(13) 0.23692(5) 0.52840(3) 0.0293(3) Uani 1 1 d . . . . .
Br15 Br 0.28814(16) 0.25961(7) 0.62883(4) 0.0491(4) Uani 1 1 d . . . . .
Br16 Br -0.12401(15) 0.23628(6) 0.62767(4) 0.0423(3) Uani 1 1 d . . . . .
Br17 Br 0.19676(13) 0.41206(6) 0.55324(3) 0.0346(3) Uani 1 1 d . . . . .
Br18 Br -0.21541(14) 0.37319(6) 0.54981(4) 0.0414(3) Uani 1 1 d . . . . .
Br19 Br 0.00889(18) 0.41555(7) 0.64853(4) 0.0530(4) Uani 1 1 d . . . . .
Bi3 Bi 0.54782(5) 0.15651(2) 0.34050(2) 0.02550(11) Uani 1 1 d . . . . .
Bi4 Bi 0.60936(5) 0.33770(2) 0.35080(2) 0.02834(12) Uani 1 1 d . . . . .
Br21 Br 0.72730(13) 0.08011(5) 0.30681(3) 0.0338(3) Uani 1 1 d . . . . .
Br22 Br 0.31091(13) 0.10154(6) 0.30169(3) 0.0377(3) Uani 1 1 d . . . . .
Br23 Br 0.55261(13) 0.07464(5) 0.40122(3) 0.0323(3) Uani 1 1 d . . . . .
Br24 Br 0.58214(14) 0.25186(5) 0.28099(3) 0.0327(3) Uani 1 1 d . . . . .
Br25 Br 0.78357(19) 0.22748(7) 0.38556(5) 0.0660(5) Uani 1 1 d . . . . .
Br26 Br 0.37318(14) 0.25372(5) 0.37387(3) 0.0335(3) Uani 1 1 d . . . . .
Br27 Br 0.83283(14) 0.40270(6) 0.33033(4) 0.0402(3) Uani 1 1 d . . . . .
Br28 Br 0.42268(13) 0.41730(6) 0.30979(3) 0.0325(3) Uani 1 1 d . . . . .
Br29 Br 0.61414(14) 0.40281(6) 0.41695(3) 0.0410(3) Uani 1 1 d . . . . .
Br1 Br 0.13879(13) 0.47495(6) 0.27273(3) 0.0326(3) Uani 1 1 d . . . . .
Br2 Br -0.06132(13) 0.52234(6) 0.24090(3) 0.0342(3) Uani 1 1 d . . . . .
Br3 Br 0.60179(13) 0.02234(6) 0.51573(3) 0.0370(3) Uani 1 1 d . . . . .
Br4 Br 0.4128(2) 0.53018(9) 0.48305(5) 0.0307(6) Uani 0.593(3) 1 d . . P . .
Br5 Br 0.4117(3) 0.47334(13) 0.51328(8) 0.0300(9) Uani 0.407(3) 1 d . . P . .
N1 N 0.5061(12) 0.4580(5) 0.1673(3) 0.043(3) Uani 1 1 d . . . . .
H1 H 0.4371 0.4811 0.1558 0.052 Uiso 1 1 calc R U . . .
C11 C 0.6118(14) 0.4413(6) 0.1482(4) 0.038(3) Uani 1 1 d . . . . .
H11 H 0.6100 0.4535 0.1221 0.046 Uiso 1 1 calc R U . . .
C12 C 0.7221(13) 0.4074(6) 0.1650(3) 0.034(3) Uani 1 1 d . . . . .
H12 H 0.7986 0.3974 0.1511 0.041 Uiso 1 1 calc R U . . .
C13 C 0.7229(12) 0.3872(5) 0.2027(3) 0.029(3) Uani 1 1 d . . . . .
C14 C 0.6094(13) 0.4057(6) 0.2220(3) 0.036(3) Uani 1 1 d . . . . .
H14 H 0.6069 0.3939 0.2480 0.043 Uiso 1 1 calc R U . . .
C15 C 0.5024(14) 0.4408(6) 0.2034(4) 0.041(3) Uani 1 1 d . . . . .
H15 H 0.4250 0.4528 0.2165 0.050 Uiso 1 1 calc R U . . .
C16 C 0.8405(13) 0.3484(6) 0.2220(3) 0.033(3) Uani 1 1 d . . . . .
H16A H 0.8035 0.3195 0.2399 0.049 Uiso 1 1 calc R U . . .
H16B H 0.9117 0.3755 0.2361 0.049 Uiso 1 1 calc R U . . .
H16C H 0.8837 0.3248 0.2025 0.049 Uiso 1 1 calc R U . . .
N2 N 0.6311(15) 0.5395(6) 0.3497(4) 0.065(3) Uani 1 1 d . U . . .
H2 H 0.6991 0.5147 0.3598 0.078 Uiso 1 1 calc R U . . .
C21 C 0.6319(17) 0.5591(7) 0.3140(4) 0.058(3) Uani 1 1 d . U . . .
H21 H 0.7056 0.5466 0.2997 0.069 Uiso 1 1 calc R U . . .
C22 C 0.5257(17) 0.5977(7) 0.2974(4) 0.056(3) Uani 1 1 d . U . . .
H22 H 0.5250 0.6111 0.2716 0.067 Uiso 1 1 calc R U . . .
C23 C 0.4196(18) 0.6169(7) 0.3187(4) 0.059(3) Uani 1 1 d . U . . .
C24 C 0.4236(18) 0.5952(7) 0.3562(4) 0.059(3) Uani 1 1 d . U . . .
H24 H 0.3528 0.6072 0.3716 0.071 Uiso 1 1 calc R U . . .
C25 C 0.5314(19) 0.5560(7) 0.3708(5) 0.065(3) Uani 1 1 d . U . . .
H25 H 0.5343 0.5406 0.3963 0.079 Uiso 1 1 calc R U . . .
C26 C 0.296(2) 0.6569(9) 0.3000(5) 0.090(5) Uani 1 1 d . U . . .
H26A H 0.2863 0.6515 0.2720 0.135 Uiso 1 1 calc R U . . .
H26B H 0.3145 0.7008 0.3063 0.135 Uiso 1 1 calc R U . . .
H26C H 0.2085 0.6439 0.3097 0.135 Uiso 1 1 calc R U . . .
N4 N -0.0776(12) 0.0559(5) 0.4025(4) 0.050(3) Uani 1 1 d . . . . .
H4 H -0.1512 0.0366 0.3902 0.059 Uiso 1 1 calc R U . . .
C41 C 0.0263(15) 0.0724(7) 0.3828(4) 0.048(4) Uani 1 1 d . . . . .
H41 H 0.0201 0.0640 0.3560 0.058 Uiso 1 1 calc R U . . .
C42 C 0.1438(13) 0.1018(6) 0.4014(3) 0.035(3) Uani 1 1 d . . . . .
H42 H 0.2189 0.1140 0.3876 0.042 Uiso 1 1 calc R U . . .
C43 C 0.1517(12) 0.1137(5) 0.4408(3) 0.028(3) Uani 1 1 d . . . . .
C44 C 0.0392(13) 0.0949(6) 0.4594(4) 0.035(3) Uani 1 1 d . . . . .
H44 H 0.0426 0.1015 0.4863 0.042 Uiso 1 1 calc R U . . .
C45 C -0.0766(13) 0.0669(6) 0.4398(4) 0.043(3) Uani 1 1 d . . . . .
H45 H -0.1550 0.0556 0.4526 0.052 Uiso 1 1 calc R U . . .
C46 C 0.2767(13) 0.1474(6) 0.4605(3) 0.035(3) Uani 1 1 d . . . . .
H46A H 0.2451 0.1792 0.4776 0.053 Uiso 1 1 calc R U . . .
H46B H 0.3281 0.1674 0.4413 0.053 Uiso 1 1 calc R U . . .
H46C H 0.3391 0.1178 0.4756 0.053 Uiso 1 1 calc R U . . .
N5 N 0.6442(18) 0.2033(8) 0.5364(4) 0.090(4) Uani 1 1 d D U . . .
H5 H 0.7028 0.1772 0.5495 0.108 Uiso 1 1 calc R U . . .
C51 C 0.5512(18) 0.2306(8) 0.5567(5) 0.085(4) Uani 1 1 d D U . . .
H51 H 0.5499 0.2210 0.5832 0.101 Uiso 1 1 calc R U . . .
C52 C 0.4586(19) 0.2724(8) 0.5386(4) 0.078(4) Uani 1 1 d D U . . .
H52 H 0.3925 0.2946 0.5516 0.093 Uiso 1 1 calc R U . . .
C53 C 0.4679(17) 0.2806(7) 0.4991(4) 0.070(4) Uani 1 1 d D U . . .
C54 C 0.5723(18) 0.2484(9) 0.4830(6) 0.084(4) Uani 1 1 d D U . . .
H54 H 0.5773 0.2563 0.4566 0.101 Uiso 1 1 calc R U . . .
C55 C 0.663(2) 0.2094(10) 0.4990(5) 0.090(4) Uiso 1 1 d D U . . .
H55 H 0.7318 0.1882 0.4866 0.108 Uiso 1 1 calc R U . . .
C56 C 0.367(2) 0.3211(9) 0.4774(6) 0.094(6) Uani 1 1 d . U . . .
H56A H 0.2790 0.3214 0.4892 0.142 Uiso 1 1 calc R U . . .
H56B H 0.3482 0.3060 0.4509 0.142 Uiso 1 1 calc R U . . .
H56C H 0.4056 0.3634 0.4775 0.142 Uiso 1 1 calc R U . . .
N3 N -0.0573(11) 0.3689(5) 0.4670(3) 0.043(3) Uani 1 1 d . . . . .
H3 H -0.1097 0.3546 0.4841 0.051 Uiso 1 1 calc R U . . .
C31 C 0.0017(19) 0.3294(7) 0.4458(4) 0.060(4) Uani 1 1 d . . . . .
H31 H -0.0122 0.2860 0.4488 0.072 Uiso 1 1 calc R U . . .
C32 C 0.083(2) 0.3506(7) 0.4194(4) 0.070(5) Uani 1 1 d . . . . .
H32 H 0.1227 0.3219 0.4031 0.084 Uiso 1 1 calc R U . . .
C33 C 0.1101(15) 0.4143(6) 0.4161(3) 0.044(3) Uani 1 1 d . . . . .
C34 C 0.0439(13) 0.4542(6) 0.4386(3) 0.035(3) Uani 1 1 d . . . . .
H34 H 0.0568 0.4979 0.4368 0.042 Uiso 1 1 calc R U . . .
C35 C -0.0413(13) 0.4302(6) 0.4638(3) 0.037(3) Uani 1 1 d . . . . .
H35 H -0.0891 0.4576 0.4792 0.044 Uiso 1 1 calc R U . . .
C36 C 0.205(2) 0.4396(9) 0.3889(5) 0.086(6) Uani 1 1 d . . . . .
H36A H 0.2113 0.4097 0.3680 0.129 Uiso 1 1 calc R U . . .
H36B H 0.3000 0.4464 0.4027 0.129 Uiso 1 1 calc R U . . .
H36C H 0.1675 0.4792 0.3781 0.129 Uiso 1 1 calc R U . . .
N6 N 0.1948(17) 0.2571(7) 0.2186(4) 0.105(4) Uani 1 1 d D U . . .
H6 H 0.2402 0.2607 0.1983 0.126 Uiso 1 1 calc R U . . .
C61 C 0.1027(19) 0.2100(7) 0.2213(5) 0.100(5) Uani 1 1 d D U . . .
H61 H 0.0841 0.1824 0.2001 0.120 Uiso 1 1 calc R U . . .
C62 C 0.0353(19) 0.1997(7) 0.2526(5) 0.094(4) Uani 1 1 d D U . . .
H62 H -0.0269 0.1655 0.2541 0.113 Uiso 1 1 calc R U . . .
C63 C 0.0629(18) 0.2420(7) 0.2818(4) 0.094(4) Uani 1 1 d D U . . .
C64 C 0.1547(17) 0.2901(7) 0.2804(4) 0.080(4) Uani 1 1 d D U . . .
H64 H 0.1762 0.3174 0.3016 0.096 Uiso 1 1 calc R U . . .
C65 C 0.2151(19) 0.2977(7) 0.2471(4) 0.099(4) Uani 1 1 d D U . . .
H65 H 0.2731 0.3331 0.2445 0.119 Uiso 1 1 calc R U . . .
C66 C 0.001(2) 0.2348(11) 0.3178(5) 0.111(7) Uani 1 1 d D U . . .
H66A H -0.0810 0.2070 0.3136 0.166 Uiso 1 1 calc R U . . .
H66B H -0.0292 0.2756 0.3263 0.166 Uiso 1 1 calc R U . . .
H66C H 0.0715 0.2171 0.3375 0.166 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 Br11 2.6799(13) . yes
Bi1 Br12 2.7709(14) . yes
Bi1 Br13 2.7133(12) . yes
Bi1 Br14 3.0215(11) . yes
Bi1 Br15 3.0545(15) . yes
Bi1 Br16 3.0909(14) . yes
Bi2 Br14 3.0369(12) . yes
Bi2 Br15 3.0818(16) . yes
Bi2 Br16 2.9475(13) . yes
Bi2 Br17 2.7547(13) . yes
Bi2 Br18 2.7350(15) . yes
Bi2 Br19 2.7088(13) . yes
Bi3 Br21 2.7411(12) . yes
Bi3 Br22 2.7546(13) . yes
Bi3 Br23 2.7565(11) . yes
Bi3 Br24 2.9697(12) . yes
Bi3 Br25 2.9988(15) . yes
Bi3 Br26 2.9965(12) . yes
Bi4 Br24 3.0489(12) . yes
Bi4 Br25 3.0570(15) . yes
Bi4 Br26 3.0702(13) . yes
Bi4 Br27 2.7167(13) . yes
Bi4 Br28 2.7429(13) . yes
Bi4 Br29 2.7034(12) . yes
Br1 Br2 2.3227(17) . yes
Br3 Br3 2.318(3) 3_656 yes
Br4 Br4 2.317(4) 3_666 yes
Br4 Br5 1.617(3) . ?
Br4 Br5 1.664(3) 3_666 ?
Br5 Br4 1.664(3) 3_666 ?
Br5 Br5 2.324(5) 3_666 yes
N1 H1 0.8800 . ?
N1 C11 1.326(15) . ?
N1 C15 1.324(15) . ?
C11 H11 0.9500 . ?
C11 C12 1.354(17) . ?
C12 H12 0.9500 . ?
C12 C13 1.391(15) . ?
C13 C14 1.402(15) . ?
C13 C16 1.489(16) . ?
C14 H14 0.9500 . ?
C14 C15 1.366(17) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
N2 H2 0.8800 . ?
N2 C21 1.323(18) . ?
N2 C25 1.32(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.38(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.392(19) . ?
C23 C24 1.392(19) . ?
C23 C26 1.54(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.38(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N4 H4 0.8800 . ?
N4 C41 1.325(17) . ?
N4 C45 1.328(17) . ?
C41 H41 0.9500 . ?
C41 C42 1.380(18) . ?
C42 H42 0.9500 . ?
C42 C43 1.395(16) . ?
C43 C44 1.382(15) . ?
C43 C46 1.490(17) . ?
C44 H44 0.9500 . ?
C44 C45 1.367(18) . ?
C45 H45 0.9500 . ?
C46 H46A 0.9800 . ?
C46 H46B 0.9800 . ?
C46 H46C 0.9800 . ?
N5 H5 0.8800 . ?
N5 C51 1.340(9) . ?
N5 C55 1.349(8) . ?
C51 H51 0.9500 . ?
C51 C52 1.36(2) . ?
C52 H52 0.9500 . ?
C52 C53 1.409(9) . ?
C53 C54 1.387(9) . ?
C53 C56 1.44(2) . ?
C54 H54 0.9500 . ?
C54 C55 1.28(2) . ?
C55 H55 0.9500 . ?
C56 H56A 0.9800 . ?
C56 H56B 0.9800 . ?
C56 H56C 0.9800 . ?
N3 H3 0.8800 . ?
N3 C31 1.300(18) . ?
N3 C35 1.332(16) . ?
C31 H31 0.9500 . ?
C31 C32 1.36(2) . ?
C32 H32 0.9500 . ?
C32 C33 1.40(2) . ?
C33 C34 1.371(16) . ?
C33 C36 1.498(18) . ?
C34 H34 0.9500 . ?
C34 C35 1.371(16) . ?
C35 H35 0.9500 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
N6 H6 0.8800 . ?
N6 C61 1.350(9) . ?
N6 C65 1.324(9) . ?
C61 H61 0.9500 . ?
C61 C62 1.354(10) . ?
C62 H62 0.9500 . ?
C62 C63 1.370(9) . ?
C63 C64 1.358(9) . ?
C63 C66 1.467(9) . ?
C64 H64 0.9500 . ?
C64 C65 1.372(9) . ?
C65 H65 0.9500 . ?
C66 H66A 0.9800 . ?
C66 H66B 0.9800 . ?
C66 H66C 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
Br11 Bi1 Br12 95.01(4) . . yes
Br11 Bi1 Br13 91.57(4) . . yes
Br11 Bi1 Br14 93.04(4) . . yes
Br11 Bi1 Br15 95.95(4) . . yes
Br11 Bi1 Br16 174.47(4) . . yes
Br12 Bi1 Br14 88.01(4) . . yes
Br12 Bi1 Br15 165.41(4) . . yes
Br12 Bi1 Br16 88.21(4) . . yes
Br13 Bi1 Br12 92.74(4) . . yes
Br13 Bi1 Br14 175.25(4) . . yes
Br13 Bi1 Br15 96.56(4) . . yes
Br13 Bi1 Br16 92.77(4) . . yes
Br14 Bi1 Br15 81.82(3) . . yes
Br14 Bi1 Br16 82.56(3) . . yes
Br15 Bi1 Br16 80.15(4) . . yes
Br14 Bi2 Br15 81.13(4) . . yes
Br16 Bi2 Br14 84.72(4) . . yes
Br16 Bi2 Br15 81.99(4) . . yes
Br17 Bi2 Br14 89.18(3) . . yes
Br17 Bi2 Br15 92.84(4) . . yes
Br17 Bi2 Br16 172.54(4) . . yes
Br18 Bi2 Br14 87.46(4) . . yes
Br18 Bi2 Br15 166.77(4) . . yes
Br18 Bi2 Br16 90.35(4) . . yes
Br18 Bi2 Br17 93.68(4) . . yes
Br19 Bi2 Br14 177.23(4) . . yes
Br19 Bi2 Br15 98.25(5) . . yes
Br19 Bi2 Br16 92.52(4) . . yes
Br19 Bi2 Br17 93.55(4) . . yes
Br19 Bi2 Br18 92.83(5) . . yes
Bi1 Br14 Bi2 81.71(3) . . yes
Bi1 Br15 Bi2 80.45(4) . . yes
Bi2 Br16 Bi1 82.00(3) . . yes
Br21 Bi3 Br22 92.76(4) . . yes
Br21 Bi3 Br23 89.96(4) . . yes
Br21 Bi3 Br24 88.92(4) . . yes
Br21 Bi3 Br25 93.66(5) . . yes
Br21 Bi3 Br26 172.60(4) . . yes
Br22 Bi3 Br23 92.44(4) . . yes
Br22 Bi3 Br24 95.92(4) . . yes
Br22 Bi3 Br25 173.48(5) . . yes
Br22 Bi3 Br26 91.72(4) . . yes
Br23 Bi3 Br24 171.61(4) . . yes
Br23 Bi3 Br25 88.71(4) . . yes
Br23 Bi3 Br26 95.73(4) . . yes
Br24 Bi3 Br25 83.06(4) . . yes
Br24 Bi3 Br26 84.76(3) . . yes
Br26 Bi3 Br25 81.77(5) . . yes
Br24 Bi4 Br25 80.80(4) . . yes
Br24 Bi4 Br26 82.17(3) . . yes
Br25 Bi4 Br26 79.65(4) . . yes
Br27 Bi4 Br24 95.18(4) . . yes
Br27 Bi4 Br25 95.61(5) . . yes
Br27 Bi4 Br26 174.87(4) . . yes
Br27 Bi4 Br28 91.19(4) . . yes
Br28 Bi4 Br24 88.32(3) . . yes
Br28 Bi4 Br25 167.63(4) . . yes
Br28 Bi4 Br26 93.12(4) . . yes
Br29 Bi4 Br24 172.69(4) . . yes
Br29 Bi4 Br25 96.18(5) . . yes
Br29 Bi4 Br26 90.75(4) . . yes
Br29 Bi4 Br27 91.73(4) . . yes
Br29 Bi4 Br28 93.92(4) . . yes
Bi3 Br24 Bi4 81.89(3) . . yes
Bi3 Br25 Bi4 81.29(4) . . yes
Bi3 Br26 Bi4 81.10(3) . . yes
Br5 Br4 Br4 44.27(11) 3_666 3_666 ?
Br5 Br4 Br4 45.89(12) . 3_666 ?
Br5 Br4 Br5 90.16(16) . 3_666 ?
Br4 Br5 Br4 89.84(16) . 3_666 ?
Br4 Br5 Br5 44.11(12) 3_666 3_666 ?
Br4 Br5 Br5 45.73(12) . 3_666 ?
C11 N1 H1 119.4 . . ?
C15 N1 H1 119.4 . . ?
C15 N1 C11 121.2(12) . . ?
N1 C11 H11 119.2 . . ?
N1 C11 C12 121.6(12) . . ?
C12 C11 H11 119.2 . . ?
C11 C12 H12 120.2 . . ?
C11 C12 C13 119.6(11) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 117.1(11) . . ?
C12 C13 C16 121.3(10) . . ?
C14 C13 C16 121.6(10) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.2(11) . . ?
C15 C14 H14 119.9 . . ?
N1 C15 C14 120.2(11) . . ?
N1 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C21 N2 H2 118.9 . . ?
C25 N2 H2 118.9 . . ?
C25 N2 C21 122.2(15) . . ?
N2 C21 H21 120.0 . . ?
N2 C21 C22 120.0(14) . . ?
C22 C21 H21 120.0 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(14) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 C26 120.4(13) . . ?
C24 C23 C22 118.1(15) . . ?
C24 C23 C26 121.4(14) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 C23 119.1(15) . . ?
C25 C24 H24 120.5 . . ?
N2 C25 C24 120.9(15) . . ?
N2 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C41 N4 H4 118.3 . . ?
C41 N4 C45 123.4(12) . . ?
C45 N4 H4 118.3 . . ?
N4 C41 H41 120.3 . . ?
N4 C41 C42 119.4(12) . . ?
C42 C41 H41 120.3 . . ?
C41 C42 H42 120.2 . . ?
C41 C42 C43 119.6(12) . . ?
C43 C42 H42 120.2 . . ?
C42 C43 C46 119.3(10) . . ?
C44 C43 C42 117.6(11) . . ?
C44 C43 C46 123.0(10) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 C43 121.1(12) . . ?
C45 C44 H44 119.5 . . ?
N4 C45 C44 118.8(12) . . ?
N4 C45 H45 120.6 . . ?
C44 C45 H45 120.6 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46B 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C51 N5 H5 114.7 . . ?
C51 N5 C55 130.5(19) . . ?
C55 N5 H5 114.7 . . ?
N5 C51 H51 120.9 . . ?
N5 C51 C52 118.2(17) . . ?
C52 C51 H51 120.9 . . ?
C51 C52 H52 122.4 . . ?
C51 C52 C53 115.2(17) . . ?
C53 C52 H52 122.4 . . ?
C52 C53 C56 118.3(16) . . ?
C54 C53 C52 118.1(17) . . ?
C54 C53 C56 123.6(16) . . ?
C53 C54 H54 115.6 . . ?
C55 C54 C53 128.8(19) . . ?
C55 C54 H54 115.6 . . ?
N5 C55 H55 125.5 . . ?
C54 C55 N5 109.0(19) . . ?
C54 C55 H55 125.5 . . ?
C53 C56 H56A 109.5 . . ?
C53 C56 H56B 109.5 . . ?
C53 C56 H56C 109.5 . . ?
H56A C56 H56B 109.5 . . ?
H56A C56 H56C 109.5 . . ?
H56B C56 H56C 109.5 . . ?
C31 N3 H3 118.8 . . ?
C31 N3 C35 122.3(12) . . ?
C35 N3 H3 118.8 . . ?
N3 C31 H31 120.1 . . ?
N3 C31 C32 119.7(14) . . ?
C32 C31 H31 120.1 . . ?
C31 C32 H32 119.7 . . ?
C31 C32 C33 120.6(13) . . ?
C33 C32 H32 119.7 . . ?
C32 C33 C36 122.6(13) . . ?
C34 C33 C32 117.4(12) . . ?
C34 C33 C36 120.0(13) . . ?
C33 C34 H34 120.4 . . ?
C33 C34 C35 119.3(12) . . ?
C35 C34 H34 120.4 . . ?
N3 C35 C34 120.5(12) . . ?
N3 C35 H35 119.7 . . ?
C34 C35 H35 119.7 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36B 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C61 N6 H6 120.8 . . ?
C65 N6 H6 120.8 . . ?
C65 N6 C61 118.4(11) . . ?
N6 C61 H61 118.0 . . ?
N6 C61 C62 123.9(14) . . ?
C62 C61 H61 118.0 . . ?
C61 C62 H62 122.3 . . ?
C61 C62 C63 115.5(14) . . ?
C63 C62 H62 122.3 . . ?
C62 C63 C66 121.0(16) . . ?
C64 C63 C62 122.8(11) . . ?
C64 C63 C66 116.2(16) . . ?
C63 C64 H64 121.2 . . ?
C63 C64 C65 117.5(13) . . ?
C65 C64 H64 121.2 . . ?
N6 C65 C64 121.7(13) . . ?
N6 C65 H65 119.1 . . ?
C64 C65 H65 119.1 . . ?
C63 C66 H66A 109.5 . . ?
C63 C66 H66B 109.5 . . ?
C63 C66 H66C 109.5 . . ?
H66A C66 H66B 109.5 . . ?
H66A C66 H66C 109.5 . . ?
H66B C66 H66C 109.5 . . ?

_refine_diff_density_max         2.464
_refine_diff_density_min         -3.986
_refine_diff_density_rms         0.253

####################################################################### 
# 
# 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_3
_database_code_depnum_ccdc_archive 'CCDC 1450026'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H14 Bi Br7 N2'
_chemical_formula_weight         954.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           63
_space_group_name_H-M_alt        'C m c m'
_space_group_name_Hall           '-C 2c 2'

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

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

_cell_length_a                   14.1671(3)
_cell_length_b                   19.7299(4)
_cell_length_c                   7.74397(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2164.56(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    5632
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      30.76

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.929
_exptl_crystal_F_000             1712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    21.064
_shelx_estimated_absorpt_T_min   0.059
_shelx_estimated_absorpt_T_max   0.817
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.15671
_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_ambient_temperature      130(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            8963
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.344
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             1235
_reflns_number_gt                1139
_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    'SHELXS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'

_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)+(0.0362P)²+29.8320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         1235
_refine_ls_number_parameters     92
_refine_ls_number_restraints     45
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0782
_refine_ls_wR_factor_gt          0.0760
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.5000 0.38401(2) 0.7500 0.01499(14) Uani 1 4 d S T P . .
Br11 Br 0.5000 0.29260(4) 0.48671(11) 0.0243(2) Uani 1 2 d S T P . .
Br12 Br 0.29969(6) 0.37834(4) 0.7500 0.0283(2) Uani 1 2 d S T P . .
Br13 Br 0.5000 0.4899(2) 1.0264(5) 0.0299(8) Uani 0.5 2 d S T P . .
N1 N 0.3232(7) 0.3744(5) 0.228(9) 0.028(10) Uani 0.5 1 d . U P . .
H1 H 0.3850 0.3703 0.2251 0.034 Uiso 0.5 1 calc R U P . .
C1 C 0.2867(8) 0.4353(6) 0.231(16) 0.034(15) Uani 0.5 1 d . U P . .
H1A H 0.3261 0.4741 0.2417 0.040 Uiso 0.5 1 calc R U P . .
C2 C 0.1922(9) 0.4420(7) 0.218(3) 0.039(7) Uani 0.5 1 d . U P . .
H2 H 0.1652 0.4860 0.2079 0.047 Uiso 0.5 1 calc R U P . .
C3 C 0.1352(10) 0.3869(7) 0.218(3) 0.044(7) Uani 0.5 1 d . U P . .
C4 C 0.1747(9) 0.3239(7) 0.227(7) 0.038(10) Uani 0.5 1 d . U P . .
H4 H 0.1360 0.2846 0.2306 0.046 Uiso 0.5 1 calc R U P . .
C5 C 0.2707(8) 0.3185(6) 0.229(14) 0.037(14) Uani 0.5 1 d . U P . .
H5 H 0.2999 0.2752 0.2325 0.044 Uiso 0.5 1 calc R U P . .
C6 C 0.0296(11) 0.3934(11) 0.180(3) 0.084(7) Uani 0.5 1 d . U P . .
H6A H 0.0195 0.4361 0.1152 0.101 Uiso 0.5 1 calc R U P . .
H6B H 0.0111 0.3556 0.1033 0.101 Uiso 0.5 1 calc R U P . .
Br1 Br 0.08311(7) 0.37558(5) 0.7500 0.0423(3) Uani 1 2 d S T P . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br11 2.7220(8) . yes
Bi1 Br11 2.7220(8) 10_557 yes
Bi1 Br12 2.8400(8) . yes
Bi1 Br12 2.8400(8) 3_656 yes
Bi1 Br13 2.992(5) . yes
Bi1 Br13 2.992(5) 10_557 yes
Bi1 Br13 3.030(5) 2_664 yes
Bi1 Br13 3.030(5) 4_567 yes
Br13 Bi1 3.030(5) 9_667 yes
N1 H1 0.8800 . ?
N1 C1 1.307(14) . ?
N1 C5 1.330(14) . ?
C1 H1A 0.9500 . ?
C1 C2 1.351(17) . ?
C2 H2 0.9500 . ?
C2 C3 1.355(18) . ?
C3 C4 1.364(18) . ?
C3 C6 1.53(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.366(17) . ?
C5 H5 0.9500 . ?
C6 C6 1.37(4) 3 ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
Br1 Br1 2.3548(19) 3_556 yes

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
Br11 Bi1 Br11 97.01(4) 10_557 . yes
Br11 Bi1 Br12 88.504(13) . 3_656 yes
Br11 Bi1 Br12 88.504(13) 10_557 3_656 yes
Br11 Bi1 Br12 88.505(13) . . yes
Br11 Bi1 Br12 88.505(13) 10_557 . yes
Br11 Bi1 Br13 85.82(5) . 10_557 yes
Br11 Bi1 Br13 85.82(5) 10_557 . yes
Br11 Bi1 Br13 96.64(5) . 2_664 yes
Br11 Bi1 Br13 96.64(5) 10_557 4_567 yes
Br11 Bi1 Br13 166.34(5) . 4_567 yes
Br11 Bi1 Br13 166.34(5) 10_557 2_664 yes
Br11 Bi1 Br13 177.17(5) . . yes
Br11 Bi1 Br13 177.17(5) 10_557 10_557 yes
Br12 Bi1 Br12 175.49(4) . 3_656 yes
Br12 Bi1 Br13 91.577(14) . . yes
Br12 Bi1 Br13 91.577(14) . 10_557 yes
Br12 Bi1 Br13 91.577(14) 3_656 . yes
Br12 Bi1 Br13 91.577(14) 3_656 10_557 yes
Br12 Bi1 Br13 91.852(16) . 2_664 yes
Br12 Bi1 Br13 91.852(16) . 4_567 yes
Br12 Bi1 Br13 91.853(16) 3_656 2_664 yes
Br12 Bi1 Br13 91.853(16) 3_656 4_567 yes
Br13 Bi1 Br13 80.53(2) . 2_664 yes
Br13 Bi1 Br13 10.83(9) . 4_567 ?
Br13 Bi1 Br13 10.83(9) 10_557 2_664 ?
Br13 Bi1 Br13 69.70(9) 2_664 4_567 ?
Br13 Bi1 Br13 80.53(2) 10_557 4_567 ?
Br13 Bi1 Br13 91.35(9) . 10_557 yes
Bi1 Br13 Bi1 169.17(9) . 9_667 yes
C1 N1 H1 118.6 . . ?
C1 N1 C5 122.8(11) . . ?
C5 N1 H1 118.6 . . ?
N1 C1 H1A 120.6 . . ?
N1 C1 C2 118.7(15) . . ?
C2 C1 H1A 120.6 . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(13) . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 119.2(13) . . ?
C2 C3 C6 121.0(15) . . ?
C4 C3 C6 119.2(15) . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(13) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 119.5(12) . . ?
N1 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C3 C6 H6A 108.2 . . ?
C3 C6 H6B 108.2 . . ?
C6 C6 C3 117(2) 3 . ?
C6 C6 H6A 108.2 3 . ?
C6 C6 H6B 108.2 3 . ?
H6A C6 H6B 107.3 . . ?

_refine_diff_density_max         1.530
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.204

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1450027'
_audit_update_record             
;
2016-01-26 deposited with the CCDC.
2016-03-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H36 Bi Br13 N4'
_chemical_formula_weight         1676.42

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                   16.0606(4)
_cell_length_b                   13.9864(3)
_cell_length_c                   19.4745(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4374.56(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(2)
_cell_measurement_reflns_used    7310
_cell_measurement_theta_min      3.79
_cell_measurement_theta_max      28.71

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.545
_exptl_crystal_F_000             3080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_exptl_absorpt_coefficient_mu    15.931
_shelx_estimated_absorpt_T_min   0.402
_shelx_estimated_absorpt_T_max   0.448
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94081
_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_ambient_temperature      130(2)
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Xcalibur, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            AtlasS2
_diffrn_detector_area_resol_mean 10.6168
_diffrn_reflns_number            19395
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.288
_diffrn_reflns_theta_max         29.097
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.879
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.879
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             5359
_reflns_number_gt                4521
_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, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'ShelXle (Hübschle, 2011)'
_computing_publication_material  'CIFTAB-2014 (Sheldrick, 2014)'

_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)+(0.0115P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_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         5359
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0346
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0362
_refine_ls_wR_factor_gt          0.0339
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.78919(2) 0.7500 0.15324(2) 0.01316(4) Uani 1 2 d S T P . .
Br1 Br 0.79078(2) 0.54519(2) 0.15021(2) 0.01660(7) Uani 1 1 d . . . . .
Br2 Br 0.74571(3) 0.7500 0.01661(2) 0.01980(10) Uani 1 2 d S T P . .
Br3 Br 0.96197(3) 0.7500 0.12060(2) 0.02405(10) Uani 1 2 d S T P . .
Br4 Br 0.84136(3) 0.7500 0.30236(2) 0.02551(10) Uani 1 2 d S T P . .
Br5 Br 0.62157(3) 0.7500 0.19437(2) 0.01952(9) Uani 1 2 d S T P . .
Br6 Br 0.80633(3) 0.7500 0.44052(2) 0.02387(10) Uani 1 2 d S T P . .
Br7 Br 0.77306(3) 0.7500 0.56168(2) 0.02747(11) Uani 1 2 d S T P . .
Br8 Br 0.54743(4) 0.7500 0.63923(2) 0.03520(13) Uani 1 2 d S T P . .
Br9 Br 0.41944(4) 0.7500 0.57968(3) 0.04195(14) Uani 1 2 d S T P . .
Br10 Br 0.71051(4) 0.7500 0.72223(2) 0.03694(12) Uani 1 2 d S T P . .
Br11 Br 0.61312(3) 0.7500 0.83005(2) 0.02371(10) Uani 1 2 d S T P . .
Br12 Br 0.51712(3) 0.7500 0.93019(2) 0.02904(11) Uani 1 2 d S T P . .
N1 N 0.55459(16) 0.52050(15) 0.12888(11) 0.0170(5) Uani 1 1 d . . . . .
C11 C 0.4935(2) 0.56640(19) 0.16252(14) 0.0224(7) Uani 1 1 d . . . . .
H11 H 0.4691 0.6218 0.1428 0.027 Uiso 1 1 calc R U . . .
C12 C 0.4661(2) 0.5342(2) 0.22492(15) 0.0300(8) Uani 1 1 d . . . . .
H12 H 0.4228 0.5667 0.2485 0.036 Uiso 1 1 calc R U . . .
C13 C 0.5023(3) 0.4542(2) 0.25290(16) 0.0347(9) Uani 1 1 d . . . . .
H13 H 0.4839 0.4306 0.2960 0.042 Uiso 1 1 calc R U . . .
C14 C 0.5653(2) 0.4083(2) 0.21841(15) 0.0314(8) Uani 1 1 d . . . . .
H14 H 0.5908 0.3533 0.2378 0.038 Uiso 1 1 calc R U . . .
C15 C 0.5912(2) 0.44228(19) 0.15564(14) 0.0230(7) Uani 1 1 d . . . . .
H15 H 0.6346 0.4108 0.1314 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5828(2) 0.55700(19) 0.06115(13) 0.0210(7) Uani 1 1 d . . . . .
H16A H 0.6444 0.5548 0.0592 0.025 Uiso 1 1 calc R U . . .
H16B H 0.5655 0.6246 0.0562 0.025 Uiso 1 1 calc R U . . .
C17 C 0.54706(19) 0.4988(2) 0.00169(14) 0.0210(7) Uani 1 1 d . . . . .
H17A H 0.5699 0.5237 -0.0420 0.025 Uiso 1 1 calc R U . . .
H17B H 0.5655 0.4315 0.0064 0.025 Uiso 1 1 calc R U . . .
N2 N 0.64747(15) 0.54948(14) 0.44239(11) 0.0146(5) Uani 1 1 d . . . . .
C21 C 0.63837(19) 0.58818(18) 0.37933(14) 0.0187(6) Uani 1 1 d . . . . .
H21 H 0.5988 0.6377 0.3723 0.022 Uiso 1 1 calc R U . . .
C22 C 0.6858(2) 0.55659(19) 0.32536(15) 0.0214(7) Uani 1 1 d . . . . .
H22 H 0.6795 0.5846 0.2812 0.026 Uiso 1 1 calc R U . . .
C23 C 0.7425(2) 0.48414(18) 0.33525(14) 0.0211(7) Uani 1 1 d . . . . .
H23 H 0.7752 0.4612 0.2980 0.025 Uiso 1 1 calc R U . . .
C24 C 0.7515(2) 0.4450(2) 0.40056(14) 0.0229(7) Uani 1 1 d . . . . .
H24 H 0.7904 0.3951 0.4085 0.028 Uiso 1 1 calc R U . . .
C25 C 0.70333(19) 0.47947(18) 0.45331(14) 0.0192(7) Uani 1 1 d . . . . .
H25 H 0.7096 0.4535 0.4981 0.023 Uiso 1 1 calc R U . . .
C26 C 0.59705(19) 0.58430(18) 0.50153(13) 0.0186(7) Uani 1 1 d . . . . .
H26A H 0.5673 0.6433 0.4879 0.022 Uiso 1 1 calc R U . . .
H26B H 0.6348 0.6006 0.5400 0.022 Uiso 1 1 calc R U . . .
C27 C 0.53398(19) 0.51054(18) 0.52590(13) 0.0175(6) Uani 1 1 d . . . . .
H27A H 0.5637 0.4503 0.5367 0.021 Uiso 1 1 calc R U . . .
H27B H 0.5080 0.5338 0.5689 0.021 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 2.8653(2) . yes
Bi1 Br1 2.8653(3) 7_575 ?
Bi1 Br2 2.7510(4) . yes
Bi1 Br3 2.8469(5) . yes
Bi1 Br4 3.0224(4) . yes
Bi1 Br5 2.8087(5) . yes
Br4 Br6 2.7489(6) . yes
Br6 Br7 2.4192(6) . yes
Br8 Br9 2.3603(8) . yes
Br10 Br11 2.6181(7) . yes
Br11 Br12 2.4861(7) . yes
N1 C11 1.343(4) . ?
N1 C15 1.347(3) . ?
N1 C16 1.485(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.369(4) . ?
C12 H12 0.9500 . ?
C12 C13 1.374(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.373(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.376(4) . ?
C15 H15 0.9500 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.528(4) . ?
C17 C17 1.513(6) 5_665 ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
N2 C21 1.350(3) . ?
N2 C25 1.345(3) . ?
N2 C26 1.490(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.371(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.377(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.392(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.373(4) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C26 C27 1.522(4) . ?
C27 C27 1.515(5) 5_666 ?
C27 H27A 0.9900 . ?
C27 H27B 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 Br1 177.427(12) 7_575 . yes
Br1 Bi1 Br4 90.990(6) 7_575 . ?
Br1 Bi1 Br4 90.991(6) . . yes
Br2 Bi1 Br1 88.989(6) . . yes
Br2 Bi1 Br1 88.990(6) . 7_575 ?
Br2 Bi1 Br3 91.800(14) . . yes
Br2 Bi1 Br4 178.606(15) . . yes
Br2 Bi1 Br5 91.867(14) . . yes
Br3 Bi1 Br1 89.236(7) . . yes
Br3 Bi1 Br1 89.236(7) . 7_575 ?
Br3 Bi1 Br4 86.806(14) . . yes
Br5 Bi1 Br1 90.828(7) . . yes
Br5 Bi1 Br1 90.829(7) . 7_575 ?
Br5 Bi1 Br3 176.333(13) . . yes
Br5 Bi1 Br4 89.527(13) . . yes
Br6 Br4 Bi1 152.09(2) . . yes
Br7 Br6 Br4 179.05(3) . . yes
Br12 Br11 Br10 178.36(3) . . yes
C11 N1 C15 121.2(2) . . ?
C11 N1 C16 119.5(2) . . ?
C15 N1 C16 119.3(3) . . ?
N1 C11 H11 119.6 . . ?
N1 C11 C12 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 H12 120.5 . . ?
C11 C12 C13 118.9(3) . . ?
C13 C12 H12 120.5 . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 119.9(3) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(3) . . ?
C15 C14 H14 120.1 . . ?
N1 C15 C14 119.5(3) . . ?
N1 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
N1 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
N1 C16 C17 112.0(2) . . ?
H16A C16 H16B 107.9 . . ?
C17 C16 H16A 109.2 . . ?
C17 C16 H16B 109.2 . . ?
C16 C17 H17A 108.9 . . ?
C16 C17 H17B 108.9 . . ?
C17 C17 C16 113.3(3) 5_665 . ?
C17 C17 H17A 108.9 5_665 . ?
C17 C17 H17B 108.9 5_665 . ?
H17A C17 H17B 107.7 . . ?
C21 N2 C26 120.9(2) . . ?
C25 N2 C21 120.5(2) . . ?
C25 N2 C26 118.6(2) . . ?
N2 C21 H21 119.7 . . ?
N2 C21 C22 120.5(3) . . ?
C22 C21 H21 119.7 . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.8(3) . . ?
C23 C22 H22 120.1 . . ?
C22 C23 H23 120.5 . . ?
C22 C23 C24 119.0(3) . . ?
C24 C23 H23 120.5 . . ?
C23 C24 H24 120.4 . . ?
C25 C24 C23 119.2(3) . . ?
C25 C24 H24 120.4 . . ?
N2 C25 C24 120.8(3) . . ?
N2 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
N2 C26 H26A 109.1 . . ?
N2 C26 H26B 109.1 . . ?
N2 C26 C27 112.4(2) . . ?
H26A C26 H26B 107.9 . . ?
C27 C26 H26A 109.1 . . ?
C27 C26 H26B 109.1 . . ?
C26 C27 H27A 108.8 . . ?
C26 C27 H27B 108.8 . . ?
C27 C27 C26 113.8(3) 5_666 . ?
C27 C27 H27A 108.8 5_666 . ?
C27 C27 H27B 108.8 5_666 . ?
H27A C27 H27B 107.7 . . ?

_refine_diff_density_max         1.049
_refine_diff_density_min         -0.882
_refine_diff_density_rms         0.128

