# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1440442'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         
'3(C27 H36 Bi N12 S6), Bi6 C12 F36 O44 S12, 3(C F3 O3 S)'
_chemical_formula_sum            'C96 H108 Bi9 F45 N36 O53 S33'
_chemical_formula_weight         6408.07
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      trigonal
_space_group_IT_number           167
_space_group_name_H-M_alt        'R -3 c'
_space_group_name_Hall           '-R 3 2"c'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y,x-y,z
3 -x+y,-x,z
4 x-y,-y,-z+1/2
5 -x,-x+y,-z+1/2
6 y,x,-z+1/2
7 -x,-y,-z
8 y,-x+y,-z
9 x-y,x,-z
10 -x+y,y,z-1/2
11 x,x-y,z-1/2
12 -y,-x,z-1/2
13 x+1/3,y+2/3,z+2/3
14 -y+1/3,x-y+2/3,z+2/3
15 -x+y+1/3,-x+2/3,z+2/3
16 x-y+1/3,-y+2/3,-z+7/6
17 -x+1/3,-x+y+2/3,-z+7/6
18 y+1/3,x+2/3,-z+7/6
19 -x+1/3,-y+2/3,-z+2/3
20 y+1/3,-x+y+2/3,-z+2/3
21 x-y+1/3,x+2/3,-z+2/3
22 -x+y+1/3,y+2/3,z+1/6
23 x+1/3,x-y+2/3,z+1/6
24 -y+1/3,-x+2/3,z+1/6
25 x+2/3,y+1/3,z+1/3
26 -y+2/3,x-y+1/3,z+1/3
27 -x+y+2/3,-x+1/3,z+1/3
28 x-y+2/3,-y+1/3,-z+5/6
29 -x+2/3,-x+y+1/3,-z+5/6
30 y+2/3,x+1/3,-z+5/6
31 -x+2/3,-y+1/3,-z+1/3
32 y+2/3,-x+y+1/3,-z+1/3
33 x-y+2/3,x+1/3,-z+1/3
34 -x+y+2/3,y+1/3,z-1/6
35 x+2/3,x-y+1/3,z-1/6
36 -y+2/3,-x+1/3,z-1/6

_symmetry_Int_Tables_number      167
_cell_length_a                   30.7421(7)
_cell_length_b                   30.7421(7)
_cell_length_c                   70.888(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     58019(2)
_cell_formula_units_Z            12
_cell_measurement_reflns_used    10175
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.0800
_cell_measurement_theta_min      4.1510
_exptl_absorpt_coefficient_mu    20.189
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.53444
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    2.2006
_exptl_crystal_F_000             36339.3471
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0549
_diffrn_reflns_av_unetI/netI     0.0517
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       37
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_l_max       63
_diffrn_reflns_limit_l_min       -85
_diffrn_reflns_number            42164
_diffrn_reflns_theta_full        71.2234
_diffrn_reflns_theta_max         71.22
_diffrn_reflns_theta_min         4.15
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9903
_diffrn_measured_fraction_theta_max 0.9903
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -39.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  116.0000   89.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -28.00    0.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   65.00  130.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -       55.1553  167.0000  144.0000 65

#__ type_ start__ end____ width___ exp.time_
  4 omega   51.00  120.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -       55.1553   57.0000 -150.0000 69

#__ type_ start__ end____ width___ exp.time_
  5 omega   39.00   75.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega   52.00   88.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -25.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
  7 omega   62.00   99.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -50.0000 -180.0000 37

#__ type_ start__ end____ width___ exp.time_
  8 omega  116.00  167.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      110.3105  111.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
  9 omega   40.00   89.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega  108.00  178.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -12.0000  -30.0000 70

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   63.00   1.0000    3.8900
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -12.0000  -30.0000 26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0428667000
_diffrn_orient_matrix_UB_12      -0.0402036000
_diffrn_orient_matrix_UB_13      0.0121212000
_diffrn_orient_matrix_UB_21      -0.0098272000
_diffrn_orient_matrix_UB_22      0.0405409000
_diffrn_orient_matrix_UB_23      0.0083686000
_diffrn_orient_matrix_UB_31      -0.0376352000
_diffrn_orient_matrix_UB_32      -0.0093045000
_diffrn_orient_matrix_UB_33      -0.0159685000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              32
_reflns_limit_h_min              0
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              85
_reflns_limit_l_min              -85
_reflns_number_gt                10295
_reflns_number_total             12404
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.6938
_refine_diff_density_min         -1.7320
_refine_diff_density_rms         0.2300
_refine_ls_d_res_high            0.8143
_refine_ls_d_res_low             10.6436
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0456
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    57
_refine_ls_number_parameters     823
_refine_ls_number_reflns         12404
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.0456
_refine_ls_shift/su_max          0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0452P)²+111.0811P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0918
_refine_ls_wR_factor_ref         0.0975
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C14(H14a,H14b), C23(H23a,H23b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6), C7(H7), C12(H12), C13(H13), C16(H16), C17(H17),
 C21(H21), C22(H22), C25(H25), C26(H26)
2.c Idealised Me refined as rotating group:
 C8(H8a,H8b,H8c), C9(H9a,H9b,H9c), C11(H11a,H11b,H11c), C18(H18a,H18b,H18c),
 C20(H20a,H20b,H20c), C27(H27a,H27b,H27c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Bi1 Bi 0.269246(10) 0.321415(10) 0.495409(4) 0.02546(8) Uani 1.000000 1 . . .
S1 S 0.24961(7) 0.33616(7) 0.53123(2) 0.0290(4) Uani 1.000000 1 . . .
S2 S 0.35961(7) 0.41754(8) 0.49858(3) 0.0357(4) Uani 1.000000 1 . . .
S3 S 0.29918(7) 0.25379(7) 0.51148(2) 0.0310(4) Uani 1.000000 1 . . .
S4 S 0.17111(7) 0.24396(7) 0.49596(2) 0.0304(4) Uani 1.000000 1 . . .
S5 S 0.27818(8) 0.31013(7) 0.45359(3) 0.0362(4) Uani 1.000000 1 . . .
S6 S 0.22098(7) 0.37169(7) 0.48619(2) 0.0291(4) Uani 1.000000 1 . . .
N1 N 0.2678(2) 0.2732(2) 0.55265(8) 0.0281(13) Uani 1.000000 1 . . .
N2 N 0.3338(2) 0.3461(2) 0.54922(8) 0.0261(12) Uani 1.000000 1 . . .
N3 N 0.4030(2) 0.3995(2) 0.52956(8) 0.0280(13) Uani 1.000000 1 . . .
N4 N 0.4391(3) 0.4030(3) 0.50297(9) 0.0393(16) Uani 1.000000 1 . . .
N5 N 0.3470(2) 0.2352(2) 0.48294(9) 0.0298(13) Uani 1.000000 1 . . .
N6 N 0.2656(2) 0.1900(2) 0.48084(8) 0.0268(13) Uani 1.000000 1 . . .
N7 N 0.1522(2) 0.2246(2) 0.45807(8) 0.0286(13) Uani 1.000000 1 . . .
N8 N 0.1895(2) 0.1877(2) 0.47049(8) 0.0254(12) Uani 1.000000 1 . . .
N9 N 0.3712(2) 0.3737(3) 0.43873(9) 0.0339(14) Uani 1.000000 1 . . .
N10 N 0.3284(2) 0.4111(2) 0.44433(8) 0.0284(13) Uani 1.000000 1 . . .
N11 N 0.2955(2) 0.4491(2) 0.46545(8) 0.0284(13) Uani 1.000000 1 . . .
N12 N 0.2894(2) 0.4697(2) 0.49402(8) 0.0301(14) Uani 1.000000 1 . . .
C1 C 0.2845(3) 0.3179(3) 0.54450(10) 0.0271(15) Uani 1.000000 1 . . .
C2 C 0.3061(3) 0.2732(3) 0.56311(10) 0.0316(16) Uani 1.000000 1 . . .
H2 H 0.3037(3) 0.2470(3) 0.57042(10) 0.038(2) Uiso 1.000000 1 R . .
C3 C 0.3467(3) 0.3178(3) 0.56063(10) 0.0281(15) Uani 1.000000 1 . . .
H3 H 0.3784(3) 0.3283(3) 0.56568(10) 0.0337(18) Uiso 1.000000 1 R . .
C4 C 0.3684(3) 0.3982(3) 0.54348(10) 0.0266(15) Uani 1.000000 1 . . .
H4a H 0.3495(3) 0.4129(3) 0.53832(10) 0.0319(18) Uiso 1.000000 1 R . .
H4b H 0.3869(3) 0.4178(3) 0.55440(10) 0.0319(18) Uiso 1.000000 1 R . .
C5 C 0.4005(3) 0.4059(3) 0.51060(10) 0.0301(16) Uani 1.000000 1 . . .
C6 C 0.4447(3) 0.3950(3) 0.53319(11) 0.0353(17) Uani 1.000000 1 . . .
H6 H 0.4553(3) 0.3912(3) 0.54504(11) 0.042(2) Uiso 1.000000 1 R . .
C7 C 0.4671(3) 0.3970(3) 0.51691(12) 0.043(2) Uani 1.000000 1 . . .
H7 H 0.4959(3) 0.3949(3) 0.51523(12) 0.052(2) Uiso 1.000000 1 R . .
C8 C 0.4517(4) 0.4091(4) 0.48293(12) 0.058(3) Uani 1.000000 1 . . .
H8a H 0.468(2) 0.4440(5) 0.4797(2) 0.088(4) Uiso 1.000000 1 GR . .
H8b H 0.474(2) 0.396(3) 0.4803(2) 0.088(4) Uiso 1.000000 1 GR . .
H8c H 0.4215(5) 0.391(2) 0.47563(12) 0.088(4) Uiso 1.000000 1 GR . .
C9 C 0.2163(3) 0.2308(3) 0.55090(11) 0.0378(18) Uani 1.000000 1 . . .
H9a H 0.2101(8) 0.2194(15) 0.5380(2) 0.057(3) Uiso 1.000000 1 GR . .
H9b H 0.2122(7) 0.2039(9) 0.5589(6) 0.057(3) Uiso 1.000000 1 GR . .
H9c H 0.1930(3) 0.2413(7) 0.5546(8) 0.057(3) Uiso 1.000000 1 GR . .
C10 C 0.3036(3) 0.2264(3) 0.49148(10) 0.0275(15) Uani 1.000000 1 . . .
C11 C 0.3971(3) 0.2697(3) 0.49016(12) 0.0363(18) Uani 1.000000 1 . . .
H11a H 0.4031(9) 0.2558(10) 0.5013(5) 0.054(3) Uiso 1.000000 1 GR . .
H11b H 0.4217(3) 0.2748(17) 0.4807(3) 0.054(3) Uiso 1.000000 1 GR . .
H11c H 0.3995(7) 0.3013(7) 0.4932(8) 0.054(3) Uiso 1.000000 1 GR . .
C12 C 0.3357(3) 0.2034(3) 0.46773(11) 0.0357(18) Uani 1.000000 1 . . .
H12 H 0.3589(3) 0.2016(3) 0.45978(11) 0.043(2) Uiso 1.000000 1 R . .
C13 C 0.2863(3) 0.1757(3) 0.46637(11) 0.0386(19) Uani 1.000000 1 . . .
H13 H 0.2685(3) 0.1511(3) 0.45735(11) 0.046(2) Uiso 1.000000 1 R . .
C14 C 0.2125(3) 0.1691(3) 0.48398(10) 0.0288(16) Uani 1.000000 1 . . .
H14a H 0.1959(3) 0.1328(3) 0.48303(10) 0.0346(19) Uiso 1.000000 1 R . .
H14b H 0.2072(3) 0.1774(3) 0.49666(10) 0.0346(19) Uiso 1.000000 1 R . .
C15 C 0.1708(3) 0.2183(3) 0.47454(10) 0.0270(15) Uani 1.000000 1 . . .
C16 C 0.1817(3) 0.1747(3) 0.45150(10) 0.0294(16) Uani 1.000000 1 . . .
H16 H 0.1907(3) 0.1537(3) 0.44529(10) 0.0353(19) Uiso 1.000000 1 R . .
C17 C 0.1593(3) 0.1975(3) 0.44386(11) 0.0351(18) Uani 1.000000 1 . . .
H17 H 0.1499(3) 0.1958(3) 0.43129(11) 0.042(2) Uiso 1.000000 1 R . .
C18 C 0.1294(3) 0.2561(3) 0.45549(12) 0.041(2) Uani 1.000000 1 . . .
H18a H 0.1086(18) 0.2524(18) 0.4662(4) 0.062(3) Uiso 1.000000 1 GR . .
H18b H 0.1553(3) 0.2907(4) 0.4544(9) 0.062(3) Uiso 1.000000 1 GR . .
H18c H 0.1093(19) 0.2460(15) 0.4442(5) 0.062(3) Uiso 1.000000 1 GR . .
C19 C 0.3266(3) 0.3659(3) 0.44591(9) 0.0287(16) Uani 1.000000 1 . . .
C20 C 0.3858(4) 0.3354(4) 0.43755(13) 0.051(2) Uani 1.000000 1 . . .
H20a H 0.3568(6) 0.3029(4) 0.4395(10) 0.076(4) Uiso 1.000000 1 GR . .
H20b H 0.400(2) 0.3366(17) 0.4253(4) 0.076(4) Uiso 1.000000 1 GR . .
H20c H 0.4105(19) 0.3416(15) 0.4470(6) 0.076(4) Uiso 1.000000 1 GR . .
C21 C 0.3994(3) 0.4230(3) 0.43294(12) 0.0382(18) Uani 1.000000 1 . . .
H21 H 0.4313(3) 0.4375(3) 0.42762(12) 0.046(2) Uiso 1.000000 1 R . .
C22 C 0.3740(3) 0.4460(3) 0.43616(10) 0.0370(18) Uani 1.000000 1 . . .
H22 H 0.3844(3) 0.4794(3) 0.43350(10) 0.044(2) Uiso 1.000000 1 R . .
C23 C 0.2866(3) 0.4195(3) 0.44828(9) 0.0306(16) Uani 1.000000 1 . . .
H23a H 0.2822(3) 0.4370(3) 0.43773(9) 0.037(2) Uiso 1.000000 1 R . .
H23b H 0.2560(3) 0.3874(3) 0.44970(9) 0.037(2) Uiso 1.000000 1 R . .
C24 C 0.2701(3) 0.4306(3) 0.48187(10) 0.0264(15) Uani 1.000000 1 . . .
C25 C 0.3300(3) 0.4996(3) 0.46741(11) 0.0375(18) Uani 1.000000 1 . . .
H25 H 0.3521(3) 0.5208(3) 0.45825(11) 0.045(2) Uiso 1.000000 1 R . .
C26 C 0.3255(3) 0.5121(3) 0.48512(11) 0.0390(19) Uani 1.000000 1 . . .
H26 H 0.3436(3) 0.5439(3) 0.49044(11) 0.047(2) Uiso 1.000000 1 R . .
C27 C 0.2748(3) 0.4670(3) 0.51398(10) 0.040(2) Uani 1.000000 1 . . .
H27a H 0.2521(18) 0.480(2) 0.51530(17) 0.061(3) Uiso 1.000000 1 GR . .
H27b H 0.259(2) 0.4327(4) 0.5181(3) 0.061(3) Uiso 1.000000 1 GR . .
H27c H 0.3042(4) 0.4867(18) 0.52150(15) 0.061(3) Uiso 1.000000 1 GR . .
Bi2 Bi 0.318692(10) 0.591222(9) 0.542189(3) 0.02167(7) Uani 1.000000 1 . . .
Bi3 Bi 0.392078(10) 0.649383(10) 0.584678(3) 0.02232(7) Uani 1.000000 1 . . .
S7 S 0.22102(7) 0.56815(7) 0.50493(3) 0.0327(4) Uani 1.000000 1 . . .
S8 S 0.20393(7) 0.47373(6) 0.56299(2) 0.0276(4) Uani 1.000000 1 . . .
S9 S 0.39278(7) 0.53083(6) 0.56492(2) 0.0255(3) Uani 1.000000 1 . . .
S10 S 0.45356(7) 0.75336(7) 0.62101(2) 0.0319(4) Uani 1.000000 1 . . .
F1 F 0.2678(3) 0.6227(3) 0.47576(9) 0.083(2) Uani 1.000000 1 . . .
F2 F 0.2362(3) 0.5436(3) 0.47162(8) 0.084(2) Uani 1.000000 1 . . .
F3 F 0.1883(2) 0.5761(2) 0.47199(8) 0.0647(16) Uani 1.000000 1 . . .
F4 F 0.1999(3) 0.4120(2) 0.58906(8) 0.0720(19) Uani 1.000000 1 . . .
F5 F 0.2325(3) 0.4072(2) 0.56315(8) 0.0683(18) Uani 1.000000 1 . . .
F6 F 0.2740(2) 0.4697(3) 0.58220(7) 0.0651(17) Uani 1.000000 1 . . .
F7 F 0.4641(2) 0.5917(2) 0.54227(8) 0.0623(16) Uani 1.000000 1 . . .
F8 F 0.4375(2) 0.5134(2) 0.53712(9) 0.0686(18) Uani 1.000000 1 . . .
F9 F 0.4848(2) 0.5501(3) 0.56066(10) 0.080(2) Uani 1.000000 1 . . .
F10 F 0.3793(2) 0.7335(3) 0.64347(9) 0.081(2) Uani 1.000000 1 . . .
F11 F 0.4443(2) 0.8061(2) 0.64760(8) 0.0598(15) Uani 1.000000 1 . . .
F12 F 0.4435(3) 0.7397(3) 0.65704(7) 0.0741(19) Uani 1.000000 1 . . .
O1 O 0.333333333333 0.666666666667 0.5339(2) 0.064(4) Uani 1.000000 3 S T P
O2 O 0.333333333333 0.666666666667 0.5973(2) 0.066(4) Uani 1.000000 3 S T P
O3 O 0.3178(2) 0.5966(3) 0.57294(9) 0.067(2) Uani 1.000000 1 . . .
O4 O 0.3973(3) 0.6492(2) 0.55214(9) 0.070(3) Uani 1.000000 1 . . .
O5 O 0.2409(2) 0.4999(2) 0.54868(7) 0.0363(12) Uani 1.000000 1 . . .
O6 O 0.1560(2) 0.4357(2) 0.55628(10) 0.0512(16) Uani 1.000000 1 . . .
O7 O 0.2025(2) 0.50583(19) 0.57774(7) 0.0349(12) Uani 1.000000 1 . . .
O8 O 0.2653(2) 0.5669(2) 0.51056(8) 0.0434(15) Uani 1.000000 1 . . .
O9 O 0.2200(2) 0.6117(2) 0.51178(7) 0.0395(13) Uani 1.000000 1 . . .
O10 O 0.1753(2) 0.5213(2) 0.50644(10) 0.0571(18) Uani 1.000000 1 . . .
O11 O 0.4112(2) 0.57290(19) 0.57762(7) 0.0336(12) Uani 1.000000 1 . . .
O12 O 0.3811(2) 0.4838(2) 0.57320(8) 0.0394(13) Uani 1.000000 1 . . .
O13 O 0.3568(2) 0.52910(19) 0.55133(7) 0.0327(11) Uani 1.000000 1 . . .
O14 O 0.4275(2) 0.7000(2) 0.61724(8) 0.0396(13) Uani 1.000000 1 . . .
O15 O 0.5063(2) 0.7750(2) 0.62449(8) 0.0428(14) Uani 1.000000 1 . . .
O16 O 0.4384(3) 0.7807(3) 0.60883(9) 0.063(2) Uani 1.000000 1 . . .
C28 C 0.2291(4) 0.5778(4) 0.47952(13) 0.050(2) Uani 1.000000 1 . . .
C29 C 0.2286(4) 0.4385(3) 0.57513(11) 0.044(2) Uani 1.000000 1 . . .
C30 C 0.4472(3) 0.5471(3) 0.55066(13) 0.043(2) Uani 1.000000 1 . . .
C31 C 0.4289(3) 0.7582(3) 0.64333(12) 0.041(2) Uani 1.000000 1 . . .
S11 S 0.49677(7) 0.56391(8) 0.41445(3) 0.0367(4) Uani 1.000000 1 . . .
F13 F 0.5130(3) 0.6452(2) 0.39671(9) 0.074(2) Uani 1.000000 1 . . .
F14 F 0.5244(3) 0.5950(3) 0.37969(8) 0.080(2) Uani 1.000000 1 . . .
F15 F 0.4498(2) 0.5778(2) 0.38617(9) 0.0671(18) Uani 1.000000 1 . . .
O17 O 0.5473(2) 0.5935(2) 0.42142(8) 0.0406(14) Uani 1.000000 1 . . .
O19 O 0.4589(2) 0.5642(3) 0.42623(10) 0.0606(19) Uani 1.000000 1 . . .
O20 O 0.4833(3) 0.5149(2) 0.40739(9) 0.0566(18) Uani 1.000000 1 . . .
C32 C 0.4961(3) 0.5970(3) 0.39328(13) 0.046(2) Uani 1.000000 1 . . .


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 S1 2.7005(17) . ?
Bi1 S2 2.879(2) . ?
Bi1 S3 2.8947(19) . ?
Bi1 S4 2.7550(19) . ?
Bi1 S6 2.7038(18) . ?
S1 C1 1.717(8) . ?
S2 C5 1.697(8) . ?
S3 C10 1.689(7) . ?
S4 C15 1.709(7) . ?
S5 C19 1.703(8) . ?
S6 C24 1.708(7) . ?
N1 C1 1.335(9) . ?
N1 C2 1.391(9) . ?
N1 C9 1.469(9) . ?
N2 C1 1.359(9) . ?
N2 C3 1.382(9) . ?
N2 C4 1.470(8) . ?
N3 C4 1.436(9) . ?
N3 C5 1.367(9) . ?
N3 C6 1.380(9) . ?
N4 C5 1.347(10) . ?
N4 C7 1.382(10) . ?
N4 C8 1.460(10) . ?
N5 C10 1.364(9) . ?
N5 C11 1.457(9) . ?
N5 C12 1.379(9) . ?
N6 C10 1.370(9) . ?
N6 C13 1.388(9) . ?
N6 C14 1.444(9) . ?
N7 C15 1.356(9) . ?
N7 C17 1.391(9) . ?
N7 C18 1.466(9) . ?
N8 C14 1.463(9) . ?
N8 C15 1.358(9) . ?
N8 C16 1.390(9) . ?
N9 C19 1.365(9) . ?
N9 C20 1.457(10) . ?
N9 C21 1.378(10) . ?
N10 C19 1.367(9) . ?
N10 C22 1.395(9) . ?
N10 C23 1.458(9) . ?
N11 C23 1.461(9) . ?
N11 C24 1.359(9) . ?
N11 C25 1.382(9) . ?
N12 C24 1.351(9) . ?
N12 C26 1.372(10) . ?
N12 C27 1.474(9) . ?
C2 C3 1.327(10) . ?
C6 C7 1.329(11) . ?
C12 C13 1.324(11) . ?
C16 C17 1.322(11) . ?
C21 C22 1.310(11) . ?
C25 C26 1.339(11) . ?
Bi2 O1 2.210(4) . ?
Bi2 O3 2.188(6) . ?
Bi2 O4 2.360(7) 3_565 ?
Bi2 O4 2.283(6) . ?
Bi3 O2 2.303(6) 2_665 ?
Bi3 O3 2.217(6) 2_665 ?
Bi3 O3 2.199(5) . ?
Bi3 O4 2.312(6) . ?
S7 O8 1.437(6) . ?
S7 O9 1.440(6) . ?
S7 O10 1.427(6) . ?
S7 C28 1.822(9) . ?
S8 O5 1.432(5) . ?
S8 O6 1.428(6) . ?
S8 O7 1.453(5) . ?
S8 C29 1.820(8) . ?
S9 O11 1.439(5) . ?
S9 O12 1.430(5) . ?
S9 O13 1.447(5) . ?
S9 C30 1.799(8) . ?
S10 O14 1.446(6) . ?
S10 O15 1.433(6) . ?
S10 O16 1.436(6) . ?
S10 C31 1.792(8) . ?
F1 C28 1.324(12) . ?
F2 C28 1.303(10) . ?
F3 C28 1.339(11) . ?
F4 C29 1.303(10) . ?
F5 C29 1.333(9) . ?
F6 C29 1.333(11) . ?
F7 C30 1.337(10) . ?
F8 C30 1.332(10) . ?
F9 C30 1.318(11) . ?
F10 C31 1.321(10) . ?
F11 C31 1.337(10) . ?
F12 C31 1.313(10) . ?
S11 O17 1.440(5) . ?
S11 O19 1.435(7) . ?
S11 O20 1.437(6) . ?
S11 C32 1.820(9) . ?
F13 C32 1.323(10) . ?
F14 C32 1.321(11) . ?
F15 C32 1.337(10) . ?

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
S2 Bi1 S1 86.34(6) . . ?
S3 Bi1 S1 85.90(5) . . ?
S3 Bi1 S2 102.49(6) . . ?
S4 Bi1 S1 83.78(5) . . ?
S4 Bi1 S2 164.49(6) . . ?
S4 Bi1 S3 88.72(6) . . ?
S6 Bi1 S1 84.18(5) . . ?
S6 Bi1 S2 87.47(6) . . ?
S6 Bi1 S3 165.46(5) . . ?
S6 Bi1 S4 79.67(6) . . ?
C1 S1 Bi1 103.4(2) . . ?
C5 S2 Bi1 105.0(3) . . ?
C10 S3 Bi1 99.3(2) . . ?
C15 S4 Bi1 97.8(2) . . ?
C24 S6 Bi1 101.7(2) . . ?
C2 N1 C1 110.0(6) . . ?
C9 N1 C1 124.5(6) . . ?
C9 N1 C2 125.5(6) . . ?
C3 N2 C1 108.9(6) . . ?
C4 N2 C1 126.6(6) . . ?
C4 N2 C3 124.5(6) . . ?
C5 N3 C4 125.8(6) . . ?
C6 N3 C4 125.5(6) . . ?
C6 N3 C5 108.7(6) . . ?
C7 N4 C5 110.5(7) . . ?
C8 N4 C5 124.6(7) . . ?
C8 N4 C7 124.7(7) . . ?
C11 N5 C10 124.1(6) . . ?
C12 N5 C10 109.3(6) . . ?
C12 N5 C11 126.3(6) . . ?
C13 N6 C10 109.1(6) . . ?
C14 N6 C10 126.3(6) . . ?
C14 N6 C13 124.6(6) . . ?
C17 N7 C15 109.6(6) . . ?
C18 N7 C15 125.3(6) . . ?
C18 N7 C17 125.1(6) . . ?
C15 N8 C14 125.9(6) . . ?
C16 N8 C14 124.7(6) . . ?
C16 N8 C15 109.3(6) . . ?
C20 N9 C19 124.5(7) . . ?
C21 N9 C19 109.2(7) . . ?
C21 N9 C20 126.2(7) . . ?
C22 N10 C19 109.2(6) . . ?
C23 N10 C19 125.0(6) . . ?
C23 N10 C22 125.3(7) . . ?
C24 N11 C23 124.3(6) . . ?
C25 N11 C23 125.7(7) . . ?
C25 N11 C24 110.0(6) . . ?
C26 N12 C24 109.9(6) . . ?
C27 N12 C24 125.1(7) . . ?
C27 N12 C26 125.1(6) . . ?
N1 C1 S1 126.3(6) . . ?
N2 C1 S1 127.3(6) . . ?
N2 C1 N1 106.3(6) . . ?
C3 C2 N1 106.8(7) . . ?
C2 C3 N2 108.0(6) . . ?
N3 C4 N2 110.1(6) . . ?
N3 C5 S2 128.8(6) . . ?
N4 C5 S2 125.6(6) . . ?
N4 C5 N3 105.6(6) . . ?
C7 C6 N3 108.6(7) . . ?
C6 C7 N4 106.6(7) . . ?
N5 C10 S3 126.1(6) . . ?
N6 C10 S3 128.4(6) . . ?
N6 C10 N5 105.5(6) . . ?
C13 C12 N5 108.3(7) . . ?
C12 C13 N6 107.6(7) . . ?
N8 C14 N6 112.6(6) . . ?
N7 C15 S4 127.2(6) . . ?
N8 C15 S4 127.0(5) . . ?
N8 C15 N7 105.8(6) . . ?
C17 C16 N8 107.8(7) . . ?
C16 C17 N7 107.4(7) . . ?
N9 C19 S5 126.2(6) . . ?
N10 C19 S5 128.3(6) . . ?
N10 C19 N9 105.3(6) . . ?
C22 C21 N9 108.9(7) . . ?
C21 C22 N10 107.3(7) . . ?
N11 C23 N10 111.4(6) . . ?
N11 C24 S6 128.1(5) . . ?
N12 C24 S6 126.3(6) . . ?
N12 C24 N11 105.5(6) . . ?
C26 C25 N11 106.5(7) . . ?
C25 C26 N12 108.0(7) . . ?
O3 Bi2 O1 100.9(4) . . ?
O4 Bi2 O1 71.5(2) . . ?
O4 Bi2 O1 70.0(2) 3_565 . ?
O4 Bi2 O3 69.2(2) 3_565 . ?
O4 Bi2 O3 71.4(2) . . ?
O3 Bi3 O2 70.9(3) . 2_665 ?
O3 Bi3 O2 70.6(3) 2_665 2_665 ?
O4 Bi3 O2 116.9(4) . 2_665 ?
O4 Bi3 O3 70.7(2) . . ?
O4 Bi3 O3 69.6(3) . 2_665 ?
O9 S7 O8 113.1(3) . . ?
O10 S7 O8 114.9(4) . . ?
O10 S7 O9 116.4(4) . . ?
C28 S7 O8 103.0(4) . . ?
C28 S7 O9 104.3(4) . . ?
C28 S7 O10 102.9(4) . . ?
O6 S8 O5 115.3(4) . . ?
O7 S8 O5 114.3(3) . . ?
O7 S8 O6 115.3(4) . . ?
C29 S8 O5 102.7(4) . . ?
C29 S8 O6 103.7(4) . . ?
C29 S8 O7 103.1(3) . . ?
O12 S9 O11 116.1(3) . . ?
O13 S9 O11 113.6(3) . . ?
O13 S9 O12 115.8(3) . . ?
C30 S9 O11 102.0(4) . . ?
C30 S9 O12 104.0(4) . . ?
C30 S9 O13 102.9(4) . . ?
O15 S10 O14 114.5(3) . . ?
O16 S10 O14 113.3(4) . . ?
O16 S10 O15 117.0(4) . . ?
C31 S10 O14 103.9(4) . . ?
C31 S10 O15 103.7(4) . . ?
C31 S10 O16 102.0(4) . . ?
Bi2 O1 Bi2 113.2(3) 2_665 . ?
Bi2 O1 Bi2 113.2(3) 3_565 . ?
Bi2 O1 Bi2 113.2(3) 3_565 2_665 ?
Bi3 O2 Bi3 105.9(4) . 3_565 ?
Bi3 O2 Bi3 105.9(4) 2_665 3_565 ?
Bi3 O2 Bi3 105.9(4) 2_665 . ?
Bi3 O3 Bi2 112.6(3) . . ?
Bi3 O3 Bi2 115.4(3) 3_565 . ?
Bi3 O4 Bi2 105.2(3) . . ?
Bi3 O4 Bi2 105.7(3) . 2_665 ?
F1 C28 S7 110.3(7) . . ?
F2 C28 S7 111.0(7) . . ?
F2 C28 F1 109.2(9) . . ?
F3 C28 S7 109.8(7) . . ?
F3 C28 F1 107.3(8) . . ?
F3 C28 F2 109.1(8) . . ?
F4 C29 S8 112.2(7) . . ?
F5 C29 S8 110.1(6) . . ?
F5 C29 F4 108.0(7) . . ?
F6 C29 S8 110.2(6) . . ?
F6 C29 F4 107.6(7) . . ?
F6 C29 F5 108.7(8) . . ?
F7 C30 S9 111.5(6) . . ?
F8 C30 S9 111.8(6) . . ?
F8 C30 F7 107.3(8) . . ?
F9 C30 S9 112.2(7) . . ?
F9 C30 F7 106.9(8) . . ?
F9 C30 F8 106.8(7) . . ?
F10 C31 S10 112.0(6) . . ?
F11 C31 S10 111.1(6) . . ?
F11 C31 F10 107.4(8) . . ?
F12 C31 S10 111.6(6) . . ?
F12 C31 F10 107.1(8) . . ?
F12 C31 F11 107.5(7) . . ?
O19 S11 O17 114.8(4) . . ?
O20 S11 O17 115.9(4) . . ?
O20 S11 O19 113.5(4) . . ?
C32 S11 O17 103.9(4) . . ?
C32 S11 O19 103.9(4) . . ?
C32 S11 O20 102.8(4) . . ?
F13 C32 S11 111.5(6) . . ?
F14 C32 S11 112.5(7) . . ?
F14 C32 F13 106.7(8) . . ?
F15 C32 S11 111.8(6) . . ?
F15 C32 F13 107.4(8) . . ?
F15 C32 F14 106.6(8) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 0.250 390.7 46.2 ?
2 0.000 0.000 0.750 390.7 45.8 ?
3 0.000 0.419 0.750 18.7 0.0 ?
4 0.000 0.436 0.250 15.0 0.0 ?
5 -0.080 0.442 0.522 33.5 2.3 ?
6 0.080 0.522 0.978 33.5 0.8 ?
7 -0.080 0.478 0.022 33.5 2.8 ?
8 0.080 0.558 0.478 33.5 1.3 ?
9 0.000 0.564 0.750 15.0 1.8 ?
10 0.000 0.581 0.250 18.7 2.5 ?
11 0.086 0.333 0.083 18.7 0.0 ?
12 0.086 0.752 0.583 18.7 2.5 ?
13 0.108 0.253 0.311 33.5 0.8 ?
14 0.103 0.333 0.583 15.0 0.0 ?
15 0.103 0.770 0.083 15.0 1.8 ?
16 0.108 0.855 0.811 33.5 1.3 ?
17 0.145 0.253 0.811 33.5 1.3 ?
18 0.145 0.892 0.311 33.5 0.8 ?
19 0.189 0.414 0.856 33.5 2.3 ?
20 0.189 0.775 0.356 33.5 2.8 ?
21 0.333 0.667 0.917 390.7 46.2 ?
22 0.333 0.667 0.417 390.7 45.8 ?
23 0.225 0.414 0.356 33.5 2.8 ?
24 0.225 0.811 0.856 33.5 2.3 ?
25 0.253 0.108 0.189 33.5 2.3 ?
26 0.253 0.145 0.689 33.5 2.8 ?
27 0.230 0.333 0.083 15.0 1.8 ?
28 0.230 0.897 0.583 15.0 0.0 ?
29 0.248 0.333 0.583 18.7 2.5 ?
30 0.248 0.914 0.083 18.7 0.0 ?
31 0.333 0.086 0.417 18.7 0.0 ?
32 0.333 0.248 0.917 18.7 2.5 ?
33 0.333 0.103 0.917 15.0 0.0 ?
34 0.333 0.230 0.417 15.0 1.8 ?
35 0.414 0.189 0.644 33.5 0.8 ?
36 0.414 0.225 0.144 33.5 1.3 ?
37 0.419 0.419 0.250 18.7 2.5 ?
38 0.419 1.000 0.750 18.7 0.0 ?
39 0.436 0.436 0.750 15.0 1.8 ?
40 0.442 0.522 0.478 33.5 1.3 ?
41 0.442 0.920 -0.022 33.5 0.8 ?
42 0.436 0.000 0.250 15.0 0.0 ?
43 0.478 0.558 -0.022 33.5 0.8 ?
44 0.478 0.920 0.478 33.5 1.3 ?
45 0.522 0.080 0.522 33.5 2.3 ?
46 0.522 0.442 0.022 33.5 2.8 ?
47 0.667 0.333 0.583 390.7 46.2 ?
48 0.667 0.333 0.083 390.7 45.8 ?
49 0.558 0.080 0.022 33.5 2.8 ?
50 0.558 0.478 0.522 33.5 2.3 ?
51 0.586 0.775 0.856 33.5 2.3 ?
52 0.586 0.811 0.356 33.5 2.8 ?
53 0.564 0.564 0.250 15.0 0.0 ?
54 0.564 0.000 0.750 15.0 1.8 ?
55 0.581 0.581 0.750 18.7 0.0 ?
56 0.581 0.000 0.250 18.7 2.5 ?
57 0.667 0.752 0.083 18.7 0.0 ?
58 0.667 0.914 0.583 18.7 2.5 ?
59 0.667 0.770 0.583 15.0 0.0 ?
60 0.667 0.897 0.083 15.0 1.8 ?
61 0.747 0.855 0.311 33.5 0.8 ?
62 0.747 0.892 0.811 33.5 1.3 ?
63 0.752 0.086 0.917 18.7 2.5 ?
64 0.752 0.667 0.417 18.7 0.0 ?
65 0.770 0.103 0.417 15.0 1.8 ?
66 0.775 0.189 0.144 33.5 1.3 ?
67 0.775 0.586 0.644 33.5 0.8 ?
68 0.770 0.667 0.917 15.0 0.0 ?
69 0.811 0.225 0.644 33.5 0.8 ?
70 0.811 0.586 0.144 33.5 1.3 ?
71 0.855 0.108 0.689 33.5 2.8 ?
72 0.855 0.747 0.189 33.5 2.3 ?
73 0.892 0.145 0.189 33.5 2.3 ?
74 0.892 0.747 0.689 33.5 2.8 ?
75 0.897 0.230 0.917 15.0 0.0 ?
76 0.897 0.667 0.417 15.0 1.8 ?
77 0.914 0.248 0.417 18.7 0.0 ?
78 0.914 0.667 0.917 18.7 2.5 ?

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1440443'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         
'C20 H24 Bi F6 N8 O6 S2 Se4, C F3 O3 S, 2(C H4 O)'
_chemical_formula_sum            'C23 H32 Bi F9 N8 O11 S3 Se4'
_chemical_formula_weight         1388.56
_chemical_oxdiff_formula         'C14 H12 N4 Se2 Bi S3 O9 F9'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.0767(5)
_cell_length_b                   15.2872(8)
_cell_length_c                   16.4710(7)
_cell_angle_alpha                71.308(4)
_cell_angle_beta                 86.504(4)
_cell_angle_gamma                82.217(4)
_cell_volume                     2144.61(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7325
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.8005
_cell_measurement_theta_min      3.0724
_exptl_absorpt_coefficient_mu    14.222
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.56199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.1501
_exptl_crystal_description       block
_exptl_crystal_F_000             1316.3246
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16544
_diffrn_reflns_theta_full        70.9370
_diffrn_reflns_theta_max         70.94
_diffrn_reflns_theta_min         3.07
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9745
_diffrn_measured_fraction_theta_max 0.9745
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -53.00  -26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -21.00    6.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -52.00  -24.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  4 omega  -95.00  -68.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -96.00  -67.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   -9.00   35.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  7 omega  -63.00  -23.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000 -120.0000 40

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00  108.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00  118.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -90.0000 82

#__ type_ start__ end____ width___ exp.time_
 10 omega  -13.00   80.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   82.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -150.0000 45

#__ type_ start__ end____ width___ exp.time_
 12 omega   92.00  125.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   30.0000 33

#__ type_ start__ end____ width___ exp.time_
 13 omega   36.00   62.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   26.00   86.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
 15 omega   35.00  122.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  120.0000 87

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  104.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 65

#__ type_ start__ end____ width___ exp.time_
 17 omega   82.00  127.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
 18 omega   36.00   82.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 46

#__ type_ start__ end____ width___ exp.time_
 19 omega   54.00   81.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
 20 omega   41.00   74.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 33

#__ type_ start__ end____ width___ exp.time_
 21 omega   43.00   74.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 31

#__ type_ start__ end____ width___ exp.time_
 22 omega   42.00   93.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   30.0000 51

#__ type_ start__ end____ width___ exp.time_
 23 omega   57.00  146.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 24 omega   94.00  145.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 51

#__ type_ start__ end____ width___ exp.time_
 25 omega   78.00  178.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 100

#__ type_ start__ end____ width___ exp.time_
 26 omega   38.00  137.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000   30.0000 99

#__ type_ start__ end____ width___ exp.time_
 27 omega  139.00  166.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 28 omega   37.00  106.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 69

#__ type_ start__ end____ width___ exp.time_
 29 omega   61.00  115.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
 30 omega   97.00  134.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   90.0000 37

#__ type_ start__ end____ width___ exp.time_
 31 omega   79.00  177.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
 32 omega   42.00   69.00   1.0000    3.2800
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 27
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0626343000
_diffrn_orient_matrix_UB_12      -0.0238258000
_diffrn_orient_matrix_UB_13      0.0925325000
_diffrn_orient_matrix_UB_21      -0.1197550000
_diffrn_orient_matrix_UB_22      -0.0496307000
_diffrn_orient_matrix_UB_23      -0.0236498000
_diffrn_orient_matrix_UB_31      0.1053176000
_diffrn_orient_matrix_UB_32      -0.0919759000
_diffrn_orient_matrix_UB_33      0.0251292000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              18
_reflns_limit_k_min              -17
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                7179
_reflns_number_total             8065
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         4.7528
_refine_diff_density_min         -2.9552
_refine_diff_density_rms         0.2053
_refine_ls_d_res_high            0.8157
_refine_ls_d_res_low             14.3717
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0413
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    50
_refine_ls_number_parameters     538
_refine_ls_number_reflns         8065
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.0413
_refine_ls_shift/su_max          2.5980
_refine_ls_shift/su_mean         0.0188
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+7.7347P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1285
_refine_ls_wR_factor_ref         0.1350
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Riding coordinates:
 O10(H10), O11(H11a)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8), C11(H11), C12(H12), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C9(H9a,H9b,H9c), C13(H13a,H13b,H13c), C18(H18a,H18b,H18c),
 C22(H22a,H22b,H22c), C23(H23a,H23b,H23c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Bi1 Bi 0.27610(3) 0.129068(18) 0.296587(16) 0.02981(12) Uani 1.000000 .
Se1 Se 0.26549(10) -0.02177(6) 0.44385(5) 0.0350(2) Uani 1.000000 .
Se2 Se 0.59415(9) 0.08225(6) 0.28729(5) 0.0366(2) Uani 1.000000 .
Se3 Se 0.34866(9) 0.19381(5) 0.42628(5) 0.03257(19) Uani 1.000000 .
Se4 Se -0.04016(9) 0.17320(6) 0.33924(6) 0.0379(2) Uani 1.000000 .
S1 S 0.1840(3) 0.03747(16) 0.13609(13) 0.0453(5) Uani 1.000000 .
S2 S 0.3581(5) 0.3436(2) 0.1279(2) 0.0938(13) Uani 1.000000 .
F1 F -0.0535(9) -0.0237(14) 0.2121(6) 0.211(9) Uani 1.000000 .
F2 F 0.095(2) -0.1244(11) 0.1681(9) 0.191(8) Uani 1.000000 .
F3 F -0.0413(9) -0.0095(13) 0.0792(6) 0.193(7) Uani 1.000000 .
F4 F 0.1344(9) 0.4126(8) 0.0448(5) 0.113(4) Uani 1.000000 .
F5 F 0.2201(10) 0.5078(5) 0.1128(5) 0.090(2) Uani 1.000000 .
F6 F 0.3372(10) 0.4938(6) 0.0003(5) 0.110(3) Uani 1.000000 .
O1 O 0.2514(7) 0.0017(4) 0.2200(3) 0.0406(13) Uani 1.000000 .
O2 O 0.1153(18) 0.1296(7) 0.1190(6) 0.150(6) Uani 1.000000 .
O3 O 0.2744(8) 0.0190(6) 0.0681(4) 0.0616(19) Uani 1.000000 .
O4 O 0.2636(7) 0.3095(4) 0.2019(4) 0.0477(14) Uani 1.000000 .
O5 O 0.3974(13) 0.2879(7) 0.0770(5) 0.097(3) Uani 1.000000 .
O6 O 0.4960(10) 0.3871(10) 0.1475(7) 0.116(4) Uani 1.000000 .
N1 N 0.1468(8) -0.1594(5) 0.3930(4) 0.0383(15) Uani 1.000000 .
N2 N 0.3847(7) -0.1648(4) 0.3678(4) 0.0343(14) Uani 1.000000 .
N3 N 0.5694(7) -0.0943(4) 0.2637(4) 0.0333(13) Uani 1.000000 .
N4 N 0.6108(8) 0.0108(5) 0.1442(4) 0.0378(15) Uani 1.000000 .
N5 N 0.4414(7) 0.3715(5) 0.3395(4) 0.0353(14) Uani 1.000000 .
N6 N 0.2021(7) 0.3838(4) 0.3573(4) 0.0298(12) Uani 1.000000 .
N7 N -0.0273(7) 0.3708(5) 0.3001(4) 0.0340(14) Uani 1.000000 .
N8 N -0.1187(7) 0.3376(5) 0.1973(4) 0.0391(15) Uani 1.000000 .
C1 C 0.2661(9) -0.1178(5) 0.3955(5) 0.0352(17) Uani 1.000000 .
C2 C 0.1883(11) -0.2336(6) 0.3635(6) 0.049(2) Uani 1.000000 .
H2 H 0.1261(11) -0.2741(6) 0.3564(6) 0.058(3) Uiso 1.000000 R
C3 C 0.3367(11) -0.2371(6) 0.3467(6) 0.045(2) Uani 1.000000 .
H3 H 0.3952(11) -0.2798(6) 0.3252(6) 0.054(2) Uiso 1.000000 R
C4 C -0.0067(10) -0.1272(6) 0.4141(6) 0.045(2) Uani 1.000000 .
H4a H -0.0123(19) -0.127(5) 0.4724(15) 0.068(3) Uiso 1.000000 GR
H4b H -0.035(3) -0.0654(19) 0.376(3) 0.068(3) Uiso 1.000000 GR
H4c H -0.0726(14) -0.168(3) 0.407(4) 0.068(3) Uiso 1.000000 GR
C5 C 0.5383(8) -0.1407(5) 0.3538(5) 0.0327(15) Uani 1.000000 .
H5a H 0.5529(8) -0.1002(5) 0.3868(5) 0.0392(19) Uiso 1.000000 R
H5b H 0.6075(8) -0.1970(5) 0.3741(5) 0.0392(19) Uiso 1.000000 R
C6 C 0.5877(8) -0.0033(5) 0.2279(5) 0.0321(15) Uani 1.000000 .
C7 C 0.5811(10) -0.1361(6) 0.2001(5) 0.0394(18) Uani 1.000000 .
H7 H 0.5723(10) -0.1980(6) 0.2070(5) 0.047(2) Uiso 1.000000 R
C8 C 0.6077(10) -0.0699(6) 0.1266(5) 0.0417(19) Uani 1.000000 .
H8 H 0.6217(10) -0.0778(6) 0.0729(5) 0.050(2) Uiso 1.000000 R
C9 C 0.6316(14) 0.1007(7) 0.0794(6) 0.060(3) Uani 1.000000 .
H9a H 0.538(2) 0.140(2) 0.070(4) 0.089(4) Uiso 1.000000 GR
H9b H 0.703(7) 0.130(3) 0.099(2) 0.089(4) Uiso 1.000000 GR
H9c H 0.667(9) 0.0906(9) 0.0265(17) 0.089(4) Uiso 1.000000 GR
C10 C 0.3279(8) 0.3225(5) 0.3701(5) 0.0306(15) Uani 1.000000 .
C11 C 0.3894(9) 0.4637(6) 0.3058(5) 0.0380(17) Uani 1.000000 .
H11 H 0.4462(9) 0.5118(6) 0.2797(5) 0.046(2) Uiso 1.000000 R
C12 C 0.2408(9) 0.4720(5) 0.3175(5) 0.0378(17) Uani 1.000000 .
H12 H 0.1761(9) 0.5271(5) 0.3017(5) 0.045(2) Uiso 1.000000 R
C13 C 0.5984(9) 0.3317(6) 0.3388(6) 0.046(2) Uani 1.000000 .
H13a H 0.635(2) 0.309(4) 0.3963(8) 0.069(3) Uiso 1.000000 GR
H13b H 0.6066(13) 0.281(3) 0.316(4) 0.069(3) Uiso 1.000000 GR
H13c H 0.6563(15) 0.3787(14) 0.304(4) 0.069(3) Uiso 1.000000 GR
C14 C 0.0506(8) 0.3630(5) 0.3773(5) 0.0322(15) Uani 1.000000 .
H14a H 0.0512(8) 0.3003(5) 0.4169(5) 0.0386(18) Uiso 1.000000 R
H14b H -0.0016(8) 0.4057(5) 0.4050(5) 0.0386(18) Uiso 1.000000 R
C15 C -0.0578(8) 0.3000(5) 0.2745(5) 0.0348(16) Uani 1.000000 .
C16 C -0.0747(9) 0.4530(6) 0.2381(6) 0.0422(19) Uani 1.000000 .
H16 H -0.0692(9) 0.5125(6) 0.2404(6) 0.051(2) Uiso 1.000000 R
C17 C -0.1296(11) 0.4326(6) 0.1744(6) 0.048(2) Uani 1.000000 .
H17 H -0.1681(11) 0.4749(6) 0.1237(6) 0.057(2) Uiso 1.000000 R
C18 C -0.1630(11) 0.2861(7) 0.1419(6) 0.052(2) Uani 1.000000 .
H18a H -0.082(3) 0.278(5) 0.104(3) 0.078(3) Uiso 1.000000 GR
H18b H -0.188(8) 0.226(2) 0.1770(7) 0.078(3) Uiso 1.000000 GR
H18c H -0.248(5) 0.321(3) 0.109(3) 0.078(3) Uiso 1.000000 GR
C19 C 0.0360(15) -0.0384(19) 0.1477(8) 0.117(8) Uani 1.000000 .
C20 C 0.271(3) 0.4500(11) 0.0712(9) 0.132(9) Uani 1.000000 .
S3 S 0.1833(2) 0.36817(13) 0.61893(13) 0.0381(4) Uani 1.000000 .
F7 F 0.1788(8) 0.5186(4) 0.4868(4) 0.0709(18) Uani 1.000000 .
F8 F 0.3916(7) 0.4353(5) 0.5103(4) 0.0705(17) Uani 1.000000 .
F9 F 0.3093(8) 0.5203(5) 0.5901(5) 0.083(2) Uani 1.000000 .
O7 O 0.1559(9) 0.3176(5) 0.5632(5) 0.0610(19) Uani 1.000000 .
O8 O 0.0536(7) 0.4113(4) 0.6519(4) 0.0486(15) Uani 1.000000 .
O9 O 0.2941(9) 0.3229(6) 0.6809(5) 0.075(2) Uani 1.000000 .
C21 C 0.2700(11) 0.4663(7) 0.5468(7) 0.050(2) Uani 1.000000 .
O10 O 0.7222(17) 0.7028(13) 0.0882(8) 0.160(7) Uani 1.000000 .
H10 H 0.6720(17) 0.6985(13) 0.1321(8) 0.240(10) Uiso 1.000000 R
C22 C 0.8654(19) 0.7216(12) 0.1001(9) 0.099(5) Uani 1.000000 .
H22a H 0.878(5) 0.713(8) 0.1597(15) 0.148(8) Uiso 1.000000 GR
H22b H 0.9385(19) 0.680(6) 0.082(7) 0.148(8) Uiso 1.000000 GR
H22c H 0.877(5) 0.785(3) 0.067(6) 0.148(8) Uiso 1.000000 GR
O11 O 0.4764(10) 0.6619(5) 0.1938(5) 0.074(2) Uani 1.000000 .
H11a H 0.4493(10) 0.6718(5) 0.2388(5) 0.112(3) Uiso 1.000000 R
C23 C 0.361(2) 0.7001(12) 0.1318(10) 0.123(7) Uani 1.000000 .
H23a H 0.267(3) 0.705(10) 0.1608(10) 0.185(11) Uiso 1.000000 GR
H23b H 0.381(10) 0.761(5) 0.096(6) 0.185(11) Uiso 1.000000 GR
H23c H 0.359(11) 0.660(6) 0.098(7) 0.185(11) Uiso 1.000000 GR


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 Se1 2.7670(8) . ?
Bi1 Se2 2.8855(9) . ?
Bi1 Se3 2.7712(8) . ?
Bi1 Se4 2.9533(9) . ?
Se1 C1 1.881(8) . ?
Se2 C6 1.875(7) . ?
Se3 C10 1.875(8) . ?
Se4 C15 1.879(8) . ?
S1 O1 1.453(6) . ?
S1 O2 1.407(9) . ?
S1 O3 1.427(7) . ?
S1 C19 1.853(19) . ?
S2 O4 1.442(6) . ?
S2 O5 1.375(8) . ?
S2 O6 1.589(10) . ?
S2 C20 1.705(15) . ?
F1 C19 1.353(18) . ?
F2 C19 1.29(3) . ?
F3 C19 1.286(15) . ?
F4 C20 1.58(3) . ?
F5 C20 1.307(17) . ?
F6 C20 1.300(15) . ?
N1 C1 1.336(11) . ?
N1 C2 1.371(11) . ?
N1 C4 1.473(11) . ?
N2 C1 1.350(10) . ?
N2 C3 1.389(11) . ?
N2 C5 1.476(10) . ?
N3 C5 1.454(9) . ?
N3 C6 1.355(10) . ?
N3 C7 1.384(10) . ?
N4 C6 1.334(10) . ?
N4 C8 1.359(10) . ?
N4 C9 1.472(10) . ?
N5 C10 1.334(10) . ?
N5 C11 1.366(10) . ?
N5 C13 1.473(10) . ?
N6 C10 1.356(9) . ?
N6 C12 1.381(10) . ?
N6 C14 1.448(9) . ?
N7 C14 1.456(9) . ?
N7 C15 1.346(10) . ?
N7 C16 1.376(10) . ?
N8 C15 1.336(10) . ?
N8 C17 1.371(11) . ?
N8 C18 1.484(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.356(13) . ?
C3 H3 0.9300 . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 0.9600 . ?
C5 H5a 0.9700 . ?
C5 H5b 0.9700 . ?
C7 H7 0.9300 . ?
C7 C8 1.339(12) . ?
C8 H8 0.9300 . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
C11 H11 0.9300 . ?
C11 C12 1.346(11) . ?
C12 H12 0.9300 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C14 H14a 0.9700 . ?
C14 H14b 0.9700 . ?
C16 H16 0.9300 . ?
C16 C17 1.327(13) . ?
C17 H17 0.9300 . ?
C18 H18a 0.9600 . ?
C18 H18b 0.9600 . ?
C18 H18c 0.9600 . ?
S3 O7 1.427(7) . ?
S3 O8 1.434(6) . ?
S3 O9 1.420(7) . ?
S3 C21 1.829(10) . ?
F7 C21 1.310(12) . ?
F8 C21 1.329(11) . ?
F9 C21 1.342(10) . ?
O10 H10 0.8200 . ?
O10 C22 1.407(19) . ?
C22 H22a 0.9600 . ?
C22 H22b 0.9600 . ?
C22 H22c 0.9600 . ?
O11 H11a 0.8200 . ?
O11 C23 1.433(18) . ?
C23 H23a 0.9600 . ?
C23 H23b 0.9600 . ?
C23 H23c 0.9600 . ?

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
Se2 Bi1 Se1 89.33(3) . . ?
Se3 Bi1 Se1 75.71(2) . . ?
Se3 Bi1 Se2 82.67(2) . . ?
Se4 Bi1 Se1 83.75(3) . . ?
Se4 Bi1 Se2 169.50(3) . . ?
Se4 Bi1 Se3 87.95(2) . . ?
C1 Se1 Bi1 100.2(2) . . ?
C6 Se2 Bi1 95.6(2) . . ?
C10 Se3 Bi1 101.0(2) . . ?
C15 Se4 Bi1 96.6(2) . . ?
O2 S1 O1 112.1(5) . . ?
O3 S1 O1 115.0(4) . . ?
O3 S1 O2 115.5(6) . . ?
C19 S1 O1 102.3(5) . . ?
C19 S1 O2 107.8(11) . . ?
C19 S1 O3 102.4(7) . . ?
O5 S2 O4 118.1(6) . . ?
O6 S2 O4 113.4(5) . . ?
O6 S2 O5 112.2(7) . . ?
C20 S2 O4 105.6(6) . . ?
C20 S2 O5 111.9(7) . . ?
C20 S2 O6 92.5(10) . . ?
C2 N1 C1 109.5(7) . . ?
C4 N1 C1 125.1(7) . . ?
C4 N1 C2 125.3(7) . . ?
C3 N2 C1 108.5(7) . . ?
C5 N2 C1 127.2(7) . . ?
C5 N2 C3 124.0(7) . . ?
C6 N3 C5 125.9(6) . . ?
C7 N3 C5 125.0(7) . . ?
C7 N3 C6 109.0(6) . . ?
C8 N4 C6 109.8(7) . . ?
C9 N4 C6 125.5(7) . . ?
C9 N4 C8 124.6(7) . . ?
C11 N5 C10 109.8(6) . . ?
C13 N5 C10 125.0(7) . . ?
C13 N5 C11 125.2(7) . . ?
C12 N6 C10 108.3(6) . . ?
C14 N6 C10 127.5(6) . . ?
C14 N6 C12 124.2(6) . . ?
C15 N7 C14 126.5(7) . . ?
C16 N7 C14 125.1(7) . . ?
C16 N7 C15 108.3(7) . . ?
C17 N8 C15 109.5(7) . . ?
C18 N8 C15 126.3(7) . . ?
C18 N8 C17 124.2(7) . . ?
N1 C1 Se1 124.1(6) . . ?
N2 C1 Se1 127.7(6) . . ?
N2 C1 N1 107.7(7) . . ?
H2 C2 N1 126.3(5) . . ?
C3 C2 N1 107.4(8) . . ?
C3 C2 H2 126.3(5) . . ?
C2 C3 N2 106.9(7) . . ?
H3 C3 N2 126.6(5) . . ?
H3 C3 C2 126.6(5) . . ?
H4a C4 N1 109.5 . . ?
H4b C4 N1 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 N1 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
N3 C5 N2 111.5(6) . . ?
H5a C5 N2 109.3(4) . . ?
H5a C5 N3 109.3(4) . . ?
H5b C5 N2 109.3(4) . . ?
H5b C5 N3 109.3(4) . . ?
H5b C5 H5a 108.0 . . ?
N3 C6 Se2 125.9(6) . . ?
N4 C6 Se2 127.4(6) . . ?
N4 C6 N3 106.5(6) . . ?
H7 C7 N3 126.8(4) . . ?
C8 C7 N3 106.4(7) . . ?
C8 C7 H7 126.8(5) . . ?
C7 C8 N4 108.2(7) . . ?
H8 C8 N4 125.9(4) . . ?
H8 C8 C7 125.9(5) . . ?
H9a C9 N4 109.5 . . ?
H9b C9 N4 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 N4 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
N5 C10 Se3 124.3(6) . . ?
N6 C10 Se3 128.4(6) . . ?
N6 C10 N5 107.2(7) . . ?
H11 C11 N5 126.3(4) . . ?
C12 C11 N5 107.3(7) . . ?
C12 C11 H11 126.3(5) . . ?
C11 C12 N6 107.4(7) . . ?
H12 C12 N6 126.3(4) . . ?
H12 C12 C11 126.3(5) . . ?
H13a C13 N5 109.5 . . ?
H13b C13 N5 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 N5 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
N7 C14 N6 111.1(6) . . ?
H14a C14 N6 109.4(4) . . ?
H14a C14 N7 109.4(4) . . ?
H14b C14 N6 109.4(4) . . ?
H14b C14 N7 109.4(4) . . ?
H14b C14 H14a 108.0 . . ?
N7 C15 Se4 127.0(6) . . ?
N8 C15 Se4 125.6(6) . . ?
N8 C15 N7 107.0(7) . . ?
H16 C16 N7 126.0(5) . . ?
C17 C16 N7 108.1(8) . . ?
C17 C16 H16 126.0(5) . . ?
C16 C17 N8 107.1(8) . . ?
H17 C17 N8 126.5(5) . . ?
H17 C17 C16 126.5(5) . . ?
H18a C18 N8 109.5 . . ?
H18b C18 N8 109.5 . . ?
H18b C18 H18a 109.5 . . ?
H18c C18 N8 109.5 . . ?
H18c C18 H18a 109.5 . . ?
H18c C18 H18b 109.5 . . ?
F1 C19 S1 104.9(15) . . ?
F2 C19 S1 109.6(11) . . ?
F2 C19 F1 110.6(18) . . ?
F3 C19 S1 109.0(15) . . ?
F3 C19 F1 107.3(14) . . ?
F3 C19 F2 115(2) . . ?
F4 C20 S2 96.0(11) . . ?
F5 C20 S2 118.2(11) . . ?
F5 C20 F4 107.7(16) . . ?
F6 C20 S2 116.4(13) . . ?
F6 C20 F4 106.6(14) . . ?
F6 C20 F5 110.0(15) . . ?
O8 S3 O7 115.6(4) . . ?
O9 S3 O7 114.9(5) . . ?
O9 S3 O8 114.1(4) . . ?
C21 S3 O7 102.6(4) . . ?
C21 S3 O8 103.9(4) . . ?
C21 S3 O9 103.3(5) . . ?
F7 C21 S3 111.3(7) . . ?
F8 C21 S3 109.9(7) . . ?
F8 C21 F7 108.9(8) . . ?
F9 C21 S3 110.8(7) . . ?
F9 C21 F7 107.6(9) . . ?
F9 C21 F8 108.3(8) . . ?
C22 O10 H10 109.4 . . ?
H22a C22 O10 109.5 . . ?
H22b C22 O10 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 O10 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?
C23 O11 H11a 109.6 . . ?
H23a C23 O11 109.5 . . ?
H23b C23 O11 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 O11 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.111 0.173 0.975 7.2 0.4 ?
2 0.111 0.827 0.025 7.2 0.6 ?

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1440444'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C28 H40 Bi F6 N8 O6 S6, C F3 O3 S'
_chemical_formula_sum            'C29 H40 Bi F9 N8 O9 S7'
_chemical_formula_weight         1249.12
_chemical_oxdiff_formula         'C21 H24 N4 S Bi F3 O3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2ybc (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.1033(3)
_cell_length_b                   13.2707(3)
_cell_length_c                   22.9733(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.6380(16)
_cell_angle_gamma                90
_cell_volume                     4589.50(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10776
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      71.3090
_cell_measurement_theta_min      3.8470
_exptl_absorpt_coefficient_mu    11.358
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59311
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.8076
_exptl_crystal_description       block
_exptl_crystal_F_000             2474.6940
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            17863
_diffrn_reflns_theta_full        71.2385
_diffrn_reflns_theta_max         71.24
_diffrn_reflns_theta_min         3.38
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9792
_diffrn_measured_fraction_theta_max 0.9791
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -20.00    5.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   40.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -58.00  -31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  126.0000  163.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega   34.00   62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega  -67.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   63.0000  120.0000 89

#__ type_ start__ end____ width___ exp.time_
  6 omega -111.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -57.0000  -30.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega -119.00  -63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -180.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega  -55.00    8.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   12.0000  -30.0000 63

#__ type_ start__ end____ width___ exp.time_
  9 omega   62.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1553  -99.0000   60.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   86.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1553 -125.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   56.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -25.0000  120.0000 38

#__ type_ start__ end____ width___ exp.time_
 12 omega   36.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -25.0000 -150.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   67.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   84.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105   38.0000  -90.0000 94

#__ type_ start__ end____ width___ exp.time_
 15 omega   53.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 16 omega   55.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   83.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000  -60.0000 30

#__ type_ start__ end____ width___ exp.time_
 18 omega   40.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega  100.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  111.0000   90.0000 75

#__ type_ start__ end____ width___ exp.time_
 20 omega   45.00  115.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 21 omega   45.00  131.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -63.0000  -30.0000 86
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0669905000
_diffrn_orient_matrix_UB_12      -0.0665029000
_diffrn_orient_matrix_UB_13      0.0295221000
_diffrn_orient_matrix_UB_21      0.0516579000
_diffrn_orient_matrix_UB_22      -0.0948961000
_diffrn_orient_matrix_UB_23      -0.0160115000
_diffrn_orient_matrix_UB_31      0.0575116000
_diffrn_orient_matrix_UB_32      0.0077415000
_diffrn_orient_matrix_UB_33      0.0582890000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -18
_reflns_limit_k_max              15
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              -14
_reflns_number_gt                8190
_reflns_number_total             8727
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.9412
_refine_diff_density_min         -2.4588
_refine_diff_density_rms         0.1815
_refine_ls_d_res_high            0.8142
_refine_ls_d_res_low             13.0735
_refine_ls_goodness_of_fit_ref   1.0077
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     575
_refine_ls_number_reflns         8727
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0344
_refine_ls_restrained_S_all      1.0077
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0686P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.0960
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C24(H24), C8(H8), C11(H11), C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17a,H17b), C4(H4a,H4b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C16(H16), C2(H2), C19(H19), C3(H3), C20(H20), C7(H7), C15(H15)
2.d Idealised Me refined as rotating group:
 C26(H26a,H26b,H26c), C13(H13a,H13b,H13c), C25(H25a,H25b,H25c), C9(H9a,H9b,
 H9c), C10(H10a,H10b,H10c), C12(H12a,H12b,H12c), C23(H23a,H23b,H23c), C22(H22a,
 H22b,H22c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Bi1 Bi 0.437470(8) 0.761081(11) 0.724594(5) 0.02054(7) Uani 1.000000 .
S6 S 0.39135(7) 0.75673(7) 0.55418(4) 0.0264(2) Uani 1.000000 .
S1 S 0.43176(6) 0.78633(7) 0.83752(4) 0.02301(17) Uani 1.000000 .
S7 S 0.11560(6) 0.17172(7) 0.50028(4) 0.02450(18) Uani 1.000000 .
S2 S 0.37685(6) 0.56094(7) 0.73983(4) 0.02559(18) Uani 1.000000 .
S3 S 0.47099(6) 0.96690(7) 0.72992(4) 0.02483(18) Uani 1.000000 .
F8 F 0.2725(2) 0.2400(2) 0.48073(18) 0.0597(10) Uani 1.000000 .
O9 O 0.15517(19) 0.1366(2) 0.55597(12) 0.0385(7) Uani 1.000000 .
O3 O 0.7321(2) 0.7797(2) 0.78929(14) 0.0363(7) Uani 1.000000 .
O4 O 0.3669(3) 0.7531(3) 0.61326(16) 0.0474(9) Uani 1.000000 .
N14 N 0.5959(2) 0.7883(2) 0.89604(12) 0.0204(6) Uani 1.000000 .
F7 F 0.1652(2) 0.3096(3) 0.42948(14) 0.0669(9) Uani 1.000000 .
N16 N 0.5205(2) 0.4391(3) 0.72773(13) 0.0285(7) Uani 1.000000 .
S5 S 0.67580(7) 0.74688(7) 0.73997(5) 0.0261(2) Uani 1.000000 .
F9 F 0.1887(2) 0.3477(2) 0.51897(16) 0.0685(9) Uani 1.000000 .
N20 N 0.51667(19) 0.4977(2) 0.81531(12) 0.0237(6) Uani 1.000000 .
N24 N 0.36372(19) 1.0266(2) 0.63414(12) 0.0236(6) Uani 1.000000 .
O1 O 0.59551(18) 0.6944(3) 0.75548(13) 0.0374(7) Uani 1.000000 .
N26 N 0.1690(2) 0.7748(3) 0.63892(16) 0.0277(7) Uani 1.000000 .
C6 C 0.5904(3) 0.4359(3) 0.81575(17) 0.0301(8) Uani 1.000000 .
H6 H 0.6307(3) 0.4222(3) 0.84753(17) 0.0361(10) Uiso 1.000000 R
N28 N 0.54507(19) 0.6367(2) 0.88237(12) 0.0203(6) Uani 1.000000 .
O7 O 0.0314(2) 0.2211(2) 0.50259(14) 0.0370(7) Uani 1.000000 .
O8 O 0.1209(3) 0.1003(3) 0.45337(15) 0.0549(9) Uani 1.000000 .
C16 C 0.3702(2) 1.0676(3) 0.57916(15) 0.0270(8) Uani 1.000000 .
H16 H 0.3234(2) 1.0887(3) 0.55320(15) 0.0324(9) Uiso 1.000000 R
C2 C 0.6563(3) 0.7232(3) 0.92425(17) 0.0256(8) Uani 1.000000 .
H2 H 0.7092(3) 0.7412(3) 0.94525(17) 0.0307(9) Uiso 1.000000 R
C19 C 0.1852(2) 0.9120(3) 0.58727(16) 0.0270(8) Uani 1.000000 .
H19 H 0.1811(2) 0.9598(3) 0.55758(16) 0.0324(9) Uiso 1.000000 R
N35 N 0.50348(19) 1.0316(2) 0.62010(12) 0.0228(6) Uani 1.000000 .
C5 C 0.4734(2) 0.4997(3) 0.76090(16) 0.0249(7) Uani 1.000000 .
C1 C 0.5282(3) 0.7351(3) 0.87096(16) 0.0196(7) Uani 1.000000 .
C29 C 0.1894(3) 0.2727(3) 0.4814(2) 0.0375(10) Uani 1.000000 .
S4 S 0.26924(5) 0.80858(7) 0.74141(4) 0.02536(18) Uani 1.000000 .
C3 C 0.6251(2) 0.6294(3) 0.91590(15) 0.0254(7) Uani 1.000000 .
H3 H 0.6521(2) 0.5704(3) 0.93004(15) 0.0305(9) Uiso 1.000000 R
C24 C 0.6013(2) 1.0230(3) 0.62921(16) 0.0258(7) Uani 1.000000 .
H24 H 0.6162(2) 0.9865(3) 0.66576(16) 0.0310(9) Uiso 1.000000 R
O2 O 0.6612(3) 0.8173(3) 0.69331(15) 0.0576(10) Uani 1.000000 .
O6 O 0.4366(3) 0.8467(3) 0.5406(2) 0.0763(13) Uani 1.000000 .
C20 C 0.1454(3) 0.8217(3) 0.58625(16) 0.0299(8) Uani 1.000000 .
H20 H 0.1085(3) 0.7954(3) 0.55560(16) 0.0359(10) Uiso 1.000000 R
C26 C 0.6373(3) 0.9646(3) 0.57982(18) 0.0379(9) Uani 1.000000 .
H26a H 0.6072(15) 0.9010(11) 0.5755(9) 0.0569(14) Uiso 1.000000 GR
H26b H 0.628(2) 1.0024(11) 0.5442(3) 0.0569(14) Uiso 1.000000 GR
H26c H 0.6998(5) 0.953(2) 0.5884(7) 0.0569(14) Uiso 1.000000 GR
C13 C 0.5729(3) 0.4039(4) 0.63119(18) 0.0382(10) Uani 1.000000 .
H13a H 0.6030(13) 0.4677(8) 0.6324(12) 0.0574(14) Uiso 1.000000 GR
H13b H 0.6126(11) 0.3528(18) 0.6474(9) 0.0574(14) Uiso 1.000000 GR
H13c H 0.5541(4) 0.387(3) 0.5914(4) 0.0574(14) Uiso 1.000000 GR
N49 N 0.23368(19) 0.9207(2) 0.64076(13) 0.0240(6) Uani 1.000000 .
C14 C 0.4458(2) 1.0058(3) 0.65946(15) 0.0222(7) Uani 1.000000 .
C18 C 0.2241(2) 0.8349(3) 0.67162(15) 0.0248(7) Uani 1.000000 .
C25 C 0.6406(3) 1.1280(3) 0.6350(2) 0.0401(10) Uani 1.000000 .
H25a H 0.6276(19) 1.1642(9) 0.5991(5) 0.0602(15) Uiso 1.000000 GR
H25b H 0.6152(16) 1.1630(9) 0.6662(10) 0.0602(15) Uiso 1.000000 GR
H25c H 0.7038(4) 1.1233(3) 0.6433(14) 0.0602(15) Uiso 1.000000 GR
C7 C 0.5925(3) 0.3997(3) 0.76150(17) 0.0319(8) Uani 1.000000 .
H7 H 0.6348(3) 0.3557(3) 0.74871(17) 0.0383(10) Uiso 1.000000 R
C17 C 0.2807(2) 1.0112(3) 0.66136(16) 0.0254(7) Uani 1.000000 .
H17a H 0.2935(2) 1.0066(3) 0.70334(16) 0.0305(9) Uiso 1.000000 R
H17b H 0.2425(2) 1.0691(3) 0.65335(16) 0.0305(9) Uiso 1.000000 R
C27 C 0.7381(3) 0.6454(3) 0.70871(19) 0.0357(9) Uani 1.000000 .
C4 C 0.4886(2) 0.5514(3) 0.86597(14) 0.0230(7) Uani 1.000000 .
H4a H 0.4281(2) 0.5749(3) 0.85743(14) 0.0276(8) Uiso 1.000000 R
H4b H 0.4889(2) 0.5052(3) 0.89870(14) 0.0276(8) Uiso 1.000000 R
C8 C 0.6020(2) 0.9002(3) 0.89659(16) 0.0259(8) Uani 1.000000 .
H8 H 0.5747(2) 0.9257(3) 0.85932(16) 0.0310(9) Uiso 1.000000 R
C11 C 0.4926(3) 0.4102(3) 0.66650(17) 0.0367(10) Uani 1.000000 .
H11 H 0.4534(3) 0.4631(3) 0.64943(17) 0.0441(11) Uiso 1.000000 R
C15 C 0.4570(2) 1.0711(3) 0.57065(16) 0.0287(8) Uani 1.000000 .
H15 H 0.4816(2) 1.0955(3) 0.53760(16) 0.0344(9) Uiso 1.000000 R
C21 C 0.1366(3) 0.6740(3) 0.65567(18) 0.0338(9) Uani 1.000000 .
H21 H 0.1577(3) 0.6623(3) 0.69657(18) 0.0405(11) Uiso 1.000000 R
O5 O 0.3245(3) 0.7241(3) 0.51135(18) 0.0559(10) Uani 1.000000 .
F1 F 0.81914(17) 0.6760(3) 0.69910(13) 0.0566(8) Uani 1.000000 .
F2 F 0.7468(2) 0.5663(2) 0.74421(14) 0.0586(8) Uani 1.000000 .
F3 F 0.69788(19) 0.6158(3) 0.65812(12) 0.0596(8) Uani 1.000000 .
F6 F 0.5210(3) 0.6708(4) 0.50527(15) 0.1052(18) Uani 1.000000 .
C9 C 0.5501(3) 0.9407(3) 0.94516(17) 0.0352(9) Uani 1.000000 .
H9a H 0.4890(5) 0.921(2) 0.9384(8) 0.0529(13) Uiso 1.000000 GR
H9b H 0.5743(14) 0.9139(19) 0.9819(2) 0.0529(13) Uiso 1.000000 GR
H9c H 0.5541(17) 1.0129(3) 0.9460(9) 0.0529(13) Uiso 1.000000 GR
F5 F 0.4438(4) 0.5705(3) 0.5539(2) 0.1158(19) Uani 1.000000 .
C10 C 0.6983(3) 0.9330(3) 0.9026(2) 0.0419(10) Uani 1.000000 .
H10a H 0.7250(7) 0.913(2) 0.9401(6) 0.0629(16) Uiso 1.000000 GR
H10b H 0.7294(6) 0.902(2) 0.8725(9) 0.0629(16) Uiso 1.000000 GR
H10c H 0.7015(3) 1.0050(4) 0.8990(14) 0.0629(16) Uiso 1.000000 GR
C28 C 0.4770(4) 0.6616(5) 0.5538(2) 0.0565(15) Uani 1.000000 .
C12 C 0.4400(3) 0.3126(5) 0.6662(2) 0.0635(17) Uani 1.000000 .
H12a H 0.4768(10) 0.2600(9) 0.6837(19) 0.095(3) Uiso 1.000000 GR
H12b H 0.3890(17) 0.3216(11) 0.6880(17) 0.095(3) Uiso 1.000000 GR
H12c H 0.421(3) 0.2946(19) 0.6267(3) 0.095(3) Uiso 1.000000 GR
F4 F 0.5348(2) 0.6697(4) 0.59910(15) 0.1067(18) Uani 1.000000 .
C23 C 0.0358(3) 0.6750(4) 0.6519(3) 0.0577(14) Uani 1.000000 .
H23a H 0.0158(3) 0.729(2) 0.6757(15) 0.087(2) Uiso 1.000000 GR
H23b H 0.0132(3) 0.685(3) 0.6121(4) 0.087(2) Uiso 1.000000 GR
H23c H 0.0146(3) 0.6117(13) 0.6656(18) 0.087(2) Uiso 1.000000 GR
C22 C 0.1751(4) 0.5929(4) 0.6197(2) 0.0547(13) Uani 1.000000 .
H22a H 0.154(2) 0.6012(18) 0.5794(3) 0.0820(19) Uiso 1.000000 GR
H22b H 0.2388(4) 0.5977(19) 0.6234(14) 0.0820(19) Uiso 1.000000 GR
H22c H 0.157(2) 0.5281(4) 0.6332(11) 0.0820(19) Uiso 1.000000 GR


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 S1 2.6242(8) . ?
Bi1 S2 2.8402(9) . ?
Bi1 S3 2.7788(9) . ?
Bi1 O1 2.590(3) . ?
Bi1 S4 2.6760(8) . ?
S6 O4 1.436(4) . ?
S6 O6 1.423(4) . ?
S6 O5 1.419(4) . ?
S6 C28 1.809(5) . ?
S1 C1 1.730(4) . ?
S7 O9 1.445(3) . ?
S7 O7 1.436(3) . ?
S7 O8 1.442(3) . ?
S7 C29 1.818(4) . ?
S2 C5 1.705(4) . ?
S3 C14 1.712(3) . ?
F8 C29 1.330(5) . ?
O3 S5 1.428(3) . ?
N14 C2 1.379(5) . ?
N14 C1 1.334(5) . ?
N14 C8 1.489(4) . ?
F7 C29 1.313(5) . ?
N16 C5 1.348(5) . ?
N16 C7 1.387(5) . ?
N16 C11 1.486(5) . ?
S5 O1 1.467(3) . ?
S5 O2 1.426(3) . ?
S5 C27 1.823(4) . ?
F9 C29 1.318(6) . ?
N20 C6 1.382(5) . ?
N20 C5 1.363(4) . ?
N20 C4 1.457(4) . ?
N24 C16 1.386(4) . ?
N24 C14 1.355(4) . ?
N24 C17 1.460(4) . ?
N26 C20 1.382(5) . ?
N26 C18 1.338(5) . ?
N26 C21 1.485(5) . ?
C6 H6 0.9300 . ?
C6 C7 1.339(5) . ?
N28 C1 1.352(4) . ?
N28 C3 1.383(4) . ?
N28 C4 1.449(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.343(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.340(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.339(5) . ?
C19 N49 1.383(4) . ?
N35 C24 1.479(4) . ?
N35 C14 1.349(4) . ?
N35 C15 1.389(4) . ?
S4 C18 1.727(4) . ?
C3 H3 0.9300 . ?
C24 H24 0.9800 . ?
C24 C26 1.511(5) . ?
C24 C25 1.516(5) . ?
C20 H20 0.9300 . ?
C26 H26a 0.9600 . ?
C26 H26b 0.9600 . ?
C26 H26c 0.9600 . ?
C13 H13a 0.9600 . ?
C13 H13b 0.9600 . ?
C13 H13c 0.9600 . ?
C13 C11 1.515(5) . ?
N49 C18 1.356(5) . ?
N49 C17 1.454(4) . ?
C25 H25a 0.9600 . ?
C25 H25b 0.9600 . ?
C25 H25c 0.9600 . ?
C7 H7 0.9300 . ?
C17 H17a 0.9700 . ?
C17 H17b 0.9700 . ?
C27 F1 1.326(5) . ?
C27 F2 1.329(5) . ?
C27 F3 1.327(5) . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C8 H8 0.9800 . ?
C8 C9 1.513(5) . ?
C8 C10 1.513(5) . ?
C11 H11 0.9800 . ?
C11 C12 1.519(7) . ?
C15 H15 0.9300 . ?
C21 H21 0.9800 . ?
C21 C23 1.517(6) . ?
C21 C22 1.504(6) . ?
F6 C28 1.348(7) . ?
C9 H9a 0.9600 . ?
C9 H9b 0.9600 . ?
C9 H9c 0.9600 . ?
F5 C28 1.309(8) . ?
C10 H10a 0.9600 . ?
C10 H10b 0.9600 . ?
C10 H10c 0.9600 . ?
C28 F4 1.307(6) . ?
C12 H12a 0.9600 . ?
C12 H12b 0.9600 . ?
C12 H12c 0.9600 . ?
C23 H23a 0.9600 . ?
C23 H23b 0.9600 . ?
C23 H23c 0.9600 . ?
C22 H22a 0.9600 . ?
C22 H22b 0.9600 . ?
C22 H22c 0.9600 . ?

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
S2 Bi1 S1 87.76(3) . . ?
S3 Bi1 S1 81.45(3) . . ?
S3 Bi1 S2 166.69(3) . . ?
O1 Bi1 S1 82.88(7) . . ?
O1 Bi1 S2 86.90(7) . . ?
O1 Bi1 S3 99.39(7) . . ?
S4 Bi1 S1 73.72(3) . . ?
S4 Bi1 S2 83.29(3) . . ?
S4 Bi1 S3 86.21(3) . . ?
S4 Bi1 O1 154.90(7) . . ?
O6 S6 O4 113.6(2) . . ?
O5 S6 O4 115.0(3) . . ?
O5 S6 O6 115.6(3) . . ?
C28 S6 O4 102.7(2) . . ?
C28 S6 O6 103.2(3) . . ?
C28 S6 O5 104.6(2) . . ?
C1 S1 Bi1 107.15(13) . . ?
O7 S7 O9 114.75(18) . . ?
O8 S7 O9 114.0(2) . . ?
O8 S7 O7 115.5(2) . . ?
C29 S7 O9 103.4(2) . . ?
C29 S7 O7 103.6(2) . . ?
C29 S7 O8 103.5(2) . . ?
C5 S2 Bi1 101.77(12) . . ?
C14 S3 Bi1 103.22(12) . . ?
C1 N14 C2 109.1(3) . . ?
C8 N14 C2 125.6(3) . . ?
C8 N14 C1 125.2(3) . . ?
C7 N16 C5 109.5(3) . . ?
C11 N16 C5 124.6(3) . . ?
C11 N16 C7 125.5(3) . . ?
O1 S5 O3 113.75(19) . . ?
O2 S5 O3 116.2(2) . . ?
O2 S5 O1 114.4(2) . . ?
C27 S5 O3 104.19(18) . . ?
C27 S5 O1 102.00(19) . . ?
C27 S5 O2 104.0(2) . . ?
C5 N20 C6 110.1(3) . . ?
C4 N20 C6 124.8(3) . . ?
C4 N20 C5 125.0(3) . . ?
C14 N24 C16 110.0(3) . . ?
C17 N24 C16 124.8(3) . . ?
C17 N24 C14 125.1(3) . . ?
S5 O1 Bi1 122.19(18) . . ?
C18 N26 C20 109.1(3) . . ?
C21 N26 C20 124.5(3) . . ?
C21 N26 C18 126.4(3) . . ?
H6 C6 N20 126.7(2) . . ?
C7 C6 N20 106.6(3) . . ?
C7 C6 H6 126.7(2) . . ?
C3 N28 C1 108.5(3) . . ?
C4 N28 C1 127.4(3) . . ?
C4 N28 C3 124.1(3) . . ?
H16 C16 N24 126.6(2) . . ?
C15 C16 N24 106.7(3) . . ?
C15 C16 H16 126.6(2) . . ?
H2 C2 N14 126.2(2) . . ?
C3 C2 N14 107.6(3) . . ?
C3 C2 H2 126.2(2) . . ?
C20 C19 H19 126.4(2) . . ?
N49 C19 H19 126.4(2) . . ?
N49 C19 C20 107.2(3) . . ?
C14 N35 C24 125.2(3) . . ?
C15 N35 C24 125.3(3) . . ?
C15 N35 C14 109.5(3) . . ?
N16 C5 S2 127.0(3) . . ?
N20 C5 S2 127.2(3) . . ?
N20 C5 N16 105.7(3) . . ?
N14 C1 S1 125.0(3) . . ?
N28 C1 S1 127.1(3) . . ?
N28 C1 N14 107.5(3) . . ?
F8 C29 S7 111.1(3) . . ?
F7 C29 S7 111.2(3) . . ?
F7 C29 F8 107.8(4) . . ?
F9 C29 S7 111.3(3) . . ?
F9 C29 F8 108.1(4) . . ?
F9 C29 F7 107.3(4) . . ?
C18 S4 Bi1 102.84(12) . . ?
C2 C3 N28 107.3(3) . . ?
H3 C3 N28 126.4(2) . . ?
H3 C3 C2 126.4(2) . . ?
H24 C24 N35 108.53(18) . . ?
C26 C24 N35 110.5(3) . . ?
C26 C24 H24 108.5(2) . . ?
C25 C24 N35 108.7(3) . . ?
C25 C24 H24 108.5(2) . . ?
C25 C24 C26 112.0(3) . . ?
C19 C20 N26 107.7(3) . . ?
H20 C20 N26 126.1(2) . . ?
H20 C20 C19 126.1(2) . . ?
H26a C26 C24 109.5 . . ?
H26b C26 C24 109.5 . . ?
H26b C26 H26a 109.5 . . ?
H26c C26 C24 109.5 . . ?
H26c C26 H26a 109.5 . . ?
H26c C26 H26b 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
C11 C13 H13a 109.5 . . ?
C11 C13 H13b 109.5 . . ?
C11 C13 H13c 109.5 . . ?
C18 N49 C19 108.8(3) . . ?
C17 N49 C19 124.6(3) . . ?
C17 N49 C18 126.4(3) . . ?
N24 C14 S3 126.4(3) . . ?
N35 C14 S3 127.2(3) . . ?
N35 C14 N24 106.1(3) . . ?
S4 C18 N26 125.6(3) . . ?
N49 C18 N26 107.2(3) . . ?
N49 C18 S4 127.2(3) . . ?
H25a C25 C24 109.5 . . ?
H25b C25 C24 109.5 . . ?
H25b C25 H25a 109.5 . . ?
H25c C25 C24 109.5 . . ?
H25c C25 H25a 109.5 . . ?
H25c C25 H25b 109.5 . . ?
C6 C7 N16 108.0(3) . . ?
H7 C7 N16 126.0(2) . . ?
H7 C7 C6 126.0(2) . . ?
N49 C17 N24 113.0(3) . . ?
H17a C17 N24 108.99(18) . . ?
H17a C17 N49 108.99(19) . . ?
H17b C17 N24 108.99(19) . . ?
H17b C17 N49 108.99(18) . . ?
H17b C17 H17a 107.8 . . ?
F1 C27 S5 110.6(3) . . ?
F2 C27 S5 111.7(3) . . ?
F2 C27 F1 107.3(4) . . ?
F3 C27 S5 110.5(3) . . ?
F3 C27 F1 108.0(4) . . ?
F3 C27 F2 108.6(4) . . ?
N28 C4 N20 112.8(3) . . ?
H4a C4 N20 109.04(18) . . ?
H4a C4 N28 109.04(18) . . ?
H4b C4 N20 109.04(18) . . ?
H4b C4 N28 109.04(17) . . ?
H4b C4 H4a 107.8 . . ?
H8 C8 N14 108.36(19) . . ?
C9 C8 N14 109.0(3) . . ?
C9 C8 H8 108.4(2) . . ?
C10 C8 N14 110.3(3) . . ?
C10 C8 H8 108.4(2) . . ?
C10 C8 C9 112.4(3) . . ?
C13 C11 N16 110.1(3) . . ?
H11 C11 N16 108.0(2) . . ?
H11 C11 C13 108.0(3) . . ?
C12 C11 N16 109.5(4) . . ?
C12 C11 C13 113.1(4) . . ?
C12 C11 H11 108.0(3) . . ?
N35 C15 C16 107.6(3) . . ?
H15 C15 C16 126.2(2) . . ?
H15 C15 N35 126.2(2) . . ?
H21 C21 N26 107.6(2) . . ?
C23 C21 N26 109.2(4) . . ?
C23 C21 H21 107.6(3) . . ?
C22 C21 N26 110.6(4) . . ?
C22 C21 H21 107.6(3) . . ?
C22 C21 C23 114.0(4) . . ?
H9a C9 C8 109.5 . . ?
H9b C9 C8 109.5 . . ?
H9b C9 H9a 109.5 . . ?
H9c C9 C8 109.5 . . ?
H9c C9 H9a 109.5 . . ?
H9c C9 H9b 109.5 . . ?
H10a C10 C8 109.5 . . ?
H10b C10 C8 109.5 . . ?
H10b C10 H10a 109.5 . . ?
H10c C10 C8 109.5 . . ?
H10c C10 H10a 109.5 . . ?
H10c C10 H10b 109.5 . . ?
F6 C28 S6 109.9(4) . . ?
F5 C28 S6 111.7(4) . . ?
F5 C28 F6 107.5(5) . . ?
F4 C28 S6 111.7(4) . . ?
F4 C28 F6 108.0(5) . . ?
F4 C28 F5 107.8(5) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H23a C23 C21 109.5 . . ?
H23b C23 C21 109.5 . . ?
H23b C23 H23a 109.5 . . ?
H23c C23 C21 109.5 . . ?
H23c C23 H23a 109.5 . . ?
H23c C23 H23b 109.5 . . ?
H22a C22 C21 109.5 . . ?
H22b C22 C21 109.5 . . ?
H22b C22 H22a 109.5 . . ?
H22c C22 C21 109.5 . . ?
H22c C22 H22a 109.5 . . ?
H22c C22 H22b 109.5 . . ?

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1440445'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C28 H40 Bi F6 N8 O6 S2 Se4, C F3 O3 S'
_chemical_formula_sum            'C29 H40 Bi F9 N8 O9 S3 Se4'
_chemical_formula_weight         1436.69
_chemical_oxdiff_formula         'C22 H24 N4 Se S O3 F3 Bi'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
F 0.07537 0.05506 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.277599990368
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn (x-z,y,z)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   15.3075(6)
_cell_length_b                   13.2282(6)
_cell_length_c                   23.4812(9)
_cell_angle_alpha                90
_cell_angle_beta                 94.758(4)
_cell_angle_gamma                90
_cell_volume                     4738.4(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7875
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      70.6497
_cell_measurement_theta_min      2.8943
_exptl_absorpt_coefficient_mu    12.868
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.26923
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    2.0138
_exptl_crystal_description       block
_exptl_crystal_F_000             2744.6384
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            20296
_diffrn_reflns_theta_full        70.7720
_diffrn_reflns_theta_max         70.77
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.9834
_diffrn_measured_fraction_theta_max 0.9834
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -23.00   12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  107.0000  176.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   18.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   39.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00  -14.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -50.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega    6.00   71.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega   44.00  110.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega   48.00  108.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
  8 omega   -8.00   73.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  150.0000 81

#__ type_ start__ end____ width___ exp.time_
  9 omega   58.00  130.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
 10 omega   60.00   94.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
 11 omega   61.00   86.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega   49.00   87.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 38

#__ type_ start__ end____ width___ exp.time_
 13 omega   92.00  147.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 55

#__ type_ start__ end____ width___ exp.time_
 14 omega   46.00   93.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 47

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00   93.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 52

#__ type_ start__ end____ width___ exp.time_
 16 omega   59.00   85.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 17 omega   58.00   84.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00   77.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
 19 omega   82.00  113.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 20 omega   51.00  124.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000 -120.0000 73

#__ type_ start__ end____ width___ exp.time_
 21 omega  102.00  175.00   1.0000    2.1400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 73
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0723757000
_diffrn_orient_matrix_UB_12      0.0693788000
_diffrn_orient_matrix_UB_13      -0.0198366000
_diffrn_orient_matrix_UB_21      0.0649997000
_diffrn_orient_matrix_UB_22      -0.0892191000
_diffrn_orient_matrix_UB_23      0.0046892000
_diffrn_orient_matrix_UB_31      -0.0272325000
_diffrn_orient_matrix_UB_32      -0.0284604000
_diffrn_orient_matrix_UB_33      -0.0625461000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -18
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              -14
_reflns_number_gt                7544
_reflns_number_total             8961
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET)
(compiled Oct 27 2011,15:02:11)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         2.1297
_refine_diff_density_min         -1.9802
_refine_diff_density_rms         0.2462
_refine_ls_d_res_high            0.8165
_refine_ls_d_res_low             13.2935
_refine_ls_goodness_of_fit_ref   1.0334
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    62
_refine_ls_number_parameters     575
_refine_ls_number_reflns         8961
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0361
_refine_ls_restrained_S_all      1.0334
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²+1.1667P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1358
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C24(H24), C17(H17), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C20(H20a,H20b), C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C22(H22), C16(H16), C15(H15), C9(H9), C3(H3), C23(H23), C10(H10), C2(H2)
2.d Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c), C19(H19a,H19b,H19c), C18(H18a,H18b,H18c), C26(H26a,H26b,
 H26c), C5(H5a,H5b,H5c), C25(H25a,H25b,H25c), C12(H12a,H12b,H12c), C13(H13a,
 H13b,H13c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Bi1 Bi 0.560110(15) 0.767480(19) 0.773444(10) 0.02654(10) Uani 1.000000 .
Se1 Se 0.52650(5) 0.98234(6) 0.76728(3) 0.03178(17) Uani 1.000000 .
Se2 Se 0.73343(5) 0.81567(6) 0.75727(3) 0.03124(17) Uani 1.000000 .
Se3 Se 0.56731(5) 0.80050(6) 0.65884(3) 0.03059(17) Uani 1.000000 .
Se4 Se 0.62689(5) 0.56212(5) 0.75711(3) 0.03197(17) Uani 1.000000 .
S1 S 0.60902(12) 0.75783(13) 0.94311(7) 0.0344(4) Uani 1.000000 .
S2 S 0.32356(13) 0.74879(14) 0.75720(8) 0.0384(4) Uani 1.000000 .
F1 F 0.4985(7) 0.6484(8) 0.9939(3) 0.149(4) Uani 1.000000 .
F2 F 0.4646(5) 0.6678(8) 0.9057(3) 0.122(3) Uani 1.000000 .
F3 F 0.5652(8) 0.5696(6) 0.9326(4) 0.143(4) Uani 1.000000 .
F4 F 0.3022(4) 0.6186(5) 0.8372(3) 0.086(2) Uani 1.000000 .
F5 F 0.1827(4) 0.6787(5) 0.7981(3) 0.0761(18) Uani 1.000000 .
F6 F 0.2522(4) 0.5681(4) 0.7538(3) 0.0799(19) Uani 1.000000 .
O1 O 0.6269(4) 0.7629(5) 0.8848(2) 0.0580(17) Uani 1.000000 .
O2 O 0.5621(6) 0.8419(6) 0.9616(4) 0.087(3) Uani 1.000000 .
O3 O 0.6798(5) 0.7259(6) 0.9811(3) 0.074(2) Uani 1.000000 .
O4 O 0.4015(3) 0.6970(4) 0.7425(2) 0.0438(13) Uani 1.000000 .
O5 O 0.3366(6) 0.8201(5) 0.8027(3) 0.076(2) Uani 1.000000 .
O6 O 0.2673(4) 0.7816(5) 0.7098(3) 0.0534(15) Uani 1.000000 .
N1 N 0.4962(4) 1.0375(4) 0.8829(2) 0.0307(12) Uani 1.000000 .
N2 N 0.6348(4) 1.0331(4) 0.8697(2) 0.0301(12) Uani 1.000000 .
N3 N 0.7648(3) 0.9299(4) 0.8631(2) 0.0283(11) Uani 1.000000 .
N4 N 0.8322(4) 0.7857(5) 0.8649(2) 0.0327(12) Uani 1.000000 .
N5 N 0.3975(4) 0.7907(4) 0.5988(2) 0.0262(11) Uani 1.000000 .
N6 N 0.4516(4) 0.6402(4) 0.6134(2) 0.0266(11) Uani 1.000000 .
N7 N 0.4785(4) 0.5020(4) 0.6804(2) 0.0329(12) Uani 1.000000 .
N8 N 0.4746(4) 0.4380(5) 0.7649(3) 0.0377(13) Uani 1.000000 .
C1 C 0.5534(4) 1.0156(5) 0.8440(3) 0.0287(13) Uani 1.000000 .
C2 C 0.5411(5) 1.0723(6) 0.9319(3) 0.0371(16) Uani 1.000000 .
H2 H 0.5163(5) 1.0934(6) 0.9648(3) 0.0445(19) Uiso 1.000000 R
C3 C 0.6273(5) 1.0708(6) 0.9243(3) 0.0370(16) Uani 1.000000 .
H3 H 0.6730(5) 1.0911(6) 0.9504(3) 0.0444(19) Uiso 1.000000 R
C4 C 0.3997(4) 1.0263(6) 0.8729(3) 0.0357(15) Uani 1.000000 .
H4 H 0.3858(4) 0.9915(6) 0.8364(3) 0.0429(18) Uiso 1.000000 R
C5 C 0.3651(6) 0.9647(8) 0.9202(4) 0.056(2) Uani 1.000000 .
H5a H 0.395(3) 0.901(2) 0.923(2) 0.085(3) Uiso 1.000000 GR
H5b H 0.375(4) 1.000(3) 0.9557(6) 0.085(3) Uiso 1.000000 GR
H5c H 0.3033(11) 0.954(5) 0.9119(16) 0.085(3) Uiso 1.000000 GR
C6 C 0.3586(6) 1.1294(7) 0.8699(5) 0.062(3) Uani 1.000000 .
H6a H 0.375(4) 1.165(2) 0.9047(13) 0.093(4) Uiso 1.000000 GR
H6b H 0.379(4) 1.166(2) 0.8382(19) 0.093(4) Uiso 1.000000 GR
H6c H 0.2960(6) 1.1228(7) 0.865(3) 0.093(4) Uiso 1.000000 GR
C7 C 0.7168(4) 1.0206(5) 0.8430(3) 0.0315(14) Uani 1.000000 .
H7a H 0.7043(4) 1.0165(5) 0.8019(3) 0.0378(16) Uiso 1.000000 R
H7b H 0.7535(4) 1.0794(5) 0.8513(3) 0.0378(16) Uiso 1.000000 R
C8 C 0.7776(4) 0.8452(5) 0.8324(3) 0.0305(14) Uani 1.000000 .
C9 C 0.8116(5) 0.9210(6) 0.9160(3) 0.0367(16) Uani 1.000000 .
H9 H 0.8139(5) 0.9684(6) 0.9454(3) 0.0441(19) Uiso 1.000000 R
C10 C 0.8533(5) 0.8311(6) 0.9170(3) 0.0367(16) Uani 1.000000 .
H10 H 0.8894(5) 0.8047(6) 0.9471(3) 0.0441(19) Uiso 1.000000 R
C11 C 0.8659(5) 0.6846(6) 0.8482(3) 0.0448(18) Uani 1.000000 .
H11 H 0.8494(5) 0.6751(6) 0.8073(3) 0.054(2) Uiso 1.000000 R
C12 C 0.9637(6) 0.6831(9) 0.8568(5) 0.076(3) Uani 1.000000 .
H12a H 0.9873(7) 0.735(4) 0.834(3) 0.114(5) Uiso 1.000000 GR
H12b H 0.9817(7) 0.694(7) 0.8965(8) 0.114(5) Uiso 1.000000 GR
H12c H 0.9850(7) 0.619(3) 0.845(4) 0.114(5) Uiso 1.000000 GR
C13 C 0.8234(8) 0.6018(7) 0.8800(5) 0.075(3) Uani 1.000000 .
H13a H 0.843(4) 0.606(4) 0.9199(8) 0.112(5) Uiso 1.000000 GR
H13b H 0.7609(8) 0.610(4) 0.876(3) 0.112(5) Uiso 1.000000 GR
H13c H 0.839(5) 0.5374(8) 0.865(3) 0.112(5) Uiso 1.000000 GR
C14 C 0.4660(4) 0.7394(5) 0.6243(3) 0.0274(13) Uani 1.000000 .
C15 C 0.3398(4) 0.7232(5) 0.5709(3) 0.0313(14) Uani 1.000000 .
H15 H 0.2876(4) 0.7393(5) 0.5497(3) 0.0376(17) Uiso 1.000000 R
C16 C 0.3728(5) 0.6305(5) 0.5800(3) 0.0322(14) Uani 1.000000 .
H16 H 0.3475(5) 0.5703(5) 0.5663(3) 0.0386(17) Uiso 1.000000 R
C17 C 0.3886(5) 0.9028(5) 0.5976(3) 0.0347(15) Uani 1.000000 .
H17 H 0.4153(5) 0.9296(5) 0.6339(3) 0.0416(18) Uiso 1.000000 R
C18 C 0.2927(5) 0.9326(6) 0.5921(4) 0.050(2) Uani 1.000000 .
H18a H 0.2664(11) 0.912(4) 0.5555(12) 0.075(3) Uiso 1.000000 GR
H18b H 0.2632(10) 0.901(4) 0.6217(17) 0.075(3) Uiso 1.000000 GR
H18c H 0.2878(5) 1.0047(8) 0.595(3) 0.075(3) Uiso 1.000000 GR
C19 C 0.4385(6) 0.9451(6) 0.5498(3) 0.0478(19) Uani 1.000000 .
H19a H 0.4992(9) 0.927(4) 0.5561(15) 0.072(3) Uiso 1.000000 GR
H19b H 0.415(3) 0.918(4) 0.5139(5) 0.072(3) Uiso 1.000000 GR
H19c H 0.433(4) 1.0174(7) 0.5490(18) 0.072(3) Uiso 1.000000 GR
C20 C 0.5083(4) 0.5563(5) 0.6312(3) 0.0329(14) Uani 1.000000 .
H20a H 0.5107(4) 0.5095(5) 0.5995(3) 0.0395(17) Uiso 1.000000 R
H20b H 0.5671(4) 0.5815(5) 0.6409(3) 0.0395(17) Uiso 1.000000 R
C21 C 0.5211(4) 0.4994(5) 0.7327(3) 0.0300(14) Uani 1.000000 .
C22 C 0.4033(5) 0.4426(5) 0.6793(3) 0.0424(17) Uani 1.000000 .
H22 H 0.3624(5) 0.4327(5) 0.6483(3) 0.051(2) Uiso 1.000000 R
C23 C 0.4013(5) 0.4024(6) 0.7315(3) 0.0434(18) Uani 1.000000 .
H23 H 0.3588(5) 0.3587(6) 0.7434(3) 0.052(2) Uiso 1.000000 R
C24 C 0.5014(5) 0.4032(6) 0.8242(3) 0.0455(19) Uani 1.000000 .
H24 H 0.5450(5) 0.4510(6) 0.8412(3) 0.055(2) Uiso 1.000000 R
C25 C 0.5452(7) 0.3009(8) 0.8212(5) 0.076(4) Uani 1.000000 .
H25a H 0.5032(17) 0.2522(18) 0.806(4) 0.115(5) Uiso 1.000000 GR
H25b H 0.593(4) 0.3053(19) 0.797(3) 0.115(5) Uiso 1.000000 GR
H25c H 0.567(5) 0.280(3) 0.8589(7) 0.115(5) Uiso 1.000000 GR
C26 C 0.4237(6) 0.4044(7) 0.8599(4) 0.052(2) Uani 1.000000 .
H26a H 0.401(3) 0.4719(12) 0.861(2) 0.077(3) Uiso 1.000000 GR
H26b H 0.3791(19) 0.360(4) 0.8431(16) 0.077(3) Uiso 1.000000 GR
H26c H 0.4418(11) 0.382(5) 0.8979(9) 0.077(3) Uiso 1.000000 GR
C27 C 0.5296(8) 0.6558(10) 0.9434(4) 0.074(3) Uani 1.000000 .
C28 C 0.2628(5) 0.6473(7) 0.7886(4) 0.050(2) Uani 1.000000 .
S3 S 0.38563(12) 0.32572(13) 0.49988(7) 0.0353(4) Uani 1.000000 .
F7 F 0.3097(4) 0.1503(4) 0.4871(3) 0.0840(19) Uani 1.000000 .
F8 F 0.2296(4) 0.2643(5) 0.5219(3) 0.082(2) Uani 1.000000 .
F9 F 0.3357(4) 0.1970(5) 0.5739(3) 0.0809(19) Uani 1.000000 .
O7 O 0.3454(4) 0.3548(4) 0.4449(2) 0.0471(13) Uani 1.000000 .
O8 O 0.3828(6) 0.4023(5) 0.5426(3) 0.076(2) Uani 1.000000 .
O9 O 0.4677(4) 0.2737(5) 0.4988(3) 0.0513(15) Uani 1.000000 .
C29 C 0.3114(6) 0.2278(7) 0.5221(4) 0.052(2) Uani 1.000000 .


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 Se1 2.8899(8) . ?
Bi1 Se2 2.7850(7) . ?
Bi1 Se3 2.7375(7) . ?
Bi1 Se4 2.9389(8) . ?
Se1 C1 1.867(6) . ?
Se2 C8 1.878(6) . ?
Se3 C14 1.872(7) . ?
Se4 C21 1.867(7) . ?
S1 O1 1.419(6) . ?
S1 O2 1.412(7) . ?
S1 O3 1.410(6) . ?
S1 C27 1.817(10) . ?
S2 O4 1.442(5) . ?
S2 O5 1.427(6) . ?
S2 O6 1.418(6) . ?
S2 C28 1.824(8) . ?
F1 C27 1.317(12) . ?
F2 C27 1.286(12) . ?
F3 C27 1.297(16) . ?
F4 C28 1.302(10) . ?
F5 C28 1.332(10) . ?
F6 C28 1.331(11) . ?
N1 C1 1.348(8) . ?
N1 C2 1.372(9) . ?
N1 C4 1.483(8) . ?
N2 C1 1.358(8) . ?
N2 C3 1.389(8) . ?
N2 C7 1.458(8) . ?
N3 C7 1.463(8) . ?
N3 C8 1.354(8) . ?
N3 C9 1.388(8) . ?
N4 C8 1.340(9) . ?
N4 C10 1.376(9) . ?
N4 C11 1.498(9) . ?
N5 C14 1.347(9) . ?
N5 C15 1.383(9) . ?
N5 C17 1.489(8) . ?
N6 C14 1.353(8) . ?
N6 C16 1.390(8) . ?
N6 C20 1.449(8) . ?
N7 C20 1.465(8) . ?
N7 C21 1.342(9) . ?
N7 C22 1.393(9) . ?
N8 C21 1.351(9) . ?
N8 C23 1.395(10) . ?
N8 C24 1.492(9) . ?
C2 C3 1.347(10) . ?
C4 C5 1.508(11) . ?
C4 C6 1.502(11) . ?
C9 C10 1.349(11) . ?
C11 C12 1.493(12) . ?
C11 C13 1.505(13) . ?
C15 C16 1.336(10) . ?
C17 C18 1.515(11) . ?
C17 C19 1.517(10) . ?
C22 C23 1.338(11) . ?
C24 C25 1.514(12) . ?
C24 C26 1.511(11) . ?
S3 O7 1.436(5) . ?
S3 O8 1.430(6) . ?
S3 O9 1.434(6) . ?
S3 C29 1.827(9) . ?
F7 C29 1.313(11) . ?
F8 C29 1.342(10) . ?
F9 C29 1.306(11) . ?

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
Se2 Bi1 Se1 86.31(2) . . ?
Se3 Bi1 Se1 79.36(2) . . ?
Se3 Bi1 Se2 73.32(2) . . ?
Se4 Bi1 Se1 164.79(2) . . ?
Se4 Bi1 Se2 81.27(2) . . ?
Se4 Bi1 Se3 88.65(2) . . ?
C1 Se1 Bi1 99.2(2) . . ?
C8 Se2 Bi1 101.1(2) . . ?
C14 Se3 Bi1 104.9(2) . . ?
C21 Se4 Bi1 98.53(19) . . ?
O2 S1 O1 113.8(5) . . ?
O3 S1 O1 115.1(5) . . ?
O3 S1 O2 115.1(5) . . ?
C27 S1 O1 102.8(4) . . ?
C27 S1 O2 103.1(6) . . ?
C27 S1 O3 104.7(5) . . ?
O5 S2 O4 115.2(4) . . ?
O6 S2 O4 114.7(4) . . ?
O6 S2 O5 115.1(4) . . ?
C28 S2 O4 101.9(4) . . ?
C28 S2 O5 103.2(4) . . ?
C28 S2 O6 104.2(4) . . ?
C2 N1 C1 109.4(6) . . ?
C4 N1 C1 124.5(6) . . ?
C4 N1 C2 126.1(6) . . ?
C3 N2 C1 109.2(6) . . ?
C7 N2 C1 125.6(5) . . ?
C7 N2 C3 125.2(6) . . ?
C8 N3 C7 126.7(5) . . ?
C9 N3 C7 124.4(6) . . ?
C9 N3 C8 108.6(6) . . ?
C10 N4 C8 109.8(6) . . ?
C11 N4 C8 126.0(6) . . ?
C11 N4 C10 124.2(6) . . ?
C15 N5 C14 109.2(5) . . ?
C17 N5 C14 125.3(6) . . ?
C17 N5 C15 125.4(6) . . ?
C16 N6 C14 108.5(6) . . ?
C20 N6 C14 127.2(6) . . ?
C20 N6 C16 124.3(5) . . ?
C21 N7 C20 125.1(6) . . ?
C22 N7 C20 124.9(6) . . ?
C22 N7 C21 109.9(6) . . ?
C23 N8 C21 109.0(6) . . ?
C24 N8 C21 126.1(6) . . ?
C24 N8 C23 124.5(6) . . ?
N1 C1 Se1 126.9(5) . . ?
N2 C1 Se1 126.1(5) . . ?
N2 C1 N1 106.7(5) . . ?
C3 C2 N1 108.1(6) . . ?
C2 C3 N2 106.6(6) . . ?
C5 C4 N1 110.1(6) . . ?
C6 C4 N1 109.0(6) . . ?
C6 C4 C5 110.7(7) . . ?
N3 C7 N2 112.5(5) . . ?
N3 C8 Se2 128.0(5) . . ?
N4 C8 Se2 124.8(5) . . ?
N4 C8 N3 107.1(6) . . ?
C10 C9 N3 107.3(6) . . ?
C9 C10 N4 107.1(6) . . ?
C12 C11 N4 109.9(7) . . ?
C13 C11 N4 110.2(7) . . ?
C13 C11 C12 113.1(8) . . ?
N5 C14 Se3 124.1(5) . . ?
N6 C14 Se3 128.1(5) . . ?
N6 C14 N5 107.2(6) . . ?
C16 C15 N5 107.4(6) . . ?
C15 C16 N6 107.7(6) . . ?
C18 C17 N5 110.3(6) . . ?
C19 C17 N5 109.3(6) . . ?
C19 C17 C18 112.6(6) . . ?
N7 C20 N6 112.7(5) . . ?
N7 C21 Se4 127.8(5) . . ?
N8 C21 Se4 125.4(5) . . ?
N8 C21 N7 106.8(6) . . ?
C23 C22 N7 106.8(7) . . ?
C22 C23 N8 107.6(7) . . ?
C25 C24 N8 108.7(7) . . ?
C26 C24 N8 110.2(7) . . ?
C26 C24 C25 114.0(7) . . ?
F1 C27 S1 110.5(8) . . ?
F2 C27 S1 112.7(8) . . ?
F2 C27 F1 108.1(11) . . ?
F3 C27 S1 111.1(9) . . ?
F3 C27 F1 107.4(11) . . ?
F3 C27 F2 106.8(10) . . ?
F4 C28 S2 110.8(6) . . ?
F5 C28 S2 110.2(6) . . ?
F5 C28 F4 108.1(8) . . ?
F6 C28 S2 111.7(6) . . ?
F6 C28 F4 109.5(8) . . ?
F6 C28 F5 106.4(7) . . ?
O8 S3 O7 113.9(4) . . ?
O9 S3 O7 115.1(3) . . ?
O9 S3 O8 115.5(5) . . ?
C29 S3 O7 102.5(4) . . ?
C29 S3 O8 104.2(4) . . ?
C29 S3 O9 103.4(4) . . ?
F7 C29 S3 110.8(6) . . ?
F8 C29 S3 110.3(6) . . ?
F8 C29 F7 108.0(8) . . ?
F9 C29 S3 110.5(7) . . ?
F9 C29 F7 109.1(8) . . ?
F9 C29 F8 108.0(8) . . ?

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1440446'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         
'2(C9 H12 Bi Cl4 N4 S2), C18 H24 Bi Cl2 N8 S4, C18 H25 Bi Cl2 N8 S4'
_chemical_formula_sum            'C54 H73 Bi4 Cl12 N24 S12'
_chemical_formula_weight         2704.49
_chemical_oxdiff_formula         'C21 H24 N2 Se Bi Cl3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   27.2866(11)
_cell_length_b                   27.1101(6)
_cell_length_c                   29.9547(11)
_cell_angle_alpha                90
_cell_angle_beta                 117.194(5)
_cell_angle_gamma                90
_cell_volume                     19709.5(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4120
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.9610
_cell_measurement_theta_min      4.5940
_exptl_absorpt_coefficient_mu    19.514
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.8227
_exptl_crystal_description       needle
_exptl_crystal_F_000             10314.2421
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            21580
_diffrn_reflns_theta_full        70.8080
_diffrn_reflns_theta_max         70.81
_diffrn_reflns_theta_min         3.26
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.7661
_diffrn_measured_fraction_theta_max 0.7661
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -33.00   -8.00   1.0000    2.7600
omega____ theta____ kappa____ phi______ frames
    -        0.0000  106.0000  119.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -37.00   -9.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   50.0000   30.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   31.00   66.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
  4 omega  -15.00   72.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -49.0000  106.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   36.00   94.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega   88.00  176.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -150.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   64.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega   63.00  103.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -106.0000   20.0000 40

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   82.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00   78.00   1.0000   11.0300
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0584410000
_diffrn_orient_matrix_UB_12      -0.0107334000
_diffrn_orient_matrix_UB_13      0.0419170000
_diffrn_orient_matrix_UB_21      0.0239022500
_diffrn_orient_matrix_UB_22      0.0369843500
_diffrn_orient_matrix_UB_23      -0.0239495000
_diffrn_orient_matrix_UB_31      -0.0062548500
_diffrn_orient_matrix_UB_32      0.0418090500
_diffrn_orient_matrix_UB_33      0.0318463000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              29
_reflns_limit_h_min              -33
_reflns_limit_k_max              31
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                9336
_reflns_number_total             14572
_reflns_odcompleteness_completeness 78.51
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.2874
_refine_diff_density_min         -1.3549
_refine_diff_density_rms         0.1869
_refine_ls_d_res_high            0.8163
_refine_ls_d_res_low             13.5551
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0217
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    115
_refine_ls_number_parameters     967
_refine_ls_number_reflns         14572
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0775
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.0217
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.0028
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0521P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1377
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C50(H50a,H50b), C23(H23a,H23b), C5(H5a,H5b), C41(H41a,H41b), C32(H32a,H32b),
 C44(H44a,H44b), C14(H14a,H14b)
2.b Aromatic/amide H refined with riding coordinates:
 C48(H48), C13(H13), C2(H2), C53(H53), C25(H25), C35(H35), C52(H52), C17(H17),
 C49(H49), C7(H7), C8(H8), C22(H22), C16(H16), C43(H43), C21(H21), C3(H3),
 C39(H39), C34(H34), C26(H26), C40(H40), C12(H12), C30(H30), C31(H31)
2.c Idealised Me refined as rotating group:
 C45(H45a,H45b,H45c), C54(H54a,H54b,H54c), C18(H18a,H18b,H18c), C27(H27a,H27b,
 H27c), C36(H36a,H36b,H36c), C29(H29a,H29b,H29c), C47(H47a,H47b,H47c), C38(H38a,
 H38b,H38c), C4(H4a,H4b,H4c), C11(H11a,H11b,H11c), C20(H20a,H20b,H20c), C9(H9a,
 H9b,H9c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Bi2 Bi 0.547583(16) 0.379657(14) 0.121540(13) 0.04316(11) Uani 1.000000 .
Bi1 Bi 0.296598(17) 0.619639(14) 0.114979(14) 0.04619(12) Uani 1.000000 .
Bi4 Bi 0.196328(16) 0.372832(14) -0.127515(14) 0.04365(11) Uani 1.000000 .
S5 S 0.65336(13) 0.37946(10) 0.21003(10) 0.0593(8) Uani 1.000000 .
S6 S 0.61864(12) 0.38038(10) 0.07386(10) 0.0538(6) Uani 1.000000 .
Cl11 Cl 0.24865(13) 0.37414(11) -0.18469(10) 0.0627(7) Uani 1.000000 .
Cl6 Cl 0.45529(11) 0.37697(10) 0.03559(10) 0.0607(7) Uani 1.000000 .
Cl5 Cl 0.49271(13) 0.37685(10) 0.17575(10) 0.0618(7) Uani 1.000000 .
S11 S 0.08853(12) 0.37025(10) -0.21248(10) 0.0566(7) Uani 1.000000 .
S4 S 0.35858(12) 0.60742(11) 0.06255(11) 0.0597(7) Uani 1.000000 .
Cl4 Cl 0.55399(12) 0.28083(10) 0.12182(10) 0.0635(7) Uani 1.000000 .
Cl9 Cl 0.19936(10) 0.27551(9) -0.12371(10) 0.0527(6) Uani 1.000000 .
Cl10 Cl 0.18411(12) 0.47274(10) -0.13302(11) 0.0642(8) Uani 1.000000 .
Cl12 Cl 0.28943(11) 0.37658(10) -0.04281(10) 0.0596(7) Uani 1.000000 .
Cl3 Cl 0.54813(10) 0.47774(9) 0.11957(9) 0.0521(6) Uani 1.000000 .
Cl2 Cl 0.29663(12) 0.52384(10) 0.13380(10) 0.0595(7) Uani 1.000000 .
S12 S 0.13005(11) 0.36869(10) -0.07513(10) 0.0533(6) Uani 1.000000 .
S1 S 0.24192(13) 0.63152(11) 0.17467(11) 0.0598(7) Uani 1.000000 .
Bi3 Bi 0.052934(16) 0.367045(14) 0.122265(13) 0.04439(11) Uani 1.000000 .
S9 S -0.03868(11) 0.35043(11) 0.02754(11) 0.0589(7) Uani 1.000000 .
S10 S 0.11477(11) 0.35636(11) 0.07016(10) 0.0558(6) Uani 1.000000 .
Cl8 Cl 0.06063(13) 0.27133(10) 0.14617(10) 0.0621(7) Uani 1.000000 .
S7 S -0.00065(13) 0.38097(11) 0.18345(12) 0.0607(7) Uani 1.000000 .
S8 S 0.14842(13) 0.38108(10) 0.21465(10) 0.0560(7) Uani 1.000000 .
Cl7 Cl 0.04681(14) 0.46066(11) 0.09717(12) 0.0724(8) Uani 1.000000 .
S3 S 0.20567(11) 0.60378(11) 0.02105(10) 0.0573(7) Uani 1.000000 .
Cl1 Cl 0.29027(17) 0.71354(12) 0.09108(14) 0.0881(11) Uani 1.000000 .
N11 N 0.6711(3) 0.4698(3) 0.1092(3) 0.050(2) Uani 1.000000 .
N23 N 0.0833(3) 0.2763(3) -0.1079(3) 0.050(2) Uani 1.000000 .
N20 N 0.1649(3) 0.2685(3) 0.1099(3) 0.057(2) Uani 1.000000 .
N2 N 0.2760(4) 0.7259(3) 0.2072(3) 0.056(2) Uani 1.000000 .
N7 N 0.3293(4) 0.5101(3) 0.0364(3) 0.051(2) Uani 1.000000 .
N19 N 0.0871(4) 0.2595(3) 0.0428(3) 0.056(2) Uani 1.000000 .
C24 C 0.6301(4) 0.4425(4) 0.0734(4) 0.047(2) Uani 1.000000 .
C50 C 0.0432(4) 0.2908(4) -0.1582(4) 0.051(3) Uani 1.000000 .
H50a H 0.0083(4) 0.2748(4) -0.1665(4) 0.061(3) Uiso 1.000000 R
H50b H 0.0376(4) 0.3261(4) -0.1591(4) 0.061(3) Uiso 1.000000 R
N22 N 0.0612(4) 0.2775(3) -0.1954(3) 0.052(2) Uani 1.000000 .
N1 N 0.1933(4) 0.7217(4) 0.1440(3) 0.062(3) Uani 1.000000 .
C42 C 0.1212(4) 0.2931(4) 0.0744(4) 0.050(3) Uani 1.000000 .
N14 N 0.0325(4) 0.4759(3) 0.2116(3) 0.057(2) Uani 1.000000 .
N10 N 0.6888(4) 0.4700(3) 0.1955(3) 0.052(2) Uani 1.000000 .
C33 C 0.1534(4) 0.4434(4) 0.2155(3) 0.049(3) Uani 1.000000 .
N16 N 0.1829(4) 0.4703(4) 0.1988(3) 0.060(2) Uani 1.000000 .
C45 C 0.2114(4) 0.2915(5) 0.1537(5) 0.084(5) Uani 1.000000 .
H45a H 0.231(3) 0.314(3) 0.1422(5) 0.126(7) Uiso 1.000000 GR
H45b H 0.1975(6) 0.309(3) 0.173(2) 0.126(7) Uiso 1.000000 GR
H45c H 0.236(2) 0.2662(6) 0.174(2) 0.126(7) Uiso 1.000000 GR
N8 N 0.4063(4) 0.5191(4) 0.1032(3) 0.064(3) Uani 1.000000 .
N24 N 0.1534(4) 0.2767(3) -0.0339(3) 0.051(2) Uani 1.000000 .
C37 C -0.0415(4) 0.2876(4) 0.0257(4) 0.055(3) Uani 1.000000 .
C10 C 0.2021(4) 0.5411(4) 0.0196(4) 0.053(3) Uani 1.000000 .
C54 C 0.2020(5) 0.2943(5) 0.0106(4) 0.067(3) Uani 1.000000 .
H54a H 0.2321(11) 0.298(3) 0.0026(10) 0.100(5) Uiso 1.000000 GR
H54b H 0.1938(12) 0.3254(17) 0.021(2) 0.100(5) Uiso 1.000000 GR
H54c H 0.212(2) 0.2708(16) 0.0372(11) 0.100(5) Uiso 1.000000 GR
N12 N 0.6011(4) 0.4730(3) 0.0357(3) 0.054(2) Uani 1.000000 .
C23 C 0.7094(4) 0.4542(4) 0.1608(4) 0.054(3) Uani 1.000000 .
H23a H 0.7131(4) 0.4185(4) 0.1620(4) 0.065(3) Uiso 1.000000 R
H23b H 0.7454(4) 0.4685(4) 0.1706(4) 0.065(3) Uiso 1.000000 R
C46 C 0.0837(4) 0.3077(4) -0.2176(4) 0.051(3) Uani 1.000000 .
N13 N -0.0480(4) 0.4703(3) 0.1486(3) 0.059(2) Uani 1.000000 .
C6 C 0.3975(4) 0.6927(4) 0.2099(4) 0.049(3) Uani 1.000000 .
C48 C 0.0869(5) 0.2306(4) -0.2408(4) 0.065(3) Uani 1.000000 .
H48 H 0.0939(5) 0.2038(4) -0.2563(4) 0.078(4) Uiso 1.000000 R
N4 N 0.4311(4) 0.7182(4) 0.1960(4) 0.062(3) Uani 1.000000 .
C28 C -0.0058(4) 0.4429(4) 0.1803(4) 0.047(2) Uani 1.000000 .
N18 N -0.0110(4) 0.2562(3) 0.0132(3) 0.058(2) Uani 1.000000 .
N3 N 0.3717(4) 0.7250(3) 0.2257(3) 0.055(2) Uani 1.000000 .
C15 C 0.3647(4) 0.5450(4) 0.0676(4) 0.052(3) Uani 1.000000 .
C18 C 0.4534(5) 0.5408(5) 0.1475(5) 0.087(5) Uani 1.000000 .
H18a H 0.474(3) 0.562(3) 0.1365(5) 0.131(7) Uiso 1.000000 GR
H18b H 0.4399(6) 0.559(3) 0.167(2) 0.131(7) Uiso 1.000000 GR
H18c H 0.477(2) 0.5149(6) 0.168(2) 0.131(7) Uiso 1.000000 GR
N15 N 0.1282(4) 0.4758(3) 0.2333(3) 0.055(2) Uani 1.000000 .
C51 C 0.1223(4) 0.3066(4) -0.0723(4) 0.047(2) Uani 1.000000 .
N21 N 0.0987(4) 0.2788(4) -0.2449(3) 0.061(3) Uani 1.000000 .
N5 N 0.1673(4) 0.5130(4) 0.0299(4) 0.067(3) Uani 1.000000 .
S2 S 0.39352(12) 0.62990(10) 0.20978(11) 0.0572(7) Uani 1.000000 .
N17 N -0.0769(4) 0.2594(4) 0.0336(4) 0.060(2) Uani 1.000000 .
C19 C 0.6615(5) 0.4417(4) 0.2149(4) 0.056(3) Uani 1.000000 .
C27 C 0.5517(5) 0.4586(5) -0.0085(4) 0.071(3) Uani 1.000000 .
H27a H 0.5606(8) 0.434(3) -0.0267(19) 0.107(5) Uiso 1.000000 GR
H27b H 0.5255(16) 0.445(3) 0.0014(4) 0.107(5) Uiso 1.000000 GR
H27c H 0.536(2) 0.4869(8) -0.0295(18) 0.107(5) Uiso 1.000000 GR
N6 N 0.2314(4) 0.5088(3) 0.0057(3) 0.054(2) Uani 1.000000 .
C5 C 0.3316(5) 0.7134(4) 0.2442(4) 0.057(3) Uani 1.000000 .
H5a H 0.3408(5) 0.7316(4) 0.2749(4) 0.069(3) Uiso 1.000000 R
H5b H 0.3335(5) 0.6784(4) 0.2519(4) 0.069(3) Uiso 1.000000 R
C41 C 0.0338(5) 0.2698(4) 0.0005(4) 0.057(3) Uani 1.000000 .
H41a H 0.0313(5) 0.3045(4) -0.0079(4) 0.069(3) Uiso 1.000000 R
H41b H 0.0300(5) 0.2510(4) -0.0285(4) 0.069(3) Uiso 1.000000 R
C32 C 0.0882(4) 0.4641(5) 0.2511(4) 0.059(3) Uani 1.000000 .
H32a H 0.0961(4) 0.4831(5) 0.2811(4) 0.071(4) Uiso 1.000000 R
H32b H 0.0905(4) 0.4293(5) 0.2595(4) 0.071(4) Uiso 1.000000 R
C1 C 0.2373(5) 0.6952(4) 0.1745(4) 0.055(3) Uani 1.000000 .
C13 C 0.2137(5) 0.4618(5) 0.0068(5) 0.073(4) Uani 1.000000 .
H13 H 0.2266(5) 0.4333(5) -0.0014(5) 0.088(4) Uiso 1.000000 R
C2 C 0.2053(5) 0.7703(5) 0.1582(5) 0.071(4) Uani 1.000000 .
H2 H 0.1820(5) 0.7969(5) 0.1429(5) 0.086(4) Uiso 1.000000 R
C36 C 0.2129(5) 0.4503(5) 0.1749(5) 0.082(4) Uani 1.000000 .
H36a H 0.237(3) 0.425(2) 0.1955(18) 0.123(6) Uiso 1.000000 GR
H36b H 0.1877(6) 0.437(3) 0.1430(17) 0.123(6) Uiso 1.000000 GR
H36c H 0.234(3) 0.4759(9) 0.170(3) 0.123(6) Uiso 1.000000 GR
C53 C 0.1343(5) 0.2289(4) -0.0442(4) 0.058(3) Uani 1.000000 .
H53 H 0.1491(5) 0.2019(4) -0.0231(4) 0.070(4) Uiso 1.000000 R
C25 C 0.6662(5) 0.5182(4) 0.0930(4) 0.061(3) Uani 1.000000 .
H25 H 0.6891(5) 0.5443(4) 0.1104(4) 0.073(4) Uiso 1.000000 R
C35 C 0.1780(5) 0.5199(4) 0.2082(5) 0.067(3) Uani 1.000000 .
H35 H 0.1954(5) 0.5461(4) 0.2011(5) 0.080(4) Uiso 1.000000 R
C52 C 0.0910(4) 0.2278(4) -0.0896(4) 0.055(3) Uani 1.000000 .
H52 H 0.0701(4) 0.2003(4) -0.1060(4) 0.066(3) Uiso 1.000000 R
C17 C 0.3981(5) 0.4693(5) 0.0939(5) 0.064(3) Uani 1.000000 .
H17 H 0.4214(5) 0.4439(5) 0.1126(5) 0.077(4) Uiso 1.000000 R
N9 N 0.6437(4) 0.4721(4) 0.2387(3) 0.059(2) Uani 1.000000 .
C49 C 0.0635(5) 0.2293(4) -0.2101(4) 0.064(3) Uani 1.000000 .
H49 H 0.0510(5) 0.2013(4) -0.2005(4) 0.077(4) Uiso 1.000000 R
C7 C 0.3885(6) 0.7723(5) 0.2213(5) 0.072(4) Uani 1.000000 .
H7 H 0.3768(6) 0.8016(5) 0.2296(5) 0.086(4) Uiso 1.000000 R
C8 C 0.4239(7) 0.7680(5) 0.2035(5) 0.089(5) Uani 1.000000 .
H8 H 0.4417(7) 0.7941(5) 0.1967(5) 0.106(6) Uiso 1.000000 R
C22 C 0.6873(5) 0.5188(4) 0.2094(4) 0.056(3) Uani 1.000000 .
H22 H 0.7024(5) 0.5457(4) 0.2008(4) 0.067(3) Uiso 1.000000 R
C44 C 0.1579(5) 0.2180(5) 0.1005(5) 0.074(4) Uani 1.000000 .
H44a H 0.1881(5) 0.2046(5) 0.0957(5) 0.089(4) Uiso 1.000000 R
H44b H 0.1562(5) 0.2009(5) 0.1282(5) 0.089(4) Uiso 1.000000 R
C16 C 0.3498(5) 0.4645(5) 0.0528(5) 0.068(3) Uani 1.000000 .
H16 H 0.3332(5) 0.4349(5) 0.0379(5) 0.082(4) Uiso 1.000000 R
C43 C 0.1096(5) 0.2134(5) 0.0580(5) 0.069(3) Uani 1.000000 .
H43 H 0.0942(5) 0.1839(5) 0.0418(5) 0.083(4) Uiso 1.000000 R
C21 C 0.6610(5) 0.5202(5) 0.2369(4) 0.067(3) Uani 1.000000 .
H21 H 0.6551(5) 0.5478(5) 0.2521(4) 0.080(4) Uiso 1.000000 R
C3 C 0.2543(6) 0.7735(4) 0.1965(5) 0.075(4) Uani 1.000000 .
H3 H 0.2715(6) 0.8022(4) 0.2135(5) 0.091(5) Uiso 1.000000 R
C39 C -0.0682(5) 0.2107(5) 0.0263(5) 0.073(4) Uani 1.000000 .
H39 H -0.0870(5) 0.1838(5) 0.0302(5) 0.088(4) Uiso 1.000000 R
C29 C -0.0959(5) 0.4497(5) 0.1056(5) 0.087(5) Uani 1.000000 .
H29a H -0.112(3) 0.424(3) 0.1170(6) 0.130(7) Uiso 1.000000 GR
H29b H -0.122(2) 0.4753(10) 0.089(2) 0.130(7) Uiso 1.000000 GR
H29c H -0.0846(9) 0.436(4) 0.0823(19) 0.130(7) Uiso 1.000000 GR
C34 C 0.1444(5) 0.5237(5) 0.2289(5) 0.077(4) Uani 1.000000 .
H34 H 0.1336(5) 0.5526(5) 0.2386(5) 0.093(5) Uiso 1.000000 R
C47 C 0.1276(6) 0.2973(5) -0.2722(5) 0.077(4) Uani 1.000000 .
H47a H 0.112(2) 0.3285(16) -0.287(3) 0.115(6) Uiso 1.000000 GR
H47b H 0.1659(8) 0.301(3) -0.2493(8) 0.115(6) Uiso 1.000000 GR
H47c H 0.124(3) 0.2742(16) -0.298(2) 0.115(6) Uiso 1.000000 GR
C26 C 0.6220(5) 0.5202(4) 0.0471(4) 0.059(3) Uani 1.000000 .
H26 H 0.6083(5) 0.5481(4) 0.0271(4) 0.071(4) Uiso 1.000000 R
C38 C -0.1173(6) 0.2782(6) 0.0493(5) 0.087(4) Uani 1.000000 .
H38a H -0.0991(10) 0.300(3) 0.078(2) 0.131(7) Uiso 1.000000 GR
H38b H -0.145(2) 0.296(3) 0.0222(14) 0.131(7) Uiso 1.000000 GR
H38c H -0.134(3) 0.2511(6) 0.058(4) 0.131(7) Uiso 1.000000 GR
C14 C 0.2770(4) 0.5202(5) -0.0062(4) 0.058(3) Uani 1.000000 .
H14a H 0.2753(4) 0.5547(5) -0.0154(4) 0.070(4) Uiso 1.000000 R
H14b H 0.2733(4) 0.5005(5) -0.0346(4) 0.070(4) Uiso 1.000000 R
C4 C 0.1458(5) 0.7019(6) 0.1012(5) 0.087(5) Uani 1.000000 .
H4a H 0.1575(6) 0.685(3) 0.080(2) 0.130(7) Uiso 1.000000 GR
H4b H 0.127(2) 0.679(3) 0.1126(5) 0.130(7) Uiso 1.000000 GR
H4c H 0.121(2) 0.7283(7) 0.083(2) 0.130(7) Uiso 1.000000 GR
C40 C -0.0282(5) 0.2089(5) 0.0126(5) 0.071(4) Uani 1.000000 .
H40 H -0.0147(5) 0.1808(5) 0.0041(5) 0.085(4) Uiso 1.000000 R
C11 C 0.1278(6) 0.5322(5) 0.0466(5) 0.087(4) Uani 1.000000 .
H11a H 0.134(3) 0.5668(10) 0.054(4) 0.130(7) Uiso 1.000000 GR
H11b H 0.0909(6) 0.527(3) 0.0207(16) 0.130(7) Uiso 1.000000 GR
H11c H 0.133(3) 0.515(3) 0.076(2) 0.130(7) Uiso 1.000000 GR
C20 C 0.6105(6) 0.4574(6) 0.2622(5) 0.087(5) Uani 1.000000 .
H20a H 0.597(3) 0.4246(14) 0.252(3) 0.131(7) Uiso 1.000000 GR
H20b H 0.6324(12) 0.458(3) 0.2980(5) 0.131(7) Uiso 1.000000 GR
H20c H 0.580(2) 0.480(2) 0.253(3) 0.131(7) Uiso 1.000000 GR
C12 C 0.1741(6) 0.4642(5) 0.0220(5) 0.080(4) Uani 1.000000 .
H12 H 0.1550(6) 0.4377(5) 0.0262(5) 0.096(5) Uiso 1.000000 R
C9 C 0.4663(5) 0.6973(5) 0.1760(5) 0.080(4) Uani 1.000000 .
H9a H 0.487(3) 0.670(2) 0.197(2) 0.119(6) Uiso 1.000000 GR
H9b H 0.4440(6) 0.686(3) 0.1423(13) 0.119(6) Uiso 1.000000 GR
H9c H 0.492(3) 0.7220(11) 0.176(3) 0.119(6) Uiso 1.000000 GR
C30 C -0.0389(5) 0.5184(5) 0.1596(5) 0.070(3) Uani 1.000000 .
H30 H -0.0631(5) 0.5438(5) 0.1426(5) 0.085(4) Uiso 1.000000 R
C31 C 0.0111(5) 0.5240(5) 0.1993(5) 0.072(4) Uani 1.000000 .
H31 H 0.0278(5) 0.5533(5) 0.2151(5) 0.087(4) Uiso 1.000000 R


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
Bi2 S5 2.892(3) . ?
Bi2 S6 2.886(3) . ?
Bi2 Cl6 2.655(2) . ?
Bi2 Cl5 2.666(3) . ?
Bi2 Cl4 2.685(3) . ?
Bi2 Cl3 2.660(3) . ?
Bi1 S4 2.804(3) . ?
Bi1 Cl2 2.657(3) . ?
Bi1 S1 2.822(3) . ?
Bi1 S3 2.806(3) . ?
Bi1 Cl1 2.629(3) . ?
Bi1 S2 2.876(3) . ?
Bi4 Cl11 2.685(3) . ?
Bi4 S11 2.880(3) . ?
Bi4 Cl9 2.641(3) . ?
Bi4 Cl10 2.725(3) . ?
Bi4 Cl12 2.648(2) . ?
Bi4 S12 2.888(3) . ?
S5 C19 1.699(11) . ?
S6 C24 1.713(10) . ?
S11 C46 1.702(10) . ?
S4 C15 1.700(11) . ?
S12 C51 1.704(10) . ?
S1 C1 1.731(12) . ?
Bi3 S9 2.832(3) . ?
Bi3 S10 2.788(3) . ?
Bi3 Cl8 2.674(3) . ?
Bi3 S7 2.844(3) . ?
Bi3 S8 2.829(3) . ?
Bi3 Cl7 2.630(3) . ?
S9 C37 1.704(12) . ?
S10 C42 1.722(11) . ?
S7 C28 1.685(11) . ?
S8 C33 1.694(11) . ?
S3 C10 1.702(11) . ?
N11 C24 1.360(12) . ?
N11 C23 1.478(11) . ?
N11 C25 1.384(13) . ?
N23 C50 1.455(12) . ?
N23 C51 1.382(12) . ?
N23 C52 1.402(13) . ?
N20 C42 1.357(12) . ?
N20 C45 1.482(13) . ?
N20 C44 1.392(14) . ?
N2 C5 1.453(13) . ?
N2 C1 1.349(13) . ?
N2 C3 1.394(14) . ?
N7 C15 1.369(12) . ?
N7 C16 1.352(14) . ?
N7 C14 1.442(12) . ?
N19 C42 1.337(12) . ?
N19 C41 1.454(13) . ?
N19 C43 1.373(15) . ?
C24 N12 1.332(12) . ?
C50 N22 1.453(13) . ?
N22 C46 1.365(14) . ?
N22 C49 1.390(14) . ?
N1 C1 1.339(14) . ?
N1 C2 1.378(15) . ?
N1 C4 1.447(14) . ?
N14 C28 1.369(12) . ?
N14 C32 1.475(13) . ?
N14 C31 1.407(15) . ?
N10 C23 1.451(14) . ?
N10 C19 1.371(15) . ?
N10 C22 1.394(13) . ?
C33 N16 1.342(14) . ?
C33 N15 1.364(14) . ?
N16 C36 1.416(16) . ?
N16 C35 1.395(15) . ?
N8 C15 1.347(13) . ?
N8 C18 1.484(14) . ?
N8 C17 1.376(15) . ?
N24 C54 1.465(12) . ?
N24 C51 1.344(11) . ?
N24 C53 1.380(14) . ?
C37 N18 1.358(14) . ?
C37 N17 1.336(14) . ?
C10 N5 1.356(15) . ?
C10 N6 1.374(14) . ?
N12 C27 1.447(13) . ?
N12 C26 1.379(14) . ?
C46 N21 1.325(14) . ?
N13 C28 1.333(13) . ?
N13 C29 1.463(14) . ?
N13 C30 1.342(15) . ?
C6 N4 1.357(14) . ?
C6 N3 1.336(13) . ?
C6 S2 1.706(11) . ?
C48 N21 1.363(14) . ?
C48 C49 1.338(17) . ?
N4 C8 1.395(17) . ?
N4 C9 1.460(15) . ?
N18 C41 1.484(14) . ?
N18 C40 1.362(15) . ?
N3 C5 1.471(14) . ?
N3 C7 1.388(15) . ?
N15 C32 1.453(14) . ?
N15 C34 1.395(15) . ?
N21 C47 1.458(14) . ?
N5 C11 1.476(16) . ?
N5 C12 1.373(15) . ?
N17 C39 1.376(15) . ?
N17 C38 1.474(16) . ?
C19 N9 1.320(14) . ?
N6 C13 1.368(15) . ?
N6 C14 1.476(14) . ?
C13 C12 1.351(19) . ?
C2 C3 1.308(16) . ?
C53 C52 1.333(14) . ?
C25 C26 1.355(14) . ?
C35 C34 1.325(18) . ?
C17 C16 1.336(15) . ?
N9 C21 1.395(15) . ?
N9 C20 1.435(16) . ?
C7 C8 1.31(2) . ?
C22 C21 1.318(17) . ?
C44 C43 1.358(16) . ?
C39 C40 1.331(18) . ?
C30 C31 1.345(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
S6 Bi2 S5 80.72(9) . . ?
Cl6 Bi2 S5 174.70(10) . . ?
Cl6 Bi2 S6 94.26(9) . . ?
Cl5 Bi2 S5 92.56(9) . . ?
Cl5 Bi2 S6 173.18(8) . . ?
Cl5 Bi2 Cl6 92.41(9) . . ?
Cl4 Bi2 S5 87.65(8) . . ?
Cl4 Bi2 S6 87.18(9) . . ?
Cl4 Bi2 Cl6 90.41(8) . . ?
Cl4 Bi2 Cl5 91.35(9) . . ?
Cl3 Bi2 S5 90.50(7) . . ?
Cl3 Bi2 S6 88.30(8) . . ?
Cl3 Bi2 Cl6 91.05(8) . . ?
Cl3 Bi2 Cl5 93.01(9) . . ?
Cl3 Bi2 Cl4 175.34(9) . . ?
Cl2 Bi1 S4 93.53(9) . . ?
S1 Bi1 S4 175.58(9) . . ?
S1 Bi1 Cl2 85.76(9) . . ?
S3 Bi1 S4 84.47(9) . . ?
S3 Bi1 Cl2 88.71(8) . . ?
S3 Bi1 S1 99.88(9) . . ?
Cl1 Bi1 S4 86.74(11) . . ?
Cl1 Bi1 Cl2 176.21(10) . . ?
Cl1 Bi1 S1 94.25(11) . . ?
Cl1 Bi1 S3 87.55(10) . . ?
S2 Bi1 S4 92.67(9) . . ?
S2 Bi1 Cl2 88.51(8) . . ?
S2 Bi1 S1 82.95(9) . . ?
S2 Bi1 S3 175.88(9) . . ?
S2 Bi1 Cl1 95.25(10) . . ?
S11 Bi4 Cl11 93.59(9) . . ?
Cl9 Bi4 Cl11 91.46(9) . . ?
Cl9 Bi4 S11 90.75(7) . . ?
Cl10 Bi4 Cl11 91.97(10) . . ?
Cl10 Bi4 S11 85.61(8) . . ?
Cl10 Bi4 Cl9 175.15(9) . . ?
Cl12 Bi4 Cl11 93.09(9) . . ?
Cl12 Bi4 S11 173.26(10) . . ?
Cl12 Bi4 Cl9 89.97(8) . . ?
Cl12 Bi4 Cl10 93.27(8) . . ?
S12 Bi4 Cl11 174.17(8) . . ?
S12 Bi4 S11 80.73(8) . . ?
S12 Bi4 Cl9 87.29(8) . . ?
S12 Bi4 Cl10 88.96(9) . . ?
S12 Bi4 Cl12 92.61(9) . . ?
C19 S5 Bi2 96.5(4) . . ?
C24 S6 Bi2 100.2(4) . . ?
C46 S11 Bi4 96.3(3) . . ?
C15 S4 Bi1 97.3(4) . . ?
C51 S12 Bi4 100.9(4) . . ?
C1 S1 Bi1 99.9(4) . . ?
S10 Bi3 S9 84.58(9) . . ?
Cl8 Bi3 S9 92.25(8) . . ?
Cl8 Bi3 S10 93.18(9) . . ?
S7 Bi3 S9 100.86(9) . . ?
S7 Bi3 S10 174.49(8) . . ?
S7 Bi3 Cl8 87.53(9) . . ?
S8 Bi3 S9 176.62(9) . . ?
S8 Bi3 S10 92.24(9) . . ?
S8 Bi3 Cl8 86.79(8) . . ?
S8 Bi3 S7 82.34(9) . . ?
Cl7 Bi3 S9 87.44(9) . . ?
Cl7 Bi3 S10 85.18(10) . . ?
Cl7 Bi3 Cl8 178.35(10) . . ?
Cl7 Bi3 S7 94.12(10) . . ?
Cl7 Bi3 S8 93.42(9) . . ?
C37 S9 Bi3 101.4(3) . . ?
C42 S10 Bi3 97.4(4) . . ?
C28 S7 Bi3 98.7(4) . . ?
C33 S8 Bi3 100.4(3) . . ?
C10 S3 Bi1 101.1(3) . . ?
C23 N11 C24 127.0(9) . . ?
C25 N11 C24 109.1(8) . . ?
C25 N11 C23 123.1(9) . . ?
C51 N23 C50 126.0(8) . . ?
C52 N23 C50 124.4(8) . . ?
C52 N23 C51 109.4(8) . . ?
C45 N20 C42 125.3(10) . . ?
C44 N20 C42 109.6(9) . . ?
C44 N20 C45 125.1(10) . . ?
C1 N2 C5 127.4(10) . . ?
C3 N2 C5 125.3(10) . . ?
C3 N2 C1 107.2(9) . . ?
C16 N7 C15 109.8(9) . . ?
C14 N7 C15 125.2(9) . . ?
C14 N7 C16 125.0(10) . . ?
C41 N19 C42 125.6(9) . . ?
C43 N19 C42 108.9(9) . . ?
C43 N19 C41 125.5(10) . . ?
N11 C24 S6 128.0(7) . . ?
N12 C24 S6 125.3(8) . . ?
N12 C24 N11 106.6(9) . . ?
N22 C50 N23 111.8(9) . . ?
C46 N22 C50 127.7(9) . . ?
C49 N22 C50 123.7(10) . . ?
C49 N22 C46 108.3(10) . . ?
C2 N1 C1 106.9(9) . . ?
C4 N1 C1 124.5(10) . . ?
C4 N1 C2 128.3(10) . . ?
N20 C42 S10 124.8(7) . . ?
N19 C42 S10 127.8(8) . . ?
N19 C42 N20 107.3(9) . . ?
C32 N14 C28 126.3(9) . . ?
C31 N14 C28 109.3(9) . . ?
C31 N14 C32 124.3(9) . . ?
C19 N10 C23 126.9(10) . . ?
C22 N10 C23 124.6(10) . . ?
C22 N10 C19 107.9(10) . . ?
N16 C33 S8 126.3(9) . . ?
N15 C33 S8 126.7(9) . . ?
N15 C33 N16 106.9(10) . . ?
C36 N16 C33 124.4(11) . . ?
C35 N16 C33 108.6(10) . . ?
C35 N16 C36 127.0(11) . . ?
C18 N8 C15 125.0(10) . . ?
C17 N8 C15 110.6(9) . . ?
C17 N8 C18 124.4(10) . . ?
C51 N24 C54 122.4(9) . . ?
C53 N24 C54 127.1(9) . . ?
C53 N24 C51 110.4(9) . . ?
N18 C37 S9 127.8(9) . . ?
N17 C37 S9 126.3(9) . . ?
N17 C37 N18 105.8(10) . . ?
N5 C10 S3 126.4(9) . . ?
N6 C10 S3 127.6(9) . . ?
N6 C10 N5 106.0(10) . . ?
C27 N12 C24 123.5(10) . . ?
C26 N12 C24 110.4(9) . . ?
C26 N12 C27 125.8(10) . . ?
N10 C23 N11 110.1(8) . . ?
N22 C46 S11 125.8(9) . . ?
N21 C46 S11 127.8(10) . . ?
N21 C46 N22 106.3(9) . . ?
C29 N13 C28 123.2(10) . . ?
C30 N13 C28 111.2(9) . . ?
C30 N13 C29 125.4(10) . . ?
N3 C6 N4 108.2(10) . . ?
S2 C6 N4 124.0(9) . . ?
S2 C6 N3 127.8(9) . . ?
C49 C48 N21 107.1(11) . . ?
C8 N4 C6 106.2(11) . . ?
C9 N4 C6 126.3(11) . . ?
C9 N4 C8 127.5(12) . . ?
N14 C28 S7 126.5(8) . . ?
N13 C28 S7 128.1(8) . . ?
N13 C28 N14 105.3(9) . . ?
C41 N18 C37 126.5(10) . . ?
C40 N18 C37 110.1(11) . . ?
C40 N18 C41 123.4(11) . . ?
C5 N3 C6 126.5(10) . . ?
C7 N3 C6 108.9(11) . . ?
C7 N3 C5 124.6(11) . . ?
N7 C15 S4 128.2(8) . . ?
N8 C15 S4 127.1(8) . . ?
N8 C15 N7 104.8(9) . . ?
C32 N15 C33 126.8(10) . . ?
C34 N15 C33 109.0(11) . . ?
C34 N15 C32 124.1(10) . . ?
N23 C51 S12 128.2(7) . . ?
N24 C51 S12 126.5(8) . . ?
N24 C51 N23 105.3(9) . . ?
C48 N21 C46 111.0(11) . . ?
C47 N21 C46 122.7(10) . . ?
C47 N21 C48 126.2(12) . . ?
C11 N5 C10 125.1(11) . . ?
C12 N5 C10 109.8(12) . . ?
C12 N5 C11 125.1(12) . . ?
C6 S2 Bi1 97.3(3) . . ?
C39 N17 C37 109.3(11) . . ?
C38 N17 C37 124.5(11) . . ?
C38 N17 C39 126.2(11) . . ?
N10 C19 S5 126.5(10) . . ?
N9 C19 S5 127.0(10) . . ?
N9 C19 N10 106.6(10) . . ?
C13 N6 C10 108.9(11) . . ?
C14 N6 C10 127.7(10) . . ?
C14 N6 C13 123.2(10) . . ?
N3 C5 N2 111.0(9) . . ?
N18 C41 N19 109.9(9) . . ?
N15 C32 N14 109.2(9) . . ?
N2 C1 S1 125.6(9) . . ?
N1 C1 S1 125.4(9) . . ?
N1 C1 N2 108.9(10) . . ?
C12 C13 N6 108.1(12) . . ?
C3 C2 N1 109.7(10) . . ?
C52 C53 N24 108.5(9) . . ?
C26 C25 N11 107.0(9) . . ?
C34 C35 N16 108.6(11) . . ?
C53 C52 N23 106.4(9) . . ?
C16 C17 N8 106.4(11) . . ?
C21 N9 C19 110.4(11) . . ?
C20 N9 C19 124.2(11) . . ?
C20 N9 C21 125.4(12) . . ?
C48 C49 N22 107.2(11) . . ?
C8 C7 N3 107.0(12) . . ?
C7 C8 N4 109.7(12) . . ?
C21 C22 N10 108.3(11) . . ?
C43 C44 N20 105.4(11) . . ?
C17 C16 N7 108.5(11) . . ?
C44 C43 N19 108.8(11) . . ?
C22 C21 N9 106.8(11) . . ?
C2 C3 N2 107.3(10) . . ?
C40 C39 N17 108.0(12) . . ?
C35 C34 N15 106.8(12) . . ?
C25 C26 N12 106.8(10) . . ?
N6 C14 N7 110.5(9) . . ?
C39 C40 N18 106.8(12) . . ?
C13 C12 N5 107.1(13) . . ?
C31 C30 N13 109.1(11) . . ?
C30 C31 N14 104.9(10) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.069 0.121 0.129 80.2 2.9 ?
2 -0.069 0.121 0.371 80.2 2.7 ?
3 0.000 0.500 0.500 215.3 4.3 ?
4 0.000 0.500 0.000 215.3 4.3 ?
5 0.069 0.879 0.629 80.2 2.1 ?
6 -0.069 0.879 0.871 80.2 1.8 ?
7 0.186 0.129 0.875 76.4 1.2 ?
8 0.226 0.350 0.406 111.8 1.3 ?
9 0.226 0.650 0.906 111.8 0.0 ?
10 0.186 0.871 0.375 76.4 2.5 ?
11 0.274 0.150 0.594 111.8 1.4 ?
12 0.274 0.850 0.094 111.8 3.1 ?
13 0.314 0.371 0.125 76.4 2.9 ?
14 0.314 0.629 0.625 76.4 1.6 ?
15 0.431 0.379 0.871 80.2 1.8 ?
16 0.431 0.621 0.371 80.2 2.7 ?
17 0.500 0.000 0.500 215.3 4.3 ?
18 0.500 0.000 1.000 215.3 4.3 ?
19 0.569 0.379 0.629 80.2 2.1 ?
20 0.569 0.621 0.129 80.2 2.9 ?
21 0.726 0.150 0.906 111.8 0.0 ?
22 0.686 0.371 0.375 76.4 2.5 ?
23 0.686 0.629 0.875 76.4 1.2 ?
24 0.726 0.850 0.406 111.8 1.3 ?
25 0.774 0.350 0.094 111.8 3.1 ?
26 0.774 0.650 0.594 111.8 1.4 ?
27 0.814 0.129 0.625 76.4 1.6 ?
28 0.814 0.871 0.125 76.4 2.9 ?

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

data_6
_database_code_depnum_ccdc_archive 'CCDC 1440447'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C18 H24 Bi2 Br6 N8 S4'
_chemical_formula_sum            'C18 H24 Bi2 Br6 N8 S4'
_chemical_formula_weight         1378.09
_chemical_oxdiff_formula         'C21 H24 N2 S Bi Br3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   9.393(2)
_cell_length_b                   17.461(2)
_cell_length_c                   11.491(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.29(3)
_cell_angle_gamma                90
_cell_volume                     1731.0(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    781
_cell_measurement_temperature    293
_cell_measurement_theta_max      69.1650
_cell_measurement_theta_min      5.1860
_exptl_absorpt_coefficient_mu    30.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.6438
_exptl_crystal_description       needle
_exptl_crystal_F_000             1238.0679
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0576
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            3383
_diffrn_reflns_theta_full        70.9917
_diffrn_reflns_theta_max         70.99
_diffrn_reflns_theta_min         4.90
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.00000
_diffrn_measured_fraction_theta_max 1.00000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   32.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00    9.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
  3 omega -117.00  -92.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega -111.00  -11.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  -77.0000  -90.0000 100

#__ type_ start__ end____ width___ exp.time_
  5 omega   55.00  104.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000    0.0000 49

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   71.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000   30.0000 30

#__ type_ start__ end____ width___ exp.time_
  7 omega   40.00   79.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   92.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -25.0000  -30.0000 53

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00  104.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -50.0000 -180.0000 63

#__ type_ start__ end____ width___ exp.time_
 10 omega   45.00   87.00   1.0000    2.7000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000   60.0000 42
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1702170000
_diffrn_orient_matrix_UB_12      -0.0112855000
_diffrn_orient_matrix_UB_13      0.0914364000
_diffrn_orient_matrix_UB_21      -0.0428460000
_diffrn_orient_matrix_UB_22      0.0187260000
_diffrn_orient_matrix_UB_23      0.1130578000
_diffrn_orient_matrix_UB_31      -0.0318171000
_diffrn_orient_matrix_UB_32      -0.0856214000
_diffrn_orient_matrix_UB_33      0.0125394000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -11
_reflns_limit_k_max              21
_reflns_limit_k_min              0
_reflns_limit_l_max              13
_reflns_limit_l_min              0
_reflns_number_gt                2016
_reflns_number_total             2520
_reflns_odcompleteness_completeness 99.33
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.1527
_refine_diff_density_min         -2.4895
_refine_diff_density_rms         0.2723
_refine_ls_d_res_high            0.8154
_refine_ls_d_res_low             9.0324
_refine_ls_goodness_of_fit_ref   0.9962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    19
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2520
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      0.9962
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0643P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1054
_refine_ls_wR_factor_ref         0.1192
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C8(H8)
2.c Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C9(H9a,H9b,H9c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Bi1 Bi 0.82414(6) 0.56728(2) 0.83902(4) 0.03083(16) Uani 1.000000 .
Br3 Br 0.9091(2) 0.50482(10) 0.65004(17) 0.0600(5) Uani 1.000000 .
Br1 Br 0.69651(19) 0.64459(8) 0.98729(13) 0.0418(4) Uani 1.000000 .
Br2 Br 1.16172(19) 0.59449(8) 1.04874(15) 0.0447(4) Uani 1.000000 .
S1 S 0.8491(4) 0.69786(18) 0.7247(3) 0.0389(8) Uani 1.000000 .
S2 S 0.5379(4) 0.55114(18) 0.6554(3) 0.0388(8) Uani 1.000000 .
N1 N 0.8157(13) 0.8136(6) 0.8733(11) 0.039(3) Uani 1.000000 .
N2 N 0.5984(13) 0.7780(6) 0.7252(10) 0.032(2) Uani 1.000000 .
N3 N 0.3947(13) 0.6859(6) 0.6726(9) 0.034(2) Uani 1.000000 .
N4 N 0.3406(14) 0.5899(6) 0.7676(12) 0.040(3) Uani 1.000000 .
C1 C 0.7520(16) 0.7629(6) 0.7767(10) 0.029(3) Uani 1.000000 .
C2 C 0.7019(18) 0.8590(7) 0.8819(13) 0.045(4) Uani 1.000000 .
H2 H 0.7154(18) 0.8977(7) 0.9410(13) 0.054(4) Uiso 1.000000 R
C3 C 0.5660(18) 0.8375(7) 0.7891(13) 0.040(3) Uani 1.000000 .
H3 H 0.4690(18) 0.8589(7) 0.7718(13) 0.048(4) Uiso 1.000000 R
C4 C 0.9798(17) 0.8159(8) 0.9563(14) 0.051(4) Uani 1.000000 .
H4a H 1.009(3) 0.769(3) 1.003(7) 0.077(6) Uiso 1.000000 GR
H4b H 1.0401(18) 0.823(6) 0.9062(16) 0.077(6) Uiso 1.000000 GR
H4c H 0.999(3) 0.858(4) 1.015(7) 0.077(6) Uiso 1.000000 GR
C5 C 0.4810(16) 0.7364(8) 0.6232(11) 0.037(3) Uani 1.000000 .
H5a H 0.4104(16) 0.7723(8) 0.5638(11) 0.045(4) Uiso 1.000000 R
H5b H 0.5299(16) 0.7063(8) 0.5782(11) 0.045(4) Uiso 1.000000 R
C6 C 0.4288(16) 0.6115(7) 0.7035(12) 0.035(3) Uani 1.000000 .
C7 C 0.2938(15) 0.7116(7) 0.7250(13) 0.036(3) Uani 1.000000 .
H7 H 0.2586(15) 0.7615(7) 0.7231(13) 0.043(4) Uiso 1.000000 R
C8 C 0.2569(15) 0.6522(8) 0.7780(13) 0.040(3) Uani 1.000000 .
H8 H 0.1861(15) 0.6524(8) 0.8161(13) 0.048(4) Uiso 1.000000 R
C9 C 0.3383(18) 0.5158(8) 0.8232(16) 0.056(5) Uani 1.000000 .
H9a H 0.322(13) 0.5225(9) 0.900(6) 0.084(7) Uiso 1.000000 GR
H9b H 0.256(8) 0.485(2) 0.765(5) 0.084(7) Uiso 1.000000 GR
H9c H 0.436(5) 0.490(3) 0.842(10) 0.084(7) Uiso 1.000000 GR


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 Br3 2.8126(16) . ?
Bi1 Br1 2.7888(14) . ?
Bi1 Br2 3.169(2) . ?
Bi1 Br2 3.0862(15) 3_767 ?
Bi1 S1 2.687(3) . ?
Bi1 S2 2.697(4) . ?
S1 C1 1.705(12) . ?
S2 C6 1.707(13) . ?
N1 C1 1.360(15) . ?
N1 C2 1.365(16) . ?
N1 C4 1.457(17) . ?
N2 C1 1.352(17) . ?
N2 C3 1.373(15) . ?
N2 C5 1.448(15) . ?
N3 C5 1.456(15) . ?
N3 C6 1.352(16) . ?
N3 C7 1.382(14) . ?
N4 C6 1.361(14) . ?
N4 C8 1.376(16) . ?
N4 C9 1.446(16) . ?
C2 C3 1.354(19) . ?
C7 C8 1.316(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Bi1 Br3 168.81(5) . . ?
Br2 Bi1 Br3 98.12(5) . . ?
Br2 Bi1 Br3 89.38(5) 3_767 . ?
Br2 Bi1 Br1 90.31(4) . . ?
Br2 Bi1 Br1 98.37(4) 3_767 . ?
S1 Bi1 Br3 81.12(7) . . ?
S1 Bi1 Br1 91.69(7) . . ?
S1 Bi1 Br2 89.44(9) . . ?
S1 Bi1 Br2 169.46(7) . 3_767 ?
S2 Bi1 Br3 81.65(8) . . ?
S2 Bi1 Br1 89.55(7) . . ?
S2 Bi1 Br2 177.07(8) . . ?
S2 Bi1 Br2 95.52(8) . 3_767 ?
S2 Bi1 S1 87.64(11) . . ?
C1 S1 Bi1 103.4(4) . . ?
C6 S2 Bi1 102.9(5) . . ?
C2 N1 C1 109.4(12) . . ?
C4 N1 C1 124.1(12) . . ?
C4 N1 C2 126.4(12) . . ?
C3 N2 C1 109.8(12) . . ?
C5 N2 C1 126.5(11) . . ?
C5 N2 C3 123.6(12) . . ?
C6 N3 C5 125.0(11) . . ?
C7 N3 C5 123.8(10) . . ?
C7 N3 C6 109.2(10) . . ?
C8 N4 C6 108.6(11) . . ?
C9 N4 C6 127.3(11) . . ?
C9 N4 C8 124.1(11) . . ?
N1 C1 S1 126.6(10) . . ?
N2 C1 S1 127.1(9) . . ?
N2 C1 N1 106.2(11) . . ?
C3 C2 N1 107.7(12) . . ?
C2 C3 N2 106.9(13) . . ?
N3 C5 N2 110.6(9) . . ?
N3 C6 S2 128.2(9) . . ?
N4 C6 S2 125.1(10) . . ?
N4 C6 N3 106.1(11) . . ?
C8 C7 N3 107.3(11) . . ?
C7 C8 N4 108.6(11) . . ?

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

data_9
_database_code_depnum_ccdc_archive 'CCDC 1440450'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H40 Bi2 Cl6 N8 S4, C2 N'
_chemical_formula_sum            'C28 H40 Bi2 Cl6 N9 S4'
_chemical_formula_weight         1261.63
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           138
_space_group_name_H-M_alt        'P 42/n c m'
_space_group_name_Hall           '-P 4ac 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/2,x,z+1/2
3 y,-x+1/2,z+1/2
4 x+1/2,-y,-z+1/2
5 -x,y+1/2,-z+1/2
6 -x+1/2,-y+1/2,z
7 y+1/2,x+1/2,-z
8 -y,-x,-z
9 -x,-y,-z
10 y-1/2,-x,-z-1/2
11 -y,x-1/2,-z-1/2
12 -x-1/2,y,z-1/2
13 x,-y-1/2,z-1/2
14 x-1/2,y-1/2,-z
15 -y-1/2,-x-1/2,z
16 y,x,z

_symmetry_Int_Tables_number      138
_cell_length_a                   19.00307(17)
_cell_length_b                   19.00307(17)
_cell_length_c                   12.04528(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4349.75(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3505
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8880
_cell_measurement_theta_min      4.3330
_exptl_absorpt_coefficient_mu    21.151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59528
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.9264
_exptl_crystal_description       needle
_exptl_crystal_F_000             2401.5888
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9430
_diffrn_reflns_theta_full        70.8761
_diffrn_reflns_theta_max         70.88
_diffrn_reflns_theta_min         3.29
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -8.00   35.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   12.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega -103.00  -61.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   12.0000  -90.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega    1.00   86.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000    0.0000 85

#__ type_ start__ end____ width___ exp.time_
  4 omega   67.00  103.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega   45.00   91.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -180.0000 46

#__ type_ start__ end____ width___ exp.time_
  6 omega   56.00  115.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega   36.00   92.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
  8 omega   53.00   79.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega  117.00  176.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   90.0000 59

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00   93.00   1.0000    1.8200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 46
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0005058000
_diffrn_orient_matrix_UB_12      -0.0513386000
_diffrn_orient_matrix_UB_13      -0.0989644000
_diffrn_orient_matrix_UB_21      -0.0064902000
_diffrn_orient_matrix_UB_22      0.0625582000
_diffrn_orient_matrix_UB_23      -0.0806790000
_diffrn_orient_matrix_UB_31      0.0808244000
_diffrn_orient_matrix_UB_32      0.0047060000
_diffrn_orient_matrix_UB_33      -0.0070736000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1773
_reflns_number_total             2182
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.1306
_refine_diff_density_min         -1.5809
_refine_diff_density_rms         0.1557
_refine_ls_d_res_high            0.8160
_refine_ls_d_res_low             13.4372
_refine_ls_goodness_of_fit_ref   1.0142
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2182
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0437
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.0142
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0526P)²+4.9723P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0973
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C6(H6a,H6b,H6c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Bi1 Bi 0.480973(12) 0.480973(12) 0.67426(2) 0.04452(14) Uani 1.000000 2 S T P
Cl1 Cl 0.38395(10) 0.38395(10) 0.6760(2) 0.0743(7) Uani 1.000000 2 S T P
Cl2 Cl 0.42843(8) 0.57157(8) 0.5 0.0639(6) Uani 1.000000 2 S T P
Cl3 Cl 0.58011(9) 0.58011(9) 0.71512(19) 0.0598(5) Uani 1.000000 2 S T P
S1 S 0.55486(8) 0.41243(9) 0.83773(12) 0.0513(4) Uani 1.000000 1 . . .
N1 N 0.5076(3) 0.2763(3) 0.8679(5) 0.0584(14) Uani 1.000000 1 . . .
N2 N 0.4448(2) 0.3548(2) 0.9519(4) 0.0417(10) Uani 1.000000 1 . . .
N3 N 0.25 0.25 0.5888(11) 0.087(4) Uani 1.000000 4 S T P
C1 C 0.5008(3) 0.3467(3) 0.8832(5) 0.0473(13) Uani 1.000000 1 . . .
C2 C 0.4561(4) 0.2411(3) 0.9238(6) 0.0640(18) Uani 1.000000 1 . . .
H2 H 0.4493(4) 0.1927(3) 0.9251(6) 0.077(2) Uiso 1.000000 1 R . .
C3 C 0.4173(3) 0.2895(3) 0.9763(6) 0.0574(15) Uani 1.000000 1 . . .
H3 H 0.3786(3) 0.2806(3) 1.0213(6) 0.0689(19) Uiso 1.000000 1 R . .
C4 C 0.5625(4) 0.2375(4) 0.8052(6) 0.073(2) Uani 1.000000 1 . . .
H4 H 0.5489(4) 0.1879(4) 0.8116(6) 0.087(2) Uiso 1.000000 1 R . .
C5 C 0.5599(5) 0.2525(5) 0.6840(6) 0.086(3) Uani 1.000000 1 . . .
H5a H 0.5124(8) 0.248(4) 0.6580(13) 0.129(4) Uiso 1.000000 1 GR . .
H5b H 0.576(4) 0.2995(15) 0.6705(8) 0.129(4) Uiso 1.000000 1 GR . .
H5c H 0.589(3) 0.220(3) 0.6452(8) 0.129(4) Uiso 1.000000 1 GR . .
C6 C 0.6311(4) 0.2417(4) 0.8608(7) 0.081(2) Uani 1.000000 1 . . .
H6a H 0.6483(15) 0.2891(8) 0.857(4) 0.121(3) Uiso 1.000000 1 GR . .
H6b H 0.6260(7) 0.228(3) 0.9372(15) 0.121(3) Uiso 1.000000 1 GR . .
H6c H 0.6637(10) 0.211(2) 0.825(3) 0.121(3) Uiso 1.000000 1 GR . .
C7 C 0.4203(3) 0.4203(3) 0.9992(6) 0.0446(18) Uani 1.000000 2 S T P
H7a H 0.4142(3) 0.4142(3) 1.0786(6) 0.054(2) Uiso 1.000000 2 RS T P
H7b H 0.4561(3) 0.4561(3) 0.9880(6) 0.054(2) Uiso 1.000000 2 RS T P
C8 C 0.25 0.25 0.7999(15) 0.162(13) Uani 1.000000 4 S T P
C9 C 0.25 0.25 0.6807(14) 0.073(4) Uani 1.000000 4 S T P


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 Cl1 2.608(3) . ?
Bi1 Cl2 2.8925(15) 16 ?
Bi1 Cl2 2.8925(15) 8_666 ?
Bi1 Cl3 2.709(2) . ?
Bi1 S1 2.7468(15) . ?
Bi1 S1 2.7468(15) 16 ?
S1 C1 1.707(6) . ?
N1 C1 1.356(8) . ?
N1 C2 1.362(9) . ?
N1 C4 1.484(8) . ?
N2 C1 1.358(7) . ?
N2 C3 1.378(7) . ?
N2 C7 1.446(6) . ?
N3 C9 1.107(16) . ?
C2 C3 1.338(8) . ?
C4 C5 1.489(9) . ?
C4 C6 1.467(11) . ?
C8 C9 1.44(2) . ?

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
Cl2 Bi1 Cl1 100.53(4) 16 . ?
Cl2 Bi1 Cl1 100.53(4) 8_666 . ?
Cl2 Bi1 Cl2 83.35(6) 8_666 16 ?
Cl3 Bi1 Cl1 169.06(7) . . ?
Cl3 Bi1 Cl2 87.59(4) . 16 ?
Cl3 Bi1 Cl2 87.59(4) . 8_666 ?
S1 Bi1 Cl1 91.16(5) . . ?
S1 Bi1 Cl1 91.16(5) 16 . ?
S1 Bi1 Cl2 93.00(5) 16 8_666 ?
S1 Bi1 Cl2 168.20(4) 16 16 ?
S1 Bi1 Cl2 168.20(4) . 8_666 ?
S1 Bi1 Cl2 93.00(5) . 16 ?
S1 Bi1 Cl3 81.03(5) . . ?
S1 Bi1 Cl3 81.03(5) 16 . ?
S1 Bi1 S1 88.33(7) 16 . ?
Bi1 Cl2 Bi1 96.65(6) 9_666 16 ?
C1 S1 Bi1 105.6(2) . . ?
C2 N1 C1 110.4(5) . . ?
C4 N1 C1 128.8(6) . . ?
C4 N1 C2 120.8(6) . . ?
C3 N2 C1 109.0(5) . . ?
C7 N2 C1 126.1(5) . . ?
C7 N2 C3 124.7(5) . . ?
N1 C1 S1 128.4(5) . . ?
N2 C1 S1 125.7(5) . . ?
N2 C1 N1 105.6(6) . . ?
C3 C2 N1 107.0(6) . . ?
C2 C3 N2 108.0(6) . . ?
C5 C4 N1 112.3(7) . . ?
C6 C4 N1 111.4(6) . . ?
C6 C4 C5 117.8(8) . . ?
N2 C7 N2 113.4(6) 16 . ?
C8 C9 N3 180.0 . . ?

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

data_10
_database_code_depnum_ccdc_archive 'CCDC 1440451'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C26 H40 Bi2 Br6 N8 S4, C2 N'
_chemical_formula_sum            'C28 H40 Bi2 Br6 N9 S4'
_chemical_formula_weight         1528.34
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.33537 0.55136 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           138
_space_group_name_H-M_alt        'P 42/n c m'
_space_group_name_Hall           '-P 4ac 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/2,x,z+1/2
3 y,-x+1/2,z+1/2
4 x+1/2,-y,-z+1/2
5 -x,y+1/2,-z+1/2
6 -x+1/2,-y+1/2,z
7 y+1/2,x+1/2,-z
8 -y,-x,-z
9 -x,-y,-z
10 y-1/2,-x,-z-1/2
11 -y,x-1/2,-z-1/2
12 -x-1/2,y,z-1/2
13 x,-y-1/2,z-1/2
14 x-1/2,y-1/2,-z
15 -y-1/2,-x-1/2,z
16 y,x,z

_symmetry_Int_Tables_number      138
_cell_length_a                   19.2248(3)
_cell_length_b                   19.2248(3)
_cell_length_c                   12.2798(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4538.55(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4243
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.6000
_cell_measurement_theta_min      4.5800
_exptl_absorpt_coefficient_mu    23.211
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.22858
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.2366
_exptl_crystal_description       needle
_exptl_crystal_F_000             2808.6716
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11356
_diffrn_reflns_theta_full        70.7864
_diffrn_reflns_theta_max         70.79
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.0000
_diffrn_measured_fraction_theta_max 1.0000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -76.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -38.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -50.00  -17.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00  -42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 59

#__ type_ start__ end____ width___ exp.time_
  4 omega   71.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  175.0000 -162.0000 55

#__ type_ start__ end____ width___ exp.time_
  5 omega    5.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -180.0000 89

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
  7 omega  105.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   61.0000  135.0000 71

#__ type_ start__ end____ width___ exp.time_
  8 omega   39.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   51.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
 11 omega   36.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 27

#__ type_ start__ end____ width___ exp.time_
 12 omega   59.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   30.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0239173000
_diffrn_orient_matrix_UB_12      -0.0029948000
_diffrn_orient_matrix_UB_13      0.1197759000
_diffrn_orient_matrix_UB_21      0.0522030000
_diffrn_orient_matrix_UB_22      -0.0578137000
_diffrn_orient_matrix_UB_23      -0.0292366000
_diffrn_orient_matrix_UB_31      0.0558324000
_diffrn_orient_matrix_UB_32      0.0553379000
_diffrn_orient_matrix_UB_33      -0.0239641000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1865
_reflns_number_total             2269
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.7352
_refine_diff_density_min         -1.5422
_refine_diff_density_rms         0.2245
_refine_ls_d_res_high            0.8164
_refine_ls_d_res_low             13.5940
_refine_ls_goodness_of_fit_ref   1.0152
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     123
_refine_ls_number_reflns         2269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0432
_refine_ls_restrained_S_all      1.0152
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0913P)²+0.8567P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1234
_refine_ls_wR_factor_ref         0.1351
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H5a,H5b,H5c} of C5, All C(H,H) groups
 At 1.5 times of:
  {H6a,H6b,H6c} of C6
2.a Riding coordinates:
 C5(H5a,H5b,H5c)
2.b Ternary CH refined with riding coordinates:
 C4(H4)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.d Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.e Idealised Me refined as rotating group:
 C6(H6a,H6b,H6c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Bi1 Bi 0.016309(15) 0.483691(15) 0.17732(3) 0.04593(19) Uani 1.000000 2 S T P
Br1 Br 0.11719(5) 0.38281(5) 0.17278(11) 0.0722(4) Uani 1.000000 2 S T P
Br2 Br -0.07523(4) 0.42477(4) 0.0 0.0572(3) Uani 1.000000 2 S T P
Br3 Br -0.08772(5) 0.58772(5) 0.21714(10) 0.0614(3) Uani 1.000000 2 S T P
S1 S 0.08531(11) 0.55710(10) 0.33688(15) 0.0522(5) Uani 1.000000 1 . . .
N1 N 0.2199(4) 0.5100(4) 0.3704(6) 0.0600(17) Uani 1.000000 1 . . .
N2 N 0.1407(3) 0.4486(3) 0.4500(5) 0.0462(13) Uani 1.000000 1 . . .
C1 C 0.1498(4) 0.5042(4) 0.3831(6) 0.0472(16) Uani 1.000000 1 . . .
C2 C 0.2531(4) 0.4597(5) 0.4279(7) 0.064(2) Uani 1.000000 1 . . .
H2 H 0.3010(4) 0.4532(5) 0.4321(7) 0.077(3) Uiso 1.000000 1 R . .
C3 C 0.2049(4) 0.4212(4) 0.4771(7) 0.061(2) Uani 1.000000 1 . . .
H3 H 0.2130(4) 0.3829(4) 0.5215(7) 0.073(2) Uiso 1.000000 1 R . .
C4 C 0.2588(5) 0.5640(5) 0.3094(8) 0.073(3) Uani 1.000000 1 . . .
H4 H 0.3079(5) 0.5511(5) 0.3168(8) 0.087(3) Uiso 1.000000 1 R . .
C5 C 0.2526(6) 0.6326(5) 0.3641(9) 0.088(3) Uani 1.000000 1 . . .
H5a H 0.2052(6) 0.6485(5) 0.3613(9) 0.106(4) Uiso 1.000000 1 R . .
H5b H 0.2668(6) 0.6281(5) 0.4387(9) 0.106(4) Uiso 1.000000 1 R . .
H5c H 0.2821(6) 0.6656(5) 0.3280(9) 0.106(4) Uiso 1.000000 1 R . .
C6 C 0.2447(6) 0.5614(6) 0.1915(8) 0.091(4) Uani 1.000000 1 . . .
H6a H 0.244(5) 0.5138(7) 0.1677(18) 0.136(5) Uiso 1.000000 1 GR . .
H6b H 0.200(2) 0.582(5) 0.1770(12) 0.136(5) Uiso 1.000000 1 GR . .
H6c H 0.280(3) 0.586(5) 0.1531(10) 0.136(5) Uiso 1.000000 1 GR . .
C7 C 0.0750(4) 0.4250(4) 0.4947(8) 0.047(2) Uani 1.000000 2 S T P
H7a H 0.0797(4) 0.4203(4) 0.5730(8) 0.056(3) Uiso 1.000000 2 RS T P
H7b H 0.0398(4) 0.4602(4) 0.4810(8) 0.056(3) Uiso 1.000000 2 RS T P
N5 N 0.25 0.25 0.0898(18) 0.126(9) Uani 1.000000 4 S T P
C14 C 0.25 0.25 0.2958(19) 0.144(14) Uani 1.000000 4 S T P
C15 C 0.25 0.25 0.1806(19) 0.079(6) Uani 1.000000 4 S T P


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br1 2.7433(14) . ?
Bi1 Br2 3.0202(8) 7_455 ?
Bi1 Br2 3.0202(8) 15_665 ?
Bi1 Br3 2.8702(13) . ?
Bi1 S1 2.7551(19) 15_665 ?
Bi1 S1 2.7551(19) . ?
S1 C1 1.702(8) . ?
N1 C1 1.361(10) . ?
N1 C2 1.357(11) . ?
N1 C4 1.483(11) . ?
N2 C1 1.359(9) . ?
N2 C3 1.382(10) . ?
N2 C7 1.451(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.330(11) . ?
C3 H3 0.9300 . ?
C4 H4 0.9800 . ?
C4 C5 1.485(14) . ?
C4 C6 1.474(11) . ?
C5 H5a 0.9598 . ?
C5 H5b 0.9601 . ?
C5 H5c 0.9600 . ?
C6 H6a 0.9600 . ?
C6 H6b 0.9600 . ?
C6 H6c 0.9600 . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
N5 C15 1.11(2) . ?
C14 C15 1.41(3) . ?

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
Br2 Bi1 Br1 97.59(2) 15_665 . ?
Br2 Bi1 Br1 97.59(2) 7_455 . ?
Br2 Bi1 Br2 85.26(3) 7_455 15_665 ?
Br3 Bi1 Br1 171.35(4) . . ?
Br3 Bi1 Br2 88.75(2) . 15_665 ?
Br3 Bi1 Br2 88.75(2) . 7_455 ?
S1 Bi1 Br1 92.07(5) . . ?
S1 Bi1 Br1 92.07(5) 15_665 . ?
S1 Bi1 Br2 170.20(4) . 7_455 ?
S1 Bi1 Br2 91.93(4) 15_665 7_455 ?
S1 Bi1 Br2 170.20(4) 15_665 15_665 ?
S1 Bi1 Br2 91.93(4) . 15_665 ?
S1 Bi1 Br3 81.80(5) . . ?
S1 Bi1 Br3 81.80(5) 15_665 . ?
S1 Bi1 S1 89.28(8) 15_665 . ?
Bi1 Br2 Bi1 94.74(3) 9_565 15_665 ?
C1 S1 Bi1 106.4(2) . . ?
C2 N1 C1 110.3(7) . . ?
C4 N1 C1 127.9(8) . . ?
C4 N1 C2 121.7(8) . . ?
C3 N2 C1 109.2(6) . . ?
C7 N2 C1 126.0(7) . . ?
C7 N2 C3 124.6(7) . . ?
N1 C1 S1 129.4(6) . . ?
N2 C1 S1 125.3(6) . . ?
N2 C1 N1 105.2(7) . . ?
H2 C2 N1 126.1(4) . . ?
C3 C2 N1 107.8(7) . . ?
C3 C2 H2 126.1(5) . . ?
C2 C3 N2 107.5(7) . . ?
H3 C3 N2 126.2(4) . . ?
H3 C3 C2 126.2(5) . . ?
H4 C4 N1 105.1(5) . . ?
C5 C4 N1 110.6(8) . . ?
C5 C4 H4 105.1(6) . . ?
C6 C4 N1 112.3(8) . . ?
C6 C4 H4 105.1(7) . . ?
C6 C4 C5 117.4(10) . . ?
H5a C5 C4 110.1 . . ?
H5b C5 C4 109.1 . . ?
H5b C5 H5a 109.5 . . ?
H5c C5 C4 109.2 . . ?
H5c C5 H5a 109.5 . . ?
H5c C5 H5b 109.5 . . ?
H6a C6 C4 109.5 . . ?
H6b C6 C4 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 C4 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?
N2 C7 N2 113.7(8) 15_665 . ?
H7a C7 N2 108.8(5) . . ?
H7a C7 N2 108.8(5) . 15_665 ?
H7b C7 N2 108.8(5) . . ?
H7b C7 N2 108.8(5) . 15_665 ?
H7b C7 H7a 107.7 . . ?
C14 C15 N5 180.0 . . ?

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

data_11
_database_code_depnum_ccdc_archive 'CCDC 1440452'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H40 Bi2 Cl6 N8 Se4, C2 N'
_chemical_formula_sum            'C28 H40 Bi2 Cl6 N9 Se4'
_chemical_formula_weight         1449.20
_chemical_oxdiff_formula         'C21 H24 N2 Se Bi Cl3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           138
_space_group_name_H-M_alt        'P 42/n c m'
_space_group_name_Hall           '-P 4ac 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/2,x,z+1/2
3 y,-x+1/2,z+1/2
4 x+1/2,-y,-z+1/2
5 -x,y+1/2,-z+1/2
6 -x+1/2,-y+1/2,z
7 y+1/2,x+1/2,-z
8 -y,-x,-z
9 -x,-y,-z
10 y-1/2,-x,-z-1/2
11 -y,x-1/2,-z-1/2
12 -x-1/2,y,z-1/2
13 x,-y-1/2,z-1/2
14 x-1/2,y-1/2,-z
15 -y-1/2,-x-1/2,z
16 y,x,z

_symmetry_Int_Tables_number      138
_cell_length_a                   19.04444(18)
_cell_length_b                   19.04444(18)
_cell_length_c                   12.15557(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4408.71(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4311
_cell_measurement_temperature    293
_cell_measurement_theta_max      70.8700
_cell_measurement_theta_min      4.6380
_exptl_absorpt_coefficient_mu    22.875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.51750
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.1832
_exptl_crystal_description       needle
_exptl_crystal_F_000             2671.5547
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9141
_diffrn_reflns_theta_full        70.9539
_diffrn_reflns_theta_max         70.95
_diffrn_reflns_theta_min         3.28
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 1.00000
_diffrn_measured_fraction_theta_max 1.00000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -97.00  -51.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 46

#__ type_ start__ end____ width___ exp.time_
  2 omega  -99.00  -55.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000  120.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega   21.00  110.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000  -60.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00   56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   37.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
  6 omega   37.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   63.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 30

#__ type_ start__ end____ width___ exp.time_
  8 omega   65.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  9 omega  104.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 74

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 11 omega   55.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 33
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0385782000
_diffrn_orient_matrix_UB_12      0.0526486000
_diffrn_orient_matrix_UB_13      0.0748175000
_diffrn_orient_matrix_UB_21      0.0709317000
_diffrn_orient_matrix_UB_22      0.0245751000
_diffrn_orient_matrix_UB_23      0.0473894000
_diffrn_orient_matrix_UB_31      0.0051755000
_diffrn_orient_matrix_UB_32      0.0562941000
_diffrn_orient_matrix_UB_33      -0.0905873000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1956
_reflns_number_total             2201
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS-1997 (Sheldrick, 2008)'
_refine_diff_density_max         1.0236
_refine_diff_density_min         -1.4481
_refine_diff_density_rms         0.1501
_refine_ls_d_res_high            0.8156
_refine_ls_d_res_low             13.4665
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0133
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0336
_refine_ls_R_factor_gt           0.0297
_refine_ls_restrained_S_all      1.0133
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0498P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0761
_refine_ls_wR_factor_ref         0.0795
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C5(H5)
2.d Idealised Me refined as rotating group:
 C4(H4a,H4b,H4c), C3(H3a,H3b,H3c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Bi1 Bi 0.480694(9) 0.019306(9) 0.827943(19) 0.03269(12) Uani 1.000000 2 S T P
Se1 Se 0.55984(2) 0.08594(3) 0.66102(4) 0.03396(15) Uani 1.000000 1 . . .
Cl2 Cl 0.57283(6) 0.07283(6) 1.0 0.0490(4) Uani 1.000000 2 S T P
Cl3 Cl 0.58038(6) -0.08038(6) 0.78597(14) 0.0461(4) Uani 1.000000 2 S T P
Cl1 Cl 0.38335(7) 0.11665(7) 0.82201(17) 0.0632(5) Uani 1.000000 2 S T P
N2 N 0.44303(17) 0.14696(17) 0.5449(3) 0.0308(7) Uani 1.000000 1 . . .
N1 N 0.5055(2) 0.2268(2) 0.6259(3) 0.0381(9) Uani 1.000000 1 . . .
C7 C 0.4201(2) 0.0799(2) 0.4999(5) 0.0314(12) Uani 1.000000 2 S T P
H7a H 0.4160(2) 0.0840(2) 0.4206(5) 0.0377(15) Uiso 1.000000 2 RS T P
H7b H 0.4554(2) 0.0446(2) 0.5155(5) 0.0377(15) Uiso 1.000000 2 RS T P
C2 C 0.5597(3) 0.2654(3) 0.6889(4) 0.0489(13) Uani 1.000000 1 . . .
H2 H 0.5470(3) 0.3152(3) 0.6846(4) 0.0587(15) Uiso 1.000000 1 R . .
C1 C 0.4992(2) 0.1565(2) 0.6119(4) 0.0304(8) Uani 1.000000 1 . . .
C6 C 0.4148(2) 0.2114(2) 0.5175(4) 0.0432(11) Uani 1.000000 1 . . .
H6 H 0.3763(2) 0.2193(2) 0.4721(4) 0.0518(13) Uiso 1.000000 1 R . .
C5 C 0.4531(3) 0.2600(2) 0.5683(4) 0.0478(12) Uani 1.000000 1 . . .
H5 H 0.4457(3) 0.3083(2) 0.5653(4) 0.0574(15) Uiso 1.000000 1 R . .
N1AA N 0.25 0.25 0.9063(9) 0.066(3) Uani 1.000000 4 S T P
C9 C 0.25 0.25 0.8140(11) 0.060(3) Uani 1.000000 4 S T P
C4 C 0.6307(3) 0.2587(3) 0.6340(5) 0.0620(15) Uani 1.000000 1 . . .
H4a H 0.6452(11) 0.2104(5) 0.635(3) 0.093(2) Uiso 1.000000 1 GR . .
H4b H 0.6274(6) 0.275(2) 0.5593(13) 0.093(2) Uiso 1.000000 1 GR . .
H4c H 0.6644(6) 0.2867(19) 0.673(2) 0.093(2) Uiso 1.000000 1 GR . .
C3 C 0.5577(4) 0.2462(3) 0.8100(4) 0.0628(17) Uani 1.000000 1 . . .
H3a H 0.5114(8) 0.254(2) 0.8384(11) 0.094(2) Uiso 1.000000 1 GR . .
H3b H 0.570(2) 0.1975(7) 0.8187(6) 0.094(2) Uiso 1.000000 1 GR . .
H3c H 0.5909(19) 0.2746(18) 0.8496(8) 0.094(2) Uiso 1.000000 1 GR . .
C8 C 0.25 0.25 0.6971(14) 0.163(11) Uani 1.000000 4 S T P


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 Se1 2.8283(5) . ?
Bi1 Se1 2.8283(5) 15_665 ?
Bi1 Cl2 2.9142(11) 9_657 ?
Bi1 Cl2 2.9142(11) . ?
Bi1 Cl3 2.7328(17) . ?
Bi1 Cl1 2.623(2) . ?
Se1 C1 1.869(4) . ?
N2 C7 1.457(4) 15_665 ?
N2 C1 1.357(5) . ?
N2 C6 1.380(5) . ?
N1 C2 1.481(6) . ?
N1 C1 1.355(6) . ?
N1 C5 1.374(6) . ?
C7 H7a 0.9700 . ?
C7 H7b 0.9700 . ?
C2 H2 0.9800 . ?
C2 C4 1.512(8) . ?
C2 C3 1.517(7) . ?
C6 H6 0.9300 . ?
C6 C5 1.331(6) . ?
C5 H5 0.9300 . ?
N1AA C9 1.122(15) . ?
C9 C8 1.42(2) . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 0.9600 . ?
C3 H3a 0.9600 . ?
C3 H3b 0.9600 . ?
C3 H3c 0.9600 . ?

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
Se1 Bi1 Se1 87.91(2) . 15_665 ?
Cl2 Bi1 Se1 92.12(3) . . ?
Cl2 Bi1 Se1 166.278(14) . 15_665 ?
Cl2 Bi1 Se1 166.278(14) 9_657 . ?
Cl2 Bi1 Se1 92.12(3) 9_657 15_665 ?
Cl2 Bi1 Cl2 84.62(4) . 9_657 ?
Cl3 Bi1 Se1 78.90(3) . 15_665 ?
Cl3 Bi1 Se1 78.90(3) . . ?
Cl3 Bi1 Cl2 87.63(3) . 9_657 ?
Cl3 Bi1 Cl2 87.63(3) . . ?
Cl1 Bi1 Se1 92.28(3) . 15_665 ?
Cl1 Bi1 Se1 92.28(3) . . ?
Cl1 Bi1 Cl2 101.43(3) . 9_657 ?
Cl1 Bi1 Cl2 101.43(3) . . ?
Cl1 Bi1 Cl3 167.66(6) . . ?
C1 Se1 Bi1 102.84(13) . 15_665 ?
Bi1 Cl2 Bi1 95.38(5) 15_665 9_657 ?
C1 N2 C7 125.3(4) . 15_665 ?
C6 N2 C7 124.9(4) . 15_665 ?
C6 N2 C1 109.5(4) . . ?
C1 N1 C2 128.1(4) . . ?
C5 N1 C2 122.7(4) . . ?
C5 N1 C1 109.1(4) . . ?
N2 C7 N2 112.6(5) 15_665 . ?
H7a C7 N2 109.1(3) . . ?
H7a C7 N2 109.1(3) . 15_665 ?
H7b C7 N2 109.1(3) . . ?
H7b C7 N2 109.1(3) . 15_665 ?
H7b C7 H7a 107.8 . . ?
H2 C2 N1 106.2(3) . . ?
C4 C2 N1 110.6(4) . . ?
C4 C2 H2 106.2(3) . . ?
C3 C2 N1 111.4(5) . . ?
C3 C2 H2 106.2(3) . . ?
C3 C2 C4 115.5(6) . . ?
N2 C1 Se1 125.7(3) . . ?
N1 C1 Se1 128.0(3) . . ?
N1 C1 N2 106.1(4) . . ?
H6 C6 N2 126.5(2) . . ?
C5 C6 N2 107.1(4) . . ?
C5 C6 H6 126.5(3) . . ?
C6 C5 N1 108.3(4) . . ?
H5 C5 N1 125.9(3) . . ?
H5 C5 C6 125.9(3) . . ?
C8 C9 N1AA 180.0 . . ?
H4a C4 C2 109.5 . . ?
H4b C4 C2 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C2 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?
H3a C3 C2 109.5 . . ?
H3b C3 C2 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C2 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?

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

data_12
_database_code_depnum_ccdc_archive 'CCDC 1440453'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-10-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'C26 H40 Bi2 Br6 N8 Se4, C2 N'
_chemical_formula_sum            'C28 H40 Bi2 Br6 N9 Se4'
_chemical_formula_weight         1715.91
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      tetragonal
_space_group_IT_number           138
_space_group_name_H-M_alt        'P 42/n c m'
_space_group_name_Hall           '-P 4ac 2ac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -y+1/2,x,z+1/2
3 y,-x+1/2,z+1/2
4 x+1/2,-y,-z+1/2
5 -x,y+1/2,-z+1/2
6 -x+1/2,-y+1/2,z
7 y+1/2,x+1/2,-z
8 -y,-x,-z
9 -x,-y,-z
10 y-1/2,-x,-z-1/2
11 -y,x-1/2,-z-1/2
12 -x-1/2,y,z-1/2
13 x,-y-1/2,z-1/2
14 x-1/2,y-1/2,-z
15 -y-1/2,-x-1/2,z
16 y,x,z

_symmetry_Int_Tables_number      138
_cell_length_a                   19.2323(2)
_cell_length_b                   19.2323(2)
_cell_length_c                   12.4100(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4590.22(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4395
_cell_measurement_temperature    293.0
_cell_measurement_theta_max      70.9210
_cell_measurement_theta_min      3.2260
_exptl_absorpt_coefficient_mu    24.877
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18959
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.4828
_exptl_crystal_description       needle
_exptl_crystal_F_000             3078.6382
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0370
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            9414
_diffrn_reflns_theta_full        70.9016
_diffrn_reflns_theta_max         70.90
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      293.0
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9858
_diffrn_measured_fraction_theta_max 0.9858
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   19.00   44.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -98.00  -73.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -99.00  -74.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -72.00  -47.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega   57.00  104.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  125.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -30.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega   58.00  112.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
  8 omega   60.00   89.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega  150.00  175.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 10 omega  103.00  176.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   30.0000 73

#__ type_ start__ end____ width___ exp.time_
 11 omega  100.00  174.00   1.0000    2.3700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -90.0000 74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0120995000
_diffrn_orient_matrix_UB_12      0.0143130000
_diffrn_orient_matrix_UB_13      -0.1208240000
_diffrn_orient_matrix_UB_21      -0.0689058000
_diffrn_orient_matrix_UB_22      -0.0407239000
_diffrn_orient_matrix_UB_23      0.0049440000
_diffrn_orient_matrix_UB_31      -0.0389308000
_diffrn_orient_matrix_UB_32      0.0674403000
_diffrn_orient_matrix_UB_33      0.0285507000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                1993
_reflns_number_total             2291
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.3622
_refine_diff_density_min         -1.0163
_refine_diff_density_rms         0.1596
_refine_ls_d_res_high            0.8158
_refine_ls_d_res_low             13.5993
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9943
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    17
_refine_ls_number_parameters     125
_refine_ls_number_reflns         2291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0288
_refine_ls_restrained_S_all      0.9943
_refine_ls_shift/su_max          0.0001
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0426P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0707
_refine_ls_wR_factor_ref         0.0746
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3)
2.d Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C6(H6a,H6b,H6c)
;
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_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
Bi1 Bi 0.483453(10) 0.016547(10) 0.17551(2) 0.03468(11) Uani 1.000000 2 S T P
Br3 Br 0.58798(3) -0.08798(3) 0.21722(7) 0.0486(2) Uani 1.000000 2 S T P
Br1 Br 0.38230(3) 0.11770(3) 0.17521(8) 0.0619(3) Uani 1.000000 2 S T P
Br2 Br 0.57610(3) 0.07610(3) 0.0 0.0463(2) Uani 1.000000 2 S T P
Se1 Se 0.56212(3) 0.08371(3) 0.33820(4) 0.03584(15) Uani 1.000000 1 . . .
N1 N 0.5079(2) 0.2223(2) 0.3765(4) 0.0383(9) Uani 1.000000 1 . . .
N2 N 0.4466(2) 0.14295(19) 0.4536(3) 0.0350(9) Uani 1.000000 1 . . .
N3 N 0.25 0.25 0.0932(11) 0.088(4) Uani 1.000000 4 S T P
C1 C 0.5017(2) 0.1529(2) 0.3884(4) 0.0342(10) Uani 1.000000 1 . . .
C2 C 0.4568(3) 0.2553(3) 0.4347(4) 0.0472(13) Uani 1.000000 1 . . .
H2 H 0.4500(3) 0.3031(3) 0.4401(4) 0.0566(16) Uiso 1.000000 1 R . .
C3 C 0.4186(3) 0.2061(3) 0.4822(4) 0.0456(12) Uani 1.000000 1 . . .
H3 H 0.3802(3) 0.2132(3) 0.5264(4) 0.0547(15) Uiso 1.000000 1 R . .
C4 C 0.5612(3) 0.2616(3) 0.3145(5) 0.0500(14) Uani 1.000000 1 . . .
H4 H 0.5487(3) 0.3108(3) 0.3213(5) 0.0600(17) Uiso 1.000000 1 R . .
C5 C 0.6317(3) 0.2539(3) 0.3659(5) 0.0656(17) Uani 1.000000 1 . . .
H5a H 0.6301(7) 0.271(2) 0.4384(14) 0.098(2) Uiso 1.000000 1 GR . .
H5b H 0.6448(11) 0.2058(4) 0.366(4) 0.098(2) Uiso 1.000000 1 GR . .
H5c H 0.6653(6) 0.280(2) 0.325(2) 0.098(2) Uiso 1.000000 1 GR . .
C6 C 0.5576(4) 0.2450(3) 0.1958(5) 0.0672(19) Uani 1.000000 1 . . .
H6a H 0.571(3) 0.1976(9) 0.1843(7) 0.101(3) Uiso 1.000000 1 GR . .
H6b H 0.5108(7) 0.251(3) 0.1707(11) 0.101(3) Uiso 1.000000 1 GR . .
H6c H 0.588(2) 0.275(2) 0.1570(7) 0.101(3) Uiso 1.000000 1 GR . .
C7 C 0.4245(2) 0.0755(2) 0.4961(6) 0.0361(15) Uani 1.000000 2 S T P
H7a H 0.4217(2) 0.0783(2) 0.5740(6) 0.0433(18) Uiso 1.000000 2 RS T P
H7b H 0.4592(2) 0.0408(2) 0.4780(6) 0.0433(18) Uiso 1.000000 2 RS T P
C8 C 0.25 0.25 0.3033(12) 0.129(9) Uani 1.000000 4 S T P
C9 C 0.25 0.25 0.1867(14) 0.073(4) Uani 1.000000 4 S T P


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 Br3 2.8896(8) . ?
Bi1 Br1 2.7511(9) . ?
Bi1 Br2 3.0382(5) 7_545 ?
Bi1 Br2 3.0382(5) 15_665 ?
Bi1 Se1 2.8344(5) 15_665 ?
Bi1 Se1 2.8344(5) . ?
Se1 C1 1.873(5) . ?
N1 C1 1.350(6) . ?
N1 C2 1.375(6) . ?
N1 C4 1.487(7) . ?
N2 C1 1.347(6) . ?
N2 C3 1.374(6) . ?
N2 C7 1.463(5) 15_665 ?
N3 C9 1.160(16) . ?
C2 C3 1.336(7) . ?
C4 C5 1.507(8) . ?
C4 C6 1.508(7) . ?
C8 C9 1.45(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Bi1 Br3 169.76(3) . . ?
Br2 Bi1 Br3 89.008(13) 15_665 . ?
Br2 Bi1 Br3 89.008(13) 7_545 . ?
Br2 Bi1 Br1 98.463(16) 7_545 . ?
Br2 Bi1 Br1 98.463(16) 15_665 . ?
Br2 Bi1 Br2 85.89(2) 7_545 15_665 ?
Se1 Bi1 Br3 79.522(17) . . ?
Se1 Bi1 Br3 79.522(17) 15_665 . ?
Se1 Bi1 Br1 93.216(18) . . ?
Se1 Bi1 Br1 93.216(18) 15_665 . ?
Se1 Bi1 Br2 168.282(14) . 15_665 ?
Se1 Bi1 Br2 168.282(14) 15_665 7_545 ?
Se1 Bi1 Br2 91.478(15) 15_665 15_665 ?
Se1 Bi1 Br2 91.478(15) . 7_545 ?
Se1 Bi1 Se1 88.80(2) . 15_665 ?
Bi1 Br2 Bi1 94.11(2) 9_655 15_665 ?
C1 Se1 Bi1 103.27(14) . 15_665 ?
C2 N1 C1 109.6(4) . . ?
C4 N1 C1 128.3(4) . . ?
C4 N1 C2 122.0(4) . . ?
C3 N2 C1 109.7(4) . . ?
C7 N2 C1 124.8(4) 15_665 . ?
C7 N2 C3 125.2(5) 15_665 . ?
N1 C1 Se1 127.7(4) . . ?
N2 C1 Se1 126.0(3) . . ?
N2 C1 N1 106.0(4) . . ?
C3 C2 N1 107.3(4) . . ?
C2 C3 N2 107.3(4) . . ?
C5 C4 N1 110.6(5) . . ?
C6 C4 N1 111.5(5) . . ?
C6 C4 C5 115.7(6) . . ?
N2 C7 N2 112.6(5) . 15_665 ?
C8 C9 N3 180.0 . . ?

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

data_13
_database_code_depnum_ccdc_archive 'CCDC 1440454'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-09-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_chemical_formula_moiety         'C26 H40 Bi4 Br12 N8 Se4, 2(C2 H3 N)'
_chemical_formula_sum            'C30 H46 Bi4 Br12 N10 Se4'
_chemical_formula_weight         2657.37
_chemical_oxdiff_formula         'C21 H24 N2 Se Bi Br3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Bi -3.68252 9.31182 33.36890 12.95100 16.58770 6.46920 0.70400 2.92380 8.79370
48.00930 13.5782003403
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.67402 1.33011 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Se -0.79210 1.18296 17.00060 5.81960 3.97310 4.35430 2.40980 0.27260 15.23720
43.81630 2.84089994431
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   12.54238(19)
_cell_length_b                   21.6905(3)
_cell_length_c                   12.37785(18)
_cell_angle_alpha                90
_cell_angle_beta                 107.2678(16)
_cell_angle_gamma                90
_cell_volume                     3215.62(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5719
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.5730
_cell_measurement_theta_min      4.2020
_exptl_absorpt_coefficient_mu    32.666
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17747
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.7443
_exptl_crystal_description       needle
_exptl_crystal_F_000             2319.9978
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0442
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14054
_diffrn_reflns_theta_full        70.8791
_diffrn_reflns_theta_max         70.88
_diffrn_reflns_theta_min         3.69
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9829
_diffrn_measured_fraction_theta_max 0.9829
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00  -59.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega  -23.00   30.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   90.0000 53

#__ type_ start__ end____ width___ exp.time_
  3 omega  -54.00  -28.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -14.00   82.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   60.0000 96

#__ type_ start__ end____ width___ exp.time_
  5 omega   25.00   93.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -30.0000 68

#__ type_ start__ end____ width___ exp.time_
  6 omega   38.00  125.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
  7 omega   95.00  174.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  120.0000 79

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   92.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega   58.00  147.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 10 omega   47.00   84.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
 11 omega   45.00   84.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 39

#__ type_ start__ end____ width___ exp.time_
 12 omega   87.00  130.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
 13 omega   93.00  168.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
 14 omega   38.00   82.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
 15 omega   63.00   93.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega  110.00  135.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 17 omega   39.00   80.00   1.0000    5.3500
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -30.0000 41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.1033016000
_diffrn_orient_matrix_UB_12      0.0423267000
_diffrn_orient_matrix_UB_13      -0.0303592000
_diffrn_orient_matrix_UB_21      -0.0254157000
_diffrn_orient_matrix_UB_22      -0.0195631000
_diffrn_orient_matrix_UB_23      0.1094283000
_diffrn_orient_matrix_UB_31      0.0722527000
_diffrn_orient_matrix_UB_32      0.0535967000
_diffrn_orient_matrix_UB_33      0.0639647000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -15
_reflns_limit_k_max              26
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                5093
_reflns_number_total             6092
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         1.8519
_refine_diff_density_min         -1.7028
_refine_diff_density_rms         0.3200
_refine_ls_d_res_high            0.8159
_refine_ls_d_res_low             11.9771
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   0.9831
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    33
_refine_ls_number_parameters     280
_refine_ls_number_reflns         6092
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0474
_refine_ls_restrained_S_all      0.9831
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0840P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1362
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7a,H7b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C9(H9), C10(H10)
2.d Idealised Me refined as rotating group:
 C5(H5a,H5b,H5c), C6(H6a,H6b,H6c), C12(H12a,H12b,H12c), C13(H13a,H13b,H13c),
 C14(H14a,H14b,H14c)
;
_atom_sites_solution_primary     direct
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_refinement_flags_posn
Bi1 Bi 0.63683(3) 0.440637(17) 0.29703(3) 0.04956(14) Uani 1.000000 .
Bi2 Bi 0.35461(3) 0.544650(18) 0.05949(3) 0.05073(14) Uani 1.000000 .
Br1 Br 0.69685(9) 0.31980(5) 0.32616(9) 0.0578(3) Uani 1.000000 .
Br2 Br 0.54836(9) 0.56824(5) 0.27490(9) 0.0561(3) Uani 1.000000 .
Br3 Br 0.22468(10) 0.50236(7) 0.17862(10) 0.0704(3) Uani 1.000000 .
Br4 Br 0.46876(10) 0.41434(5) 0.06366(9) 0.0587(3) Uani 1.000000 .
Br5 Br 0.19883(11) 0.52108(8) -0.14647(11) 0.0795(4) Uani 1.000000 .
Br6 Br 0.28481(12) 0.66047(6) 0.06322(11) 0.0734(3) Uani 1.000000 .
Se1 Se 0.47177(9) 0.42999(5) 0.39897(10) 0.0559(3) Uani 1.000000 .
Se2 Se 0.78853(10) 0.47487(6) 0.50730(10) 0.0629(3) Uani 1.000000 .
N1 N 0.4382(7) 0.3003(4) 0.4088(8) 0.059(2) Uani 1.000000 .
N2 N 0.5761(6) 0.3310(4) 0.5492(6) 0.0524(19) Uani 1.000000 .
N3 N 0.7715(7) 0.3573(4) 0.6145(7) 0.059(2) Uani 1.000000 .
N4 N 0.9266(7) 0.3680(5) 0.5743(9) 0.071(3) Uani 1.000000 .
C1 C 0.4981(8) 0.3490(5) 0.4535(8) 0.048(2) Uani 1.000000 .
C2 C 0.4784(12) 0.2501(6) 0.4788(13) 0.082(4) Uani 1.000000 .
H2 H 0.4502(12) 0.2092(6) 0.4665(13) 0.098(4) Uiso 1.000000 R
C3 C 0.5614(11) 0.2685(6) 0.5643(11) 0.071(3) Uani 1.000000 .
H3 H 0.6037(11) 0.2438(6) 0.6253(11) 0.085(4) Uiso 1.000000 R
C4 C 0.3432(10) 0.2986(7) 0.3029(12) 0.077(4) Uani 1.000000 .
C5 C 0.3575(16) 0.2491(11) 0.2287(15) 0.151(9) Uani 1.000000 .
H5a H 0.430(7) 0.253(5) 0.215(13) 0.227(14) Uiso 1.000000 GR
H5b H 0.354(15) 0.2092(11) 0.265(7) 0.227(14) Uiso 1.000000 GR
H5c H 0.298(9) 0.251(5) 0.157(6) 0.227(14) Uiso 1.000000 GR
C6 C 0.2375(13) 0.2937(15) 0.3293(19) 0.218(15) Uani 1.000000 .
H6a H 0.1755(15) 0.295(13) 0.259(3) 0.33(2) Uiso 1.000000 GR
H6b H 0.236(10) 0.255(6) 0.37(2) 0.33(2) Uiso 1.000000 GR
H6c H 0.230(11) 0.328(7) 0.38(2) 0.33(2) Uiso 1.000000 GR
C7 C 0.6595(9) 0.3705(6) 0.6242(8) 0.066(3) Uani 1.000000 .
H7a H 0.6405(9) 0.4142(6) 0.6047(8) 0.079(4) Uiso 1.000000 R
H7b H 0.6594(9) 0.3638(6) 0.7033(8) 0.079(4) Uiso 1.000000 R
C8 C 0.8304(8) 0.3963(5) 0.5660(8) 0.056(2) Uani 1.000000 .
C9 C 0.8322(10) 0.3043(7) 0.6506(10) 0.081(4) Uani 1.000000 .
H9 H 0.8111(10) 0.2701(7) 0.6877(10) 0.097(5) Uiso 1.000000 R
C10 C 0.9275(10) 0.3106(6) 0.6227(12) 0.086(4) Uani 1.000000 .
H10 H 0.9853(10) 0.2808(6) 0.6342(12) 0.103(5) Uiso 1.000000 R
C11 C 1.0186(10) 0.3927(7) 0.5350(14) 0.082(4) Uani 1.000000 .
H11 H 1.0117(10) 0.4387(7) 0.5315(14) 0.099(5) Uiso 1.000000 R
C12 C 1.1302(11) 0.3769(8) 0.6158(17) 0.131(8) Uani 1.000000 .
H12a H 1.146(6) 0.404(5) 0.682(6) 0.196(11) Uiso 1.000000 GR
H12b H 1.130(4) 0.334(2) 0.640(11) 0.196(11) Uiso 1.000000 GR
H12c H 1.1882(19) 0.382(7) 0.578(4) 0.196(11) Uiso 1.000000 GR
C13 C 1.0037(13) 0.3687(10) 0.4134(18) 0.136(7) Uani 1.000000 .
H13a H 1.068(7) 0.381(7) 0.389(6) 0.204(11) Uiso 1.000000 GR
H13b H 0.999(14) 0.3235(11) 0.413(3) 0.204(11) Uiso 1.000000 GR
H13c H 0.935(8) 0.386(6) 0.362(3) 0.204(11) Uiso 1.000000 GR
H4 H 0.343(8) 0.334(5) 0.256(9) 0.05(3) Uiso 1.000000 .
N5 N 0.908(2) 0.7077(13) -0.026(3) 0.238(13) Uani 1.000000 .
C14 C 0.9789(18) 0.6031(10) 0.044(2) 0.157(9) Uani 1.000000 .
H14a H 0.919(4) 0.578(3) 0.055(15) 0.235(14) Uiso 1.000000 GR
H14b H 1.007(14) 0.585(3) -0.014(7) 0.235(14) Uiso 1.000000 GR
H14c H 1.039(10) 0.6059(13) 0.115(8) 0.235(14) Uiso 1.000000 GR
C15 C 0.9392(19) 0.6605(12) 0.011(2) 0.148(9) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br1 2.7212(11) . ?
Bi1 Br2 2.9641(11) . ?
Bi1 Br4 3.0820(12) . ?
Bi1 Se1 2.7353(12) . ?
Bi1 Se2 2.8294(12) . ?
Bi2 Br2 3.0707(11) . ?
Bi2 Br3 2.6644(12) . ?
Bi2 Br4 3.1619(12) . ?
Bi2 Br4 3.1666(12) 3_665 ?
Bi2 Br5 2.7606(13) . ?
Bi2 Br6 2.6653(13) . ?
Se1 C1 1.876(9) . ?
Se2 C8 1.866(11) . ?
N1 C1 1.319(13) . ?
N1 C2 1.389(15) . ?
N1 C4 1.488(15) . ?
N2 C1 1.351(11) . ?
N2 C3 1.388(14) . ?
N2 C7 1.453(14) . ?
N3 C7 1.473(13) . ?
N3 C8 1.373(14) . ?
N3 C9 1.379(14) . ?
N4 C8 1.330(13) . ?
N4 C10 1.380(15) . ?
N4 C11 1.479(15) . ?
C2 H2 0.9500 . ?
C2 C3 1.308(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.46(2) . ?
C4 C6 1.460(19) . ?
C4 H4 0.96(11) . ?
C5 H5a 0.9800 . ?
C5 H5b 0.9800 . ?
C5 H5c 0.9800 . ?
C6 H6a 0.9800 . ?
C6 H6b 0.9800 . ?
C6 H6c 0.9800 . ?
C7 H7a 0.9900 . ?
C7 H7b 0.9900 . ?
C9 H9 0.9500 . ?
C9 C10 1.346(17) . ?
C10 H10 0.9500 . ?
C11 H11 1.0000 . ?
C11 C12 1.499(18) . ?
C11 C13 1.55(2) . ?
C12 H12a 0.9800 . ?
C12 H12b 0.9800 . ?
C12 H12c 0.9800 . ?
C13 H13a 0.9800 . ?
C13 H13b 0.9800 . ?
C13 H13c 0.9800 . ?
N5 C15 1.14(3) . ?
C14 H14a 0.9800 . ?
C14 H14b 0.9800 . ?
C14 H14c 0.9800 . ?
C14 C15 1.36(3) . ?

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
Br2 Bi1 Br1 173.13(4) . . ?
Br4 Bi1 Br1 91.79(3) . . ?
Br4 Bi1 Br2 87.31(3) . . ?
Se1 Bi1 Br1 94.30(4) . . ?
Se1 Bi1 Br2 78.91(3) . . ?
Se1 Bi1 Br4 90.91(3) . . ?
Se2 Bi1 Br1 92.68(3) . . ?
Se2 Bi1 Br2 88.34(3) . . ?
Se2 Bi1 Br4 175.45(3) . . ?
Se2 Bi1 Se1 89.55(4) . . ?
Br3 Bi2 Br2 91.90(4) . . ?
Br4 Bi2 Br2 84.09(3) . . ?
Br4 Bi2 Br2 83.38(3) 3_665 . ?
Br4 Bi2 Br3 173.42(4) 3_665 . ?
Br4 Bi2 Br3 91.81(4) . . ?
Br5 Bi2 Br2 173.44(4) . . ?
Br5 Bi2 Br3 93.77(4) . . ?
Br5 Bi2 Br4 92.43(4) . . ?
Br5 Bi2 Br4 90.69(4) . 3_665 ?
Br6 Bi2 Br2 90.42(4) . . ?
Br6 Bi2 Br3 93.26(4) . . ?
Br6 Bi2 Br4 172.64(4) . . ?
Br6 Bi2 Br4 91.37(4) . 3_665 ?
Br6 Bi2 Br5 92.55(5) . . ?
Bi2 Br2 Bi1 95.90(3) . . ?
Bi2 Br4 Bi1 91.73(3) . . ?
Bi2 Br4 Bi1 91.01(3) 3_665 . ?
C1 Se1 Bi1 99.7(3) . . ?
C8 Se2 Bi1 98.8(3) . . ?
C2 N1 C1 108.1(9) . . ?
C4 N1 C1 126.7(10) . . ?
C4 N1 C2 125.2(11) . . ?
C3 N2 C1 108.1(10) . . ?
C7 N2 C1 125.9(9) . . ?
C7 N2 C3 126.1(9) . . ?
C8 N3 C7 124.5(10) . . ?
C9 N3 C7 125.7(10) . . ?
C9 N3 C8 109.8(9) . . ?
C10 N4 C8 109.9(10) . . ?
C11 N4 C8 125.8(10) . . ?
C11 N4 C10 124.3(10) . . ?
N1 C1 Se1 125.6(7) . . ?
N2 C1 Se1 126.2(8) . . ?
N2 C1 N1 108.1(9) . . ?
H2 C2 N1 125.7(7) . . ?
C3 C2 N1 108.6(11) . . ?
C3 C2 H2 125.7(8) . . ?
C2 C3 N2 107.2(10) . . ?
H3 C3 N2 126.4(7) . . ?
H3 C3 C2 126.4(8) . . ?
C5 C4 N1 110.9(12) . . ?
C6 C4 N1 110.3(13) . . ?
C6 C4 C5 112.2(16) . . ?
H4 C4 N1 111(6) . . ?
H4 C4 C5 101(7) . . ?
H4 C4 C6 111(6) . . ?
H5a C5 C4 109.5 . . ?
H5b C5 C4 109.5 . . ?
H5b C5 H5a 109.5 . . ?
H5c C5 C4 109.5 . . ?
H5c C5 H5a 109.5 . . ?
H5c C5 H5b 109.5 . . ?
H6a C6 C4 109.5 . . ?
H6b C6 C4 109.5 . . ?
H6b C6 H6a 109.5 . . ?
H6c C6 C4 109.5 . . ?
H6c C6 H6a 109.5 . . ?
H6c C6 H6b 109.5 . . ?
N3 C7 N2 110.9(9) . . ?
H7a C7 N2 109.5(6) . . ?
H7a C7 N3 109.5(6) . . ?
H7b C7 N2 109.5(5) . . ?
H7b C7 N3 109.5(5) . . ?
H7b C7 H7a 108.0 . . ?
N3 C8 Se2 127.4(8) . . ?
N4 C8 Se2 126.5(9) . . ?
N4 C8 N3 106.0(10) . . ?
H9 C9 N3 126.9(7) . . ?
C10 C9 N3 106.2(11) . . ?
C10 C9 H9 126.9(8) . . ?
C9 C10 N4 108.1(11) . . ?
H10 C10 N4 126.0(7) . . ?
H10 C10 C9 126.0(8) . . ?
H11 C11 N4 108.0(7) . . ?
C12 C11 N4 111.2(13) . . ?
C12 C11 H11 108.0(9) . . ?
C13 C11 N4 108.4(13) . . ?
C13 C11 H11 108.0(10) . . ?
C13 C11 C12 112.9(13) . . ?
H12a C12 C11 109.5 . . ?
H12b C12 C11 109.5 . . ?
H12b C12 H12a 109.5 . . ?
H12c C12 C11 109.5 . . ?
H12c C12 H12a 109.5 . . ?
H12c C12 H12b 109.5 . . ?
H13a C13 C11 109.5 . . ?
H13b C13 C11 109.5 . . ?
H13b C13 H13a 109.5 . . ?
H13c C13 C11 109.5 . . ?
H13c C13 H13a 109.5 . . ?
H13c C13 H13b 109.5 . . ?
H14b C14 H14a 109.5 . . ?
H14c C14 H14a 109.5 . . ?
H14c C14 H14b 109.5 . . ?
C15 C14 H14a 109.5 . . ?
C15 C14 H14b 109.5 . . ?
C15 C14 H14c 109.5 . . ?
C14 C15 N5 174(4) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.076 0.162 0.663 15.1 3.9 ?
2 -0.076 0.338 0.163 15.1 4.0 ?
3 0.076 0.662 0.837 15.1 4.4 ?
4 0.076 0.838 0.337 15.1 4.5 ?
5 0.249 0.135 0.372 14.9 2.9 ?
6 0.249 0.365 0.872 14.9 3.4 ?
7 0.751 0.635 0.128 14.9 1.1 ?
8 0.751 0.865 0.628 14.9 1.6 ?

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

data_14
_database_code_depnum_ccdc_archive 'CCDC 1440455'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-11-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C25 H27 N O8, C3 H7'
_chemical_formula_sum            'C28 H34 N O8'
_chemical_formula_weight         512.58
_chemical_oxdiff_formula         'C10 H19 N2 O4'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.0626(4)
_cell_length_b                   12.3582(8)
_cell_length_c                   13.8011(9)
_cell_angle_alpha                91.927(5)
_cell_angle_beta                 99.512(5)
_cell_angle_gamma                101.537(5)
_cell_volume                     1325.66(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3681
_cell_measurement_temperature    293
_cell_measurement_theta_max      71.1640
_cell_measurement_theta_min      4.7690
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.2840
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             547.9116
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0170
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            8480
_diffrn_reflns_theta_full        71.2286
_diffrn_reflns_theta_max         71.23
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9776
_diffrn_measured_fraction_theta_max 0.9776
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -30.00   13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega   47.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   19.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -53.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   12.0000 -150.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega -119.00  -71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000   30.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega  -38.00   20.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   57.0000 -150.0000 58

#__ type_ start__ end____ width___ exp.time_
  6 omega  -29.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
  7 omega  -45.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   38.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  8 omega -100.00  -66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000   12.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega    9.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1553 -103.0000   -7.0000 76

#__ type_ start__ end____ width___ exp.time_
 10 omega   26.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1553   77.0000   90.0000 55

#__ type_ start__ end____ width___ exp.time_
 11 omega   47.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       55.1553 -125.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000 -120.0000 52

#__ type_ start__ end____ width___ exp.time_
 13 omega   55.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -38.0000 -180.0000 38

#__ type_ start__ end____ width___ exp.time_
 14 omega   71.00   97.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -103.0000   85.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000   60.0000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega   81.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105   77.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
 17 omega   87.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105   50.0000 -120.0000 89

#__ type_ start__ end____ width___ exp.time_
 18 omega   38.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000 -180.0000 71

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -50.0000  120.0000 60

#__ type_ start__ end____ width___ exp.time_
 20 omega   68.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   87.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105 -111.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 22 omega  117.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105   50.0000  150.0000 61

#__ type_ start__ end____ width___ exp.time_
 23 omega   40.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -25.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 24 omega   88.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105   50.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 25 omega   39.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -50.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
 26 omega  120.00  171.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  111.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 27 omega   54.00  127.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105  -77.0000 -150.0000 73

#__ type_ start__ end____ width___ exp.time_
 28 omega  106.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      110.3105   25.0000  -60.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0236272000
_diffrn_orient_matrix_UB_12      0.0841084000
_diffrn_orient_matrix_UB_13      0.0788754000
_diffrn_orient_matrix_UB_21      0.0055607000
_diffrn_orient_matrix_UB_22      0.0894926000
_diffrn_orient_matrix_UB_23      -0.0751430000
_diffrn_orient_matrix_UB_31      -0.1966014000
_diffrn_orient_matrix_UB_32      -0.0343751000
_diffrn_orient_matrix_UB_33      -0.0316799000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              14
_reflns_limit_k_min              -14
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3987
_reflns_number_total             5015
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.3717
_refine_diff_density_min         -0.2757
_refine_diff_density_rms         0.0442
_refine_ls_d_res_high            0.8142
_refine_ls_d_res_low             13.5789
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0805
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     341
_refine_ls_number_reflns         5015
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0610
_refine_ls_restrained_S_all      1.0805
_refine_ls_shift/su_max          0.0099
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1068P)²+0.2188P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1799
_refine_ls_wR_factor_ref         0.1964
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1)
2.b Secondary CH2 refined with riding coordinates:
 C28(H28a,H28b), C27(H27a,H27b)
2.c Aromatic/amide H refined with riding coordinates:
 C12(H12), C3(H3), C21(H21), C19(H19), C4(H4), C6(H6), C10(H10), C7(H7)
2.d Idealised Me refined as rotating group:
 C16(H16a,H16b,H16c), C24(H24a,H24b,H24c), C23(H23a,H23b,H23c), C15(H15a,H15b,
 H15c), C25(H25a,H25b,H25c), C14(H14a,H14b,H14c), C26(H26a,H26b,H26c)
;
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_refinement_flags_posn
O5 O 0.4483(2) -0.01937(12) 0.84023(12) 0.0678(4) Uani 1.000000 .
O7 O 0.7559(2) 0.43892(14) 1.07934(12) 0.0759(5) Uani 1.000000 .
O3 O 0.9444(2) 0.05835(12) 0.69846(13) 0.0707(5) Uani 1.000000 .
C17 C 0.6853(3) 0.21225(15) 0.83806(13) 0.0517(4) Uani 1.000000 .
O6 O 0.4200(2) 0.25736(14) 0.78185(12) 0.0762(5) Uani 1.000000 .
C9 C 0.8322(3) -0.01803(16) 0.73822(15) 0.0555(5) Uani 1.000000 .
O8 O 0.9566(2) 0.17363(15) 0.88756(12) 0.0765(5) Uani 1.000000 .
C20 C 0.7414(3) 0.36309(16) 1.00173(14) 0.0576(5) Uani 1.000000 .
O4 O 0.7724(2) -0.30247(13) 0.80062(15) 0.0805(5) Uani 1.000000 .
C18 C 0.5638(3) 0.27491(16) 0.85282(15) 0.0561(5) Uani 1.000000 .
C12 C 0.6017(3) -0.16630(17) 0.82357(16) 0.0599(5) Uani 1.000000 .
H12 H 0.5252(3) -0.21543(17) 0.85308(16) 0.0719(6) Uiso 1.000000 R
C8 C 0.6915(2) 0.01758(15) 0.76588(14) 0.0516(4) Uani 1.000000 .
C22 C 0.8358(3) 0.23001(16) 0.90701(14) 0.0546(5) Uani 1.000000 .
C3 C 0.8035(3) 0.28610(17) 0.65811(15) 0.0627(5) Uani 1.000000 .
H3 H 0.8444(3) 0.32740(17) 0.71792(15) 0.0752(6) Uiso 1.000000 R
C21 C 0.8649(3) 0.30428(16) 0.98986(14) 0.0556(5) Uani 1.000000 .
H21 H 0.9658(3) 0.31356(16) 1.03586(14) 0.0667(6) Uiso 1.000000 R
C11 C 0.7381(3) -0.19853(16) 0.79183(16) 0.0606(5) Uani 1.000000 .
C19 C 0.5904(3) 0.35000(17) 0.93359(15) 0.0598(5) Uani 1.000000 .
H19 H 0.5082(3) 0.39101(17) 0.94198(15) 0.0717(6) Uiso 1.000000 R
C2 C 0.7026(3) 0.18222(15) 0.65662(14) 0.0544(5) Uani 1.000000 .
C1 C 0.6466(3) 0.13075(15) 0.74812(14) 0.0522(4) Uani 1.000000 .
H1 H 0.5207(3) 0.11397(15) 0.73169(14) 0.0626(5) Uiso 1.000000 R
C13 C 0.5806(3) -0.05839(16) 0.81060(14) 0.0537(5) Uani 1.000000 .
N1 N 0.8292(3) 0.31453(18) 0.39396(15) 0.0799(6) Uani 1.000000 .
C5 C 0.7854(3) 0.26910(18) 0.48500(15) 0.0637(5) Uani 1.000000 .
O2 O 0.7955(3) 0.25426(19) 0.31931(14) 0.1086(7) Uani 1.000000 .
C4 C 0.8455(3) 0.33058(18) 0.57276(16) 0.0713(6) Uani 1.000000 .
H4 H 0.9137(3) 0.40117(18) 0.57481(16) 0.0855(8) Uiso 1.000000 R
C6 C 0.6859(4) 0.1649(2) 0.48014(17) 0.0845(8) Uani 1.000000 .
H6 H 0.6469(4) 0.1235(2) 0.42026(17) 0.1014(9) Uiso 1.000000 R
C10 C 0.8553(3) -0.12535(17) 0.75016(16) 0.0608(5) Uani 1.000000 .
H10 H 0.9487(3) -0.14788(17) 0.73038(16) 0.0730(6) Uiso 1.000000 R
C7 C 0.6451(4) 0.1229(2) 0.56637(17) 0.0880(9) Uani 1.000000 .
H7 H 0.5765(4) 0.0524(2) 0.56388(17) 0.1056(11) Uiso 1.000000 R
C16 C 0.3422(3) -0.0886(2) 0.8959(2) 0.0748(7) Uani 1.000000 .
H16a H 0.282(2) -0.1544(8) 0.8562(5) 0.1122(10) Uiso 1.000000 GR
H16b H 0.4123(4) -0.1083(14) 0.9531(8) 0.1122(10) Uiso 1.000000 GR
H16c H 0.2604(17) -0.0497(6) 0.9160(13) 0.1122(10) Uiso 1.000000 GR
C24 C 0.9097(4) 0.4571(2) 1.15057(17) 0.0775(7) Uani 1.000000 .
H24a H 1.0059(5) 0.4872(16) 1.1200(4) 0.1162(10) Uiso 1.000000 GR
H24b H 0.9020(12) 0.5082(14) 1.2028(8) 0.1162(10) Uiso 1.000000 GR
H24c H 0.9249(14) 0.3881(4) 1.1770(11) 0.1162(10) Uiso 1.000000 GR
C23 C 0.2982(3) 0.3247(2) 0.7840(2) 0.0855(8) Uani 1.000000 .
H23a H 0.2048(14) 0.3015(12) 0.7298(10) 0.1283(12) Uiso 1.000000 GR
H23b H 0.255(2) 0.3179(14) 0.8448(7) 0.1283(12) Uiso 1.000000 GR
H23c H 0.3518(8) 0.4005(3) 0.7788(16) 0.1283(12) Uiso 1.000000 GR
C15 C 0.6403(4) -0.3876(2) 0.8220(3) 0.0985(10) Uani 1.000000 .
H15a H 0.5358(9) -0.3882(14) 0.7770(12) 0.1478(15) Uiso 1.000000 GR
H15b H 0.6729(15) -0.4577(3) 0.8155(19) 0.1478(15) Uiso 1.000000 GR
H15c H 0.623(2) -0.3745(12) 0.8882(7) 0.1478(15) Uiso 1.000000 GR
C25 C 1.0872(4) 0.1593(3) 0.9643(2) 0.0967(9) Uani 1.000000 .
H25a H 1.154(2) 0.1111(18) 0.9406(6) 0.1451(14) Uiso 1.000000 GR
H25b H 1.160(2) 0.2298(4) 0.9870(13) 0.1451(14) Uiso 1.000000 GR
H25c H 1.0363(4) 0.127(2) 1.0177(8) 0.1451(14) Uiso 1.000000 GR
O1 O 0.8986(5) 0.4109(2) 0.39647(16) 0.1487(13) Uani 1.000000 .
C14 C 1.0777(4) 0.0246(2) 0.6592(2) 0.0889(8) Uani 1.000000 .
H14a H 1.0300(4) -0.0363(13) 0.6111(13) 0.1333(13) Uiso 1.000000 GR
H14b H 1.138(2) 0.0852(6) 0.6285(15) 0.1333(13) Uiso 1.000000 GR
H14c H 1.1557(17) 0.0020(18) 0.7111(3) 0.1333(13) Uiso 1.000000 GR
C28 C 0.5411(14) 0.5379(10) 0.4759(10) 0.227(5) Uani 1.000000 .
H28a H 0.6145(14) 0.5060(10) 0.4392(10) 0.273(6) Uiso 1.000000 R
H28b H 0.4599(14) 0.5671(10) 0.4296(10) 0.273(6) Uiso 1.000000 R
C27 C 0.6441(18) 0.6258(13) 0.5452(7) 0.298(6) Uani 1.000000 .
H27a H 0.5731(18) 0.6515(13) 0.5875(7) 0.357(8) Uiso 1.000000 R
H27b H 0.7348(18) 0.5987(13) 0.5863(7) 0.357(8) Uiso 1.000000 R
C26 C 0.7148(13) 0.7117(11) 0.4934(7) 0.312(7) Uani 1.000000 .
H26a H 0.746(13) 0.6821(11) 0.435(4) 0.469(11) Uiso 1.000000 GR
H26b H 0.632(5) 0.757(5) 0.475(7) 0.469(11) Uiso 1.000000 GR
H26c H 0.816(8) 0.756(5) 0.534(3) 0.469(11) Uiso 1.000000 GR


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
O5 C13 1.368(2) . ?
O5 C16 1.422(3) . ?
O7 C20 1.373(2) . ?
O7 C24 1.423(3) . ?
O3 C9 1.366(2) . ?
O3 C14 1.407(3) . ?
C17 C18 1.400(3) . ?
C17 C22 1.387(3) . ?
C17 C1 1.521(2) . ?
O6 C18 1.364(2) . ?
O6 C23 1.412(3) . ?
C9 C8 1.399(3) . ?
C9 C10 1.387(3) . ?
O8 C22 1.361(2) . ?
O8 C25 1.407(3) . ?
C20 C21 1.372(3) . ?
C20 C19 1.387(3) . ?
O4 C11 1.372(2) . ?
O4 C15 1.416(3) . ?
C18 C19 1.386(3) . ?
C12 C11 1.371(3) . ?
C12 C13 1.392(3) . ?
C8 C1 1.531(3) . ?
C8 C13 1.396(3) . ?
C22 C21 1.400(3) . ?
C3 C2 1.373(3) . ?
C3 C4 1.381(3) . ?
C11 C10 1.384(3) . ?
C2 C1 1.527(3) . ?
C2 C7 1.384(3) . ?
N1 C5 1.461(3) . ?
N1 O2 1.210(3) . ?
N1 O1 1.207(3) . ?
C5 C4 1.370(3) . ?
C5 C6 1.367(3) . ?
C6 C7 1.377(3) . ?
C28 C28 1.30(2) 2_666 ?
C28 C27 1.447(16) . ?
C27 C26 1.381(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
C16 O5 C13 117.76(17) . . ?
C24 O7 C20 117.20(17) . . ?
C14 O3 C9 119.17(18) . . ?
C22 C17 C18 117.05(17) . . ?
C1 C17 C18 118.82(17) . . ?
C1 C17 C22 124.13(17) . . ?
C23 O6 C18 119.71(18) . . ?
C8 C9 O3 116.37(17) . . ?
C10 C9 O3 122.06(18) . . ?
C10 C9 C8 121.56(18) . . ?
C25 O8 C22 119.57(18) . . ?
C21 C20 O7 123.92(19) . . ?
C19 C20 O7 114.84(18) . . ?
C19 C20 C21 121.24(18) . . ?
C15 O4 C11 117.7(2) . . ?
O6 C18 C17 115.19(17) . . ?
C19 C18 C17 121.78(19) . . ?
C19 C18 O6 123.02(18) . . ?
C13 C12 C11 118.47(19) . . ?
C1 C8 C9 125.53(17) . . ?
C13 C8 C9 116.72(17) . . ?
C13 C8 C1 117.72(17) . . ?
O8 C22 C17 115.91(17) . . ?
C21 C22 C17 122.28(18) . . ?
C21 C22 O8 121.77(18) . . ?
C4 C3 C2 121.43(19) . . ?
C22 C21 C20 118.58(19) . . ?
C12 C11 O4 123.8(2) . . ?
C10 C11 O4 114.85(19) . . ?
C10 C11 C12 121.30(19) . . ?
C18 C19 C20 119.05(19) . . ?
C1 C2 C3 123.62(17) . . ?
C7 C2 C3 117.68(19) . . ?
C7 C2 C1 118.67(18) . . ?
C8 C1 C17 115.79(15) . . ?
C2 C1 C17 113.54(15) . . ?
C2 C1 C8 114.31(16) . . ?
C12 C13 O5 122.29(18) . . ?
C8 C13 O5 115.14(17) . . ?
C8 C13 C12 122.57(18) . . ?
O2 N1 C5 118.9(2) . . ?
O1 N1 C5 118.4(2) . . ?
O1 N1 O2 122.6(2) . . ?
C4 C5 N1 119.74(19) . . ?
C6 C5 N1 118.6(2) . . ?
C6 C5 C4 121.6(2) . . ?
C5 C4 C3 118.94(19) . . ?
C7 C6 C5 118.2(2) . . ?
C11 C10 C9 119.29(19) . . ?
C6 C7 C2 122.2(2) . . ?
C26 C27 C28 108.7(9) . . ?

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

data_15
_database_code_depnum_ccdc_archive 'CCDC 1440456'
_audit_update_record             
;
2015-12-03 deposited with the CCDC.
2016-02-08 downloaded from the CCDC.
;
_audit_creation_date             2015-11-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_formula_moiety         'C23 H17 N3 O2'
_chemical_formula_sum            'C23 H17 N3 O2'
_chemical_formula_weight         367.41
_chemical_oxdiff_formula         'C10 H19 N2 O4'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-C 2yc (x+z,y,-x)'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y,-z
3 -x,-y,-z
4 x-1/2,-y,z
5 x+1/2,y+1/2,z+1/2
6 -x+1,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z+1/2
8 x,-y+1/2,z+1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   17.2917(6)
_cell_length_b                   10.6763(4)
_cell_length_c                   39.6733(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.757(4)
_cell_angle_gamma                90
_cell_volume                     7320.7(5)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    4283
_cell_measurement_temperature    293
_cell_measurement_theta_max      22.3020
_cell_measurement_theta_min      3.7720
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92276
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.3333
_exptl_crystal_description       block
_exptl_crystal_F_000             3073.3744
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.14
_diffrn_reflns_av_R_equivalents  0.0525
_diffrn_reflns_av_unetI/netI     0.0770
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            21069
_diffrn_reflns_theta_full        29.0039
_diffrn_reflns_theta_max         29.00
_diffrn_reflns_theta_min         3.02
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1293
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9980
_diffrn_measured_fraction_theta_max 0.9980
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    2.75   89.00   0.7500   31.5400
omega____ theta____ kappa____ phi______ frames
    -       20.2949   57.0000  -90.0000 115

#__ type_ start__ end____ width___ exp.time_
  2 omega   -1.00   80.00   0.7500   31.5400
omega____ theta____ kappa____ phi______ frames
    -       20.2949   57.0000    0.0000 108

#__ type_ start__ end____ width___ exp.time_
  3 omega  -29.00   17.50   0.7500   31.5400
omega____ theta____ kappa____ phi______ frames
    -       20.2949   19.0000 -180.0000 62

#__ type_ start__ end____ width___ exp.time_
  4 omega   46.00   82.00   0.7500   31.5400
omega____ theta____ kappa____ phi______ frames
    -       20.2949   19.0000 -180.0000 48

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   79.00   0.7500   31.5400
omega____ theta____ kappa____ phi______ frames
    -       20.2949   38.0000 -150.0000 68
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0396646000
_diffrn_orient_matrix_UB_12      -0.0011645000
_diffrn_orient_matrix_UB_13      0.0051508000
_diffrn_orient_matrix_UB_21      -0.0032619000
_diffrn_orient_matrix_UB_22      -0.0643777000
_diffrn_orient_matrix_UB_23      0.0041302000
_diffrn_orient_matrix_UB_31      0.0100731000
_diffrn_orient_matrix_UB_32      -0.0163502000
_diffrn_orient_matrix_UB_33      -0.0166195000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              23
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              53
_reflns_limit_l_min              -53
_reflns_number_gt                4242
_reflns_number_total             8475
_reflns_odcompleteness_completeness 99.80
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.6345
_refine_diff_density_min         -0.5633
_refine_diff_density_rms         0.1421
_refine_ls_d_res_high            0.7329
_refine_ls_d_res_low             6.7515
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0547
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    68
_refine_ls_number_parameters     505
_refine_ls_number_reflns         8475
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1578
_refine_ls_R_factor_gt           0.0776
_refine_ls_restrained_S_all      1.0547
_refine_ls_shift/su_max          0.0005
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2182
_refine_ls_wR_factor_ref         0.2932
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1a), C24(H24)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C7(H7), C8(H8), C11(H11), C13(H13), C14(H14),
 C15(H15), C16(H16), C19(H19), C20(H20), C22(H22), C23(H23), C26(H26), C28(H28),
  C29(H29), C30(H30), C31(H31), C34(H34), C36(H36), C37(H37), C38(H38),
 C39(H39), C42(H42), C43(H43), C45(H45), C46(H46), N1(H1), N2(H2), N4(H4),
 N5(H5a)
;
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_refinement_flags_posn
O1 O 0.5612(2) -0.1122(4) 0.22900(9) 0.1245(14) Uani 1.000000 .
O2 O 0.5181(2) -0.2819(4) 0.20646(9) 0.1259(14) Uani 1.000000 .
N1 N 0.16062(18) 0.0615(3) 0.31703(8) 0.0734(9) Uani 1.000000 .
H1 H 0.14897(18) 0.1331(3) 0.30831(8) 0.0881(11) Uiso 1.000000 R
N2 N 0.37782(18) -0.1870(3) 0.41100(7) 0.0700(9) Uani 1.000000 .
H2 H 0.38713(18) -0.1477(3) 0.42961(7) 0.0840(10) Uiso 1.000000 R
N3 N 0.5138(2) -0.1974(4) 0.22722(9) 0.0856(11) Uani 1.000000 .
C1 C 0.28179(18) -0.2242(3) 0.32664(8) 0.0563(9) Uani 1.000000 .
H1a H 0.25396(18) -0.3033(3) 0.32313(8) 0.0676(10) Uiso 1.000000 R
C2 C 0.22298(18) -0.1204(3) 0.32628(8) 0.0546(8) Uani 1.000000 .
C3 C 0.2229(2) -0.0105(3) 0.30899(10) 0.0661(10) Uani 1.000000 .
H3 H 0.2601(2) 0.0126(3) 0.29373(10) 0.0793(12) Uiso 1.000000 R
C4 C 0.1198(2) 0.0008(4) 0.34130(9) 0.0645(10) Uani 1.000000 .
C5 C 0.0555(2) 0.0386(5) 0.35891(12) 0.0822(12) Uani 1.000000 .
H5 H 0.0331(2) 0.1168(5) 0.35534(12) 0.0986(15) Uiso 1.000000 R
C6 C 0.0267(2) -0.0437(5) 0.38158(13) 0.0931(14) Uani 1.000000 .
H6 H -0.0160(2) -0.0205(5) 0.39380(13) 0.1118(17) Uiso 1.000000 R
C7 C 0.0591(2) -0.1604(5) 0.38698(12) 0.0900(14) Uani 1.000000 .
H7 H 0.0373(2) -0.2142(5) 0.40249(12) 0.1079(16) Uiso 1.000000 R
C8 C 0.1236(2) -0.1994(4) 0.36976(10) 0.0745(11) Uani 1.000000 .
H8 H 0.1448(2) -0.2784(4) 0.37341(10) 0.0894(13) Uiso 1.000000 R
C9 C 0.15547(18) -0.1165(3) 0.34682(9) 0.0570(9) Uani 1.000000 .
C10 C 0.32578(18) -0.2326(3) 0.36017(8) 0.0541(8) Uani 1.000000 .
C11 C 0.3261(2) -0.1494(4) 0.38600(9) 0.0660(10) Uani 1.000000 .
H11 H 0.2958(2) -0.0775(4) 0.38670(9) 0.0792(12) Uiso 1.000000 R
C12 C 0.41227(19) -0.2969(4) 0.40172(8) 0.0583(9) Uani 1.000000 .
C13 C 0.4689(2) -0.3687(4) 0.41867(10) 0.0692(10) Uani 1.000000 .
H13 H 0.4885(2) -0.3462(4) 0.43990(10) 0.0830(12) Uiso 1.000000 R
C14 C 0.4936(2) -0.4726(4) 0.40259(11) 0.0759(11) Uani 1.000000 .
H14 H 0.5315(2) -0.5223(4) 0.41301(11) 0.0911(14) Uiso 1.000000 R
C15 C 0.4636(2) -0.5075(4) 0.37068(11) 0.0739(11) Uani 1.000000 .
H15 H 0.4817(2) -0.5797(4) 0.36040(11) 0.0887(13) Uiso 1.000000 R
C16 C 0.4076(2) -0.4354(3) 0.35441(10) 0.0627(9) Uani 1.000000 .
H16 H 0.3879(2) -0.4588(3) 0.33325(10) 0.0753(11) Uiso 1.000000 R
C17 C 0.38097(18) -0.3283(3) 0.36979(8) 0.0547(8) Uani 1.000000 .
C18 C 0.33980(18) -0.2114(3) 0.29866(8) 0.0557(8) Uani 1.000000 .
C19 C 0.3381(2) -0.2927(4) 0.27162(9) 0.0666(10) Uani 1.000000 .
H19 H 0.2983(2) -0.3508(4) 0.26928(9) 0.0799(12) Uiso 1.000000 R
C20 C 0.3957(2) -0.2885(4) 0.24773(9) 0.0721(11) Uani 1.000000 .
H20 H 0.3954(2) -0.3444(4) 0.22976(9) 0.0865(13) Uiso 1.000000 R
C21 C 0.4525(2) -0.1998(4) 0.25146(9) 0.0649(10) Uani 1.000000 .
C22 C 0.4539(2) -0.1140(4) 0.27737(9) 0.0688(10) Uani 1.000000 .
H22 H 0.4922(2) -0.0529(4) 0.27878(9) 0.0825(12) Uiso 1.000000 R
C23 C 0.3981(2) -0.1199(4) 0.30096(9) 0.0626(9) Uani 1.000000 .
H23 H 0.3987(2) -0.0628(4) 0.31868(9) 0.0751(11) Uiso 1.000000 R
O3 O 0.36260(17) -0.1964(3) -0.01272(7) 0.0844(9) Uani 1.000000 .
O4 O 0.32174(18) -0.3113(3) 0.02703(8) 0.0893(9) Uani 1.000000 .
N4 N 0.16923(17) 0.2288(3) 0.17002(7) 0.0649(8) Uani 1.000000 .
H4 H 0.12874(17) 0.2441(3) 0.18139(7) 0.0779(10) Uiso 1.000000 R
N5 N 0.2107(2) 0.4915(3) 0.03729(8) 0.0733(9) Uani 1.000000 .
H5a H 0.2142(2) 0.5641(3) 0.02807(8) 0.0879(11) Uiso 1.000000 R
N6 N 0.33682(16) -0.2087(3) 0.01530(8) 0.0600(7) Uani 1.000000 .
C24 C 0.28381(18) 0.2372(3) 0.09247(8) 0.0520(8) Uani 1.000000 .
H24 H 0.33483(18) 0.2750(3) 0.09670(8) 0.0625(10) Uiso 1.000000 R
C25 C 0.24879(18) 0.2191(3) 0.12655(8) 0.0523(8) Uani 1.000000 .
C26 C 0.17779(19) 0.2561(3) 0.13641(8) 0.0589(9) Uani 1.000000 .
H26 H 0.14047(19) 0.2943(3) 0.12251(8) 0.0706(11) Uiso 1.000000 R
C27 C 0.2356(2) 0.1734(3) 0.18242(9) 0.0605(9) Uani 1.000000 .
C28 C 0.2567(3) 0.1344(4) 0.21517(9) 0.0787(12) Uani 1.000000 .
H28 H 0.2223(3) 0.1395(4) 0.23267(9) 0.0944(14) Uiso 1.000000 R
C29 C 0.3291(3) 0.0893(5) 0.22025(11) 0.1011(15) Uani 1.000000 .
H29 H 0.3443(3) 0.0618(5) 0.24169(11) 0.1213(19) Uiso 1.000000 R
C30 C 0.3814(3) 0.0825(5) 0.19462(11) 0.1007(16) Uani 1.000000 .
H30 H 0.4310(3) 0.0524(5) 0.19942(11) 0.1208(19) Uiso 1.000000 R
C31 C 0.3620(2) 0.1190(4) 0.16225(10) 0.0766(11) Uani 1.000000 .
H31 H 0.3973(2) 0.1129(4) 0.14513(10) 0.0920(14) Uiso 1.000000 R
C32 C 0.2871(2) 0.1658(3) 0.15583(8) 0.0565(8) Uani 1.000000 .
C33 C 0.23923(19) 0.3266(3) 0.06978(8) 0.0532(8) Uani 1.000000 .
C34 C 0.2631(2) 0.4402(3) 0.05930(9) 0.0629(9) Uani 1.000000 .
H34 H 0.3093(2) 0.4781(3) 0.06626(9) 0.0755(11) Uiso 1.000000 R
C35 C 0.1514(2) 0.4087(3) 0.03222(9) 0.0624(9) Uani 1.000000 .
C36 C 0.0862(2) 0.4152(4) 0.01071(10) 0.0772(12) Uani 1.000000 .
H36 H 0.0772(2) 0.4844(4) -0.00311(10) 0.0926(14) Uiso 1.000000 R
C37 C 0.0361(2) 0.3168(4) 0.01062(10) 0.0760(11) Uani 1.000000 .
H37 H -0.0077(2) 0.3190(4) -0.00356(10) 0.0912(14) Uiso 1.000000 R
C38 C 0.0489(2) 0.2128(4) 0.03126(10) 0.0689(10) Uani 1.000000 .
H38 H 0.0133(2) 0.1475(4) 0.03078(10) 0.0827(12) Uiso 1.000000 R
C39 C 0.11299(19) 0.2052(3) 0.05219(8) 0.0565(8) Uani 1.000000 .
H39 H 0.12084(19) 0.1356(3) 0.06595(8) 0.0678(10) Uiso 1.000000 R
C40 C 0.16627(19) 0.3026(3) 0.05271(8) 0.0528(8) Uani 1.000000 .
C41 C 0.29757(17) 0.1154(3) 0.07314(8) 0.0461(7) Uani 1.000000 .
C42 C 0.33434(18) 0.1225(3) 0.04247(8) 0.0543(8) Uani 1.000000 .
H42 H 0.35029(18) 0.2001(3) 0.03463(8) 0.0651(10) Uiso 1.000000 R
C43 C 0.34762(19) 0.0169(3) 0.02345(8) 0.0546(8) Uani 1.000000 .
H43 H 0.37220(19) 0.0226(3) 0.00298(8) 0.0656(10) Uiso 1.000000 R
C44 C 0.32377(17) -0.0965(3) 0.03543(8) 0.0485(7) Uani 1.000000 .
C45 C 0.28601(19) -0.1082(3) 0.06522(8) 0.0584(9) Uani 1.000000 .
H45 H 0.26960(19) -0.1861(3) 0.07262(8) 0.0700(11) Uiso 1.000000 R
C46 C 0.27299(19) -0.0022(3) 0.08389(8) 0.0561(8) Uani 1.000000 .
H46 H 0.24730(19) -0.0089(3) 0.10406(8) 0.0673(10) Uiso 1.000000 R


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
O1 N3 1.224(5) . ?
O2 N3 1.226(5) . ?
N1 C3 1.368(4) . ?
N1 C4 1.374(5) . ?
N2 C11 1.375(5) . ?
N2 C12 1.372(5) . ?
N3 C21 1.454(5) . ?
C1 C2 1.504(4) . ?
C1 C10 1.515(5) . ?
C1 C18 1.525(4) . ?
C2 C3 1.359(5) . ?
C2 C9 1.445(4) . ?
C4 C5 1.391(5) . ?
C4 C9 1.410(5) . ?
C5 C6 1.362(6) . ?
C6 C7 1.381(7) . ?
C7 C8 1.388(5) . ?
C8 C9 1.396(5) . ?
C10 C11 1.356(5) . ?
C10 C17 1.442(5) . ?
C12 C13 1.399(5) . ?
C12 C17 1.402(5) . ?
C13 C14 1.356(6) . ?
C14 C15 1.404(6) . ?
C15 C16 1.382(5) . ?
C16 C17 1.382(5) . ?
C18 C19 1.379(5) . ?
C18 C23 1.406(5) . ?
C19 C20 1.396(5) . ?
C20 C21 1.369(5) . ?
C21 C22 1.376(5) . ?
C22 C23 1.366(5) . ?
O3 N6 1.217(4) . ?
O4 N6 1.222(4) . ?
N4 C26 1.378(4) . ?
N4 C27 1.369(4) . ?
N5 C34 1.354(5) . ?
N5 C35 1.364(5) . ?
N6 C44 1.460(4) . ?
C24 C25 1.511(4) . ?
C24 C33 1.508(5) . ?
C24 C41 1.533(4) . ?
C25 C26 1.359(4) . ?
C25 C32 1.437(5) . ?
C27 C28 1.402(5) . ?
C27 C32 1.404(4) . ?
C28 C29 1.351(6) . ?
C29 C30 1.384(6) . ?
C30 C31 1.374(6) . ?
C31 C32 1.403(5) . ?
C33 C34 1.350(5) . ?
C33 C40 1.437(5) . ?
C35 C36 1.395(6) . ?
C35 C40 1.413(5) . ?
C36 C37 1.361(6) . ?
C37 C38 1.393(5) . ?
C38 C39 1.367(5) . ?
C39 C40 1.389(5) . ?
C41 C42 1.392(4) . ?
C41 C46 1.396(4) . ?
C42 C43 1.380(4) . ?
C43 C44 1.369(4) . ?
C44 C45 1.373(4) . ?
C45 C46 1.375(4) . ?

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
C4 N1 C3 108.9(3) . . ?
C12 N2 C11 109.5(3) . . ?
O2 N3 O1 122.2(4) . . ?
C21 N3 O1 118.4(4) . . ?
C21 N3 O2 119.4(4) . . ?
C10 C1 C2 111.9(3) . . ?
C18 C1 C2 112.8(3) . . ?
C18 C1 C10 108.7(3) . . ?
C3 C2 C1 129.2(3) . . ?
C9 C2 C1 125.0(3) . . ?
C9 C2 C3 105.7(3) . . ?
C2 C3 N1 110.9(3) . . ?
C5 C4 N1 130.6(4) . . ?
C9 C4 N1 107.2(3) . . ?
C9 C4 C5 122.1(4) . . ?
C6 C5 C4 117.3(4) . . ?
C7 C6 C5 122.0(4) . . ?
C8 C7 C6 121.5(4) . . ?
C9 C8 C7 118.0(4) . . ?
C4 C9 C2 107.2(3) . . ?
C8 C9 C2 133.8(3) . . ?
C8 C9 C4 119.0(3) . . ?
C11 C10 C1 128.0(3) . . ?
C17 C10 C1 125.8(3) . . ?
C17 C10 C11 106.1(3) . . ?
C10 C11 N2 109.9(3) . . ?
C13 C12 N2 130.0(3) . . ?
C17 C12 N2 106.8(3) . . ?
C17 C12 C13 123.2(3) . . ?
C14 C13 C12 116.6(4) . . ?
C15 C14 C13 121.9(4) . . ?
C16 C15 C14 120.5(4) . . ?
C17 C16 C15 119.5(4) . . ?
C12 C17 C10 107.7(3) . . ?
C16 C17 C10 134.1(3) . . ?
C16 C17 C12 118.2(3) . . ?
C19 C18 C1 120.8(3) . . ?
C23 C18 C1 120.1(3) . . ?
C23 C18 C19 119.1(3) . . ?
C20 C19 C18 120.6(3) . . ?
C21 C20 C19 118.2(3) . . ?
C20 C21 N3 118.5(3) . . ?
C22 C21 N3 119.1(4) . . ?
C22 C21 C20 122.5(3) . . ?
C23 C22 C21 119.0(3) . . ?
C22 C23 C18 120.5(3) . . ?
C27 N4 C26 109.0(3) . . ?
C35 N5 C34 108.5(3) . . ?
O4 N6 O3 122.2(3) . . ?
C44 N6 O3 118.6(3) . . ?
C44 N6 O4 119.2(3) . . ?
C33 C24 C25 113.8(3) . . ?
C41 C24 C25 114.3(3) . . ?
C41 C24 C33 108.9(3) . . ?
C26 C25 C24 127.7(3) . . ?
C32 C25 C24 125.9(3) . . ?
C32 C25 C26 106.3(3) . . ?
C25 C26 N4 110.0(3) . . ?
C28 C27 N4 130.8(3) . . ?
C32 C27 N4 107.4(3) . . ?
C32 C27 C28 121.7(4) . . ?
C29 C28 C27 117.3(4) . . ?
C30 C29 C28 122.2(4) . . ?
C31 C30 C29 121.7(4) . . ?
C32 C31 C30 118.0(4) . . ?
C27 C32 C25 107.3(3) . . ?
C31 C32 C25 133.4(3) . . ?
C31 C32 C27 119.2(3) . . ?
C34 C33 C24 126.6(3) . . ?
C40 C33 C24 126.4(3) . . ?
C40 C33 C34 106.7(3) . . ?
C33 C34 N5 110.9(3) . . ?
C36 C35 N5 130.4(4) . . ?
C40 C35 N5 108.2(3) . . ?
C40 C35 C36 121.4(4) . . ?
C37 C36 C35 117.7(4) . . ?
C38 C37 C36 121.6(4) . . ?
C39 C38 C37 121.0(4) . . ?
C40 C39 C38 119.3(3) . . ?
C35 C40 C33 105.7(3) . . ?
C39 C40 C33 135.5(3) . . ?
C39 C40 C35 118.9(3) . . ?
C42 C41 C24 118.2(3) . . ?
C46 C41 C24 123.8(3) . . ?
C46 C41 C42 117.9(3) . . ?
C43 C42 C41 121.4(3) . . ?
C44 C43 C42 118.4(3) . . ?
C43 C44 N6 118.8(3) . . ?
C45 C44 N6 118.8(3) . . ?
C45 C44 C43 122.3(3) . . ?
C46 C45 C44 118.6(3) . . ?
C45 C46 C41 121.3(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
