# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_469r
_database_code_depnum_ccdc_archive 'CCDC 833206'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H17 Bi Br N'
_chemical_formula_sum            'C15 H17 Bi Br N'
_chemical_formula_weight         500.19

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'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   13.213(2)
_cell_length_b                   11.4688(17)
_cell_length_c                   11.0325(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.611(2)
_cell_angle_gamma                90.00
_cell_volume                     1531.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    3422
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.73

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.169
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             928
_exptl_absorpt_coefficient_mu    14.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.055
_exptl_absorpt_correction_T_max  0.100
_exptl_absorpt_process_details   'Bruker, 2001.'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      297(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7149
_diffrn_reflns_av_R_equivalents  0.0649
_diffrn_reflns_av_sigmaI/netI    0.0796
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2690
_reflns_number_gt                2208
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0215P)²+34.3071P] 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         2690
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1044
_refine_ls_R_factor_gt           0.0822
_refine_ls_wR_factor_ref         0.1524
_refine_ls_wR_factor_gt          0.1445
_refine_ls_goodness_of_fit_ref   1.223
_refine_ls_restrained_S_all      1.223
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.29394(6) 1.10089(6) 0.40799(6) 0.0364(2) Uani 1 1 d . . .
Br1 Br 0.3486(2) 1.1020(2) 0.1886(2) 0.0691(7) Uani 1 1 d . . .
C1 C 0.3388(15) 0.9138(16) 0.4492(17) 0.041(4) Uani 1 1 d . . .
C2 C 0.2984(13) 0.8565(14) 0.5299(14) 0.028(4) Uani 1 1 d . . .
C3 C 0.3295(15) 0.7405(17) 0.5639(16) 0.042(5) Uani 1 1 d . . .
H3 H 0.3053 0.7024 0.6217 0.050 Uiso 1 1 calc R . .
C4 C 0.3937(17) 0.6823(18) 0.515(2) 0.052(5) Uani 1 1 d . . .
H4 H 0.4103 0.6042 0.5363 0.063 Uiso 1 1 calc R . .
C5 C 0.4340(14) 0.7373(17) 0.4355(19) 0.043(5) Uani 1 1 d . . .
H5 H 0.4799 0.6982 0.4035 0.052 Uiso 1 1 calc R . .
C6 C 0.4064(13) 0.8504(18) 0.4030(17) 0.041(5) Uani 1 1 d . . .
H6 H 0.4337 0.8875 0.3474 0.049 Uiso 1 1 calc R . .
C7 C 0.2189(16) 0.9165(17) 0.5747(19) 0.048(5) Uani 1 1 d . . .
H7A H 0.1445 0.9078 0.5076 0.058 Uiso 1 1 calc R . .
H7B H 0.2215 0.8800 0.6553 0.058 Uiso 1 1 calc R . .
C8 C 0.3463(18) 1.0565(18) 0.7199(19) 0.058(6) Uani 1 1 d . . .
H8A H 0.3746 1.1338 0.7214 0.087 Uiso 1 1 calc R . .
H8B H 0.4005 1.0004 0.7208 0.087 Uiso 1 1 calc R . .
H8C H 0.3297 1.0453 0.7963 0.087 Uiso 1 1 calc R . .
C9 C 0.1565(18) 1.1085(19) 0.605(2) 0.067(6) Uani 1 1 d . . .
H9A H 0.0965 1.1101 0.5198 0.100 Uiso 1 1 calc R . .
H9B H 0.1815 1.1866 0.6325 0.100 Uiso 1 1 calc R . .
H9C H 0.1319 1.0741 0.6683 0.100 Uiso 1 1 calc R . .
C10 C 0.1177(14) 1.0634(14) 0.2755(16) 0.031(4) Uani 1 1 d . . .
C11 C 0.0416(17) 1.1509(19) 0.2538(19) 0.053(5) Uani 1 1 d . . .
H11 H 0.0649 1.2213 0.2982 0.063 Uiso 1 1 calc R . .
C12 C -0.0680(19) 1.139(2) 0.169(2) 0.064(7) Uani 1 1 d . . .
H12 H -0.1180 1.1994 0.1563 0.077 Uiso 1 1 calc R . .
C13 C -0.1008(17) 1.035(2) 0.1032(19) 0.059(6) Uani 1 1 d . . .
H13 H -0.1741 1.0247 0.0453 0.071 Uiso 1 1 calc R . .
C14 C -0.0274(17) 0.9472(18) 0.1219(19) 0.050(5) Uani 1 1 d . . .
H14 H -0.0504 0.8775 0.0759 0.060 Uiso 1 1 calc R . .
C15 C 0.0817(17) 0.9608(17) 0.2093(17) 0.047(5) Uani 1 1 d . . .
H15 H 0.1310 0.8994 0.2230 0.056 Uiso 1 1 calc R . .
N1 N 0.2450(12) 1.0411(12) 0.5992(13) 0.035(4) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.224(19) . ?
Bi1 C10 2.241(16) . ?
Bi1 N1 2.536(13) . ?
Bi1 Br1 2.789(2) . ?
C1 C2 1.37(2) . ?
C1 C6 1.40(2) . ?
C2 C3 1.40(2) . ?
C2 C7 1.50(2) . ?
C3 C4 1.35(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.35(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.36(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.47(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N1 1.47(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.43(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.37(2) . ?
C10 C11 1.37(2) . ?
C11 C12 1.38(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.37(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.35(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.39(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?

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
C1 Bi1 C10 94.0(6) . . ?
C1 Bi1 N1 72.8(6) . . ?
C10 Bi1 N1 86.9(5) . . ?
C1 Bi1 Br1 92.4(5) . . ?
C10 Bi1 Br1 89.9(4) . . ?
N1 Bi1 Br1 164.6(3) . . ?
C2 C1 C6 117.3(18) . . ?
C2 C1 Bi1 116.9(13) . . ?
C6 C1 Bi1 125.8(14) . . ?
C1 C2 C3 118.6(17) . . ?
C1 C2 C7 120.1(16) . . ?
C3 C2 C7 121.2(15) . . ?
C4 C3 C2 121.9(18) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.2(19) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 118.9(18) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C1 123.0(19) . . ?
C5 C6 H6 118.5 . . ?
C1 C6 H6 118.5 . . ?
N1 C7 C2 111.3(14) . . ?
N1 C7 H7A 109.4 . . ?
C2 C7 H7A 109.4 . . ?
N1 C7 H7B 109.4 . . ?
C2 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 117.6(17) . . ?
C15 C10 Bi1 124.2(13) . . ?
C11 C10 Bi1 118.1(13) . . ?
C10 C11 C12 123(2) . . ?
C10 C11 H11 118.6 . . ?
C12 C11 H11 118.6 . . ?
C13 C12 C11 118(2) . . ?
C13 C12 H12 121.0 . . ?
C11 C12 H12 121.0 . . ?
C14 C13 C12 121(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C10 C15 C14 120.8(19) . . ?
C10 C15 H15 119.6 . . ?
C14 C15 H15 119.6 . . ?
C9 N1 C7 113.5(15) . . ?
C9 N1 C8 110.9(15) . . ?
C7 N1 C8 110.2(15) . . ?
C9 N1 Bi1 112.4(13) . . ?
C7 N1 Bi1 103.3(9) . . ?
C8 N1 Bi1 106.1(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 Bi1 C1 C2 -72.1(13) . . . . ?
N1 Bi1 C1 C2 13.4(12) . . . . ?
Br1 Bi1 C1 C2 -162.2(12) . . . . ?
C10 Bi1 C1 C6 109.5(14) . . . . ?
N1 Bi1 C1 C6 -165.0(15) . . . . ?
Br1 Bi1 C1 C6 19.5(14) . . . . ?
C6 C1 C2 C3 2(2) . . . . ?
Bi1 C1 C2 C3 -176.7(11) . . . . ?
C6 C1 C2 C7 -175.4(16) . . . . ?
Bi1 C1 C2 C7 6(2) . . . . ?
C1 C2 C3 C4 -3(2) . . . . ?
C7 C2 C3 C4 174.3(17) . . . . ?
C2 C3 C4 C5 3(3) . . . . ?
C3 C4 C5 C6 -2(3) . . . . ?
C4 C5 C6 C1 1(3) . . . . ?
C2 C1 C6 C5 -1(2) . . . . ?
Bi1 C1 C6 C5 177.6(13) . . . . ?
C1 C2 C7 N1 -36(2) . . . . ?
C3 C2 C7 N1 146.6(16) . . . . ?
C1 Bi1 C10 C15 -23.9(15) . . . . ?
N1 Bi1 C10 C15 -96.4(15) . . . . ?
Br1 Bi1 C10 C15 68.5(14) . . . . ?
C1 Bi1 C10 C11 159.6(14) . . . . ?
N1 Bi1 C10 C11 87.1(14) . . . . ?
Br1 Bi1 C10 C11 -108.0(14) . . . . ?
C15 C10 C11 C12 0(3) . . . . ?
Bi1 C10 C11 C12 176.7(16) . . . . ?
C10 C11 C12 C13 -1(3) . . . . ?
C11 C12 C13 C14 0(3) . . . . ?
C12 C13 C14 C15 1(3) . . . . ?
C11 C10 C15 C14 1(3) . . . . ?
Bi1 C10 C15 C14 -175.4(13) . . . . ?
C13 C14 C15 C10 -2(3) . . . . ?
C2 C7 N1 C9 163.3(16) . . . . ?
C2 C7 N1 C8 -71.6(19) . . . . ?
C2 C7 N1 Bi1 41.3(16) . . . . ?
C1 Bi1 N1 C9 -152.2(14) . . . . ?
C10 Bi1 N1 C9 -57.0(13) . . . . ?
Br1 Bi1 N1 C9 -135.3(13) . . . . ?
C1 Bi1 N1 C7 -29.6(11) . . . . ?
C10 Bi1 N1 C7 65.6(11) . . . . ?
Br1 Bi1 N1 C7 -13(2) . . . . ?
C1 Bi1 N1 C8 86.3(12) . . . . ?
C10 Bi1 N1 C8 -178.5(12) . . . . ?
Br1 Bi1 N1 C8 103.3(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.732
_refine_diff_density_min         -3.637
_refine_diff_density_rms         0.236
####################################################################### 
# 
# 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_nm12
_database_code_depnum_ccdc_archive 'CCDC 833207'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 Bi Br F5 N'
_chemical_formula_sum            'C15 H12 Bi Br F5 N'
_chemical_formula_weight         590.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.493(3)
_cell_length_b                   20.012(4)
_cell_length_c                   19.786(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.90(4)
_cell_angle_gamma                90.00
_cell_volume                     3350.6(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    64
_cell_measurement_theta_min      5.403
_cell_measurement_theta_max      25.085

_exptl_crystal_description       ?
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2176
_exptl_absorpt_coefficient_mu    12.955
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.0477
_exptl_absorpt_correction_T_max  0.1123
_exptl_absorpt_process_details   
;

        (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)

;

_exptl_special_details           ?

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 197
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            9751
_diffrn_reflns_av_R_equivalents  0.0352
_diffrn_reflns_av_sigmaI/netI    0.0665
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.61
_diffrn_reflns_theta_max         27.51
_reflns_number_total             7587
_reflns_number_gt                5687
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0862P)²+0.0000P] 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         7587
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0813
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1370
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.039
_refine_ls_shift/su_mean         0.001

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1535(18) 0.8122(7) 0.7917(6) 0.042(3) Uani 1 1 d . . .
C2 C 0.2369(16) 0.7786(6) 0.7427(6) 0.032(3) Uani 1 1 d . . .
C3 C 0.2300(15) 0.7077(6) 0.7421(7) 0.037(3) Uani 1 1 d . . .
H3 H 0.2795 0.6835 0.7085 0.044 Uiso 1 1 calc R . .
C4 C 0.1510(17) 0.6733(7) 0.7905(7) 0.048(4) Uani 1 1 d . . .
H4 H 0.1486 0.6259 0.7904 0.057 Uiso 1 1 calc R . .
C5 C 0.0774(18) 0.7083(7) 0.8379(8) 0.049(4) Uani 1 1 d . . .
H5 H 0.0278 0.6847 0.8720 0.059 Uiso 1 1 calc R . .
C6 C 0.0736(15) 0.7770(6) 0.8374(6) 0.032(3) Uani 1 1 d . . .
H6 H 0.0153 0.8002 0.8689 0.038 Uiso 1 1 calc R . .
C7 C 0.3112(16) 0.8161(7) 0.6887(6) 0.038(3) Uani 1 1 d . . .
H7A H 0.3975 0.7891 0.6719 0.045 Uiso 1 1 calc R . .
H7B H 0.2316 0.8245 0.6501 0.045 Uiso 1 1 calc R . .
C8 C 0.417(2) 0.9230(8) 0.6603(8) 0.055(4) Uani 1 1 d . . .
H8A H 0.3740 0.9043 0.6168 0.083 Uiso 1 1 calc R . .
H8B H 0.5325 0.9259 0.6610 0.083 Uiso 1 1 calc R . .
H8C H 0.3735 0.9678 0.6660 0.083 Uiso 1 1 calc R . .
C9 C 0.5164(14) 0.8698(8) 0.7641(8) 0.047(3) Uani 1 1 d . . .
H9A H 0.5963 0.8444 0.7421 0.071 Uiso 1 1 calc R . .
H9B H 0.4856 0.8450 0.8036 0.071 Uiso 1 1 calc R . .
H9C H 0.5602 0.9133 0.7788 0.071 Uiso 1 1 calc R . .
C10 C 0.0081(15) 0.9342(5) 0.6840(5) 0.028(2) Uani 1 1 d . . .
C11 C 0.0208(14) 0.9934(6) 0.6498(6) 0.030(2) Uani 1 1 d . . .
C12 C -0.0639(16) 1.0075(6) 0.5895(6) 0.035(3) Uani 1 1 d . . .
C13 C -0.1674(15) 0.9605(7) 0.5616(5) 0.037(3) Uani 1 1 d . . .
C14 C -0.1787(15) 0.8997(7) 0.5935(6) 0.036(3) Uani 1 1 d . . .
C15 C -0.0907(14) 0.8883(5) 0.6549(6) 0.029(2) Uani 1 1 d . . .
C16 C 0.5647(14) 0.8999(4) 1.1064(4) 0.021(2) Uani 1 1 d . . .
C17 C 0.6704(12) 0.8656(5) 1.1530(5) 0.019(2) Uani 1 1 d . . .
C18 C 0.6544(14) 0.8728(5) 1.2220(5) 0.025(2) Uani 1 1 d . . .
H18 H 0.7283 0.8518 1.2540 0.031 Uiso 1 1 calc R . .
C19 C 0.5329(14) 0.9097(5) 1.2445(5) 0.026(2) Uani 1 1 d . . .
H19 H 0.5203 0.9122 1.2916 0.032 Uiso 1 1 calc R . .
C20 C 0.4275(15) 0.9438(5) 1.1982(5) 0.029(2) Uani 1 1 d . . .
H20 H 0.3479 0.9716 1.2142 0.034 Uiso 1 1 calc R . .
C21 C 0.4398(14) 0.9368(5) 1.1271(5) 0.025(2) Uani 1 1 d . . .
H21 H 0.3646 0.9568 1.0950 0.030 Uiso 1 1 calc R . .
C22 C 0.7962(14) 0.8219(5) 1.1282(5) 0.027(2) Uani 1 1 d . . .
H22A H 0.8832 0.8172 1.1644 0.032 Uiso 1 1 calc R . .
H22B H 0.7518 0.7769 1.1181 0.032 Uiso 1 1 calc R . .
C23 C 0.9561(16) 0.7982(7) 1.0367(7) 0.041(3) Uani 1 1 d . . .
H23A H 1.0514 0.7895 1.0670 0.061 Uiso 1 1 calc R . .
H23B H 0.9864 0.8146 0.9930 0.061 Uiso 1 1 calc R . .
H23C H 0.8953 0.7568 1.0298 0.061 Uiso 1 1 calc R . .
C24 C 0.9606(14) 0.9085(6) 1.0863(7) 0.036(3) Uani 1 1 d . . .
H24A H 0.8956 0.9435 1.1046 0.054 Uiso 1 1 calc R . .
H24B H 1.0073 0.9254 1.0460 0.054 Uiso 1 1 calc R . .
H24C H 1.0450 0.8956 1.1207 0.054 Uiso 1 1 calc R . .
C25 C 0.5460(13) 0.7875(5) 0.9818(5) 0.025(2) Uani 1 1 d . . .
C26 C 0.6214(12) 0.7482(6) 0.9363(5) 0.022(2) Uani 1 1 d . . .
C27 C 0.5779(16) 0.6827(6) 0.9202(5) 0.032(3) Uani 1 1 d . . .
C28 C 0.4522(15) 0.6569(6) 0.9482(5) 0.030(3) Uani 1 1 d . . .
C29 C 0.3712(15) 0.6927(6) 0.9924(6) 0.034(3) Uani 1 1 d . . .
C30 C 0.4162(13) 0.7569(5) 1.0087(5) 0.023(2) Uani 1 1 d . . .
Bi1 Bi 0.16244(5) 0.924495(19) 0.788009(18) 0.02074(12) Uani 1 1 d . . .
Bi2 Bi 0.62283(5) 0.895660(19) 0.998550(18) 0.02100(12) Uani 1 1 d . . .
F1 F 0.1204(10) 1.0421(4) 0.6766(4) 0.046(2) Uani 1 1 d . . .
F2 F -0.0459(12) 1.0663(4) 0.5584(4) 0.058(2) Uani 1 1 d . . .
F3 F -0.2464(11) 0.9719(5) 0.5033(3) 0.062(3) Uani 1 1 d . . .
F4 F -0.2752(10) 0.8531(4) 0.5662(4) 0.057(2) Uani 1 1 d . . .
F5 F -0.1128(10) 0.8288(4) 0.6844(4) 0.0461(19) Uani 1 1 d . . .
F6 F 0.7379(9) 0.7748(4) 0.9047(3) 0.0413(18) Uani 1 1 d . . .
F7 F 0.6650(11) 0.6473(4) 0.8805(4) 0.054(2) Uani 1 1 d . . .
F8 F 0.4062(11) 0.5931(4) 0.9325(4) 0.052(2) Uani 1 1 d . . .
F9 F 0.2427(9) 0.6658(4) 1.0197(4) 0.0453(19) Uani 1 1 d . . .
F10 F 0.3366(8) 0.7887(3) 1.0550(3) 0.0356(16) Uani 1 1 d . . .
Br1 Br -0.11051(14) 0.93332(6) 0.85258(6) 0.0334(3) Uani 1 1 d . . .
Br2 Br 0.31107(15) 0.93161(6) 0.95506(5) 0.0311(3) Uani 1 1 d . . .
N1 N 0.3751(11) 0.8802(5) 0.7152(5) 0.033(2) Uani 1 1 d . . .
N2 N 0.8594(11) 0.8487(5) 1.0673(5) 0.0256(19) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.371(16) . ?
C1 C2 1.418(17) . ?
C1 Bi1 2.250(13) . ?
C2 C3 1.419(16) . ?
C2 C7 1.490(16) . ?
C3 C4 1.396(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(17) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.472(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 N1 1.453(18) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 N1 1.491(16) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C15 1.340(16) . ?
C10 C11 1.373(15) . ?
C10 Bi1 2.352(11) . ?
C11 F1 1.369(14) . ?
C11 C12 1.368(16) . ?
C12 F2 1.343(14) . ?
C12 C13 1.371(19) . ?
C13 F3 1.305(13) . ?
C13 C14 1.378(19) . ?
C14 F4 1.325(14) . ?
C14 C15 1.391(16) . ?
C15 F5 1.345(13) . ?
C16 C21 1.383(15) . ?
C16 C17 1.409(14) . ?
C16 Bi2 2.233(9) . ?
C17 C18 1.391(14) . ?
C17 C22 1.496(15) . ?
C18 C19 1.374(16) . ?
C18 H18 0.9500 . ?
C19 C20 1.401(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.426(14) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 N2 1.462(14) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 N2 1.464(14) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 N2 1.503(15) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.393(15) . ?
C25 C30 1.405(14) . ?
C25 Bi2 2.277(11) . ?
C26 F6 1.326(12) . ?
C26 C27 1.390(16) . ?
C27 F7 1.330(13) . ?
C27 C28 1.347(17) . ?
C28 C29 1.363(17) . ?
C28 F8 1.363(13) . ?
C29 F9 1.368(13) . ?
C29 C30 1.370(16) . ?
C30 F10 1.346(12) . ?
Bi1 N1 2.563(9) . ?
Bi1 Br1 2.7466(17) . ?
Bi2 N2 2.511(9) . ?
Bi2 Br2 2.8070(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.7(12) . . ?
C6 C1 Bi1 123.7(9) . . ?
C2 C1 Bi1 115.6(9) . . ?
C1 C2 C3 117.2(12) . . ?
C1 C2 C7 121.2(11) . . ?
C3 C2 C7 121.2(11) . . ?
C4 C3 C2 120.6(12) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 119.6(12) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 121.3(13) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 120.4(12) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
N1 C7 C2 110.4(9) . . ?
N1 C7 H7A 109.6 . . ?
C2 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C2 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 116.9(11) . . ?
C15 C10 Bi1 126.9(8) . . ?
C11 C10 Bi1 116.2(8) . . ?
F1 C11 C12 116.9(10) . . ?
F1 C11 C10 119.7(10) . . ?
C12 C11 C10 123.4(11) . . ?
F2 C12 C13 120.7(11) . . ?
F2 C12 C11 120.6(12) . . ?
C13 C12 C11 118.7(11) . . ?
F3 C13 C12 120.0(13) . . ?
F3 C13 C14 120.6(13) . . ?
C12 C13 C14 119.2(10) . . ?
F4 C14 C13 120.0(11) . . ?
F4 C14 C15 120.5(12) . . ?
C13 C14 C15 119.5(11) . . ?
C10 C15 F5 121.8(10) . . ?
C10 C15 C14 122.2(11) . . ?
F5 C15 C14 116.1(10) . . ?
C21 C16 C17 121.9(9) . . ?
C21 C16 Bi2 122.8(7) . . ?
C17 C16 Bi2 115.2(7) . . ?
C18 C17 C16 118.8(10) . . ?
C18 C17 C22 121.0(9) . . ?
C16 C17 C22 120.2(9) . . ?
C19 C18 C17 120.8(10) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.5(10) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 120.0(10) . . ?
C19 C20 H20 120.0 . . ?
C21 C20 H20 120.0 . . ?
C16 C21 C20 117.9(10) . . ?
C16 C21 H21 121.1 . . ?
C20 C21 H21 121.1 . . ?
N2 C22 C17 112.3(9) . . ?
N2 C22 H22A 109.1 . . ?
C17 C22 H22A 109.1 . . ?
N2 C22 H22B 109.1 . . ?
C17 C22 H22B 109.1 . . ?
H22A C22 H22B 107.9 . . ?
N2 C23 H23A 109.5 . . ?
N2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
N2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
N2 C24 H24A 109.5 . . ?
N2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
N2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C30 114.7(10) . . ?
C26 C25 Bi2 119.3(7) . . ?
C30 C25 Bi2 125.7(8) . . ?
F6 C26 C27 117.7(10) . . ?
F6 C26 C25 118.7(10) . . ?
C27 C26 C25 123.5(10) . . ?
F7 C27 C28 122.6(11) . . ?
F7 C27 C26 119.1(11) . . ?
C28 C27 C26 118.2(10) . . ?
C27 C28 C29 121.5(11) . . ?
C27 C28 F8 119.2(11) . . ?
C29 C28 F8 119.3(11) . . ?
C28 C29 F9 120.6(11) . . ?
C28 C29 C30 119.9(11) . . ?
F9 C29 C30 119.5(11) . . ?
F10 C30 C29 117.3(10) . . ?
F10 C30 C25 120.4(10) . . ?
C29 C30 C25 122.2(11) . . ?
C1 Bi1 C10 95.3(4) . . ?
C1 Bi1 N1 72.5(4) . . ?
C10 Bi1 N1 84.5(4) . . ?
C1 Bi1 Br1 91.0(4) . . ?
C10 Bi1 Br1 88.4(3) . . ?
N1 Bi1 Br1 161.3(2) . . ?
C16 Bi2 C25 95.2(4) . . ?
C16 Bi2 N2 74.2(4) . . ?
C25 Bi2 N2 85.9(3) . . ?
C16 Bi2 Br2 90.2(3) . . ?
C25 Bi2 Br2 87.0(3) . . ?
N2 Bi2 Br2 162.2(2) . . ?
C8 N1 C7 110.7(10) . . ?
C8 N1 C9 109.4(11) . . ?
C7 N1 C9 111.2(11) . . ?
C8 N1 Bi1 116.5(8) . . ?
C7 N1 Bi1 104.3(7) . . ?
C9 N1 Bi1 104.5(7) . . ?
C22 N2 C23 110.3(9) . . ?
C22 N2 C24 109.1(9) . . ?
C23 N2 C24 108.9(10) . . ?
C22 N2 Bi2 104.5(6) . . ?
C23 N2 Bi2 119.1(7) . . ?
C24 N2 Bi2 104.5(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2(2) . . . . ?
Bi1 C1 C2 C3 -178.1(9) . . . . ?
C6 C1 C2 C7 174.1(13) . . . . ?
Bi1 C1 C2 C7 -5.7(16) . . . . ?
C1 C2 C3 C4 -3(2) . . . . ?
C7 C2 C3 C4 -175.8(12) . . . . ?
C2 C3 C4 C5 1(2) . . . . ?
C3 C4 C5 C6 3(2) . . . . ?
C2 C1 C6 C5 2(2) . . . . ?
Bi1 C1 C6 C5 -178.0(11) . . . . ?
C4 C5 C6 C1 -4(2) . . . . ?
C1 C2 C7 N1 36.1(17) . . . . ?
C3 C2 C7 N1 -151.8(12) . . . . ?
C15 C10 C11 F1 -179.6(11) . . . . ?
Bi1 C10 C11 F1 0.6(15) . . . . ?
C15 C10 C11 C12 1.5(19) . . . . ?
Bi1 C10 C11 C12 -178.3(9) . . . . ?
F1 C11 C12 F2 1.2(17) . . . . ?
C10 C11 C12 F2 -179.8(11) . . . . ?
F1 C11 C12 C13 -178.8(11) . . . . ?
C10 C11 C12 C13 0.2(19) . . . . ?
F2 C12 C13 F3 1.9(18) . . . . ?
C11 C12 C13 F3 -178.1(11) . . . . ?
F2 C12 C13 C14 177.6(11) . . . . ?
C11 C12 C13 C14 -2.4(18) . . . . ?
F3 C13 C14 F4 -2.6(19) . . . . ?
C12 C13 C14 F4 -178.3(11) . . . . ?
F3 C13 C14 C15 178.6(11) . . . . ?
C12 C13 C14 C15 3.0(19) . . . . ?
C11 C10 C15 F5 -179.5(11) . . . . ?
Bi1 C10 C15 F5 0.3(17) . . . . ?
C11 C10 C15 C14 -0.9(18) . . . . ?
Bi1 C10 C15 C14 178.9(9) . . . . ?
F4 C14 C15 C10 180.0(12) . . . . ?
C13 C14 C15 C10 -1(2) . . . . ?
F4 C14 C15 F5 -1.4(18) . . . . ?
C13 C14 C15 F5 177.4(11) . . . . ?
C21 C16 C17 C18 -4.3(16) . . . . ?
Bi2 C16 C17 C18 172.0(8) . . . . ?
C21 C16 C17 C22 175.1(10) . . . . ?
Bi2 C16 C17 C22 -8.6(12) . . . . ?
C16 C17 C18 C19 3.3(16) . . . . ?
C22 C17 C18 C19 -176.0(10) . . . . ?
C17 C18 C19 C20 -3.3(17) . . . . ?
C18 C19 C20 C21 4.0(17) . . . . ?
C17 C16 C21 C20 4.9(16) . . . . ?
Bi2 C16 C21 C20 -171.0(8) . . . . ?
C19 C20 C21 C16 -4.8(16) . . . . ?
C18 C17 C22 N2 -145.0(10) . . . . ?
C16 C17 C22 N2 35.6(14) . . . . ?
C30 C25 C26 F6 175.1(9) . . . . ?
Bi2 C25 C26 F6 1.1(12) . . . . ?
C30 C25 C26 C27 -2.8(15) . . . . ?
Bi2 C25 C26 C27 -176.8(8) . . . . ?
F6 C26 C27 F7 7.6(15) . . . . ?
C25 C26 C27 F7 -174.5(10) . . . . ?
F6 C26 C27 C28 -175.1(10) . . . . ?
C25 C26 C27 C28 2.8(16) . . . . ?
F7 C27 C28 C29 175.5(11) . . . . ?
C26 C27 C28 C29 -1.7(18) . . . . ?
F7 C27 C28 F8 -3.7(17) . . . . ?
C26 C27 C28 F8 179.2(10) . . . . ?
C27 C28 C29 F9 179.3(11) . . . . ?
F8 C28 C29 F9 -1.6(18) . . . . ?
C27 C28 C29 C30 0.8(19) . . . . ?
F8 C28 C29 C30 180.0(11) . . . . ?
C28 C29 C30 F10 -176.9(10) . . . . ?
F9 C29 C30 F10 4.6(16) . . . . ?
C28 C29 C30 C25 -0.9(18) . . . . ?
F9 C29 C30 C25 -179.4(10) . . . . ?
C26 C25 C30 F10 177.7(9) . . . . ?
Bi2 C25 C30 F10 -8.7(14) . . . . ?
C26 C25 C30 C29 1.8(16) . . . . ?
Bi2 C25 C30 C29 175.4(9) . . . . ?
C6 C1 Bi1 C10 -111.1(12) . . . . ?
C2 C1 Bi1 C10 68.8(11) . . . . ?
C6 C1 Bi1 N1 166.4(13) . . . . ?
C2 C1 Bi1 N1 -13.7(9) . . . . ?
C6 C1 Bi1 Br1 -22.6(12) . . . . ?
C2 C1 Bi1 Br1 157.3(10) . . . . ?
C15 C10 Bi1 C1 20.0(11) . . . . ?
C11 C10 Bi1 C1 -160.2(9) . . . . ?
C15 C10 Bi1 N1 91.8(11) . . . . ?
C11 C10 Bi1 N1 -88.4(9) . . . . ?
C15 C10 Bi1 Br1 -70.9(11) . . . . ?
C11 C10 Bi1 Br1 108.9(9) . . . . ?
C21 C16 Bi2 C25 -109.8(9) . . . . ?
C17 C16 Bi2 C25 74.0(8) . . . . ?
C21 C16 Bi2 N2 166.0(10) . . . . ?
C17 C16 Bi2 N2 -10.2(7) . . . . ?
C21 C16 Bi2 Br2 -22.8(9) . . . . ?
C17 C16 Bi2 Br2 161.0(7) . . . . ?
C26 C25 Bi2 C16 -149.3(8) . . . . ?
C30 C25 Bi2 C16 37.4(9) . . . . ?
C26 C25 Bi2 N2 -75.6(8) . . . . ?
C30 C25 Bi2 N2 111.1(9) . . . . ?
C26 C25 Bi2 Br2 120.7(8) . . . . ?
C30 C25 Bi2 Br2 -52.6(9) . . . . ?
C2 C7 N1 C8 -167.9(11) . . . . ?
C2 C7 N1 C9 70.3(13) . . . . ?
C2 C7 N1 Bi1 -41.8(11) . . . . ?
C1 Bi1 N1 C8 152.8(11) . . . . ?
C10 Bi1 N1 C8 55.4(10) . . . . ?
Br1 Bi1 N1 C8 123.5(10) . . . . ?
C1 Bi1 N1 C7 30.4(8) . . . . ?
C10 Bi1 N1 C7 -67.0(8) . . . . ?
Br1 Bi1 N1 C7 1.2(13) . . . . ?
C1 Bi1 N1 C9 -86.4(9) . . . . ?
C10 Bi1 N1 C9 176.2(9) . . . . ?
Br1 Bi1 N1 C9 -115.7(9) . . . . ?
C17 C22 N2 C23 -168.0(10) . . . . ?
C17 C22 N2 C24 72.4(11) . . . . ?
C17 C22 N2 Bi2 -38.9(10) . . . . ?
C16 Bi2 N2 C22 26.7(6) . . . . ?
C25 Bi2 N2 C22 -69.9(7) . . . . ?
Br2 Bi2 N2 C22 -3.1(12) . . . . ?
C16 Bi2 N2 C23 150.3(9) . . . . ?
C25 Bi2 N2 C23 53.6(9) . . . . ?
Br2 Bi2 N2 C23 120.4(9) . . . . ?
C16 Bi2 N2 C24 -87.9(7) . . . . ?
C25 Bi2 N2 C24 175.4(7) . . . . ?
Br2 Bi2 N2 C24 -117.8(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.986
_refine_diff_density_max         2.169
_refine_diff_density_min         -1.696
_refine_diff_density_rms         0.306
####################################################################### 
# 
# 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_nm13a
_database_code_depnum_ccdc_archive 'CCDC 833208'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H12 Bi F10 N'
_chemical_formula_sum            'C21 H12 Bi F10 N'
_chemical_formula_weight         677.30

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   6.6570(10)
_cell_length_b                   16.639(2)
_cell_length_c                   18.698(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.530(10)
_cell_angle_gamma                90.00
_cell_volume                     2071.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    70
_cell_measurement_theta_min      6.603
_cell_measurement_theta_max      26.934

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_diffrn    2.172
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1272
_exptl_absorpt_coefficient_mu    8.611
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_correction_T_min  0.052
_exptl_absorpt_correction_T_max  0.180
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 197
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5067
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_av_sigmaI/netI    0.0505
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.68
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3620
_reflns_number_gt                2916
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'Siemens SHELXTL'
_computing_structure_refinement  'Siemens SHELXTL'
_computing_molecular_graphics    'Siemens SHELXTL'
_computing_publication_material  'Siemens SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0313P)²+6.8253P] 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         3620
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0799
_refine_ls_wR_factor_gt          0.0750
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.09307(4) 0.276316(16) 0.112188(13) 0.02349(10) Uani 1 1 d . . .
C2 C 0.3221(10) 0.2289(4) 0.2518(3) 0.0255(15) Uani 1 1 d . . .
C7 C 0.1388(11) 0.1747(5) 0.2567(4) 0.0302(17) Uani 1 1 d . . .
H7A H 0.1633 0.1336 0.2925 0.036 Uiso 1 1 calc R . .
H7B H 0.0241 0.2062 0.2717 0.036 Uiso 1 1 calc R . .
C1 C 0.3445(10) 0.2790(4) 0.1918(3) 0.0258(15) Uani 1 1 d . . .
C6 C 0.5078(11) 0.3297(5) 0.1893(4) 0.0301(16) Uani 1 1 d . . .
H6 H 0.5231 0.3633 0.1500 0.036 Uiso 1 1 calc R . .
C3 C 0.4620(11) 0.2319(5) 0.3064(4) 0.0338(18) Uani 1 1 d . . .
H3 H 0.4457 0.1994 0.3464 0.041 Uiso 1 1 calc R . .
C4 C 0.6267(11) 0.2826(5) 0.3027(4) 0.0340(17) Uani 1 1 d . . .
H4 H 0.7213 0.2835 0.3396 0.041 Uiso 1 1 calc R . .
C5 C 0.6495(11) 0.3319(5) 0.2436(4) 0.0302(16) Uani 1 1 d . . .
H5 H 0.7594 0.3662 0.2406 0.036 Uiso 1 1 calc R . .
C16 C 0.2389(11) 0.2024(4) 0.0236(4) 0.0251(16) Uani 1 1 d . . .
C21 C 0.4247(11) 0.1666(5) 0.0252(4) 0.0303(16) Uani 1 1 d . . .
C11 C 0.1876(11) 0.4658(5) 0.1090(4) 0.0281(16) Uani 1 1 d . . .
C10 C 0.1913(11) 0.4014(4) 0.0640(4) 0.0282(16) Uani 1 1 d . . .
C15 C 0.2302(10) 0.4190(4) -0.0059(4) 0.0251(15) Uani 1 1 d . . .
C17 C 0.1177(11) 0.1829(5) -0.0336(4) 0.0301(17) Uani 1 1 d . . .
N1 N 0.0933(9) 0.1366(4) 0.1882(3) 0.0285(14) Uani 1 1 d . . .
C14 C 0.2617(10) 0.4957(5) -0.0306(4) 0.0294(17) Uani 1 1 d . . .
C13 C 0.2610(10) 0.5583(4) 0.0173(4) 0.0288(17) Uani 1 1 d . . .
C20 C 0.4850(11) 0.1131(5) -0.0267(4) 0.0309(17) Uani 1 1 d . . .
C12 C 0.2231(11) 0.5441(5) 0.0874(4) 0.0310(17) Uani 1 1 d . . .
C9 C -0.1111(12) 0.1040(5) 0.1846(5) 0.043(2) Uani 1 1 d . . .
H9A H -0.1403 0.0867 0.1367 0.064 Uiso 1 1 calc R . .
H9B H -0.2051 0.1450 0.1982 0.064 Uiso 1 1 calc R . .
H9C H -0.1219 0.0592 0.2167 0.064 Uiso 1 1 calc R . .
C8 C 0.2407(14) 0.0729(5) 0.1729(5) 0.045(2) Uani 1 1 d . . .
H8A H 0.3729 0.0958 0.1713 0.068 Uiso 1 1 calc R . .
H8B H 0.2091 0.0486 0.1276 0.068 Uiso 1 1 calc R . .
H8C H 0.2359 0.0328 0.2097 0.068 Uiso 1 1 calc R . .
C18 C 0.1729(12) 0.1308(5) -0.0867(4) 0.0369(19) Uani 1 1 d . . .
C19 C 0.3570(13) 0.0956(5) -0.0824(4) 0.0377(19) Uani 1 1 d . . .
F6 F -0.0676(7) 0.2171(3) -0.0391(3) 0.0460(12) Uani 1 1 d . . .
F5 F 0.2289(7) 0.3602(3) -0.0556(2) 0.0385(11) Uani 1 1 d . . .
F3 F 0.2921(7) 0.6335(3) -0.0058(3) 0.0473(12) Uani 1 1 d . . .
F1 F 0.1447(8) 0.4538(3) 0.1797(2) 0.0431(12) Uani 1 1 d . . .
F10 F 0.5572(7) 0.1833(3) 0.0776(3) 0.0483(12) Uani 1 1 d . . .
F9 F 0.6666(7) 0.0769(3) -0.0231(3) 0.0522(13) Uani 1 1 d . . .
F4 F 0.2935(7) 0.5102(3) -0.1003(2) 0.0440(12) Uani 1 1 d . . .
F2 F 0.2169(8) 0.6049(3) 0.1345(3) 0.0510(13) Uani 1 1 d . . .
F8 F 0.4149(8) 0.0434(3) -0.1335(3) 0.0553(14) Uani 1 1 d . . .
F7 F 0.0500(8) 0.1149(4) -0.1423(3) 0.0610(15) Uani 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.230(7) . ?
Bi1 C16 2.287(7) . ?
Bi1 C10 2.363(7) . ?
Bi1 N1 2.725(6) . ?
C2 C3 1.377(10) . ?
C2 C1 1.406(10) . ?
C2 C7 1.521(10) . ?
C7 N1 1.458(9) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C1 C6 1.377(10) . ?
C6 C5 1.380(10) . ?
C6 H6 0.9300 . ?
C3 C4 1.385(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(11) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 C17 1.372(10) . ?
C16 C21 1.373(10) . ?
C21 F10 1.342(8) . ?
C21 C20 1.379(10) . ?
C11 C10 1.363(10) . ?
C11 F1 1.368(8) . ?
C11 C12 1.385(11) . ?
C10 C15 1.367(10) . ?
C15 F5 1.349(8) . ?
C15 C14 1.373(10) . ?
C17 F6 1.361(8) . ?
C17 C18 1.370(11) . ?
N1 C9 1.465(9) . ?
N1 C8 1.474(10) . ?
C14 F4 1.345(8) . ?
C14 C13 1.374(11) . ?
C13 F3 1.340(8) . ?
C13 C12 1.359(11) . ?
C20 F9 1.352(9) . ?
C20 C19 1.371(11) . ?
C12 F2 1.342(9) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C18 F7 1.343(9) . ?
C18 C19 1.360(11) . ?
C19 F8 1.351(9) . ?

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
C1 Bi1 C16 100.0(3) . . ?
C1 Bi1 C10 91.6(3) . . ?
C16 Bi1 C10 94.4(2) . . ?
C1 Bi1 N1 70.9(2) . . ?
C16 Bi1 N1 85.5(2) . . ?
C10 Bi1 N1 162.1(2) . . ?
C3 C2 C1 119.7(7) . . ?
C3 C2 C7 120.9(6) . . ?
C1 C2 C7 119.4(6) . . ?
N1 C7 C2 111.4(5) . . ?
N1 C7 H7A 109.3 . . ?
C2 C7 H7A 109.3 . . ?
N1 C7 H7B 109.3 . . ?
C2 C7 H7B 109.3 . . ?
H7A C7 H7B 108.0 . . ?
C6 C1 C2 118.6(6) . . ?
C6 C1 Bi1 125.3(5) . . ?
C2 C1 Bi1 115.8(5) . . ?
C1 C6 C5 121.7(7) . . ?
C1 C6 H6 119.1 . . ?
C5 C6 H6 119.1 . . ?
C2 C3 C4 121.0(7) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 119.5(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 119.5(7) . . ?
C6 C5 H5 120.3 . . ?
C4 C5 H5 120.3 . . ?
C17 C16 C21 116.0(6) . . ?
C17 C16 Bi1 116.2(5) . . ?
C21 C16 Bi1 127.3(5) . . ?
F10 C21 C16 120.8(6) . . ?
F10 C21 C20 117.0(7) . . ?
C16 C21 C20 122.2(7) . . ?
C10 C11 F1 119.1(7) . . ?
C10 C11 C12 123.7(7) . . ?
F1 C11 C12 117.2(7) . . ?
C11 C10 C15 115.3(7) . . ?
C11 C10 Bi1 116.8(5) . . ?
C15 C10 Bi1 127.5(5) . . ?
F5 C15 C10 120.2(6) . . ?
F5 C15 C14 116.3(6) . . ?
C10 C15 C14 123.4(7) . . ?
F6 C17 C18 117.3(7) . . ?
F6 C17 C16 119.1(7) . . ?
C18 C17 C16 123.7(7) . . ?
C7 N1 C9 112.7(6) . . ?
C7 N1 C8 110.5(6) . . ?
C9 N1 C8 110.2(6) . . ?
C7 N1 Bi1 94.9(4) . . ?
C9 N1 Bi1 107.2(5) . . ?
C8 N1 Bi1 120.6(5) . . ?
F4 C14 C15 121.2(7) . . ?
F4 C14 C13 119.7(7) . . ?
C15 C14 C13 119.0(6) . . ?
F3 C13 C12 120.3(7) . . ?
F3 C13 C14 119.8(7) . . ?
C12 C13 C14 119.9(7) . . ?
F9 C20 C19 119.5(7) . . ?
F9 C20 C21 121.3(7) . . ?
C19 C20 C21 119.2(7) . . ?
F2 C12 C13 120.6(7) . . ?
F2 C12 C11 120.8(7) . . ?
C13 C12 C11 118.7(7) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
F7 C18 C19 120.2(7) . . ?
F7 C18 C17 121.3(7) . . ?
C19 C18 C17 118.5(7) . . ?
F8 C19 C18 119.9(8) . . ?
F8 C19 C20 119.7(7) . . ?
C18 C19 C20 120.5(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 C2 C7 N1 -140.1(7) . . . . ?
C1 C2 C7 N1 42.3(9) . . . . ?
C3 C2 C1 C6 0.3(10) . . . . ?
C7 C2 C1 C6 177.8(7) . . . . ?
C3 C2 C1 Bi1 -174.5(5) . . . . ?
C7 C2 C1 Bi1 3.0(8) . . . . ?
C16 Bi1 C1 C6 80.3(6) . . . . ?
C10 Bi1 C1 C6 -14.4(6) . . . . ?
N1 Bi1 C1 C6 161.9(7) . . . . ?
C16 Bi1 C1 C2 -105.2(5) . . . . ?
C10 Bi1 C1 C2 160.0(5) . . . . ?
N1 Bi1 C1 C2 -23.6(5) . . . . ?
C2 C1 C6 C5 0.6(11) . . . . ?
Bi1 C1 C6 C5 174.9(5) . . . . ?
C1 C2 C3 C4 -1.1(11) . . . . ?
C7 C2 C3 C4 -178.6(7) . . . . ?
C2 C3 C4 C5 1.0(12) . . . . ?
C1 C6 C5 C4 -0.7(11) . . . . ?
C3 C4 C5 C6 -0.1(11) . . . . ?
C1 Bi1 C16 C17 175.0(5) . . . . ?
C10 Bi1 C16 C17 -92.6(6) . . . . ?
N1 Bi1 C16 C17 105.4(5) . . . . ?
C1 Bi1 C16 C21 4.3(7) . . . . ?
C10 Bi1 C16 C21 96.7(7) . . . . ?
N1 Bi1 C16 C21 -65.4(6) . . . . ?
C17 C16 C21 F10 178.0(7) . . . . ?
Bi1 C16 C21 F10 -11.2(10) . . . . ?
C17 C16 C21 C20 -1.1(11) . . . . ?
Bi1 C16 C21 C20 169.6(6) . . . . ?
F1 C11 C10 C15 178.4(6) . . . . ?
C12 C11 C10 C15 -1.0(11) . . . . ?
F1 C11 C10 Bi1 5.4(9) . . . . ?
C12 C11 C10 Bi1 -173.9(6) . . . . ?
C1 Bi1 C10 C11 -61.7(6) . . . . ?
C16 Bi1 C10 C11 -161.9(6) . . . . ?
N1 Bi1 C10 C11 -73.0(9) . . . . ?
C1 Bi1 C10 C15 126.3(6) . . . . ?
C16 Bi1 C10 C15 26.2(7) . . . . ?
N1 Bi1 C10 C15 115.0(8) . . . . ?
C11 C10 C15 F5 -177.2(6) . . . . ?
Bi1 C10 C15 F5 -5.1(10) . . . . ?
C11 C10 C15 C14 -0.6(11) . . . . ?
Bi1 C10 C15 C14 171.4(5) . . . . ?
C21 C16 C17 F6 -179.2(7) . . . . ?
Bi1 C16 C17 F6 9.0(9) . . . . ?
C21 C16 C17 C18 0.3(11) . . . . ?
Bi1 C16 C17 C18 -171.5(6) . . . . ?
C2 C7 N1 C9 -162.8(6) . . . . ?
C2 C7 N1 C8 73.4(8) . . . . ?
C2 C7 N1 Bi1 -51.9(6) . . . . ?
C1 Bi1 N1 C7 40.6(4) . . . . ?
C16 Bi1 N1 C7 142.8(4) . . . . ?
C10 Bi1 N1 C7 52.5(8) . . . . ?
C1 Bi1 N1 C9 156.2(5) . . . . ?
C16 Bi1 N1 C9 -101.6(5) . . . . ?
C10 Bi1 N1 C9 168.1(7) . . . . ?
C1 Bi1 N1 C8 -76.8(6) . . . . ?
C16 Bi1 N1 C8 25.4(6) . . . . ?
C10 Bi1 N1 C8 -64.9(9) . . . . ?
F5 C15 C14 F4 -1.3(10) . . . . ?
C10 C15 C14 F4 -178.0(7) . . . . ?
F5 C15 C14 C13 178.8(6) . . . . ?
C10 C15 C14 C13 2.2(11) . . . . ?
F4 C14 C13 F3 0.0(10) . . . . ?
C15 C14 C13 F3 179.8(6) . . . . ?
F4 C14 C13 C12 178.1(6) . . . . ?
C15 C14 C13 C12 -2.1(11) . . . . ?
F10 C21 C20 F9 2.5(11) . . . . ?
C16 C21 C20 F9 -178.3(7) . . . . ?
F10 C21 C20 C19 -178.3(7) . . . . ?
C16 C21 C20 C19 0.9(12) . . . . ?
F3 C13 C12 F2 -0.2(11) . . . . ?
C14 C13 C12 F2 -178.3(6) . . . . ?
F3 C13 C12 C11 178.7(6) . . . . ?
C14 C13 C12 C11 0.6(11) . . . . ?
C10 C11 C12 F2 179.9(7) . . . . ?
F1 C11 C12 F2 0.5(10) . . . . ?
C10 C11 C12 C13 1.1(11) . . . . ?
F1 C11 C12 C13 -178.3(6) . . . . ?
F6 C17 C18 F7 0.8(12) . . . . ?
C16 C17 C18 F7 -178.7(7) . . . . ?
F6 C17 C18 C19 -179.7(7) . . . . ?
C16 C17 C18 C19 0.7(13) . . . . ?
F7 C18 C19 F8 -1.2(12) . . . . ?
C17 C18 C19 F8 179.3(7) . . . . ?
F7 C18 C19 C20 178.4(8) . . . . ?
C17 C18 C19 C20 -1.0(12) . . . . ?
F9 C20 C19 F8 -0.9(11) . . . . ?
C21 C20 C19 F8 179.9(7) . . . . ?
F9 C20 C19 C18 179.5(7) . . . . ?
C21 C20 C19 C18 0.3(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.737
_refine_diff_density_min         -1.283
_refine_diff_density_rms         0.147
####################################################################### 
# 
# 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_nm15a
_database_code_depnum_ccdc_archive 'CCDC 833209'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_date             2008-08-08T11:19:10-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H23 Bi Br N'
_chemical_formula_sum            'C18 H23 Bi Br N'
_chemical_formula_weight         542.26
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   8.898(2)
_cell_length_b                   14.817(5)
_cell_length_c                   13.896(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.386(14)
_cell_angle_gamma                90
_cell_volume                     1812.4(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    33
_cell_measurement_theta_min      7.432
_cell_measurement_theta_max      24.995
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       blocks
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.4
_exptl_crystal_density_diffrn    1.987
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    11.927
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   
;
        (See: Walker, N. & Stuart, D. (1983) Acta Cryst. A39, 158-166)
;
_exptl_absorpt_correction_T_min  0.0527
_exptl_absorpt_correction_T_max  0.087

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       '2θ/ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 197
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_av_unetI/netI     0.0541
_diffrn_reflns_number            9790
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.56
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_reflns_number_total             4160
_reflns_number_gt                3475
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Siemens XSCANS'
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0437P)²+1.7545P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.00109(14)
_refine_ls_number_reflns         4160
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.481
_refine_diff_density_min         -1.48
_refine_diff_density_rms         0.158

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4787(6) 1.0283(4) 0.2534(4) 0.0263(11) Uani 1 1 d . . .
C2 C 0.4981(6) 1.0709(4) 0.3434(4) 0.0289(12) Uani 1 1 d . . .
C3 C 0.6247(6) 1.1224(4) 0.3729(4) 0.0319(12) Uani 1 1 d . . .
H3 H 0.6373 1.1507 0.4349 0.038 Uiso 1 1 calc R . .
C4 C 0.7347(6) 1.1333(4) 0.3121(5) 0.0359(13) Uani 1 1 d . . .
H4 H 0.8234 1.1679 0.333 0.043 Uiso 1 1 calc R . .
C5 C 0.7138(7) 1.0932(4) 0.2205(5) 0.0406(15) Uani 1 1 d . . .
H5 H 0.7872 1.1018 0.1781 0.049 Uiso 1 1 calc R . .
C6 C 0.5861(7) 1.0404(4) 0.1908(5) 0.0352(13) Uani 1 1 d . . .
H6 H 0.5722 1.0129 0.1284 0.042 Uiso 1 1 calc R . .
C7 C 0.3792(7) 1.0574(4) 0.4100(4) 0.0307(12) Uani 1 1 d . . .
H7A H 0.4034 1.0019 0.4489 0.037 Uiso 1 1 calc R . .
H7B H 0.383 1.1089 0.4556 0.037 Uiso 1 1 calc R . .
C8 C 0.1753(8) 1.1385(4) 0.3113(5) 0.0466(17) Uani 1 1 d . . .
H8A H 0.0764 1.1315 0.2705 0.07 Uiso 1 1 calc R . .
H8B H 0.2503 1.1596 0.2712 0.07 Uiso 1 1 calc R . .
H8C H 0.1667 1.1827 0.3627 0.07 Uiso 1 1 calc R . .
C9 C 0.1195(7) 1.0226(4) 0.4231(4) 0.0344(13) Uani 1 1 d . . .
H9A H 0.1247 1.0664 0.4764 0.052 Uiso 1 1 calc R . .
H9B H 0.148 0.9627 0.4496 0.052 Uiso 1 1 calc R . .
H9C H 0.0158 1.0207 0.3879 0.052 Uiso 1 1 calc R . .
C10 C 0.3068(6) 0.8329(4) 0.3192(4) 0.0256(11) Uani 1 1 d . . .
C11 C 0.4508(6) 0.7983(4) 0.3574(4) 0.0287(11) Uani 1 1 d . . .
C12 C 0.4586(7) 0.7277(4) 0.4234(4) 0.0337(13) Uani 1 1 d . . .
H12 H 0.5555 0.704 0.4489 0.04 Uiso 1 1 calc R . .
C13 C 0.3310(7) 0.6905(4) 0.4536(4) 0.0345(13) Uani 1 1 d . . .
C14 C 0.1908(7) 0.7245(4) 0.4148(4) 0.0335(13) Uani 1 1 d . . .
H14 H 0.102 0.6992 0.4344 0.04 Uiso 1 1 calc R . .
C15 C 0.1759(6) 0.7948(4) 0.3477(4) 0.0292(12) Uani 1 1 d . . .
C18 C 0.0171(7) 0.8204(5) 0.3036(5) 0.0423(15) Uani 1 1 d . . .
H16A H -0.0506 0.8156 0.353 0.063 Uiso 1 1 calc R . .
H16B H -0.0181 0.7796 0.2494 0.063 Uiso 1 1 calc R . .
H16C H 0.0165 0.8826 0.2796 0.063 Uiso 1 1 calc R . .
C16 C 0.5961(6) 0.8315(4) 0.3267(5) 0.0373(14) Uani 1 1 d . . .
H18A H 0.6194 0.8919 0.3536 0.056 Uiso 1 1 calc R . .
H18B H 0.5846 0.8343 0.2555 0.056 Uiso 1 1 calc R . .
H18C H 0.6789 0.7902 0.3508 0.056 Uiso 1 1 calc R . .
C17 C 0.3431(10) 0.6152(5) 0.5271(5) 0.0531(19) Uani 1 1 d . . .
H17A H 0.3272 0.6394 0.5905 0.08 Uiso 1 1 calc R . .
H17B H 0.4443 0.5879 0.5326 0.08 Uiso 1 1 calc R . .
H17C H 0.2658 0.5694 0.5061 0.08 Uiso 1 1 calc R . .
N1 N 0.2248(5) 1.0499(3) 0.3561(3) 0.0270(10) Uani 1 1 d . . .
Br1 Br 0.37799(9) 0.85998(5) 0.06234(5) 0.04947(19) Uani 1 1 d . . .
Bi1 Bi 0.26334(2) 0.949196(14) 0.211061(13) 0.02733(9) Uani 1 1 d . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
C1 C2 1.389(8) . ?
C1 C6 1.394(7) . ?
C1 Bi1 2.251(5) . ?
C2 C3 1.373(8) . ?
C2 C7 1.517(8) . ?
C3 C4 1.392(8) . ?
C3 H3 0.95 . ?
C4 C5 1.392(9) . ?
C4 H4 0.95 . ?
C5 C6 1.391(9) . ?
C5 H5 0.95 . ?
C6 H6 0.95 . ?
C7 N1 1.470(7) . ?
C7 H7A 0.99 . ?
C7 H7B 0.99 . ?
C8 N1 1.492(7) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 N1 1.470(7) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 C15 1.402(7) . ?
C10 C11 1.410(7) . ?
C10 Bi1 2.282(5) . ?
C11 C12 1.386(8) . ?
C11 C16 1.503(8) . ?
C12 C13 1.382(8) . ?
C12 H12 0.95 . ?
C13 C14 1.380(9) . ?
C13 C17 1.505(9) . ?
C14 C15 1.391(8) . ?
C14 H14 0.95 . ?
C15 C18 1.505(8) . ?
C18 H16A 0.98 . ?
C18 H16B 0.98 . ?
C18 H16C 0.98 . ?
C16 H18A 0.98 . ?
C16 H18B 0.98 . ?
C16 H18C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
N1 Bi1 2.570(5) . ?
Br1 Bi1 2.7702(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.8(5) . . ?
C2 C1 Bi1 117.5(4) . . ?
C6 C1 Bi1 122.6(4) . . ?
C3 C2 C1 120.7(5) . . ?
C3 C2 C7 120.4(5) . . ?
C1 C2 C7 118.9(5) . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.5(5) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 119.4(6) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
N1 C7 C2 112.5(5) . . ?
N1 C7 H7A 109.1 . . ?
C2 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 119.6(5) . . ?
C15 C10 Bi1 115.0(4) . . ?
C11 C10 Bi1 125.4(4) . . ?
C12 C11 C10 118.6(5) . . ?
C12 C11 C16 118.2(5) . . ?
C10 C11 C16 123.1(5) . . ?
C13 C12 C11 122.5(5) . . ?
C13 C12 H12 118.7 . . ?
C11 C12 H12 118.7 . . ?
C14 C13 C12 118.1(5) . . ?
C14 C13 C17 120.5(6) . . ?
C12 C13 C17 121.4(6) . . ?
C13 C14 C15 121.9(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 119.3(5) . . ?
C14 C15 C18 117.0(5) . . ?
C10 C15 C18 123.6(5) . . ?
C15 C18 H16A 109.5 . . ?
C15 C18 H16B 109.5 . . ?
H16A C18 H16B 109.5 . . ?
C15 C18 H16C 109.5 . . ?
H16A C18 H16C 109.5 . . ?
H16B C18 H16C 109.5 . . ?
C11 C16 H18A 109.5 . . ?
C11 C16 H18B 109.5 . . ?
H18A C16 H18B 109.5 . . ?
C11 C16 H18C 109.5 . . ?
H18A C16 H18C 109.5 . . ?
H18B C16 H18C 109.5 . . ?
C13 C17 H17A 109.5 . . ?
C13 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C13 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C7 N1 C9 109.4(4) . . ?
C7 N1 C8 110.0(5) . . ?
C9 N1 C8 109.2(4) . . ?
C7 N1 Bi1 102.8(3) . . ?
C9 N1 Bi1 120.5(4) . . ?
C8 N1 Bi1 104.4(4) . . ?
C1 Bi1 C10 99.52(19) . . ?
C1 Bi1 N1 72.46(17) . . ?
C10 Bi1 N1 87.21(16) . . ?
C1 Bi1 Br1 92.94(14) . . ?
C10 Bi1 Br1 94.89(13) . . ?
N1 Bi1 Br1 165.39(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.3(8) . . . . ?
Bi1 C1 C2 C3 -178.2(4) . . . . ?
C6 C1 C2 C7 179.5(5) . . . . ?
Bi1 C1 C2 C7 3.7(7) . . . . ?
C1 C2 C3 C4 0.7(9) . . . . ?
C7 C2 C3 C4 178.9(5) . . . . ?
C2 C3 C4 C5 1.3(9) . . . . ?
C3 C4 C5 C6 -1.8(10) . . . . ?
C4 C5 C6 C1 0.2(10) . . . . ?
C2 C1 C6 C5 1.8(9) . . . . ?
Bi1 C1 C6 C5 177.5(4) . . . . ?
C3 C2 C7 N1 146.7(5) . . . . ?
C1 C2 C7 N1 -35.1(7) . . . . ?
C15 C10 C11 C12 -0.7(8) . . . . ?
Bi1 C10 C11 C12 179.4(4) . . . . ?
C15 C10 C11 C16 176.5(5) . . . . ?
Bi1 C10 C11 C16 -3.5(8) . . . . ?
C10 C11 C12 C13 -0.5(8) . . . . ?
C16 C11 C12 C13 -177.8(5) . . . . ?
C11 C12 C13 C14 1.1(9) . . . . ?
C11 C12 C13 C17 -178.6(6) . . . . ?
C12 C13 C14 C15 -0.6(9) . . . . ?
C17 C13 C14 C15 179.2(6) . . . . ?
C13 C14 C15 C10 -0.6(9) . . . . ?
C13 C14 C15 C18 174.5(6) . . . . ?
C11 C10 C15 C14 1.2(8) . . . . ?
Bi1 C10 C15 C14 -178.8(4) . . . . ?
C11 C10 C15 C18 -173.6(6) . . . . ?
Bi1 C10 C15 C18 6.4(7) . . . . ?
C2 C7 N1 C9 171.1(5) . . . . ?
C2 C7 N1 C8 -68.9(6) . . . . ?
C2 C7 N1 Bi1 41.8(5) . . . . ?
C2 C1 Bi1 C10 -69.1(4) . . . . ?
C6 C1 Bi1 C10 115.2(5) . . . . ?
C2 C1 Bi1 N1 14.9(4) . . . . ?
C6 C1 Bi1 N1 -160.8(5) . . . . ?
C2 C1 Bi1 Br1 -164.6(4) . . . . ?
C6 C1 Bi1 Br1 19.7(5) . . . . ?
C15 C10 Bi1 C1 150.3(4) . . . . ?
C11 C10 Bi1 C1 -29.7(5) . . . . ?
C15 C10 Bi1 N1 78.6(4) . . . . ?
C11 C10 Bi1 N1 -101.4(4) . . . . ?
C15 C10 Bi1 Br1 -115.9(4) . . . . ?
C11 C10 Bi1 Br1 64.1(4) . . . . ?
C7 N1 Bi1 C1 -30.3(3) . . . . ?
C9 N1 Bi1 C1 -152.3(4) . . . . ?
C8 N1 Bi1 C1 84.7(4) . . . . ?
C7 N1 Bi1 C10 70.6(3) . . . . ?
C9 N1 Bi1 C10 -51.4(4) . . . . ?
C8 N1 Bi1 C10 -174.5(4) . . . . ?
C7 N1 Bi1 Br1 -28.1(6) . . . . ?
C9 N1 Bi1 Br1 -150.1(4) . . . . ?
C8 N1 Bi1 Br1 86.8(5) . . . . ?

####################################################################### 
# 
# 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_165ale
_database_code_depnum_ccdc_archive 'CCDC 1430429'
_audit_update_record             
;
2015-10-09 deposited with the CCDC.
2016-02-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C57 H14 Bi F30 N'
_chemical_formula_sum            'C57 H14 Bi F30 N'
_chemical_formula_weight         1491.67

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

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

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

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

_cell_length_a                   11.304(2)
_cell_length_b                   11.753(2)
_cell_length_c                   20.370(4)
_cell_angle_alpha                85.226(4)
_cell_angle_beta                 75.497(5)
_cell_angle_gamma                86.735(4)
_cell_volume                     2609.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    2844
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      19.24

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.899
_exptl_crystal_F_000             1432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_absorpt_coefficient_mu    3.528
_shelx_estimated_absorpt_T_min   0.511
_shelx_estimated_absorpt_T_max   0.569
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27664
_diffrn_reflns_av_unetI/netI     0.1130
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.035
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             10566
_reflns_number_gt                6506
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1465P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10566
_refine_ls_number_parameters     622
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.1385
_refine_ls_R_factor_gt           0.0894
_refine_ls_wR_factor_ref         0.2560
_refine_ls_wR_factor_gt          0.2231
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_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
C1 C 0.1650(18) 0.4096(15) 0.1853(10) 0.1079(14) Uani 1 1 d D . . . .
C2 C 0.0364(17) 0.4186(15) 0.1868(10) 0.1079(14) Uani 1 1 d D . . . .
C3 C 0.0128(18) 0.4275(15) 0.1188(10) 0.1079(14) Uani 1 1 d D . . . .
H3 H -0.0676 0.4308 0.1151 0.130 Uiso 1 1 calc R U . . .
C4 C 0.0944(18) 0.4307(15) 0.0677(11) 0.1079(14) Uani 1 1 d D . . . .
H4 H 0.0692 0.4427 0.0275 0.130 Uiso 1 1 calc R U . . .
C5 C 0.2161(18) 0.4196(15) 0.0597(10) 0.1079(14) Uani 1 1 d D . . . .
H5 H 0.2722 0.4189 0.0177 0.130 Uiso 1 1 calc R U . . .
C6 C 0.2503(18) 0.4088(15) 0.1247(10) 0.1079(14) Uani 1 1 d D . . . .
H6 H 0.3326 0.4012 0.1247 0.130 Uiso 1 1 calc R U . . .
C7 C -0.058(2) 0.4223(16) 0.2515(11) 0.1079(14) Uani 1 1 d . . . . .
C8 C -0.1237(18) 0.2308(15) 0.2557(11) 0.1079(14) Uani 1 1 d . . . . .
H8A H -0.1290 0.1583 0.2814 0.162 Uiso 1 1 calc R U . . .
H8B H -0.2043 0.2590 0.2537 0.162 Uiso 1 1 calc R U . . .
H8C H -0.0747 0.2219 0.2104 0.162 Uiso 1 1 calc R U . . .
C9 C -0.1472(19) 0.3148(16) 0.3575(11) 0.1079(14) Uani 1 1 d . . . . .
H9A H -0.1146 0.3672 0.3815 0.162 Uiso 1 1 calc R U . . .
H9B H -0.2286 0.3401 0.3556 0.162 Uiso 1 1 calc R U . . .
H9C H -0.1491 0.2401 0.3806 0.162 Uiso 1 1 calc R U . . .
C10 C 0.3840(10) 0.2718(9) 0.2337(5) 0.048(3) Uani 1 1 d . . . . .
C11 C 0.5061(12) 0.3026(10) 0.1988(6) 0.054(3) Uani 1 1 d . . . . .
C12 C 0.5853(13) 0.2292(11) 0.1601(7) 0.066(4) Uani 1 1 d . . . . .
H12 H 0.6621 0.2544 0.1370 0.079 Uiso 1 1 calc R U . . .
C13 C 0.5573(12) 0.1192(10) 0.1534(7) 0.062(3) Uani 1 1 d . . . . .
C14 C 0.4436(13) 0.0839(11) 0.1908(7) 0.066(4) Uani 1 1 d . . . . .
H14 H 0.4228 0.0087 0.1898 0.079 Uiso 1 1 calc R U . . .
C15 C 0.3599(10) 0.1583(10) 0.2298(6) 0.053(3) Uani 1 1 d . . . . .
C16 C 0.5553(11) 0.4166(12) 0.2065(7) 0.059(3) Uani 1 1 d . . . . .
C17 C 0.6115(14) 0.4880(12) 0.1510(9) 0.076(4) Uani 1 1 d . . . . .
C18 C 0.6724(13) 0.5856(15) 0.1588(10) 0.090(5) Uani 1 1 d . . . . .
C19 C 0.674(2) 0.6061(16) 0.2214(13) 0.1079(14) Uani 1 1 d . . . . .
C20 C 0.628(2) 0.5441(16) 0.2735(12) 0.1079(14) Uani 1 1 d . . . . .
C21 C 0.5647(13) 0.4458(13) 0.2670(9) 0.075(4) Uani 1 1 d . . . . .
C23 C 0.2402(17) 0.1075(15) 0.2683(10) 0.1079(14) Uani 1 1 d D . . . .
C24 C 0.2028(18) 0.1105(15) 0.3430(10) 0.1079(14) Uani 1 1 d D . . . .
C25 C 0.0860(18) 0.0516(15) 0.3721(10) 0.1079(14) Uani 1 1 d D . . . .
C26 C 0.0389(18) 0.0052(15) 0.3375(11) 0.1079(14) Uani 1 1 d D . . . .
C27 C 0.0536(18) -0.0023(15) 0.2715(11) 0.1079(14) Uani 1 1 d D . . . .
C28 C 0.1701(18) 0.0531(16) 0.2354(11) 0.1079(14) Uani 1 1 d D . . . .
C29 C 0.6430(13) 0.0377(11) 0.1111(7) 0.064(3) Uani 1 1 d . . . . .
C30 C 0.6097(14) -0.0329(13) 0.0706(8) 0.077(4) Uani 1 1 d . . . . .
C31 C 0.6910(16) -0.1019(12) 0.0288(9) 0.085(5) Uani 1 1 d . . . . .
C32 C 0.8102(17) -0.1079(13) 0.0302(10) 0.093(5) Uani 1 1 d . . . . .
C33 C 0.8488(14) -0.0431(13) 0.0711(9) 0.084(5) Uani 1 1 d . . . . .
C34 C 0.7702(15) 0.0334(12) 0.1084(8) 0.077(4) Uani 1 1 d . . . . .
C35 C 0.2769(11) 0.5566(10) 0.3056(6) 0.054(3) Uani 1 1 d . . . . .
C36 C 0.2931(12) 0.5620(10) 0.3727(7) 0.062(3) Uani 1 1 d . . . . .
C37 C 0.3357(13) 0.6574(11) 0.3902(7) 0.066(3) Uani 1 1 d . . . . .
H37 H 0.3486 0.6586 0.4335 0.079 Uiso 1 1 calc R U . . .
C38 C 0.3612(12) 0.7549(11) 0.3446(7) 0.060(3) Uani 1 1 d . . . . .
C39 C 0.3375(13) 0.7527(11) 0.2831(7) 0.064(3) Uani 1 1 d . . . . .
H39 H 0.3509 0.8174 0.2530 0.076 Uiso 1 1 calc R U . . .
C40 C 0.2947(11) 0.6591(10) 0.2640(7) 0.057(3) Uani 1 1 d . . . . .
C41 C 0.2645(15) 0.4669(10) 0.4262(7) 0.069(4) Uani 1 1 d . . . . .
C42 C 0.148(2) 0.4285(16) 0.4505(12) 0.1079(14) Uani 1 1 d . U . . .
C43 C 0.121(2) 0.3401(16) 0.5086(12) 0.1079(14) Uani 1 1 d . . . . .
C44 C 0.208(2) 0.3094(16) 0.5329(12) 0.1079(14) Uani 1 1 d . . . . .
C45 C 0.312(2) 0.3342(16) 0.5204(12) 0.1079(14) Uani 1 1 d . . . . .
C46 C 0.349(2) 0.4199(12) 0.4622(7) 0.085(5) Uani 1 1 d . . . . .
C47 C 0.4091(15) 0.8584(12) 0.3661(8) 0.070(4) Uani 1 1 d . . . . .
C48 C 0.3539(17) 0.9057(12) 0.4272(10) 0.083(5) Uani 1 1 d . . . . .
C49 C 0.394(2) 1.0039(15) 0.4495(11) 0.099(6) Uani 1 1 d . . . . .
C50 C 0.493(2) 1.0532(17) 0.4049(13) 0.1079(14) Uani 1 1 d . . . . .
C51 C 0.5521(16) 1.0094(15) 0.3474(10) 0.090(5) Uani 1 1 d . . . . .
C52 C 0.5033(16) 0.9111(14) 0.3299(9) 0.080(4) Uani 1 1 d . . . . .
C53 C 0.2608(12) 0.6757(11) 0.1958(8) 0.065(4) Uani 1 1 d . . . . .
C54 C 0.1349(13) 0.6789(12) 0.1928(9) 0.074(4) Uani 1 1 d . . . . .
C55 C 0.0990(14) 0.7012(13) 0.1360(10) 0.075(4) Uani 1 1 d . . . . .
C56 C 0.1826(16) 0.7197(13) 0.0756(10) 0.081(5) Uani 1 1 d . . . . .
C57 C 0.3031(16) 0.7205(14) 0.0755(9) 0.084(5) Uani 1 1 d . . . . .
C58 C 0.3435(13) 0.6975(13) 0.1349(7) 0.069(4) Uani 1 1 d . . . . .
N1 N -0.0689(13) 0.3101(15) 0.2875(10) 0.112(5) Uani 1 1 d . . . . .
F17 F 0.6051(10) 0.4657(8) 0.0882(5) 0.100(3) Uani 1 1 d . . . . .
F18 F 0.7244(10) 0.6476(8) 0.1040(7) 0.118(4) Uani 1 1 d . . . . .
F19 F 0.7379(14) 0.6987(12) 0.2270(8) 0.1617(17) Uani 1 1 d . . . . .
F20 F 0.6340(14) 0.5624(12) 0.3380(8) 0.1617(17) Uani 1 1 d . . . . .
F21 F 0.5190(9) 0.3777(10) 0.3228(5) 0.100(3) Uani 1 1 d . . . . .
F24 F 0.2584(14) 0.1573(12) 0.3738(8) 0.1617(17) Uani 1 1 d . . . . .
F25 F 0.0523(14) 0.0675(12) 0.4390(8) 0.1617(17) Uani 1 1 d . . . . .
F26 F -0.0887(14) -0.0393(12) 0.3652(8) 0.1617(17) Uani 1 1 d . . . . .
F27 F 0.0005(15) -0.0465(12) 0.2256(8) 0.1617(17) Uani 1 1 d . . . . .
F28 F 0.2024(12) 0.0548(11) 0.1653(9) 0.159(6) Uani 1 1 d . . . . .
F30 F 0.4884(9) -0.0350(8) 0.0704(5) 0.096(3) Uani 1 1 d . . . . .
F31 F 0.6497(10) -0.1725(9) -0.0090(6) 0.117(3) Uani 1 1 d . . . . .
F32 F 0.8894(10) -0.1795(8) -0.0094(6) 0.114(3) Uani 1 1 d . . . . .
F33 F 0.9676(9) -0.0452(9) 0.0717(6) 0.116(3) Uani 1 1 d . . . . .
F34 F 0.8132(8) 0.0964(9) 0.1485(6) 0.108(3) Uani 1 1 d . . . . .
F42 F 0.0602(14) 0.4702(12) 0.4216(8) 0.1617(17) Uani 1 1 d . . . . .
F43 F 0.0037(14) 0.3100(12) 0.5237(8) 0.1617(17) Uani 1 1 d . . . . .
F44 F 0.1810(13) 0.2262(12) 0.5899(8) 0.1617(17) Uani 1 1 d . . . . .
F45 F 0.4079(15) 0.2965(12) 0.5446(8) 0.1617(17) Uani 1 1 d . . . . .
F46 F 0.4648(11) 0.4556(8) 0.4455(5) 0.101(3) Uani 1 1 d . . . . .
F48 F 0.2529(10) 0.8589(8) 0.4713(5) 0.099(3) Uani 1 1 d . . . . .
F49 F 0.3352(13) 1.0462(9) 0.5066(6) 0.125(4) Uani 1 1 d . . . . .
F50 F 0.5333(14) 1.1502(9) 0.4247(7) 0.144(5) Uani 1 1 d . . . . .
F51 F 0.6456(12) 1.0585(11) 0.3065(7) 0.150(5) Uani 1 1 d . . . . .
F52 F 0.5664(9) 0.8742(8) 0.2679(6) 0.101(3) Uani 1 1 d . . . . .
F54 F 0.0511(8) 0.6645(8) 0.2527(5) 0.095(3) Uani 1 1 d . . . . .
F55 F -0.0180(8) 0.7028(9) 0.1355(6) 0.108(3) Uani 1 1 d . . . . .
F56 F 0.1510(10) 0.7357(9) 0.0168(5) 0.110(3) Uani 1 1 d . . . . .
F57 F 0.3892(10) 0.7374(12) 0.0185(5) 0.125(4) Uani 1 1 d . . . . .
F58 F 0.4595(8) 0.6957(9) 0.1311(5) 0.099(3) Uani 1 1 d . . . . .
Bi01 Bi 0.21402(4) 0.37934(4) 0.28542(2) 0.0547(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.36(2) . ?
C1 C2 1.44(2) . ?
C1 Bi01 2.239(18) . ?
C2 C3 1.47(2) . ?
C2 C7 1.47(3) . ?
C3 C4 1.21(2) . ?
C3 H3 0.9300 . ?
C4 C5 1.34(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.46(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.45(3) . ?
C8 N1 1.43(2) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 N1 1.48(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.390(16) . ?
C10 C11 1.437(17) . ?
C10 Bi01 2.309(11) . ?
C11 C12 1.356(18) . ?
C11 C16 1.514(17) . ?
C12 C13 1.372(18) . ?
C12 H12 0.9300 . ?
C13 C14 1.387(18) . ?
C13 C29 1.488(18) . ?
C14 C15 1.390(17) . ?
C14 H14 0.9300 . ?
C15 C23 1.51(2) . ?
C16 C21 1.34(2) . ?
C16 C17 1.39(2) . ?
C17 F17 1.347(18) . ?
C17 C18 1.41(2) . ?
C18 F18 1.307(19) . ?
C18 C19 1.32(3) . ?
C19 C20 1.25(3) . ?
C19 F19 1.37(2) . ?
C20 F20 1.37(2) . ?
C20 C21 1.43(2) . ?
C21 F21 1.342(18) . ?
C23 C28 1.37(2) . ?
C23 C24 1.48(2) . ?
C24 F24 1.18(2) . ?
C24 C25 1.49(2) . ?
C25 C26 1.167(19) . ?
C25 F25 1.35(2) . ?
C26 C27 1.32(2) . ?
C26 F26 1.52(2) . ?
C27 F27 1.38(2) . ?
C27 C28 1.49(2) . ?
C28 F28 1.38(2) . ?
C29 C30 1.35(2) . ?
C29 C34 1.42(2) . ?
C30 C31 1.37(2) . ?
C30 F30 1.374(17) . ?
C31 F31 1.351(18) . ?
C31 C32 1.35(2) . ?
C32 C33 1.34(2) . ?
C32 F32 1.351(17) . ?
C33 F33 1.345(17) . ?
C33 C34 1.36(2) . ?
C34 F34 1.339(18) . ?
C35 C40 1.408(17) . ?
C35 C36 1.432(18) . ?
C35 Bi01 2.338(12) . ?
C36 C37 1.352(18) . ?
C36 C41 1.484(18) . ?
C37 C38 1.410(18) . ?
C37 H37 0.9300 . ?
C38 C39 1.348(18) . ?
C38 C47 1.499(19) . ?
C39 C40 1.349(17) . ?
C39 H39 0.9300 . ?
C40 C53 1.526(19) . ?
C41 C42 1.37(2) . ?
C41 C46 1.41(2) . ?
C42 F42 1.33(2) . ?
C42 C43 1.49(3) . ?
C43 C44 1.23(3) . ?
C43 F43 1.35(2) . ?
C44 C45 1.19(3) . ?
C44 F44 1.44(2) . ?
C45 F45 1.34(2) . ?
C45 C46 1.48(3) . ?
C46 F46 1.34(2) . ?
C47 C52 1.29(2) . ?
C47 C48 1.39(2) . ?
C48 F48 1.37(2) . ?
C48 C49 1.41(2) . ?
C49 F49 1.31(2) . ?
C49 C50 1.38(3) . ?
C50 C51 1.32(3) . ?
C50 F50 1.38(2) . ?
C51 F51 1.300(19) . ?
C51 C52 1.42(2) . ?
C52 F52 1.377(19) . ?
C53 C58 1.37(2) . ?
C53 C54 1.439(18) . ?
C54 C55 1.32(2) . ?
C54 F54 1.349(18) . ?
C55 F55 1.324(16) . ?
C55 C56 1.36(2) . ?
C56 F56 1.329(18) . ?
C56 C57 1.36(2) . ?
C57 F57 1.323(18) . ?
C57 C58 1.40(2) . ?
C58 F58 1.293(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 120.1(17) . . ?
C6 C1 Bi01 122.6(14) . . ?
C2 C1 Bi01 117.0(14) . . ?
C1 C2 C3 113.2(16) . . ?
C1 C2 C7 121.3(18) . . ?
C3 C2 C7 125.5(18) . . ?
C4 C3 C2 122.2(19) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 130(2) . . ?
C3 C4 H4 115.0 . . ?
C5 C4 H4 115.0 . . ?
C4 C5 C6 112.4(18) . . ?
C4 C5 H5 123.8 . . ?
C6 C5 H5 123.8 . . ?
C1 C6 C5 121.9(18) . . ?
C1 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
N1 C7 C2 110.4(16) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 114.0(10) . . ?
C15 C10 Bi01 113.5(8) . . ?
C11 C10 Bi01 132.1(8) . . ?
C12 C11 C10 121.9(12) . . ?
C12 C11 C16 116.5(12) . . ?
C10 C11 C16 121.5(10) . . ?
C11 C12 C13 123.0(13) . . ?
C11 C12 H12 118.5 . . ?
C13 C12 H12 118.5 . . ?
C12 C13 C14 116.4(12) . . ?
C12 C13 C29 123.7(13) . . ?
C14 C13 C29 119.8(11) . . ?
C13 C14 C15 121.5(12) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C15 C10 122.7(11) . . ?
C14 C15 C23 115.6(12) . . ?
C10 C15 C23 121.7(11) . . ?
C21 C16 C17 115.4(14) . . ?
C21 C16 C11 121.2(13) . . ?
C17 C16 C11 122.5(12) . . ?
F17 C17 C16 119.4(13) . . ?
F17 C17 C18 118.9(15) . . ?
C16 C17 C18 121.7(16) . . ?
F18 C18 C19 125.0(18) . . ?
F18 C18 C17 117.9(18) . . ?
C19 C18 C17 117.1(18) . . ?
C20 C19 C18 125(2) . . ?
C20 C19 F19 119(2) . . ?
C18 C19 F19 116(2) . . ?
C19 C20 F20 125(2) . . ?
C19 C20 C21 119(2) . . ?
F20 C20 C21 116(2) . . ?
C16 C21 F21 119.2(14) . . ?
C16 C21 C20 121.8(17) . . ?
F21 C21 C20 118.9(16) . . ?
C28 C23 C24 119.9(17) . . ?
C28 C23 C15 120.9(17) . . ?
C24 C23 C15 119.1(15) . . ?
F24 C24 C23 122.8(19) . . ?
F24 C24 C25 126(2) . . ?
C23 C24 C25 111.3(16) . . ?
C26 C25 F25 131(2) . . ?
C26 C25 C24 121(2) . . ?
F25 C25 C24 107.6(17) . . ?
C25 C26 C27 137(2) . . ?
C25 C26 F26 121(2) . . ?
C27 C26 F26 101.1(16) . . ?
C26 C27 F27 141.6(19) . . ?
C26 C27 C28 107.9(17) . . ?
F27 C27 C28 110.5(17) . . ?
C23 C28 F28 119.7(17) . . ?
C23 C28 C27 123.0(18) . . ?
F28 C28 C27 117.1(17) . . ?
C30 C29 C34 114.9(13) . . ?
C30 C29 C13 124.0(13) . . ?
C34 C29 C13 121.0(13) . . ?
C29 C30 C31 123.2(15) . . ?
C29 C30 F30 118.8(12) . . ?
C31 C30 F30 118.0(14) . . ?
F31 C31 C32 120.0(14) . . ?
F31 C31 C30 119.6(15) . . ?
C32 C31 C30 120.1(16) . . ?
C33 C32 F32 120.4(17) . . ?
C33 C32 C31 119.6(15) . . ?
F32 C32 C31 119.9(16) . . ?
C32 C33 F33 120.6(15) . . ?
C32 C33 C34 120.4(16) . . ?
F33 C33 C34 118.8(16) . . ?
F34 C34 C33 118.1(15) . . ?
F34 C34 C29 120.2(12) . . ?
C33 C34 C29 121.4(15) . . ?
C40 C35 C36 115.5(11) . . ?
C40 C35 Bi01 130.6(9) . . ?
C36 C35 Bi01 113.8(8) . . ?
C37 C36 C35 120.1(12) . . ?
C37 C36 C41 116.7(13) . . ?
C35 C36 C41 123.2(12) . . ?
C36 C37 C38 121.7(13) . . ?
C36 C37 H37 119.1 . . ?
C38 C37 H37 119.1 . . ?
C39 C38 C37 118.1(12) . . ?
C39 C38 C47 122.0(12) . . ?
C37 C38 C47 119.8(12) . . ?
C38 C39 C40 121.6(12) . . ?
C38 C39 H39 119.2 . . ?
C40 C39 H39 119.2 . . ?
C39 C40 C35 122.5(12) . . ?
C39 C40 C53 114.5(11) . . ?
C35 C40 C53 122.9(11) . . ?
C42 C41 C46 114.6(16) . . ?
C42 C41 C36 121.9(16) . . ?
C46 C41 C36 123.0(15) . . ?
F42 C42 C41 119(2) . . ?
F42 C42 C43 121(2) . . ?
C41 C42 C43 120.0(19) . . ?
C44 C43 F43 133(2) . . ?
C44 C43 C42 116(2) . . ?
F43 C43 C42 111.6(19) . . ?
C45 C44 C43 134(3) . . ?
C45 C44 F44 110(2) . . ?
C43 C44 F44 115(2) . . ?
C44 C45 F45 134(2) . . ?
C44 C45 C46 115(2) . . ?
F45 C45 C46 111(2) . . ?
F46 C46 C41 120.1(13) . . ?
F46 C46 C45 119.3(18) . . ?
C41 C46 C45 120.6(19) . . ?
C52 C47 C48 114.6(15) . . ?
C52 C47 C38 123.4(16) . . ?
C48 C47 C38 122.0(14) . . ?
F48 C48 C47 121.4(13) . . ?
F48 C48 C49 114.1(17) . . ?
C47 C48 C49 124.5(18) . . ?
F49 C49 C50 123.9(19) . . ?
F49 C49 C48 121(2) . . ?
C50 C49 C48 115(2) . . ?
C51 C50 F50 121(2) . . ?
C51 C50 C49 123.4(19) . . ?
F50 C50 C49 116(2) . . ?
F51 C51 C50 121.6(19) . . ?
F51 C51 C52 121.3(19) . . ?
C50 C51 C52 116.9(17) . . ?
C47 C52 F52 121.0(15) . . ?
C47 C52 C51 125.9(17) . . ?
F52 C52 C51 113.2(16) . . ?
C58 C53 C54 115.2(14) . . ?
C58 C53 C40 123.9(12) . . ?
C54 C53 C40 120.6(14) . . ?
C55 C54 F54 119.9(14) . . ?
C55 C54 C53 123.6(16) . . ?
F54 C54 C53 116.4(14) . . ?
C54 C55 F55 121.6(17) . . ?
C54 C55 C56 120.5(14) . . ?
F55 C55 C56 118.0(15) . . ?
F56 C56 C55 122.4(15) . . ?
F56 C56 C57 119.0(17) . . ?
C55 C56 C57 118.6(15) . . ?
F57 C57 C56 121.8(16) . . ?
F57 C57 C58 116.1(15) . . ?
C56 C57 C58 122.0(16) . . ?
F58 C58 C53 120.9(12) . . ?
F58 C58 C57 119.1(14) . . ?
C53 C58 C57 120.1(14) . . ?
C8 N1 C7 112.9(17) . . ?
C8 N1 C9 105.7(16) . . ?
C7 N1 C9 111.6(16) . . ?
C1 Bi01 C10 89.3(6) . . ?
C1 Bi01 C35 104.4(6) . . ?
C10 Bi01 C35 108.8(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1(2) . . . . ?
Bi01 C1 C2 C3 -174.5(12) . . . . ?
C6 C1 C2 C7 -178.6(17) . . . . ?
Bi01 C1 C2 C7 7(2) . . . . ?
C1 C2 C3 C4 -2(3) . . . . ?
C7 C2 C3 C4 175.5(19) . . . . ?
C2 C3 C4 C5 5(3) . . . . ?
C3 C4 C5 C6 -4(3) . . . . ?
C2 C1 C6 C5 1(3) . . . . ?
Bi01 C1 C6 C5 175.0(12) . . . . ?
C4 C5 C6 C1 0(3) . . . . ?
C1 C2 C7 N1 -74(2) . . . . ?
C3 C2 C7 N1 108(2) . . . . ?
C15 C10 C11 C12 6.2(17) . . . . ?
Bi01 C10 C11 C12 -166.2(9) . . . . ?
C15 C10 C11 C16 -170.3(11) . . . . ?
Bi01 C10 C11 C16 17.3(17) . . . . ?
C10 C11 C12 C13 -3(2) . . . . ?
C16 C11 C12 C13 174.0(12) . . . . ?
C11 C12 C13 C14 -2(2) . . . . ?
C11 C12 C13 C29 179.9(13) . . . . ?
C12 C13 C14 C15 4(2) . . . . ?
C29 C13 C14 C15 -178.6(12) . . . . ?
C13 C14 C15 C10 0(2) . . . . ?
C13 C14 C15 C23 -179.4(13) . . . . ?
C11 C10 C15 C14 -5.0(17) . . . . ?
Bi01 C10 C15 C14 168.9(10) . . . . ?
C11 C10 C15 C23 174.7(13) . . . . ?
Bi01 C10 C15 C23 -11.5(16) . . . . ?
C12 C11 C16 C21 -115.5(14) . . . . ?
C10 C11 C16 C21 61.2(17) . . . . ?
C12 C11 C16 C17 53.6(18) . . . . ?
C10 C11 C16 C17 -129.7(13) . . . . ?
C21 C16 C17 F17 -179.1(13) . . . . ?
C11 C16 C17 F17 11(2) . . . . ?
C21 C16 C17 C18 -1(2) . . . . ?
C11 C16 C17 C18 -170.6(13) . . . . ?
F17 C17 C18 F18 -3(2) . . . . ?
C16 C17 C18 F18 179.1(13) . . . . ?
F17 C17 C18 C19 178.4(15) . . . . ?
C16 C17 C18 C19 0(2) . . . . ?
F18 C18 C19 C20 -177.1(19) . . . . ?
C17 C18 C19 C20 2(3) . . . . ?
F18 C18 C19 F19 -1(3) . . . . ?
C17 C18 C19 F19 177.5(15) . . . . ?
C18 C19 C20 F20 177.2(19) . . . . ?
F19 C19 C20 F20 2(3) . . . . ?
C18 C19 C20 C21 -3(3) . . . . ?
F19 C19 C20 C21 -178.3(16) . . . . ?
C17 C16 C21 F21 -176.2(13) . . . . ?
C11 C16 C21 F21 -6(2) . . . . ?
C17 C16 C21 C20 0(2) . . . . ?
C11 C16 C21 C20 169.9(14) . . . . ?
C19 C20 C21 C16 2(3) . . . . ?
F20 C20 C21 C16 -178.2(15) . . . . ?
C19 C20 C21 F21 178.0(18) . . . . ?
F20 C20 C21 F21 -2(2) . . . . ?
C14 C15 C23 C28 -54(2) . . . . ?
C10 C15 C23 C28 126.1(17) . . . . ?
C14 C15 C23 C24 121.8(16) . . . . ?
C10 C15 C23 C24 -58(2) . . . . ?
C28 C23 C24 F24 -179(2) . . . . ?
C15 C23 C24 F24 5(3) . . . . ?
C28 C23 C24 C25 -1(3) . . . . ?
C15 C23 C24 C25 -177.2(14) . . . . ?
F24 C24 C25 C26 -178(2) . . . . ?
C23 C24 C25 C26 4(3) . . . . ?
F24 C24 C25 F25 4(3) . . . . ?
C23 C24 C25 F25 -174.2(16) . . . . ?
F25 C25 C26 C27 168(2) . . . . ?
C24 C25 C26 C27 -9(4) . . . . ?
F25 C25 C26 F26 7(4) . . . . ?
C24 C25 C26 F26 -170.9(16) . . . . ?
C25 C26 C27 F27 -174(3) . . . . ?
F26 C26 C27 F27 -10(3) . . . . ?
C25 C26 C27 C28 9(4) . . . . ?
F26 C26 C27 C28 172.8(14) . . . . ?
C24 C23 C28 F28 177.1(17) . . . . ?
C15 C23 C28 F28 -7(3) . . . . ?
C24 C23 C28 C27 2(3) . . . . ?
C15 C23 C28 C27 177.6(16) . . . . ?
C26 C27 C28 C23 -4(3) . . . . ?
F27 C27 C28 C23 177.8(18) . . . . ?
C26 C27 C28 F28 -179.7(17) . . . . ?
F27 C27 C28 F28 2(2) . . . . ?
C12 C13 C29 C30 -137.9(16) . . . . ?
C14 C13 C29 C30 44(2) . . . . ?
C12 C13 C29 C34 39(2) . . . . ?
C14 C13 C29 C34 -138.8(15) . . . . ?
C34 C29 C30 C31 -1(2) . . . . ?
C13 C29 C30 C31 175.6(15) . . . . ?
C34 C29 C30 F30 179.6(13) . . . . ?
C13 C29 C30 F30 -3(2) . . . . ?
C29 C30 C31 F31 178.3(15) . . . . ?
F30 C30 C31 F31 -3(2) . . . . ?
C29 C30 C31 C32 5(3) . . . . ?
F30 C30 C31 C32 -176.1(16) . . . . ?
F31 C31 C32 C33 -175.6(16) . . . . ?
C30 C31 C32 C33 -2(3) . . . . ?
F31 C31 C32 F32 4(3) . . . . ?
C30 C31 C32 F32 177.5(16) . . . . ?
F32 C32 C33 F33 2(3) . . . . ?
C31 C32 C33 F33 -177.9(16) . . . . ?
F32 C32 C33 C34 176.6(16) . . . . ?
C31 C32 C33 C34 -4(3) . . . . ?
C32 C33 C34 F34 -179.9(16) . . . . ?
F33 C33 C34 F34 -6(2) . . . . ?
C32 C33 C34 C29 7(3) . . . . ?
F33 C33 C34 C29 -178.4(14) . . . . ?
C30 C29 C34 F34 -177.3(14) . . . . ?
C13 C29 C34 F34 6(2) . . . . ?
C30 C29 C34 C33 -5(2) . . . . ?
C13 C29 C34 C33 178.3(14) . . . . ?
C40 C35 C36 C37 -6.8(18) . . . . ?
Bi01 C35 C36 C37 176.4(10) . . . . ?
C40 C35 C36 C41 172.8(12) . . . . ?
Bi01 C35 C36 C41 -4.0(16) . . . . ?
C35 C36 C37 C38 2(2) . . . . ?
C41 C36 C37 C38 -177.4(13) . . . . ?
C36 C37 C38 C39 3(2) . . . . ?
C36 C37 C38 C47 -179.6(13) . . . . ?
C37 C38 C39 C40 -2(2) . . . . ?
C47 C38 C39 C40 179.9(13) . . . . ?
C38 C39 C40 C35 -3(2) . . . . ?
C38 C39 C40 C53 174.1(13) . . . . ?
C36 C35 C40 C39 7.2(19) . . . . ?
Bi01 C35 C40 C39 -176.7(10) . . . . ?
C36 C35 C40 C53 -169.4(12) . . . . ?
Bi01 C35 C40 C53 6.8(18) . . . . ?
C37 C36 C41 C42 117.1(17) . . . . ?
C35 C36 C41 C42 -62.5(19) . . . . ?
C37 C36 C41 C46 -53.8(18) . . . . ?
C35 C36 C41 C46 126.6(15) . . . . ?
C46 C41 C42 F42 177.8(15) . . . . ?
C36 C41 C42 F42 6(3) . . . . ?
C46 C41 C42 C43 -3(2) . . . . ?
C36 C41 C42 C43 -174.4(15) . . . . ?
F42 C42 C43 C44 -178.1(19) . . . . ?
C41 C42 C43 C44 2(3) . . . . ?
F42 C42 C43 F43 2(3) . . . . ?
C41 C42 C43 F43 -177.6(16) . . . . ?
F43 C43 C44 C45 180(2) . . . . ?
C42 C43 C44 C45 0(4) . . . . ?
F43 C43 C44 F44 -1(4) . . . . ?
C42 C43 C44 F44 178.5(16) . . . . ?
C43 C44 C45 F45 -176(2) . . . . ?
F44 C44 C45 F45 5(4) . . . . ?
C43 C44 C45 C46 -1(4) . . . . ?
F44 C44 C45 C46 -180.0(14) . . . . ?
C42 C41 C46 F46 -176.4(14) . . . . ?
C36 C41 C46 F46 -5(2) . . . . ?
C42 C41 C46 C45 1(2) . . . . ?
C36 C41 C46 C45 172.9(14) . . . . ?
C44 C45 C46 F46 178.3(18) . . . . ?
F45 C45 C46 F46 -6(2) . . . . ?
C44 C45 C46 C41 0(3) . . . . ?
F45 C45 C46 C41 176.5(14) . . . . ?
C39 C38 C47 C52 -51(2) . . . . ?
C37 C38 C47 C52 131.0(15) . . . . ?
C39 C38 C47 C48 128.3(15) . . . . ?
C37 C38 C47 C48 -49(2) . . . . ?
C52 C47 C48 F48 -179.8(13) . . . . ?
C38 C47 C48 F48 1(2) . . . . ?
C52 C47 C48 C49 1(2) . . . . ?
C38 C47 C48 C49 -179.0(14) . . . . ?
F48 C48 C49 F49 -2(2) . . . . ?
C47 C48 C49 F49 177.6(15) . . . . ?
F48 C48 C49 C50 -178.6(15) . . . . ?
C47 C48 C49 C50 1(2) . . . . ?
F49 C49 C50 C51 179.9(18) . . . . ?
C48 C49 C50 C51 -4(3) . . . . ?
F49 C49 C50 F50 2(3) . . . . ?
C48 C49 C50 F50 178.9(15) . . . . ?
F50 C50 C51 F51 -3(3) . . . . ?
C49 C50 C51 F51 179.8(17) . . . . ?
F50 C50 C51 C52 -178.4(15) . . . . ?
C49 C50 C51 C52 4(3) . . . . ?
C48 C47 C52 F52 -179.6(13) . . . . ?
C38 C47 C52 F52 0(2) . . . . ?
C48 C47 C52 C51 0(2) . . . . ?
C38 C47 C52 C51 179.7(14) . . . . ?
F51 C51 C52 C47 -178.0(15) . . . . ?
C50 C51 C52 C47 -2(3) . . . . ?
F51 C51 C52 F52 2(2) . . . . ?
C50 C51 C52 F52 177.2(16) . . . . ?
C39 C40 C53 C58 65.3(17) . . . . ?
C35 C40 C53 C58 -117.9(15) . . . . ?
C39 C40 C53 C54 -109.2(14) . . . . ?
C35 C40 C53 C54 67.6(17) . . . . ?
C58 C53 C54 C55 0(2) . . . . ?
C40 C53 C54 C55 174.9(13) . . . . ?
C58 C53 C54 F54 -176.1(12) . . . . ?
C40 C53 C54 F54 -1.1(18) . . . . ?
F54 C54 C55 F55 -4(2) . . . . ?
C53 C54 C55 F55 179.7(13) . . . . ?
F54 C54 C55 C56 177.8(14) . . . . ?
C53 C54 C55 C56 2(2) . . . . ?
C54 C55 C56 F56 175.9(14) . . . . ?
F55 C55 C56 F56 -2(2) . . . . ?
C54 C55 C56 C57 -3(2) . . . . ?
F55 C55 C56 C57 178.7(14) . . . . ?
F56 C56 C57 F57 0(2) . . . . ?
C55 C56 C57 F57 179.6(15) . . . . ?
F56 C56 C57 C58 -176.1(15) . . . . ?
C55 C56 C57 C58 3(2) . . . . ?
C54 C53 C58 F58 -179.2(13) . . . . ?
C40 C53 C58 F58 6(2) . . . . ?
C54 C53 C58 C57 0(2) . . . . ?
C40 C53 C58 C57 -174.9(13) . . . . ?
F57 C57 C58 F58 1(2) . . . . ?
C56 C57 C58 F58 177.6(15) . . . . ?
F57 C57 C58 C53 -178.0(14) . . . . ?
C56 C57 C58 C53 -1(3) . . . . ?
C2 C7 N1 C8 -71(2) . . . . ?
C2 C7 N1 C9 170.5(16) . . . . ?

_refine_diff_density_max         1.986
_refine_diff_density_min         -1.679
_refine_diff_density_rms         0.173

_shelxl_version_number           2014/6

