# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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 1000479'
_audit_update_record             
;
2014-05-01 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-01-20
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C27 H36 N2 S'
_chemical_formula_sum            'C27 H36 N2 S'
_chemical_formula_weight         420.67
_chemical_oxdiff_formula         'C27 H36 N2 S'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.33537 0.55136 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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'
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

_cell_length_a                   19.2174(14)
_cell_length_b                   6.8155(4)
_cell_length_c                   20.0755(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.338(8)
_cell_angle_gamma                90
_cell_volume                     2578.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2162
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.6964
_cell_measurement_theta_min      4.6381
_exptl_absorpt_coefficient_mu    1.205
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72964
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.0837
_exptl_crystal_description       plate
_exptl_crystal_F_000             915.5451
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_diffrn_reflns_av_R_equivalents  0.0313
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            9769
_diffrn_reflns_theta_full        70.832564
_diffrn_reflns_theta_max         70.83
_diffrn_reflns_theta_min         4.64
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.972217
_diffrn_measured_fraction_theta_max 0.972217
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega -102.00  -75.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00  -34.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -34.00   37.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000 -120.0000 71

#__ type_ start__ end____ width___ exp.time_
  4 omega   26.00  120.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  150.0000 94

#__ type_ start__ end____ width___ exp.time_
  5 omega   28.00   73.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  150.0000 45

#__ type_ start__ end____ width___ exp.time_
  6 omega   -9.00   90.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -19.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
  7 omega   41.00   84.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 43

#__ type_ start__ end____ width___ exp.time_
  8 omega   37.00   92.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 55

#__ type_ start__ end____ width___ exp.time_
  9 omega   41.00   68.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -82.0000  105.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   39.00   85.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 11 omega   94.00  174.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000 -120.0000 80

#__ type_ start__ end____ width___ exp.time_
 12 omega   64.00   93.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
 13 omega   56.00  103.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 47

#__ type_ start__ end____ width___ exp.time_
 14 omega   61.00   88.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   54.00   90.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 16 omega   44.00   90.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 46

#__ type_ start__ end____ width___ exp.time_
 17 omega   92.00  128.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -82.0000  105.0000 36

#__ type_ start__ end____ width___ exp.time_
 18 omega   78.00  178.00   1.0000    1.6400
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000 -150.0000 100
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0185700000
_diffrn_orient_matrix_UB_12      0.0698933000
_diffrn_orient_matrix_UB_13      -0.0673389000
_diffrn_orient_matrix_UB_21      0.0583244000
_diffrn_orient_matrix_UB_22      0.1340303000
_diffrn_orient_matrix_UB_23      0.0397595000
_diffrn_orient_matrix_UB_31      0.0541348000
_diffrn_orient_matrix_UB_32      -0.1681676000
_diffrn_orient_matrix_UB_33      0.0033816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              15
_reflns_limit_h_min              -23
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -14
_reflns_number_gt                3670
_reflns_number_total             4829
_reflns_odcompleteness_completeness 99.32
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.453638
_refine_diff_density_min         -0.360232
_refine_diff_density_rms         0.078292
_refine_ls_d_res_high            0.816166
_refine_ls_d_res_low             9.421175
_refine_ls_goodness_of_fit_ref   1.064470
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4829
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.083202
_refine_ls_R_factor_gt           0.062640
_refine_ls_restrained_S_all      1.064470
_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)+(0.0668P)²+2.7025P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.178639
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
S1 S 0.94067(4) 0.02359(10) 0.24606(4) 0.0460(2) Uani 1.000000 .
N1 N 1.05891(11) -0.1965(3) 0.24470(12) 0.0350(5) Uani 1.000000 .
N2 N 0.96425(11) -0.3716(3) 0.24196(12) 0.0352(5) Uani 1.000000 .
C16 C 1.12085(13) 0.0639(4) 0.19684(15) 0.0364(6) Uani 1.000000 .
C3 C 1.02010(14) -0.5015(4) 0.24118(15) 0.0393(6) Uani 1.000000 .
H3 H 1.01726(14) -0.6406(4) 0.23966(15) 0.0471(8) Uiso 1.000000 R
C19 C 1.19998(15) 0.1406(5) 0.32711(16) 0.0442(7) Uani 1.000000 .
H19 H 1.22688(15) 0.1689(5) 0.37102(16) 0.0531(8) Uiso 1.000000 R
C15 C 1.10896(13) -0.0366(4) 0.25403(14) 0.0340(6) Uani 1.000000 .
C1 C 0.98763(13) -0.1818(4) 0.24408(14) 0.0349(6) Uani 1.000000 .
C6 C 0.77559(15) -0.4926(4) 0.17537(16) 0.0433(7) Uani 1.000000 .
H6 H 0.74290(15) -0.4987(4) 0.13326(16) 0.0519(8) Uiso 1.000000 R
C5 C 0.84562(14) -0.4381(4) 0.17609(15) 0.0385(6) Uani 1.000000 .
C17 C 1.17541(14) 0.2037(4) 0.20731(16) 0.0404(7) Uani 1.000000 .
H17 H 1.18546(14) 0.2757(4) 0.16978(16) 0.0485(8) Uiso 1.000000 R
C7 C 0.75280(16) -0.5377(4) 0.23432(17) 0.0468(8) Uani 1.000000 .
H7 H 0.70493(16) -0.5758(4) 0.23264(17) 0.0561(9) Uiso 1.000000 R
C18 C 1.21461(15) 0.2379(4) 0.27143(17) 0.0433(7) Uani 1.000000 .
H18 H 1.25237(15) 0.3302(4) 0.27729(17) 0.0519(8) Uiso 1.000000 R
C8 C 0.79966(15) -0.5277(4) 0.29604(16) 0.0451(7) Uani 1.000000 .
H8 H 0.78326(15) -0.5569(4) 0.33659(16) 0.0541(9) Uiso 1.000000 R
C10 C 0.92064(17) -0.4652(5) 0.36853(16) 0.0473(7) Uani 1.000000 .
H10 H 0.97000(17) -0.4536(5) 0.35994(16) 0.0568(9) Uiso 1.000000 R
C4 C 0.89126(13) -0.4287(4) 0.23933(14) 0.0343(6) Uani 1.000000 .
C2 C 1.07839(14) -0.3932(4) 0.24296(15) 0.0398(7) Uani 1.000000 .
H2 H 1.12477(14) -0.4415(4) 0.24304(15) 0.0477(8) Uiso 1.000000 R
C9 C 0.87055(14) -0.4757(4) 0.29991(15) 0.0381(6) Uani 1.000000 .
C20 C 1.14605(14) 0.0008(4) 0.31971(15) 0.0384(6) Uani 1.000000 .
C24 C 1.07849(16) 0.0211(5) 0.12623(15) 0.0447(7) Uani 1.000000 .
H24 H 1.03289(16) -0.0419(5) 0.13151(15) 0.0537(8) Uiso 1.000000 R
C21 C 1.12855(17) -0.1041(5) 0.38125(16) 0.0494(8) Uani 1.000000 .
H21 H 1.08393(17) -0.1804(5) 0.36530(16) 0.0593(9) Uiso 1.000000 R
C25 C 1.1183(2) -0.1246(6) 0.08950(18) 0.0646(10) Uani 1.000000 .
H25a H 1.1646(6) -0.0698(17) 0.0861(12) 0.0969(15) Uiso 1.000000 G
H25b H 1.1251(13) -0.2480(14) 0.1150(7) 0.0969(15) Uiso 1.000000 G
H25c H 1.0907(7) -0.150(3) 0.0438(5) 0.0969(15) Uiso 1.000000 G
C22 C 1.1866(2) -0.2516(7) 0.4113(2) 0.0735(11) Uani 1.000000 .
H22a H 1.1931(11) -0.346(3) 0.3762(5) 0.1103(17) Uiso 1.000000 G
H22b H 1.2313(4) -0.1816(8) 0.4275(14) 0.1103(17) Uiso 1.000000 G
H22c H 1.1726(7) -0.321(3) 0.4492(10) 0.1103(17) Uiso 1.000000 G
C13 C 0.86928(17) -0.3876(5) 0.11033(16) 0.0479(7) Uani 1.000000 .
H13 H 0.92136(17) -0.3598(5) 0.12176(16) 0.0575(9) Uiso 1.000000 R
C14 C 0.8582(2) -0.5608(6) 0.06098(19) 0.0697(11) Uani 1.000000 .
H14a H 0.8824(13) -0.6768(12) 0.0833(5) 0.1045(16) Uiso 1.000000 G
H14b H 0.8073(2) -0.588(3) 0.0473(11) 0.1045(16) Uiso 1.000000 G
H14c H 0.8777(14) -0.5285(17) 0.0208(7) 0.1045(16) Uiso 1.000000 G
C11 C 0.8325(2) -0.2027(6) 0.07802(18) 0.0645(10) Uani 1.000000 .
H11a H 0.7812(3) -0.2254(14) 0.0661(12) 0.0967(15) Uiso 1.000000 G
H11b H 0.8422(12) -0.0936(11) 0.1103(5) 0.0967(15) Uiso 1.000000 G
H11c H 0.8504(10) -0.170(2) 0.0369(8) 0.0967(15) Uiso 1.000000 G
C12 C 0.9177(2) -0.6505(6) 0.41056(19) 0.0685(11) Uani 1.000000 .
H12a H 0.8701(5) -0.665(2) 0.4207(12) 0.1028(16) Uiso 1.000000 G
H12b H 0.9284(15) -0.7650(7) 0.3849(6) 0.1028(16) Uiso 1.000000 G
H12c H 0.9526(11) -0.6409(19) 0.4531(7) 0.1028(16) Uiso 1.000000 G
C26 C 1.0602(2) 0.2060(6) 0.08369(18) 0.0623(10) Uani 1.000000 .
H26a H 1.0346(12) 0.2977(17) 0.1078(6) 0.0935(15) Uiso 1.000000 G
H26b H 1.1039(2) 0.268(2) 0.0759(11) 0.0935(15) Uiso 1.000000 G
H26c H 1.0302(11) 0.1713(8) 0.0399(5) 0.0935(15) Uiso 1.000000 G
C23 C 1.1140(3) 0.0396(7) 0.4343(2) 0.0817(13) Uani 1.000000 .
H23a H 1.1575(5) 0.113(3) 0.4527(12) 0.123(2) Uiso 1.000000 G
H23b H 1.0767(12) 0.131(3) 0.4135(4) 0.123(2) Uiso 1.000000 G
H23c H 1.0985(16) -0.0321(8) 0.4711(8) 0.123(2) Uiso 1.000000 G
C1a C 0.9060(3) -0.2834(6) 0.4072(2) 0.0819(14) Uani 1.000000 .
H1aa H 0.9096(17) -0.1666(7) 0.3796(7) 0.123(2) Uiso 1.000000 G
H1ab H 0.8582(7) -0.291(2) 0.4171(14) 0.123(2) Uiso 1.000000 G
H1ac H 0.9409(11) -0.275(3) 0.4499(8) 0.123(2) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C1 1.670(3) .
N1 C15 1.441(3) .
N1 C1 1.371(3) .
N1 C2 1.394(3) .
N2 C3 1.393(3) .
N2 C1 1.368(3) .
N2 C4 1.447(3) .
C16 C15 1.394(4) .
C16 C17 1.402(4) .
C16 C24 1.518(4) .
C3 H3 0.9500 .
C3 C2 1.336(4) .
C19 H19 0.9500 .
C19 C18 1.376(4) .
C19 C20 1.394(4) .
C15 C20 1.394(4) .
C6 H6 0.9500 .
C6 C5 1.393(4) .
C6 C7 1.375(4) .
C5 C4 1.395(4) .
C5 C13 1.518(4) .
C17 H17 0.9500 .
C17 C18 1.377(4) .
C7 H7 0.9500 .
C7 C8 1.383(4) .
C18 H18 0.9500 .
C8 H8 0.9500 .
C8 C9 1.395(4) .
C10 H10 1.0000 .
C10 C9 1.519(4) .
C10 C12 1.526(5) .
C10 C1a 1.517(5) .
C4 C9 1.389(4) .
C2 H2 0.9500 .
C20 C21 1.521(4) .
C24 H24 1.0000 .
C24 C25 1.529(4) .
C24 C26 1.524(4) .
C21 H21 1.0000 .
C21 C22 1.534(5) .
C21 C23 1.513(5) .
C25 H25a 0.9800 .
C25 H25b 0.9800 .
C25 H25c 0.9800 .
C22 H22a 0.9800 .
C22 H22b 0.9800 .
C22 H22c 0.9800 .
C13 H13 1.0000 .
C13 C14 1.529(5) .
C13 C11 1.526(5) .
C14 H14a 0.9800 .
C14 H14b 0.9800 .
C14 H14c 0.9800 .
C11 H11a 0.9800 .
C11 H11b 0.9800 .
C11 H11c 0.9800 .
C12 H12a 0.9800 .
C12 H12b 0.9800 .
C12 H12c 0.9800 .
C26 H26a 0.9800 .
C26 H26b 0.9800 .
C26 H26c 0.9800 .
C23 H23a 0.9800 .
C23 H23b 0.9800 .
C23 H23c 0.9800 .
C1a H1aa 0.9800 .
C1a H1ab 0.9800 .
C1a H1ac 0.9800 .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C15 125.8(2) . .
C2 N1 C15 123.7(2) . .
C2 N1 C1 110.1(2) . .
C1 N2 C3 110.6(2) . .
C4 N2 C3 124.9(2) . .
C4 N2 C1 124.5(2) . .
C17 C16 C15 116.7(3) . .
C24 C16 C15 122.0(3) . .
C24 C16 C17 121.2(3) . .
H3 C3 N2 126.50(14) . .
C2 C3 N2 107.0(2) . .
C2 C3 H3 126.50(17) . .
C18 C19 H19 119.69(18) . .
C20 C19 H19 119.69(18) . .
C20 C19 C18 120.6(3) . .
C16 C15 N1 118.5(2) . .
C20 C15 N1 117.7(2) . .
C20 C15 C16 123.6(3) . .
N1 C1 S1 127.2(2) . .
N2 C1 S1 128.16(19) . .
N2 C1 N1 104.6(2) . .
C5 C6 H6 119.29(18) . .
C7 C6 H6 119.29(17) . .
C7 C6 C5 121.4(3) . .
C4 C5 C6 117.0(3) . .
C13 C5 C6 120.3(3) . .
C13 C5 C4 122.6(3) . .
H17 C17 C16 119.65(17) . .
C18 C17 C16 120.7(3) . .
C18 C17 H17 119.65(17) . .
H7 C7 C6 120.05(17) . .
C8 C7 C6 119.9(3) . .
C8 C7 H7 120.05(17) . .
C17 C18 C19 121.1(3) . .
H18 C18 C19 119.46(17) . .
H18 C18 C17 119.46(17) . .
H8 C8 C7 119.36(17) . .
C9 C8 C7 121.3(3) . .
C9 C8 H8 119.36(18) . .
C9 C10 H10 107.50(16) . .
C12 C10 H10 107.5(2) . .
C12 C10 C9 112.1(3) . .
C1a C10 H10 107.5(2) . .
C1a C10 C9 110.7(3) . .
C1a C10 C12 111.2(3) . .
C5 C4 N2 118.5(2) . .
C9 C4 N2 118.2(2) . .
C9 C4 C5 123.3(2) . .
C3 C2 N1 107.7(2) . .
H2 C2 N1 126.15(14) . .
H2 C2 C3 126.15(17) . .
C10 C9 C8 120.0(3) . .
C4 C9 C8 117.0(3) . .
C4 C9 C10 122.9(3) . .
C15 C20 C19 117.2(3) . .
C21 C20 C19 120.9(3) . .
C21 C20 C15 121.9(3) . .
H24 C24 C16 107.69(15) . .
C25 C24 C16 110.4(2) . .
C25 C24 H24 107.7(2) . .
C26 C24 C16 112.8(3) . .
C26 C24 H24 107.69(19) . .
C26 C24 C25 110.4(3) . .
H21 C21 C20 107.27(16) . .
C22 C21 C20 111.5(3) . .
C22 C21 H21 107.3(2) . .
C23 C21 C20 111.6(3) . .
C23 C21 H21 107.3(2) . .
C23 C21 C22 111.6(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 . .
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 . .
H13 C13 C5 107.51(16) . .
C14 C13 C5 111.2(3) . .
C14 C13 H13 107.5(2) . .
C11 C13 C5 111.3(3) . .
C11 C13 H13 107.5(2) . .
C11 C13 C14 111.6(3) . .
H14a C14 C13 109.5 . .
H14b C14 C13 109.5 . .
H14b C14 H14a 109.5 . .
H14c C14 C13 109.5 . .
H14c C14 H14a 109.5 . .
H14c C14 H14b 109.5 . .
H11a C11 C13 109.5 . .
H11b C11 C13 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C13 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
H12a C12 C10 109.5 . .
H12b C12 C10 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C10 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
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 . .
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 . .
H1aa C1a C10 109.5 . .
H1ab C1a C10 109.5 . .
H1ab C1a H1aa 109.5 . .
H1ac C1a C10 109.5 . .
H1ac C1a H1aa 109.5 . .
H1ac C1a H1ab 109.5 . .

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

data_5
_database_code_depnum_ccdc_archive 'CCDC 1000480'
_audit_update_record             
;
2014-05-01 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-01-20
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C27 H36 N2 Te'
_chemical_formula_sum            'C27 H36 N2 Te'
_chemical_formula_weight         516.20
_chemical_oxdiff_formula         'C27 H36 N2 Te'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Te -0.06053 6.77227 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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'
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

_cell_length_a                   19.1643(5)
_cell_length_b                   7.15496(17)
_cell_length_c                   20.1107(8)
_cell_angle_alpha                90
_cell_angle_beta                 106.852(4)
_cell_angle_gamma                90
_cell_volume                     2639.17(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4614
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.7555
_cell_measurement_theta_min      3.7772
_exptl_absorpt_coefficient_mu    8.989
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.48037
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.2991
_exptl_crystal_description       plate
_exptl_crystal_F_000             1058.3297
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.27
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0436
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10829
_diffrn_reflns_theta_full        70.892111
_diffrn_reflns_theta_max         70.89
_diffrn_reflns_theta_min         3.78
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.978372
_diffrn_measured_fraction_theta_max 0.978372
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -45.00   37.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   25.0000  150.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -54.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   63.0000   30.0000 70

#__ type_ start__ end____ width___ exp.time_
  3 omega   28.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000   60.0000 94

#__ type_ start__ end____ width___ exp.time_
  4 omega   18.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   90.0000 50

#__ type_ start__ end____ width___ exp.time_
  5 omega  -14.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  6 omega   47.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
  7 omega   42.00   67.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega  101.00  131.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 30

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
 10 omega   46.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 48

#__ type_ start__ end____ width___ exp.time_
 11 omega   39.00  137.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  -90.0000 98

#__ type_ start__ end____ width___ exp.time_
 12 omega   43.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 13 omega  103.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000   30.0000 73

#__ type_ start__ end____ width___ exp.time_
 14 omega  152.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 25

#__ type_ start__ end____ width___ exp.time_
 15 omega   64.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   45.00  167.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -180.0000 122
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0064458000
_diffrn_orient_matrix_UB_12      -0.1742350000
_diffrn_orient_matrix_UB_13      -0.0465433000
_diffrn_orient_matrix_UB_21      -0.0526001000
_diffrn_orient_matrix_UB_22      0.1064781000
_diffrn_orient_matrix_UB_23      -0.0607211000
_diffrn_orient_matrix_UB_31      0.0650757000
_diffrn_orient_matrix_UB_32      0.0689040000
_diffrn_orient_matrix_UB_33      -0.0236193000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -23
_reflns_limit_k_max              8
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              -13
_reflns_number_gt                4169
_reflns_number_total             4976
_reflns_odcompleteness_completeness 99.88
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.009294
_refine_diff_density_min         -1.104919
_refine_diff_density_rms         0.094040
_refine_ls_d_res_high            0.815871
_refine_ls_d_res_low             11.692600
_refine_ls_goodness_of_fit_ref   1.040163
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    56
_refine_ls_number_parameters     278
_refine_ls_number_reflns         4976
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.044398
_refine_ls_R_factor_gt           0.035393
_refine_ls_restrained_S_all      1.040163
_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)+(0.0461P)²+0.3314P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.095047
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
Te1 Te 0.562749(11) 0.18067(3) 0.231272(14) 0.04373(10) Uani 1.000000 .
C20 C 0.34207(19) 0.0782(5) 0.3182(2) 0.0431(8) Uani 1.000000 .
H20 H 0.34142(19) 0.0449(5) 0.3638(2) 0.0517(10) Uiso 1.000000 R
N2 N 0.52205(13) 0.5976(3) 0.23184(13) 0.0280(5) Uani 1.000000 .
C1 C 0.50166(16) 0.4162(4) 0.23224(16) 0.0290(6) Uani 1.000000 .
C4 C 0.59533(16) 0.6617(4) 0.23682(17) 0.0292(6) Uani 1.000000 .
C3 C 0.46433(17) 0.7162(4) 0.23049(18) 0.0335(7) Uani 1.000000 .
H3 H 0.46506(17) 0.8489(4) 0.22967(18) 0.0402(8) Uiso 1.000000 R
N1 N 0.43014(13) 0.4222(3) 0.23155(13) 0.0287(5) Uani 1.000000 .
C17 C 0.34229(17) 0.1729(4) 0.18314(17) 0.0319(7) Uani 1.000000 .
C16 C 0.38688(16) 0.2652(4) 0.24121(16) 0.0283(6) Uani 1.000000 .
C7 C 0.73122(19) 0.8040(5) 0.2464(2) 0.0467(9) Uani 1.000000 .
H7 H 0.77803(19) 0.8540(5) 0.2497(2) 0.0561(11) Uiso 1.000000 R
C10 C 0.6207(2) 0.6735(6) 0.3690(2) 0.0514(10) Uani 1.000000 .
H10 H 0.5666(2) 0.6567(6) 0.3560(2) 0.0616(12) Uiso 1.000000 R
C5 C 0.61467(18) 0.6883(4) 0.17577(18) 0.0342(7) Uani 1.000000 .
C9 C 0.64176(19) 0.7033(5) 0.30246(18) 0.0375(7) Uani 1.000000 .
C19 C 0.29673(19) -0.0123(5) 0.2621(2) 0.0422(8) Uani 1.000000 .
H19 H 0.26463(19) -0.1065(5) 0.2691(2) 0.0507(10) Uiso 1.000000 R
C25 C 0.3424(2) 0.2229(6) 0.10958(18) 0.0447(9) Uani 1.000000 .
H25 H 0.3886(2) 0.2918(6) 0.11254(18) 0.0536(10) Uiso 1.000000 R
C21 C 0.38922(18) 0.2188(5) 0.30941(17) 0.0351(7) Uani 1.000000 .
C22 C 0.4412(2) 0.3124(5) 0.37185(19) 0.0464(9) Uani 1.000000 .
H22 H 0.4781(2) 0.3824(5) 0.35512(19) 0.0557(11) Uiso 1.000000 R
C11 C 0.6404(3) 0.8412(7) 0.4181(3) 0.0798(16) Uani 1.000000 .
H11a H 0.6935(3) 0.856(3) 0.4340(16) 0.120(2) Uiso 1.000000 G
H11b H 0.6182(17) 0.9545(11) 0.3935(6) 0.120(2) Uiso 1.000000 G
H11c H 0.6221(18) 0.821(2) 0.4582(10) 0.120(2) Uiso 1.000000 G
C2 C 0.40697(17) 0.6068(4) 0.23056(18) 0.0341(7) Uani 1.000000 .
H2 H 0.35970(17) 0.6481(4) 0.23004(18) 0.0410(8) Uiso 1.000000 R
C24 C 0.4823(3) 0.1705(7) 0.4255(2) 0.0696(14) Uani 1.000000 .
H24a H 0.4483(4) 0.109(3) 0.4467(13) 0.104(2) Uiso 1.000000 G
H24b H 0.5048(16) 0.077(3) 0.4028(4) 0.104(2) Uiso 1.000000 G
H24c H 0.5203(12) 0.2345(10) 0.4616(10) 0.104(2) Uiso 1.000000 G
C18 C 0.29737(18) 0.0323(5) 0.19545(19) 0.0406(8) Uani 1.000000 .
H18 H 0.26656(18) -0.0343(5) 0.15727(19) 0.0487(10) Uiso 1.000000 R
C13 C 0.5645(2) 0.6441(5) 0.10409(18) 0.0445(9) Uani 1.000000 .
H13 H 0.5205(2) 0.5790(5) 0.11001(18) 0.0534(10) Uiso 1.000000 R
C14 C 0.5390(3) 0.8250(6) 0.0633(2) 0.0617(12) Uani 1.000000 .
H14a H 0.5125(16) 0.902(2) 0.0882(9) 0.0925(18) Uiso 1.000000 G
H14b H 0.5815(3) 0.894(2) 0.0586(15) 0.0925(18) Uiso 1.000000 G
H14c H 0.5068(14) 0.7943(6) 0.0171(6) 0.0925(18) Uiso 1.000000 G
C8 C 0.7102(2) 0.7735(5) 0.3057(2) 0.0477(9) Uani 1.000000 .
H8 H 0.7434(2) 0.8012(5) 0.3497(2) 0.0572(11) Uiso 1.000000 R
C26 C 0.2786(3) 0.3526(7) 0.0760(2) 0.0653(13) Uani 1.000000 .
H26a H 0.2327(3) 0.2904(19) 0.0747(16) 0.0979(19) Uiso 1.000000 G
H26b H 0.2833(10) 0.468(2) 0.1031(10) 0.0979(19) Uiso 1.000000 G
H26c H 0.2789(11) 0.383(4) 0.0285(6) 0.0979(19) Uiso 1.000000 G
C15 C 0.6016(2) 0.5121(6) 0.0644(2) 0.0629(12) Uani 1.000000 .
H15a H 0.6466(9) 0.570(2) 0.0605(15) 0.0944(18) Uiso 1.000000 G
H15b H 0.6132(16) 0.3935(18) 0.0896(9) 0.0944(18) Uiso 1.000000 G
H15c H 0.5687(7) 0.489(4) 0.0179(6) 0.0944(18) Uiso 1.000000 G
C6 C 0.6839(2) 0.7614(5) 0.1828(2) 0.0433(9) Uani 1.000000 .
H6 H 0.6988(2) 0.7823(5) 0.1422(2) 0.0519(10) Uiso 1.000000 R
C27 C 0.3403(3) 0.0490(7) 0.0651(2) 0.0678(13) Uani 1.000000 .
H27a H 0.3794(12) -0.037(2) 0.0892(8) 0.1017(19) Uiso 1.000000 G
H27b H 0.2931(7) -0.013(3) 0.0571(15) 0.1017(19) Uiso 1.000000 G
H27c H 0.3472(18) 0.0853(8) 0.0204(7) 0.1017(19) Uiso 1.000000 G
C23 C 0.4016(2) 0.4544(7) 0.4049(2) 0.0682(13) Uani 1.000000 .
H23a H 0.3792(16) 0.551(3) 0.3707(6) 0.1024(19) Uiso 1.000000 G
H23b H 0.3637(13) 0.3906(11) 0.4202(16) 0.1024(19) Uiso 1.000000 G
H23c H 0.4366(4) 0.513(4) 0.4450(11) 0.1024(19) Uiso 1.000000 G
C12 C 0.6560(3) 0.4955(6) 0.4057(2) 0.0680(13) Uani 1.000000 .
H12a H 0.6423(15) 0.3892(10) 0.3738(6) 0.1020(19) Uiso 1.000000 G
H12b H 0.7092(3) 0.5097(18) 0.4202(15) 0.1020(19) Uiso 1.000000 G
H12c H 0.6392(14) 0.473(3) 0.4466(10) 0.1020(19) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Te1 C1 2.055(3) .
C20 H20 0.9500 .
C20 C19 1.371(5) .
C20 C21 1.398(5) .
N2 C1 1.356(4) .
N2 C4 1.453(4) .
N2 C3 1.388(4) .
C1 N1 1.367(4) .
C4 C5 1.395(4) .
C4 C9 1.393(5) .
C3 H3 0.9500 .
C3 C2 1.350(4) .
N1 C16 1.442(4) .
N1 C2 1.392(4) .
C17 C16 1.397(4) .
C17 C25 1.523(5) .
C17 C18 1.392(4) .
C16 C21 1.399(4) .
C7 H7 0.9500 .
C7 C8 1.382(6) .
C7 C6 1.371(6) .
C10 H10 1.0000 .
C10 C9 1.520(5) .
C10 C11 1.530(6) .
C10 C12 1.528(6) .
C5 C13 1.516(5) .
C5 C6 1.395(5) .
C9 C8 1.388(5) .
C19 H19 0.9500 .
C19 C18 1.382(5) .
C25 H25 1.0000 .
C25 C26 1.528(6) .
C25 C27 1.527(5) .
C21 C22 1.514(5) .
C22 H22 1.0000 .
C22 C24 1.524(5) .
C22 C23 1.530(5) .
C11 H11a 0.9800 .
C11 H11b 0.9800 .
C11 H11c 0.9800 .
C2 H2 0.9500 .
C24 H24a 0.9800 .
C24 H24b 0.9800 .
C24 H24c 0.9800 .
C18 H18 0.9500 .
C13 H13 1.0000 .
C13 C14 1.534(5) .
C13 C15 1.538(5) .
C14 H14a 0.9800 .
C14 H14b 0.9800 .
C14 H14c 0.9800 .
C8 H8 0.9500 .
C26 H26a 0.9800 .
C26 H26b 0.9800 .
C26 H26c 0.9800 .
C15 H15a 0.9800 .
C15 H15b 0.9800 .
C15 H15c 0.9800 .
C6 H6 0.9500 .
C27 H27a 0.9800 .
C27 H27b 0.9800 .
C27 H27c 0.9800 .
C23 H23a 0.9800 .
C23 H23b 0.9800 .
C23 H23c 0.9800 .
C12 H12a 0.9800 .
C12 H12b 0.9800 .
C12 H12c 0.9800 .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C19 C20 H20 119.5(2) . .
C21 C20 H20 119.5(2) . .
C21 C20 C19 120.9(3) . .
C4 N2 C1 125.2(2) . .
C3 N2 C1 110.8(3) . .
C3 N2 C4 123.9(2) . .
N2 C1 Te1 128.2(2) . .
N1 C1 Te1 126.7(2) . .
N1 C1 N2 105.0(2) . .
C5 C4 N2 118.7(3) . .
C9 C4 N2 118.1(3) . .
C9 C4 C5 123.0(3) . .
H3 C3 N2 126.57(17) . .
C2 C3 N2 106.9(3) . .
C2 C3 H3 126.57(19) . .
C16 N1 C1 126.0(2) . .
C2 N1 C1 110.2(2) . .
C2 N1 C16 123.2(2) . .
C25 C17 C16 121.9(3) . .
C18 C17 C16 116.9(3) . .
C18 C17 C25 121.2(3) . .
C17 C16 N1 119.5(3) . .
C21 C16 N1 117.4(3) . .
C21 C16 C17 123.1(3) . .
C8 C7 H7 120.3(2) . .
C6 C7 H7 120.3(2) . .
C6 C7 C8 119.4(3) . .
C9 C10 H10 107.8(2) . .
C11 C10 H10 107.8(3) . .
C11 C10 C9 112.3(4) . .
C12 C10 H10 107.8(3) . .
C12 C10 C9 110.4(3) . .
C12 C10 C11 110.5(4) . .
C13 C5 C4 123.5(3) . .
C6 C5 C4 116.7(3) . .
C6 C5 C13 119.8(3) . .
C10 C9 C4 123.0(3) . .
C8 C9 C4 117.2(3) . .
C8 C9 C10 119.8(3) . .
H19 C19 C20 119.7(2) . .
C18 C19 C20 120.5(3) . .
C18 C19 H19 119.7(2) . .
H25 C25 C17 107.99(19) . .
C26 C25 C17 110.2(3) . .
C26 C25 H25 108.0(2) . .
C27 C25 C17 111.8(3) . .
C27 C25 H25 108.0(2) . .
C27 C25 C26 110.7(4) . .
C16 C21 C20 117.2(3) . .
C22 C21 C20 120.5(3) . .
C22 C21 C16 122.3(3) . .
H22 C22 C21 107.54(19) . .
C24 C22 C21 111.9(3) . .
C24 C22 H22 107.5(2) . .
C23 C22 C21 111.3(3) . .
C23 C22 H22 107.5(2) . .
C23 C22 C24 110.7(3) . .
H11a C11 C10 109.5 . .
H11b C11 C10 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C10 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
N1 C2 C3 107.1(3) . .
H2 C2 C3 126.46(19) . .
H2 C2 N1 126.46(16) . .
H24a C24 C22 109.5 . .
H24b C24 C22 109.5 . .
H24b C24 H24a 109.5 . .
H24c C24 C22 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
C19 C18 C17 121.3(3) . .
H18 C18 C17 119.4(2) . .
H18 C18 C19 119.4(2) . .
H13 C13 C5 107.95(19) . .
C14 C13 C5 110.4(3) . .
C14 C13 H13 108.0(2) . .
C15 C13 C5 111.1(3) . .
C15 C13 H13 108.0(2) . .
C15 C13 C14 111.4(3) . .
H14a C14 C13 109.5 . .
H14b C14 C13 109.5 . .
H14b C14 H14a 109.5 . .
H14c C14 C13 109.5 . .
H14c C14 H14a 109.5 . .
H14c C14 H14b 109.5 . .
C9 C8 C7 121.7(4) . .
H8 C8 C7 119.2(2) . .
H8 C8 C9 119.2(2) . .
H26a C26 C25 109.5 . .
H26b C26 C25 109.5 . .
H26b C26 H26a 109.5 . .
H26c C26 C25 109.5 . .
H26c C26 H26a 109.5 . .
H26c C26 H26b 109.5 . .
H15a C15 C13 109.5 . .
H15b C15 C13 109.5 . .
H15b C15 H15a 109.5 . .
H15c C15 C13 109.5 . .
H15c C15 H15a 109.5 . .
H15c C15 H15b 109.5 . .
C5 C6 C7 122.0(3) . .
H6 C6 C7 119.0(2) . .
H6 C6 C5 119.0(2) . .
H27a C27 C25 109.5 . .
H27b C27 C25 109.5 . .
H27b C27 H27a 109.5 . .
H27c C27 C25 109.5 . .
H27c C27 H27a 109.5 . .
H27c C27 H27b 109.5 . .
H23a C23 C22 109.5 . .
H23b C23 C22 109.5 . .
H23b C23 H23a 109.5 . .
H23c C23 C22 109.5 . .
H23c C23 H23a 109.5 . .
H23c C23 H23b 109.5 . .
H12a C12 C10 109.5 . .
H12b C12 C10 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C10 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .

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

data_6
_database_code_depnum_ccdc_archive 'CCDC 1000481'
_audit_update_record             
;
2014-05-01 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2013-12-21
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C27 H36 Bi Cl3 N2 S, C H Cl3'
_chemical_formula_sum            'C28 H37 Bi Cl6 N2 S'
_chemical_formula_weight         855.38
_chemical_oxdiff_formula         'C27 H36 N2 S Bi Cl3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Bi -3.68252 9.31182 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.33537 0.55136 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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

_cell_length_a                   9.6999(3)
_cell_length_b                   14.6885(5)
_cell_length_c                   23.7580(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.507(3)
_cell_angle_gamma                90
_cell_volume                     3378.65(18)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7210
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      73.8670
_cell_measurement_theta_min      3.5359
_exptl_absorpt_coefficient_mu    15.342
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31991
_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            'light yellow'
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.6815
_exptl_crystal_description       needle
_exptl_crystal_F_000             1678.5403
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_unetI/netI     0.0631
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            13786
_diffrn_reflns_theta_full        74.052720
_diffrn_reflns_theta_max         74.05
_diffrn_reflns_theta_min         3.54
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.933207
_diffrn_measured_fraction_theta_max 0.933207
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -86.00  -53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000 -150.0000 33

#__ type_ start__ end____ width___ exp.time_
  2 omega  -91.00  -34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000    0.0000 57

#__ type_ start__ end____ width___ exp.time_
  3 omega  -51.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000  -90.0000 40

#__ type_ start__ end____ width___ exp.time_
  4 omega  -63.00  -35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
  5 omega   26.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -60.0000 92

#__ type_ start__ end____ width___ exp.time_
  7 omega   49.00   90.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  8 omega   21.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
  9 omega   19.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  120.0000 50

#__ type_ start__ end____ width___ exp.time_
 11 omega   72.00  137.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   30.0000 65

#__ type_ start__ end____ width___ exp.time_
 12 omega   57.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 47

#__ type_ start__ end____ width___ exp.time_
 13 omega   39.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 53

#__ type_ start__ end____ width___ exp.time_
 14 omega  129.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   38.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   89.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
 17 omega   45.00   89.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 44

#__ type_ start__ end____ width___ exp.time_
 18 omega   45.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  165.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000  -90.0000 86
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0245640000
_diffrn_orient_matrix_UB_12      -0.0157585000
_diffrn_orient_matrix_UB_13      -0.0627076000
_diffrn_orient_matrix_UB_21      -0.1372727000
_diffrn_orient_matrix_UB_22      -0.0527229000
_diffrn_orient_matrix_UB_23      -0.0072391000
_diffrn_orient_matrix_UB_31      -0.0765806000
_diffrn_orient_matrix_UB_32      0.0892420000
_diffrn_orient_matrix_UB_33      -0.0153522000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              28
_reflns_limit_l_min              0
_reflns_number_gt                5567
_reflns_number_total             6399
_reflns_odcompleteness_completeness 99.86
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         3.472201
_refine_diff_density_min         -6.806860
_refine_diff_density_rms         0.384947
_refine_ls_d_res_high            0.801776
_refine_ls_d_res_low             12.487082
_refine_ls_goodness_of_fit_ref   1.023013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6399
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.082781
_refine_ls_R_factor_gt           0.072701
_refine_ls_restrained_S_all      1.023013
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1708P)²+40.7035P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.242118
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 0.09591(4) 0.06347(3) 0.326974(15) 0.0235(2) Uani 1.000000 .
Cl1 Cl 0.2811(3) -0.05838(18) 0.31154(14) 0.0371(7) Uani 1.000000 .
S1 S -0.0808(2) 0.21465(17) 0.35836(10) 0.0246(5) Uani 1.000000 .
Cl2 Cl 0.2161(3) 0.17965(18) 0.27438(10) 0.0292(5) Uani 1.000000 .
Cl3 Cl 0.2128(3) 0.10318(18) 0.41943(10) 0.0312(6) Uani 1.000000 .
C25 C -0.2048(12) 0.1798(8) 0.2083(4) 0.029(2) Uani 1.000000 .
N2 N -0.3548(9) 0.2232(6) 0.3746(3) 0.0214(17) Uani 1.000000 .
N1 N -0.3072(9) 0.1178(6) 0.3140(3) 0.0219(17) Uani 1.000000 .
C1 C -0.2483(10) 0.1822(6) 0.3485(4) 0.0166(18) Uani 1.000000 .
C20 C -0.1340(11) -0.0946(8) 0.2720(4) 0.026(2) Uani 1.000000 .
C22 C -0.2701(14) -0.0669(7) 0.3572(5) 0.032(3) Uani 1.000000 .
C9 C -0.3294(12) 0.2522(8) 0.4747(4) 0.028(2) Uani 1.000000 .
C16 C -0.2284(10) 0.0539(7) 0.2820(4) 0.019(2) Uani 1.000000 .
C19 C -0.0748(13) -0.0665(7) 0.2233(5) 0.030(3) Uani 1.000000 .
C26 C -0.3529(13) 0.1836(8) 0.1812(5) 0.036(3) Uani 1.000000 .
C21 C -0.2135(9) -0.0359(7) 0.3028(4) 0.0205(19) Uani 1.000000 .
C4 C -0.3432(10) 0.2868(7) 0.4202(4) 0.0211(19) Uani 1.000000 .
C13 C -0.3634(14) 0.4149(9) 0.3484(5) 0.037(3) Uani 1.000000 .
C2 C -0.4476(10) 0.1164(7) 0.3186(4) 0.022(2) Uani 1.000000 .
C5 C -0.3510(11) 0.3784(7) 0.4078(4) 0.026(2) Uani 1.000000 .
C17 C -0.1755(11) 0.0850(7) 0.2314(4) 0.0221(19) Uani 1.000000 .
C10 C -0.3144(12) 0.1501(8) 0.4876(4) 0.029(2) Uani 1.000000 .
C11 C -0.4223(16) 0.1175(10) 0.5264(6) 0.050(3) Uani 1.000000 .
C12 C -0.1675(13) 0.1319(9) 0.5130(5) 0.039(3) Uani 1.000000 .
C15 C -0.2918(15) 0.5070(9) 0.3421(6) 0.043(3) Uani 1.000000 .
C18 C -0.0948(11) 0.0218(8) 0.2035(4) 0.029(2) Uani 1.000000 .
C8 C -0.3294(15) 0.3135(9) 0.5195(5) 0.042(3) Uani 1.000000 .
C23 C -0.1584(18) -0.0654(10) 0.4054(6) 0.049(4) Uani 1.000000 .
C14 C -0.5119(16) 0.4205(11) 0.3249(7) 0.053(4) Uani 1.000000 .
C24 C -0.3356(15) -0.1618(9) 0.3506(6) 0.042(3) Uani 1.000000 .
Cl6 Cl 0.0495(13) 0.4197(5) 0.4438(5) 0.176(5) Uani 1.000000 .
Cl5 Cl 0.1213(15) 0.3235(6) 0.5406(3) 0.201(6) Uani 1.000000 .
Cl4 Cl 0.3035(9) 0.3382(6) 0.4555(8) 0.295(10) Uani 1.000000 .
C28 C 0.1399(15) 0.3269(10) 0.4702(6) 0.045(3) Uani 1.000000 .
C3 C -0.4774(10) 0.1822(8) 0.3563(4) 0.025(2) Uani 1.000000 .
C6 C -0.3492(13) 0.4390(7) 0.4545(5) 0.031(3) Uani 1.000000 .
C7 C -0.3404(13) 0.4049(8) 0.5096(5) 0.036(3) Uani 1.000000 .
C27 C -0.1051(11) 0.2105(8) 0.1658(4) 0.030(2) Uani 1.000000 .
H6 H -0.3538(13) 0.5015(7) 0.4484(5) 0.037(3) Uiso 1.000000 R
H7 H -0.3422(13) 0.4449(8) 0.5398(5) 0.043(3) Uiso 1.000000 R
H8 H -0.3218(15) 0.2921(9) 0.5564(5) 0.050(4) Uiso 1.000000 R
H18 H -0.0538(11) 0.0396(8) 0.1709(4) 0.034(3) Uiso 1.000000 R
H19 H -0.0214(13) -0.1069(7) 0.2038(5) 0.037(3) Uiso 1.000000 R
H20 H -0.1203(11) -0.1541(8) 0.2844(4) 0.031(3) Uiso 1.000000 R
H25 H -0.1986(12) 0.2226(8) 0.2400(4) 0.035(3) Uiso 1.000000 R
H22 H -0.3427(14) -0.0241(7) 0.3666(5) 0.039(3) Uiso 1.000000 R
H26a H -0.364(3) 0.138(4) 0.152(3) 0.054(4) Uiso 1.000000 G
H26b H -0.4175(13) 0.173(6) 0.2095(9) 0.054(4) Uiso 1.000000 G
H26c H -0.370(3) 0.243(2) 0.165(3) 0.054(4) Uiso 1.000000 G
H13 H -0.3164(14) 0.3714(9) 0.3248(5) 0.044(3) Uiso 1.000000 R
H2 H -0.5104(10) 0.0778(7) 0.2996(4) 0.026(2) Uiso 1.000000 R
H10 H -0.3268(12) 0.1166(8) 0.4520(4) 0.035(3) Uiso 1.000000 R
H11a H -0.406(7) 0.145(6) 0.5628(16) 0.075(5) Uiso 1.000000 G
H11b H -0.5125(18) 0.134(7) 0.511(3) 0.075(5) Uiso 1.000000 G
H11c H -0.417(8) 0.0525(13) 0.530(4) 0.075(5) Uiso 1.000000 G
H12a H -0.1016(13) 0.155(6) 0.488(2) 0.058(4) Uiso 1.000000 G
H12b H -0.155(4) 0.162(6) 0.549(2) 0.058(4) Uiso 1.000000 G
H12c H -0.154(4) 0.0675(10) 0.518(4) 0.058(4) Uiso 1.000000 G
H15a H -0.339(6) 0.5526(16) 0.363(4) 0.064(5) Uiso 1.000000 G
H15b H -0.198(3) 0.503(2) 0.357(4) 0.064(5) Uiso 1.000000 G
H15c H -0.294(9) 0.523(3) 0.3030(7) 0.064(5) Uiso 1.000000 G
H23a H -0.082(6) -0.102(7) 0.396(2) 0.074(6) Uiso 1.000000 G
H23b H -0.128(9) -0.0040(14) 0.412(3) 0.074(6) Uiso 1.000000 G
H23c H -0.195(4) -0.089(8) 0.4390(14) 0.074(6) Uiso 1.000000 G
H14a H -0.555(4) 0.362(2) 0.327(5) 0.080(6) Uiso 1.000000 G
H14b H -0.561(3) 0.464(6) 0.346(3) 0.080(6) Uiso 1.000000 G
H14c H -0.5142(17) 0.439(8) 0.2861(16) 0.080(6) Uiso 1.000000 G
H24a H -0.408(7) -0.1604(19) 0.321(3) 0.064(4) Uiso 1.000000 G
H24b H -0.266(3) -0.2050(15) 0.341(4) 0.064(4) Uiso 1.000000 G
H24c H -0.374(9) -0.179(3) 0.3854(14) 0.064(4) Uiso 1.000000 G
H28 H 0.1018(15) 0.2712(10) 0.4526(6) 0.054(4) Uiso 1.000000 R
H3 H -0.5647(10) 0.1969(8) 0.3677(4) 0.030(3) Uiso 1.000000 R
H27a H -0.110(7) 0.170(4) 0.1341(18) 0.045(4) Uiso 1.000000 G
H27b H -0.129(6) 0.271(2) 0.153(3) 0.045(4) Uiso 1.000000 G
H27c H -0.0129(16) 0.210(6) 0.1830(12) 0.045(4) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Cl1 2.578(3) .
Bi1 S1 2.929(2) .
Bi1 Cl2 2.452(3) .
Bi1 Cl3 2.479(2) .
S1 C1 1.696(10) .
C25 C26 1.539(16) .
C25 C17 1.517(15) .
C25 C27 1.509(14) .
C25 H25 0.9800 .
N2 C1 1.375(12) .
N2 C4 1.430(12) .
N2 C3 1.379(13) .
N1 C1 1.355(12) .
N1 C16 1.455(12) .
N1 C2 1.372(13) .
C20 C19 1.384(16) .
C20 C21 1.394(14) .
C20 H20 0.9300 .
C22 C21 1.505(16) .
C22 C23 1.528(19) .
C22 C24 1.535(16) .
C22 H22 0.9800 .
C9 C4 1.389(14) .
C9 C10 1.535(15) .
C9 C8 1.394(15) .
C16 C21 1.413(15) .
C16 C17 1.411(15) .
C19 C18 1.390(16) .
C19 H19 0.9300 .
C26 H26a 0.9600 .
C26 H26b 0.9600 .
C26 H26c 0.9600 .
C4 C5 1.379(14) .
C13 C5 1.508(16) .
C13 C15 1.532(17) .
C13 C14 1.515(19) .
C13 H13 0.9800 .
C2 C3 1.361(14) .
C2 H2 0.9300 .
C5 C6 1.422(15) .
C17 C18 1.407(14) .
C10 C11 1.514(17) .
C10 C12 1.536(16) .
C10 H10 0.9800 .
C11 H11a 0.9600 .
C11 H11b 0.9600 .
C11 H11c 0.9600 .
C12 H12a 0.9600 .
C12 H12b 0.9600 .
C12 H12c 0.9600 .
C15 H15a 0.9600 .
C15 H15b 0.9600 .
C15 H15c 0.9600 .
C18 H18 0.9300 .
C8 C7 1.365(18) .
C8 H8 0.9300 .
C23 H23a 0.9600 .
C23 H23b 0.9600 .
C23 H23c 0.9600 .
C14 H14a 0.9600 .
C14 H14b 0.9600 .
C14 H14c 0.9600 .
C24 H24a 0.9600 .
C24 H24b 0.9600 .
C24 H24c 0.9600 .
Cl6 C28 1.718(17) .
Cl5 C28 1.694(15) .
Cl4 C28 1.654(15) .
C28 H28 0.9800 .
C3 H3 0.9300 .
C6 C7 1.399(18) .
C6 H6 0.9300 .
C7 H7 0.9300 .
C27 H27a 0.9600 .
C27 H27b 0.9600 .
C27 H27c 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
S1 Bi1 Cl1 170.47(9) . .
Cl2 Bi1 Cl1 93.08(9) . .
Cl2 Bi1 S1 84.60(8) . .
Cl3 Bi1 Cl1 90.27(10) . .
Cl3 Bi1 S1 80.73(8) . .
Cl3 Bi1 Cl2 94.70(9) . .
C1 S1 Bi1 108.8(3) . .
C17 C25 C26 109.5(9) . .
C27 C25 C26 109.2(9) . .
C27 C25 C17 113.8(10) . .
H25 C25 C26 108.0(6) . .
H25 C25 C17 108.0(5) . .
H25 C25 C27 108.0(6) . .
C4 N2 C1 126.9(8) . .
C3 N2 C1 108.9(8) . .
C3 N2 C4 123.3(9) . .
C16 N1 C1 123.4(8) . .
C2 N1 C1 110.2(8) . .
C2 N1 C16 126.0(8) . .
N2 C1 S1 123.7(7) . .
N1 C1 S1 130.1(7) . .
N1 C1 N2 106.1(8) . .
C21 C20 C19 121.7(10) . .
H20 C20 C19 119.2(6) . .
H20 C20 C21 119.2(7) . .
C23 C22 C21 111.1(11) . .
C24 C22 C21 111.0(10) . .
C24 C22 C23 111.1(10) . .
H22 C22 C21 107.8(6) . .
H22 C22 C23 107.8(8) . .
H22 C22 C24 107.8(7) . .
C10 C9 C4 123.1(9) . .
C8 C9 C4 118.0(10) . .
C8 C9 C10 118.9(10) . .
C21 C16 N1 117.7(9) . .
C17 C16 N1 117.8(9) . .
C17 C16 C21 124.5(9) . .
C18 C19 C20 120.3(10) . .
H19 C19 C20 119.8(6) . .
H19 C19 C18 119.8(6) . .
H26a C26 C25 109.5 . .
H26b C26 C25 109.5 . .
H26b C26 H26a 109.5 . .
H26c C26 C25 109.5 . .
H26c C26 H26a 109.5 . .
H26c C26 H26b 109.5 . .
C22 C21 C20 120.4(10) . .
C16 C21 C20 116.2(9) . .
C16 C21 C22 123.3(9) . .
C9 C4 N2 117.8(9) . .
C5 C4 N2 118.3(9) . .
C5 C4 C9 123.9(9) . .
C15 C13 C5 113.2(10) . .
C14 C13 C5 112.5(11) . .
C14 C13 C15 110.1(11) . .
H13 C13 C5 106.9(6) . .
H13 C13 C15 106.9(7) . .
H13 C13 C14 106.9(9) . .
C3 C2 N1 107.1(9) . .
H2 C2 N1 126.5(5) . .
H2 C2 C3 126.5(6) . .
C13 C5 C4 123.2(9) . .
C6 C5 C4 116.5(10) . .
C6 C5 C13 120.3(10) . .
C16 C17 C25 122.4(9) . .
C18 C17 C25 122.1(9) . .
C18 C17 C16 115.4(10) . .
C11 C10 C9 111.7(10) . .
C12 C10 C9 108.9(9) . .
C12 C10 C11 111.5(10) . .
H10 C10 C9 108.2(5) . .
H10 C10 C11 108.2(7) . .
H10 C10 C12 108.2(6) . .
H11a C11 C10 109.5 . .
H11b C11 C10 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C10 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
H12a C12 C10 109.5 . .
H12b C12 C10 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C10 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
H15a C15 C13 109.5 . .
H15b C15 C13 109.5 . .
H15b C15 H15a 109.5 . .
H15c C15 C13 109.5 . .
H15c C15 H15a 109.5 . .
H15c C15 H15b 109.5 . .
C17 C18 C19 121.8(10) . .
H18 C18 C19 119.1(6) . .
H18 C18 C17 119.1(6) . .
C7 C8 C9 120.5(11) . .
H8 C8 C9 119.8(7) . .
H8 C8 C7 119.8(7) . .
H23a C23 C22 109.5 . .
H23b C23 C22 109.5 . .
H23b C23 H23a 109.5 . .
H23c C23 C22 109.5 . .
H23c C23 H23a 109.5 . .
H23c C23 H23b 109.5 . .
H14a C14 C13 109.5 . .
H14b C14 C13 109.5 . .
H14b C14 H14a 109.5 . .
H14c C14 C13 109.5 . .
H14c C14 H14a 109.5 . .
H14c C14 H14b 109.5 . .
H24a C24 C22 109.5 . .
H24b C24 C22 109.5 . .
H24b C24 H24a 109.5 . .
H24c C24 C22 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
Cl5 C28 Cl6 107.5(10) . .
Cl4 C28 Cl6 108.5(11) . .
Cl4 C28 Cl5 111.9(12) . .
H28 C28 Cl6 109.6(5) . .
H28 C28 Cl5 109.6(5) . .
H28 C28 Cl4 109.6(5) . .
C2 C3 N2 107.6(9) . .
H3 C3 N2 126.2(6) . .
H3 C3 C2 126.2(6) . .
C7 C6 C5 120.2(10) . .
H6 C6 C5 119.9(7) . .
H6 C6 C7 119.9(6) . .
C6 C7 C8 120.9(10) . .
H7 C7 C8 119.6(7) . .
H7 C7 C6 119.6(6) . .
H27a C27 C25 109.5 . .
H27b C27 C25 109.5 . .
H27b C27 H27a 109.5 . .
H27c C27 C25 109.5 . .
H27c C27 H27a 109.5 . .
H27c C27 H27b 109.5 . .

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

data_7
_database_code_depnum_ccdc_archive 'CCDC 1000482'
_audit_update_record             
;
2014-05-01 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2013-12-21
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C27 H36 Bi Br3 N2 S, C H Cl3'
_chemical_formula_sum            'C28 H37 Bi Br3 Cl3 N2 S'
_chemical_formula_weight         988.73
_chemical_oxdiff_formula         'C27 H36 N2 S Bi Br3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Bi -3.68252 9.31182 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.33537 0.55136 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Br -0.67402 1.33011 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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

_cell_length_a                   10.0168(4)
_cell_length_b                   12.5839(6)
_cell_length_c                   15.6771(7)
_cell_angle_alpha                73.883(4)
_cell_angle_beta                 76.522(4)
_cell_angle_gamma                74.563(4)
_cell_volume                     1802.72(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9315
_cell_measurement_temperature    156(9)
_cell_measurement_theta_max      70.7684
_cell_measurement_theta_min      3.7413
_exptl_absorpt_coefficient_mu    16.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35919
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.8214
_exptl_crystal_description       needle
_exptl_crystal_F_000             941.0416
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0507
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12304
_diffrn_reflns_theta_full        70.905115
_diffrn_reflns_theta_max         70.91
_diffrn_reflns_theta_min         3.74
_diffrn_ambient_temperature      156(9)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.973408
_diffrn_measured_fraction_theta_max 0.973408
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -52.00   32.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   63.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  2 omega  -91.00  -56.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  3 omega -101.00  -26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  4 omega   23.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -120.0000 78

#__ type_ start__ end____ width___ exp.time_
  5 omega   53.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  6 omega   74.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000  -30.0000 51

#__ type_ start__ end____ width___ exp.time_
  7 omega   41.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega   48.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 63

#__ type_ start__ end____ width___ exp.time_
  9 omega   27.00   53.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega  -13.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   60.0000 83

#__ type_ start__ end____ width___ exp.time_
 11 omega   61.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000  -30.0000 31

#__ type_ start__ end____ width___ exp.time_
 12 omega   82.00  108.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   68.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega  104.00  173.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   60.0000 69

#__ type_ start__ end____ width___ exp.time_
 15 omega  105.00  155.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 16 omega   39.00  143.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000    0.0000 104

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   81.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 44

#__ type_ start__ end____ width___ exp.time_
 18 omega   37.00  114.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 77

#__ type_ start__ end____ width___ exp.time_
 19 omega   42.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000    0.0000 42

#__ type_ start__ end____ width___ exp.time_
 20 omega   43.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 52

#__ type_ start__ end____ width___ exp.time_
 21 omega   96.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega  139.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -30.0000 36

#__ type_ start__ end____ width___ exp.time_
 23 omega   41.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 33

#__ type_ start__ end____ width___ exp.time_
 24 omega   38.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  150.0000 54

#__ type_ start__ end____ width___ exp.time_
 25 omega   85.00  126.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 26 omega   36.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 27 omega   89.00  175.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  120.0000 86

#__ type_ start__ end____ width___ exp.time_
 28 omega   45.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  150.0000 62
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0903260000
_diffrn_orient_matrix_UB_12      0.1214574000
_diffrn_orient_matrix_UB_13      -0.0148669000
_diffrn_orient_matrix_UB_21      -0.1234360000
_diffrn_orient_matrix_UB_22      -0.0430173000
_diffrn_orient_matrix_UB_23      0.0676728000
_diffrn_orient_matrix_UB_31      0.0532662000
_diffrn_orient_matrix_UB_32      0.0206986000
_diffrn_orient_matrix_UB_33      0.0773363000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              15
_reflns_limit_k_min              -14
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                6526
_reflns_number_total             6772
_reflns_odcompleteness_completeness 99.91
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         3.481717
_refine_diff_density_min         -4.608478
_refine_diff_density_rms         0.325816
_refine_ls_d_res_high            0.815807
_refine_ls_d_res_low             11.804876
_refine_ls_goodness_of_fit_ref   1.029333
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    58
_refine_ls_number_parameters     350
_refine_ls_number_reflns         6772
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.060451
_refine_ls_R_factor_gt           0.059308
_refine_ls_restrained_S_all      1.029333
_refine_ls_shift/su_max          0.0175
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1229P)²+5.7125P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.163590
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 0.94518(2) 0.06391(2) 0.224196(15) 0.02296(13) Uani 1.000000 .
Br2 Br 0.76114(9) 0.12378(7) 0.36032(5) 0.0337(2) Uani 1.000000 .
Br3 Br 0.82470(11) -0.10777(8) 0.22607(6) 0.0396(2) Uani 1.000000 .
Br4 Br 0.80966(9) 0.20890(8) 0.10165(5) 0.0350(2) Uani 1.000000 .
S1 S 1.06460(19) 0.24166(16) 0.24729(16) 0.0341(4) Uani 1.000000 .
N1 N 1.3211(6) 0.2690(5) 0.2533(4) 0.0200(11) Uani 1.000000 .
N2 N 1.3352(6) 0.1262(5) 0.1983(4) 0.0205(11) Uani 1.000000 .
C8 C 1.2093(8) 0.0142(7) 0.0434(5) 0.0271(15) Uani 1.000000 .
C3 C 1.4722(7) 0.1333(6) 0.1978(5) 0.0225(13) Uani 1.000000 .
C5 C 1.2875(7) -0.0595(6) 0.2172(5) 0.0221(13) Uani 1.000000 .
C2 C 1.4630(8) 0.2217(6) 0.2322(5) 0.0237(14) Uani 1.000000 .
C6 C 1.2373(8) -0.1301(6) 0.1824(5) 0.0271(15) Uani 1.000000 .
C4 C 1.2962(7) 0.0480(6) 0.1626(5) 0.0212(13) Uani 1.000000 .
C9 C 1.2624(7) 0.0863(6) 0.0749(4) 0.0212(13) Uani 1.000000 .
C1 C 1.2425(7) 0.2111(5) 0.2326(4) 0.0206(13) Uani 1.000000 .
C7 C 1.1980(8) -0.0927(6) 0.0975(5) 0.0263(15) Uani 1.000000 .
C16 C 1.2633(8) 0.3661(6) 0.2933(5) 0.0270(15) Uani 1.000000 .
C10 C 1.2895(8) 0.1981(6) 0.0140(5) 0.0259(15) Uani 1.000000 .
C13 C 1.3266(9) -0.0998(6) 0.3108(5) 0.0316(17) Uani 1.000000 .
C21 C 1.2345(9) 0.3469(7) 0.3867(6) 0.0331(17) Uani 1.000000 .
C14 C 1.1926(13) -0.0896(11) 0.3815(6) 0.061(3) Uani 1.000000 .
C17 C 1.2379(9) 0.4733(6) 0.2362(6) 0.0348(18) Uani 1.000000 .
C22 C 1.2614(10) 0.2271(8) 0.4479(6) 0.041(2) Uani 1.000000 .
C25 C 1.2725(11) 0.4900(7) 0.1332(7) 0.045(2) Uani 1.000000 .
C20 C 1.1786(12) 0.4415(10) 0.4236(8) 0.054(3) Uani 1.000000 .
C15 C 1.4152(12) -0.2193(8) 0.3263(7) 0.050(2) Uani 1.000000 .
C26 C 1.3727(11) 0.5720(9) 0.0912(8) 0.055(3) Uani 1.000000 .
C19 C 1.1499(13) 0.5479(9) 0.3679(9) 0.064(4) Uani 1.000000 .
C24 C 1.3694(12) 0.2147(13) 0.5075(8) 0.064(3) Uani 1.000000 .
C12 C 1.4120(11) 0.1754(9) -0.0623(7) 0.053(3) Uani 1.000000 .
C18 C 1.1780(11) 0.5640(8) 0.2764(9) 0.053(3) Uani 1.000000 .
C11 C 1.1610(9) 0.2730(7) -0.0266(6) 0.042(2) Uani 1.000000 .
Cl1 Cl 0.6942(10) 0.4168(5) 0.4381(3) 0.153(3) Uani 1.000000 .
Cl3 Cl 0.6279(15) 0.4597(5) 0.2631(8) 0.310(9) Uani 1.000000 .
Cl2 Cl 0.7928(4) 0.5880(4) 0.2951(3) 0.0839(10) Uani 1.000000 .
C28 C 0.7464(18) 0.4542(10) 0.3247(9) 0.078(4) Uani 1.000000 .
C23 C 1.1235(13) 0.2005(10) 0.5043(9) 0.061(3) Uani 1.000000 .
C27 C 1.1333(15) 0.5347(12) 0.0936(9) 0.074(4) Uani 1.000000 .
H18 H 1.1568(11) 0.6368(8) 0.2406(9) 0.064(3) Uiso 1.000000 R
H19 H 1.1104(13) 0.6101(9) 0.3934(9) 0.077(4) Uiso 1.000000 R
H20 H 1.1607(12) 0.4328(10) 0.4858(8) 0.065(3) Uiso 1.000000 R
H8 H 1.1821(8) 0.0375(7) -0.0128(5) 0.0326(18) Uiso 1.000000 R
H7 H 1.1634(8) -0.1403(6) 0.0763(5) 0.0315(17) Uiso 1.000000 R
H6 H 1.2301(8) -0.2025(6) 0.2163(5) 0.0325(18) Uiso 1.000000 R
H3 H 1.5545(7) 0.0855(6) 0.1774(5) 0.0269(16) Uiso 1.000000 R
H2 H 1.5375(8) 0.2466(6) 0.2404(5) 0.0285(17) Uiso 1.000000 R
H10 H 1.3161(8) 0.2396(6) 0.0496(5) 0.0311(17) Uiso 1.000000 R
H13 H 1.3821(9) -0.0494(6) 0.3163(5) 0.038(2) Uiso 1.000000 R
H14a H 1.139(5) -0.013(2) 0.370(4) 0.091(5) Uiso 1.000000 G
H14b H 1.138(5) -0.140(6) 0.379(4) 0.091(5) Uiso 1.000000 G
H14c H 1.2172(13) -0.109(8) 0.4404(8) 0.091(5) Uiso 1.000000 G
H22 H 1.3002(10) 0.1730(8) 0.4093(6) 0.049(2) Uiso 1.000000 R
H25 H 1.3190(11) 0.4165(7) 0.1189(7) 0.054(3) Uiso 1.000000 R
H15a H 1.375(5) -0.2667(18) 0.306(5) 0.076(4) Uiso 1.000000 G
H15b H 1.509(3) -0.2187(13) 0.294(5) 0.076(4) Uiso 1.000000 G
H15c H 1.418(8) -0.248(3) 0.3895(10) 0.076(4) Uiso 1.000000 G
H26a H 1.327(4) 0.646(2) 0.102(5) 0.083(4) Uiso 1.000000 G
H26b H 1.456(4) 0.545(4) 0.118(5) 0.083(4) Uiso 1.000000 G
H26c H 1.398(8) 0.577(6) 0.0274(13) 0.083(4) Uiso 1.000000 G
H24a H 1.454(4) 0.235(8) 0.4702(9) 0.095(5) Uiso 1.000000 G
H24b H 1.331(4) 0.264(6) 0.548(5) 0.095(5) Uiso 1.000000 G
H24c H 1.391(8) 0.138(2) 0.541(5) 0.095(5) Uiso 1.000000 G
H12a H 1.496(2) 0.136(7) -0.0374(8) 0.079(4) Uiso 1.000000 G
H12b H 1.391(4) 0.130(6) -0.095(4) 0.079(4) Uiso 1.000000 G
H12c H 1.427(6) 0.2461(9) -0.102(3) 0.079(4) Uiso 1.000000 G
H11a H 1.130(5) 0.232(2) -0.059(4) 0.063(3) Uiso 1.000000 G
H11b H 1.087(3) 0.294(5) 0.0208(8) 0.063(3) Uiso 1.000000 G
H11c H 1.186(2) 0.340(3) -0.067(4) 0.063(3) Uiso 1.000000 G
H28 H 0.8308(18) 0.3982(10) 0.3082(9) 0.094(5) Uiso 1.000000 R
H23a H 1.079(5) 0.257(5) 0.538(5) 0.092(5) Uiso 1.000000 G
H23b H 1.063(4) 0.200(8) 0.4654(10) 0.092(5) Uiso 1.000000 G
H23c H 1.1418(16) 0.127(4) 0.545(5) 0.092(5) Uiso 1.000000 G
H27a H 1.070(5) 0.485(5) 0.123(5) 0.110(6) Uiso 1.000000 G
H27b H 1.090(6) 0.609(4) 0.103(7) 0.110(6) Uiso 1.000000 G
H27c H 1.154(2) 0.538(9) 0.0301(18) 0.110(6) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Br2 2.6152(8) .
Bi1 Br3 2.7314(9) .
Bi1 Br4 2.6103(8) .
Bi1 S1 2.9396(18) .
S1 C1 1.694(7) .
N1 C2 1.387(9) .
N1 C1 1.346(9) .
N1 C16 1.449(9) .
N2 C3 1.397(9) .
N2 C4 1.431(9) .
N2 C1 1.360(9) .
C8 C9 1.407(10) .
C8 C7 1.393(10) .
C8 H8 0.9300 .
C3 C2 1.338(10) .
C3 H3 0.9300 .
C5 C6 1.406(10) .
C5 C4 1.398(9) .
C5 C13 1.520(10) .
C2 H2 0.9300 .
C6 C7 1.395(11) .
C6 H6 0.9300 .
C4 C9 1.414(10) .
C9 C10 1.517(9) .
C7 H7 0.9300 .
C16 C21 1.390(12) .
C16 C17 1.393(11) .
C10 C12 1.528(11) .
C10 C11 1.534(11) .
C10 H10 0.9800 .
C13 C14 1.531(13) .
C13 C15 1.514(11) .
C13 H13 0.9800 .
C21 C22 1.538(12) .
C21 C20 1.392(12) .
C14 H14a 0.9600 .
C14 H14b 0.9600 .
C14 H14c 0.9600 .
C17 C25 1.535(14) .
C17 C18 1.386(13) .
C22 C24 1.539(15) .
C22 C23 1.522(14) .
C22 H22 0.9800 .
C25 C26 1.540(14) .
C25 C27 1.562(15) .
C25 H25 0.9800 .
C20 C19 1.379(18) .
C20 H20 0.9300 .
C15 H15a 0.9600 .
C15 H15b 0.9600 .
C15 H15c 0.9600 .
C26 H26a 0.9600 .
C26 H26b 0.9600 .
C26 H26c 0.9600 .
C19 C18 1.364(18) .
C19 H19 0.9300 .
C24 H24a 0.9600 .
C24 H24b 0.9600 .
C24 H24c 0.9600 .
C12 H12a 0.9600 .
C12 H12b 0.9600 .
C12 H12c 0.9600 .
C18 H18 0.9300 .
C11 H11a 0.9600 .
C11 H11b 0.9600 .
C11 H11c 0.9600 .
Cl1 C28 1.700(14) .
Cl3 C28 1.673(17) .
Cl2 C28 1.775(16) .
C28 H28 0.9800 .
C23 H23a 0.9600 .
C23 H23b 0.9600 .
C23 H23c 0.9600 .
C27 H27a 0.9600 .
C27 H27b 0.9600 .
C27 H27c 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
Br3 Bi1 Br2 93.28(3) . .
Br4 Bi1 Br2 94.71(3) . .
Br4 Bi1 Br3 93.76(3) . .
S1 Bi1 Br2 80.75(4) . .
S1 Bi1 Br3 172.70(5) . .
S1 Bi1 Br4 90.94(5) . .
C1 S1 Bi1 114.1(2) . .
C1 N1 C2 110.5(6) . .
C16 N1 C2 125.5(6) . .
C16 N1 C1 124.0(6) . .
C4 N2 C3 126.2(6) . .
C1 N2 C3 109.3(6) . .
C1 N2 C4 124.3(6) . .
C7 C8 C9 119.3(7) . .
H8 C8 C9 120.3(4) . .
H8 C8 C7 120.3(4) . .
C2 C3 N2 107.3(6) . .
H3 C3 N2 126.3(4) . .
H3 C3 C2 126.3(4) . .
C4 C5 C6 116.7(6) . .
C13 C5 C6 120.3(6) . .
C13 C5 C4 123.0(6) . .
C3 C2 N1 107.0(6) . .
H2 C2 N1 126.5(4) . .
H2 C2 C3 126.5(4) . .
C7 C6 C5 120.6(6) . .
H6 C6 C5 119.7(4) . .
H6 C6 C7 119.7(4) . .
C5 C4 N2 118.6(6) . .
C9 C4 N2 117.5(6) . .
C9 C4 C5 123.8(6) . .
C4 C9 C8 117.6(6) . .
C10 C9 C8 120.4(6) . .
C10 C9 C4 121.9(6) . .
N1 C1 S1 125.5(5) . .
N2 C1 S1 128.7(5) . .
N2 C1 N1 105.9(6) . .
C6 C7 C8 121.9(7) . .
H7 C7 C8 119.1(4) . .
H7 C7 C6 119.1(4) . .
C21 C16 N1 118.1(7) . .
C17 C16 N1 118.3(7) . .
C17 C16 C21 123.5(7) . .
C12 C10 C9 109.4(6) . .
C11 C10 C9 113.2(6) . .
C11 C10 C12 109.1(7) . .
H10 C10 C9 108.3(4) . .
H10 C10 C12 108.3(6) . .
H10 C10 C11 108.3(5) . .
C14 C13 C5 109.3(7) . .
C15 C13 C5 112.2(7) . .
C15 C13 C14 111.4(8) . .
H13 C13 C5 107.9(4) . .
H13 C13 C14 107.9(6) . .
H13 C13 C15 107.9(6) . .
C22 C21 C16 122.2(7) . .
C20 C21 C16 117.1(8) . .
C20 C21 C22 120.7(8) . .
H14a C14 C13 109.5 . .
H14b C14 C13 109.5 . .
H14b C14 H14a 109.5 . .
H14c C14 C13 109.5 . .
H14c C14 H14a 109.5 . .
H14c C14 H14b 109.5 . .
C25 C17 C16 121.5(7) . .
C18 C17 C16 117.0(9) . .
C18 C17 C25 121.5(8) . .
C24 C22 C21 110.9(9) . .
C23 C22 C21 110.0(8) . .
C23 C22 C24 111.5(9) . .
H22 C22 C21 108.1(4) . .
H22 C22 C24 108.1(6) . .
H22 C22 C23 108.1(6) . .
C26 C25 C17 111.0(8) . .
C27 C25 C17 109.4(9) . .
C27 C25 C26 110.8(8) . .
H25 C25 C17 108.5(4) . .
H25 C25 C26 108.5(6) . .
H25 C25 C27 108.5(7) . .
C19 C20 C21 120.1(10) . .
H20 C20 C21 120.0(6) . .
H20 C20 C19 120.0(6) . .
H15a C15 C13 109.5 . .
H15b C15 C13 109.5 . .
H15b C15 H15a 109.5 . .
H15c C15 C13 109.5 . .
H15c C15 H15a 109.5 . .
H15c C15 H15b 109.5 . .
H26a C26 C25 109.5 . .
H26b C26 C25 109.5 . .
H26b C26 H26a 109.5 . .
H26c C26 C25 109.5 . .
H26c C26 H26a 109.5 . .
H26c C26 H26b 109.5 . .
C18 C19 C20 121.6(9) . .
H19 C19 C20 119.2(6) . .
H19 C19 C18 119.2(6) . .
H24a C24 C22 109.5 . .
H24b C24 C22 109.5 . .
H24b C24 H24a 109.5 . .
H24c C24 C22 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
H12a C12 C10 109.5 . .
H12b C12 C10 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C10 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
C19 C18 C17 120.8(9) . .
H18 C18 C17 119.6(6) . .
H18 C18 C19 119.6(6) . .
H11a C11 C10 109.5 . .
H11b C11 C10 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C10 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
Cl3 C28 Cl1 115.1(12) . .
Cl2 C28 Cl1 109.6(7) . .
Cl2 C28 Cl3 108.6(7) . .
H28 C28 Cl1 107.8(5) . .
H28 C28 Cl3 107.8(6) . .
H28 C28 Cl2 107.8(5) . .
H23a C23 C22 109.5 . .
H23b C23 C22 109.5 . .
H23b C23 H23a 109.5 . .
H23c C23 C22 109.5 . .
H23c C23 H23a 109.5 . .
H23c C23 H23b 109.5 . .
H27a C27 C25 109.5 . .
H27b C27 C25 109.5 . .
H27b C27 H27a 109.5 . .
H27c C27 C25 109.5 . .
H27c C27 H27a 109.5 . .
H27c C27 H27b 109.5 . .

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

data_8
_database_code_depnum_ccdc_archive 'CCDC 1000483'
_audit_update_record             
;
2014-05-01 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2013-11-23
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C27 H36 Bi Cl3 N2 Se, C H2 Cl2'
_chemical_formula_sum            'C28 H38 Bi Cl5 N2 Se'
_chemical_formula_weight         867.83
_chemical_oxdiff_formula         'C10 H20 N2 Bi Cl'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Bi -3.68252 9.31182 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Se -0.79210 1.18296 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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

_cell_length_a                   10.75451(16)
_cell_length_b                   16.0772(2)
_cell_length_c                   19.7995(4)
_cell_angle_alpha                90
_cell_angle_beta                 104.6833(16)
_cell_angle_gamma                90
_cell_volume                     3311.58(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7933
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.6937
_cell_measurement_theta_min      3.5864
_exptl_absorpt_coefficient_mu    15.567
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29252
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.7405
_exptl_crystal_description       needle
_exptl_crystal_F_000             1680.4989
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15584
_diffrn_reflns_theta_full        70.832176
_diffrn_reflns_theta_max         70.83
_diffrn_reflns_theta_min         3.59
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.981975
_diffrn_measured_fraction_theta_max 0.981209
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   35.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000 -180.0000 77

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   16.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   37.0000   72.0000 64

#__ type_ start__ end____ width___ exp.time_
  3 omega   32.00  124.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
  4 omega  -13.00   23.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000   90.0000 36

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   30.0000 60

#__ type_ start__ end____ width___ exp.time_
  6 omega   27.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -99.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
  7 omega   42.00   94.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   67.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   38.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000 -150.0000 104

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -127.0000   51.0000 80

#__ type_ start__ end____ width___ exp.time_
 11 omega  101.00  145.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -150.0000 61

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 48

#__ type_ start__ end____ width___ exp.time_
 14 omega   86.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
 15 omega   84.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   43.00   91.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 48

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 27

#__ type_ start__ end____ width___ exp.time_
 18 omega  142.00  168.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  151.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 72
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1438755000
_diffrn_orient_matrix_UB_12      -0.0016472000
_diffrn_orient_matrix_UB_13      0.0379958000
_diffrn_orient_matrix_UB_21      -0.0046514000
_diffrn_orient_matrix_UB_22      -0.0957294000
_diffrn_orient_matrix_UB_23      0.0036468000
_diffrn_orient_matrix_UB_31      0.0343716000
_diffrn_orient_matrix_UB_32      -0.0057529000
_diffrn_orient_matrix_UB_33      -0.0707711000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              19
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                5722
_reflns_number_total             6266
_reflns_odcompleteness_completeness 99.93
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         3.151804
_refine_diff_density_min         -1.794651
_refine_diff_density_rms         0.165710
_refine_ls_d_res_high            0.816168
_refine_ls_d_res_low             12.313944
_refine_ls_goodness_of_fit_ref   1.040928
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    59
_refine_ls_number_parameters     342
_refine_ls_number_reflns         6266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.041741
_refine_ls_R_factor_gt           0.038398
_refine_ls_restrained_S_all      1.040928
_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)+(0.0684P)²+1.7822P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.106819
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 0.711177(17) 0.172721(10) 0.043670(9) 0.02860(9) Uani 1.000000 .
Se1 Se 0.71364(5) 0.33929(3) -0.02097(3) 0.03044(13) Uani 1.000000 .
Cl2 Cl 0.51401(13) 0.17701(8) 0.08737(8) 0.0406(3) Uani 1.000000 .
Cl1 Cl 0.82600(14) 0.26315(8) 0.14050(7) 0.0444(3) Uani 1.000000 .
Cl3 Cl 0.80631(15) 0.04326(9) 0.11692(8) 0.0539(4) Uani 1.000000 .
N2 N 0.6637(3) 0.2613(2) -0.15768(19) 0.0234(7) Uani 1.000000 .
N1 N 0.6718(3) 0.3958(2) -0.1622(2) 0.0239(8) Uani 1.000000 .
C4 C 0.6660(5) 0.1782(3) -0.1305(3) 0.0242(9) Uani 1.000000 .
C1 C 0.6794(4) 0.3310(3) -0.1177(3) 0.0237(9) Uani 1.000000 .
C16 C 0.6839(4) 0.4816(3) -0.1393(2) 0.0238(9) Uani 1.000000 .
C13 C 0.4198(5) 0.1848(3) -0.1547(3) 0.0305(10) Uani 1.000000 .
H13 H 0.4361(5) 0.2395(3) -0.1725(3) 0.0366(12) Uiso 1.000000 R
C21 C 0.8044(4) 0.5186(3) -0.1261(3) 0.0285(10) Uani 1.000000 .
C2 C 0.6499(4) 0.3668(3) -0.2302(2) 0.0285(9) Uani 1.000000 .
H2 H 0.6407(4) 0.3991(3) -0.2702(2) 0.0342(11) Uiso 1.000000 R
C17 C 0.5737(4) 0.5212(3) -0.1288(2) 0.0267(9) Uani 1.000000 .
C7 C 0.6714(5) 0.0192(3) -0.0777(3) 0.0359(11) Uani 1.000000 .
H7 H 0.6732(5) -0.0346(3) -0.0601(3) 0.0430(13) Uiso 1.000000 R
C18 C 0.5904(5) 0.6005(3) -0.1005(3) 0.0355(11) Uani 1.000000 .
H18 H 0.5202(5) 0.6287(3) -0.0922(3) 0.0426(13) Uiso 1.000000 R
C25 C 0.4407(4) 0.4817(3) -0.1508(3) 0.0305(10) Uani 1.000000 .
H25 H 0.4499(4) 0.4269(3) -0.1707(3) 0.0366(12) Uiso 1.000000 R
C19 C 0.7096(5) 0.6384(3) -0.0843(3) 0.0334(11) Uani 1.000000 .
H19 H 0.7191(5) 0.6911(3) -0.0643(3) 0.0401(13) Uiso 1.000000 R
C3 C 0.6446(5) 0.2827(3) -0.2276(3) 0.0297(10) Uani 1.000000 .
H3 H 0.6308(5) 0.2463(3) -0.2653(3) 0.0357(12) Uiso 1.000000 R
C20 C 0.8158(5) 0.5985(3) -0.0978(3) 0.0321(10) Uani 1.000000 .
H20 H 0.8950(5) 0.6253(3) -0.0877(3) 0.0385(13) Uiso 1.000000 R
C23 C 0.9878(6) 0.5330(4) -0.1822(4) 0.0557(17) Uani 1.000000 .
H23a H 0.9285(15) 0.551(3) -0.2244(14) 0.084(3) Uiso 1.000000 G
H23b H 1.020(4) 0.5803(17) -0.1535(11) 0.084(3) Uiso 1.000000 G
H23c H 1.058(3) 0.5041(11) -0.194(2) 0.084(3) Uiso 1.000000 G
C22 C 0.9196(4) 0.4752(3) -0.1430(3) 0.0324(10) Uani 1.000000 .
H22 H 0.8859(4) 0.4286(3) -0.1742(3) 0.0389(12) Uiso 1.000000 R
C5 C 0.5493(5) 0.1415(3) -0.1274(3) 0.0292(10) Uani 1.000000 .
C8 C 0.7855(5) 0.0580(3) -0.0820(3) 0.0355(11) Uani 1.000000 .
H8 H 0.8629(5) 0.0294(3) -0.0677(3) 0.0426(13) Uiso 1.000000 R
C6 C 0.5550(5) 0.0614(3) -0.0998(3) 0.0334(11) Uani 1.000000 .
H6 H 0.4797(5) 0.0357(3) -0.0960(3) 0.0401(13) Uiso 1.000000 R
C15 C 0.3521(6) 0.1985(5) -0.0969(3) 0.0509(16) Uani 1.000000 .
H15a H 0.336(4) 0.1457(5) -0.0780(17) 0.076(2) Uiso 1.000000 G
H15b H 0.405(2) 0.232(3) -0.0607(12) 0.076(2) Uiso 1.000000 G
H15c H 0.272(2) 0.227(3) -0.1155(6) 0.076(2) Uiso 1.000000 G
C14 C 0.3351(5) 0.1357(4) -0.2153(3) 0.0438(13) Uani 1.000000 .
H14a H 0.3813(17) 0.126(3) -0.2502(11) 0.066(2) Uiso 1.000000 G
H14b H 0.313(4) 0.0833(13) -0.1985(5) 0.066(2) Uiso 1.000000 G
H14c H 0.258(2) 0.1668(13) -0.2353(16) 0.066(2) Uiso 1.000000 G
C9 C 0.7852(5) 0.1382(3) -0.1074(3) 0.0303(10) Uani 1.000000 .
C24 C 1.0122(6) 0.4394(4) -0.0789(3) 0.0519(16) Uani 1.000000 .
H24a H 1.053(4) 0.4838(5) -0.0491(13) 0.078(2) Uiso 1.000000 G
H24b H 0.9660(10) 0.405(3) -0.0542(15) 0.078(2) Uiso 1.000000 G
H24c H 1.076(3) 0.407(3) -0.0929(4) 0.078(2) Uiso 1.000000 G
C11 C 0.9597(5) 0.1392(4) -0.1707(3) 0.0450(13) Uani 1.000000 .
H11a H 0.977(4) 0.0814(8) -0.1604(12) 0.068(2) Uiso 1.000000 G
H11b H 0.8962(19) 0.145(3) -0.2144(5) 0.068(2) Uiso 1.000000 G
H11c H 1.037(2) 0.1665(19) -0.1737(16) 0.068(2) Uiso 1.000000 G
C26 C 0.3521(5) 0.5340(4) -0.2075(3) 0.0458(14) Uani 1.000000 .
H26a H 0.337(4) 0.5868(12) -0.1884(7) 0.069(2) Uiso 1.000000 G
H26b H 0.392(2) 0.543(2) -0.2452(11) 0.069(2) Uiso 1.000000 G
H26c H 0.2719(17) 0.5055(14) -0.2246(17) 0.069(2) Uiso 1.000000 G
C12 C 1.0132(6) 0.1746(4) -0.0431(4) 0.0572(19) Uani 1.000000 .
H12a H 0.981(2) 0.199(3) -0.0065(7) 0.086(3) Uiso 1.000000 G
H12b H 1.035(4) 0.1175(5) -0.0321(16) 0.086(3) Uiso 1.000000 G
H12c H 1.088(2) 0.205(3) -0.0473(11) 0.086(3) Uiso 1.000000 G
C10 C 0.9093(5) 0.1795(3) -0.1123(3) 0.0359(12) Uani 1.000000 .
H10 H 0.8914(5) 0.2383(3) -0.1239(3) 0.0431(15) Uiso 1.000000 R
C27 C 0.3825(6) 0.4688(4) -0.0884(3) 0.0472(14) Uani 1.000000 .
H27a H 0.436(2) 0.432(2) -0.0556(12) 0.071(2) Uiso 1.000000 G
H27b H 0.377(4) 0.5214(6) -0.0663(15) 0.071(2) Uiso 1.000000 G
H27c H 0.2980(19) 0.445(3) -0.1044(5) 0.071(2) Uiso 1.000000 G
Cl4 Cl 1.1176(2) 0.33315(11) -0.22821(11) 0.0695(5) Uani 1.000000 .
C28 C 0.8815(9) -0.1564(9) -0.1854(5) 0.128(6) Uani 1.000000 .
H28a H 0.946(3) -0.189(4) -0.1528(16) 0.153(7) Uiso 1.000000 R
H28b H 0.937(4) -0.113(3) -0.160(2) 0.153(7) Uiso 1.000000 R
Cl5 Cl 0.7282(3) -0.15984(13) -0.17248(17) 0.0895(7) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Se1 2.9711(5) .
Bi1 Cl2 2.4859(13) .
Bi1 Cl1 2.4727(12) .
Bi1 Cl3 2.5942(13) .
Se1 C1 1.861(5) .
N2 C4 1.437(6) .
N2 C1 1.358(6) .
N2 C3 1.390(6) .
N1 C1 1.354(6) .
N1 C16 1.447(5) .
N1 C2 1.387(6) .
C4 C5 1.403(6) .
C4 C9 1.404(7) .
C16 C21 1.389(6) .
C16 C17 1.406(6) .
C13 H13 0.9800 .
C13 C5 1.528(7) .
C13 C15 1.519(8) .
C13 C14 1.529(7) .
C21 C20 1.394(7) .
C21 C22 1.531(6) .
C2 H2 0.9300 .
C2 C3 1.356(7) .
C17 C18 1.387(7) .
C17 C25 1.524(6) .
C7 H7 0.9300 .
C7 C8 1.399(7) .
C7 C6 1.393(7) .
C18 H18 0.9300 .
C18 C19 1.382(7) .
C25 H25 0.9800 .
C25 C26 1.528(7) .
C25 C27 1.533(7) .
C19 H19 0.9300 .
C19 C20 1.393(7) .
C3 H3 0.9300 .
C20 H20 0.9300 .
C23 H23a 0.9600 .
C23 H23b 0.9600 .
C23 H23c 0.9600 .
C23 C22 1.514(7) .
C22 H22 0.9800 .
C22 C24 1.514(7) .
C5 C6 1.394(7) .
C8 H8 0.9300 .
C8 C9 1.384(7) .
C6 H6 0.9300 .
C15 H15a 0.9600 .
C15 H15b 0.9600 .
C15 H15c 0.9600 .
C14 H14a 0.9600 .
C14 H14b 0.9600 .
C14 H14c 0.9600 .
C9 C10 1.515(7) .
C24 H24a 0.9600 .
C24 H24b 0.9600 .
C24 H24c 0.9600 .
C11 H11a 0.9600 .
C11 H11b 0.9600 .
C11 H11c 0.9600 .
C11 C10 1.539(8) .
C26 H26a 0.9600 .
C26 H26b 0.9600 .
C26 H26c 0.9600 .
C12 H12a 0.9600 .
C12 H12b 0.9600 .
C12 H12c 0.9600 .
C12 C10 1.535(9) .
C10 H10 0.9800 .
C27 H27a 0.9600 .
C27 H27b 0.9600 .
C27 H27c 0.9600 .
Cl4 C28 1.721(10) 2_754
C28 H28a 0.9700 .
C28 H28b 0.9700 .
C28 Cl5 1.732(9) .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl2 Bi1 Se1 103.09(3) . .
Cl1 Bi1 Se1 75.33(3) . .
Cl1 Bi1 Cl2 90.93(5) . .
Cl3 Bi1 Se1 156.73(4) . .
Cl3 Bi1 Cl2 94.48(5) . .
Cl3 Bi1 Cl1 89.40(5) . .
C1 Se1 Bi1 110.94(13) . .
C1 N2 C4 124.1(4) . .
C3 N2 C4 125.9(4) . .
C3 N2 C1 110.0(4) . .
C16 N1 C1 122.9(4) . .
C2 N1 C1 109.9(4) . .
C2 N1 C16 127.2(4) . .
C5 C4 N2 118.5(4) . .
C9 C4 N2 118.4(4) . .
C9 C4 C5 123.1(4) . .
N2 C1 Se1 128.5(3) . .
N1 C1 Se1 125.3(3) . .
N1 C1 N2 106.1(4) . .
C21 C16 N1 118.3(4) . .
C17 C16 N1 117.7(4) . .
C17 C16 C21 123.9(4) . .
C5 C13 H13 107.8(3) . .
C15 C13 H13 107.8(3) . .
C15 C13 C5 111.6(4) . .
C14 C13 H13 107.8(3) . .
C14 C13 C5 110.5(4) . .
C14 C13 C15 111.2(5) . .
C20 C21 C16 117.0(4) . .
C22 C21 C16 122.1(4) . .
C22 C21 C20 120.9(4) . .
H2 C2 N1 126.4(3) . .
C3 C2 N1 107.2(4) . .
C3 C2 H2 126.4(3) . .
C18 C17 C16 116.7(4) . .
C25 C17 C16 122.3(4) . .
C25 C17 C18 121.0(4) . .
C8 C7 H7 120.2(3) . .
C6 C7 H7 120.2(3) . .
C6 C7 C8 119.7(4) . .
H18 C18 C17 119.5(3) . .
C19 C18 C17 121.1(5) . .
C19 C18 H18 119.5(3) . .
H25 C25 C17 107.8(3) . .
C26 C25 C17 110.2(4) . .
C26 C25 H25 107.8(3) . .
C27 C25 C17 111.9(4) . .
C27 C25 H25 107.8(3) . .
C27 C25 C26 111.1(4) . .
H19 C19 C18 119.7(3) . .
C20 C19 C18 120.7(4) . .
C20 C19 H19 119.7(3) . .
C2 C3 N2 106.8(4) . .
H3 C3 N2 126.6(3) . .
H3 C3 C2 126.6(3) . .
C19 C20 C21 120.5(4) . .
H20 C20 C21 119.7(3) . .
H20 C20 C19 119.7(3) . .
H23b C23 H23a 109.5 . .
H23c C23 H23a 109.5 . .
H23c C23 H23b 109.5 . .
C22 C23 H23a 109.5 . .
C22 C23 H23b 109.5 . .
C22 C23 H23c 109.5 . .
C23 C22 C21 110.9(4) . .
H22 C22 C21 107.2(3) . .
H22 C22 C23 107.2(4) . .
C24 C22 C21 112.8(4) . .
C24 C22 C23 111.2(5) . .
C24 C22 H22 107.2(3) . .
C13 C5 C4 122.6(4) . .
C6 C5 C4 117.0(4) . .
C6 C5 C13 120.3(4) . .
H8 C8 C7 119.4(3) . .
C9 C8 C7 121.1(5) . .
C9 C8 H8 119.4(3) . .
C5 C6 C7 121.4(5) . .
H6 C6 C7 119.3(3) . .
H6 C6 C5 119.3(3) . .
H15a C15 C13 109.5 . .
H15b C15 C13 109.5 . .
H15b C15 H15a 109.5 . .
H15c C15 C13 109.5 . .
H15c C15 H15a 109.5 . .
H15c C15 H15b 109.5 . .
H14a C14 C13 109.5 . .
H14b C14 C13 109.5 . .
H14b C14 H14a 109.5 . .
H14c C14 C13 109.5 . .
H14c C14 H14a 109.5 . .
H14c C14 H14b 109.5 . .
C8 C9 C4 117.6(5) . .
C10 C9 C4 121.7(4) . .
C10 C9 C8 120.7(4) . .
H24a C24 C22 109.5 . .
H24b C24 C22 109.5 . .
H24b C24 H24a 109.5 . .
H24c C24 C22 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
C10 C11 H11a 109.5 . .
C10 C11 H11b 109.5 . .
C10 C11 H11c 109.5 . .
H26a C26 C25 109.5 . .
H26b C26 C25 109.5 . .
H26b C26 H26a 109.5 . .
H26c C26 C25 109.5 . .
H26c C26 H26a 109.5 . .
H26c C26 H26b 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
C10 C12 H12a 109.5 . .
C10 C12 H12b 109.5 . .
C10 C12 H12c 109.5 . .
C11 C10 C9 110.3(4) . .
C12 C10 C9 112.0(5) . .
C12 C10 C11 109.5(5) . .
H10 C10 C9 108.3(3) . .
H10 C10 C11 108.3(3) . .
H10 C10 C12 108.3(3) . .
H27a C27 C25 109.5 . .
H27b C27 C25 109.5 . .
H27b C27 H27a 109.5 . .
H27c C27 C25 109.5 . .
H27c C27 H27a 109.5 . .
H27c C27 H27b 109.5 . .
H28a C28 Cl4 115.3(18) . 2_744
H28b C28 Cl4 115.3(18) . 2_744
H28b C28 H28a 79(9) . .
Cl5 C28 Cl4 112.9(5) . 2_744
Cl5 C28 H28a 115.3(18) . .
Cl5 C28 H28b 115.3(18) . .

####################################################################### 
# 
# 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 1000484'
_audit_update_record             
;
2014-05-01 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2013-11-23
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C27 H36 Bi Br3 N2 Se, C H2 Cl2'
_chemical_formula_sum            'C28 H38 Bi Br3 Cl2 N2 Se'
_chemical_formula_weight         1001.18
_chemical_oxdiff_formula         'C20 H20 N2 Bi Br3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Bi -3.68252 9.31182 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Br -0.67402 1.33011 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Se -0.79210 1.18296 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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

_cell_length_a                   10.7722(2)
_cell_length_b                   16.3835(3)
_cell_length_c                   20.0651(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.228(2)
_cell_angle_gamma                90
_cell_volume                     3447.26(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7451
_cell_measurement_temperature    150.01(10)
_cell_measurement_theta_max      70.6416
_cell_measurement_theta_min      3.5181
_exptl_absorpt_coefficient_mu    16.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.18629
_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            'reddish brown'
_exptl_crystal_colour_modifier   reddish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.9289
_exptl_crystal_description       needle
_exptl_crystal_F_000             1884.0418
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0443
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14315
_diffrn_reflns_theta_full        70.762520
_diffrn_reflns_theta_max         70.76
_diffrn_reflns_theta_min         3.52
_diffrn_ambient_temperature      150.01(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.981582
_diffrn_measured_fraction_theta_max 0.981582
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -35.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  123.0000 -105.0000 35

#__ type_ start__ end____ width___ exp.time_
  2 omega  -62.00  -11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
  3 omega   -4.00   28.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   77.0000 -180.0000 32

#__ type_ start__ end____ width___ exp.time_
  4 omega    0.00   26.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   38.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega    7.00   71.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000   30.0000 64

#__ type_ start__ end____ width___ exp.time_
  6 omega   61.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
  7 omega   23.00   95.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000    0.0000 72

#__ type_ start__ end____ width___ exp.time_
  8 omega   45.00  117.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
  9 omega   44.00  133.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000    0.0000 89

#__ type_ start__ end____ width___ exp.time_
 10 omega   51.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000   90.0000 41

#__ type_ start__ end____ width___ exp.time_
 11 omega   40.00   80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 40

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 13 omega   67.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 14 omega   36.00   68.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -120.0000 32

#__ type_ start__ end____ width___ exp.time_
 15 omega   59.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 16 omega   40.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  150.0000 58

#__ type_ start__ end____ width___ exp.time_
 17 omega   38.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 34

#__ type_ start__ end____ width___ exp.time_
 18 omega   61.00  113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 19 omega   51.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 41

#__ type_ start__ end____ width___ exp.time_
 20 omega   39.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -120.0000 65
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0083036000
_diffrn_orient_matrix_UB_12      0.0525869000
_diffrn_orient_matrix_UB_13      0.0645688000
_diffrn_orient_matrix_UB_21      -0.0698418000
_diffrn_orient_matrix_UB_22      0.0699778000
_diffrn_orient_matrix_UB_23      -0.0446345000
_diffrn_orient_matrix_UB_31      -0.1288484000
_diffrn_orient_matrix_UB_32      -0.0345018000
_diffrn_orient_matrix_UB_33      0.0078227000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              24
_reflns_limit_l_min              0
_reflns_number_gt                5865
_reflns_number_total             6502
_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 1.171.35.19 (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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         5.305794
_refine_diff_density_min         -2.778693
_refine_diff_density_rms         0.247891
_refine_ls_d_res_high            0.816513
_refine_ls_d_res_low             12.552525
_refine_ls_goodness_of_fit_ref   1.033522
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    59
_refine_ls_number_parameters     342
_refine_ls_number_reflns         6502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.059270
_refine_ls_R_factor_gt           0.055031
_refine_ls_restrained_S_all      1.033522
_refine_ls_shift/su_max          0.4444
_refine_ls_shift/su_mean         0.0081
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1045P)²+9.3305P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.156362
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 0.71550(3) 0.672708(16) 0.034691(13) 0.03087(13) Uani 1.000000 .
Br1 Br 0.84217(9) 0.76332(6) 0.13504(4) 0.0473(2) Uani 1.000000 .
Br2 Br 0.80919(10) 0.53196(6) 0.10376(5) 0.0563(3) Uani 1.000000 .
Br3 Br 0.50752(9) 0.67494(5) 0.08235(5) 0.0425(2) Uani 1.000000 .
Se1 Se 0.70597(9) 0.83850(4) -0.02742(4) 0.0330(2) Uani 1.000000 .
Cl1 Cl 1.1499(7) 0.8369(2) -0.2300(2) 0.137(2) Uani 1.000000 .
Cl2 Cl 1.2128(15) 0.8360(3) -0.3588(8) 0.368(10) Uani 1.000000 .
N1 N 0.6581(5) 0.7668(3) -0.1636(3) 0.0241(11) Uani 1.000000 .
N2 N 0.6641(5) 0.8984(3) -0.1644(3) 0.0256(11) Uani 1.000000 .
C1 C 0.6723(7) 0.8332(4) -0.1225(4) 0.0280(15) Uani 1.000000 .
C2 C 0.6393(7) 0.7910(5) -0.2319(3) 0.0307(15) Uani 1.000000 .
H2 H 0.6263(7) 0.7571(5) -0.2700(3) 0.0368(18) Uiso 1.000000 R
C3 C 0.6437(7) 0.8729(5) -0.2316(3) 0.0307(15) Uani 1.000000 .
H3 H 0.6347(7) 0.9064(5) -0.2699(3) 0.0368(18) Uiso 1.000000 R
C4 C 0.6806(7) 0.9820(4) -0.1394(3) 0.0266(14) Uani 1.000000 .
C5 C 0.8007(7) 1.0144(5) -0.1270(4) 0.0327(15) Uani 1.000000 .
C6 C 0.8159(8) 1.0932(5) -0.0973(4) 0.0377(17) Uani 1.000000 .
H6 H 0.8956(8) 1.1180(5) -0.0876(4) 0.045(2) Uiso 1.000000 R
C7 C 0.7124(8) 1.1333(5) -0.0826(4) 0.0413(18) Uani 1.000000 .
H7 H 0.7247(8) 1.1843(5) -0.0617(4) 0.050(2) Uiso 1.000000 R
C8 C 0.5931(8) 1.1006(5) -0.0978(4) 0.0380(17) Uani 1.000000 .
H8 H 0.5252(8) 1.1298(5) -0.0882(4) 0.046(2) Uiso 1.000000 R
C9 C 0.5718(7) 1.0225(5) -0.1282(3) 0.0301(14) Uani 1.000000 .
C10 C 0.4381(7) 0.9866(5) -0.1481(4) 0.0327(15) Uani 1.000000 .
H10 H 0.4439(7) 0.9331(5) -0.1690(4) 0.0393(18) Uiso 1.000000 R
C11 C 0.3515(8) 1.0415(7) -0.2018(5) 0.052(2) Uani 1.000000 .
H11a H 0.338(6) 1.0926(19) -0.1811(11) 0.079(3) Uiso 1.000000 G
H11b H 0.392(3) 1.051(4) -0.2391(19) 0.079(3) Uiso 1.000000 G
H11c H 0.271(3) 1.015(2) -0.219(3) 0.079(3) Uiso 1.000000 G
C12 C 0.3815(9) 0.9743(7) -0.0860(5) 0.056(2) Uani 1.000000 .
C13 C 0.9155(7) 0.9708(5) -0.1430(4) 0.0366(16) Uani 1.000000 .
H13 H 0.8833(7) 0.9208(5) -0.1679(4) 0.044(2) Uiso 1.000000 R
C14 C 0.9769(10) 1.0212(7) -0.1902(5) 0.056(2) Uani 1.000000 .
H14a H 0.914(2) 1.034(4) -0.2312(18) 0.084(4) Uiso 1.000000 G
H14b H 1.010(7) 1.071(2) -0.1675(16) 0.084(4) Uiso 1.000000 G
H14c H 1.045(5) 0.991(2) -0.202(3) 0.084(4) Uiso 1.000000 G
C15 C 1.0113(9) 0.9446(8) -0.0787(5) 0.061(3) Uani 1.000000 .
H15a H 1.055(5) 0.9918(9) -0.056(2) 0.092(4) Uiso 1.000000 G
H15b H 0.9676(13) 0.917(4) -0.0483(19) 0.092(4) Uiso 1.000000 G
H15c H 1.072(5) 0.908(4) -0.0907(7) 0.092(4) Uiso 1.000000 G
C16 C 0.6638(7) 0.6834(4) -0.1390(3) 0.0271(14) Uani 1.000000 .
C17 C 0.7823(8) 0.6457(5) -0.1194(4) 0.0328(15) Uani 1.000000 .
C18 C 0.7849(8) 0.5668(5) -0.0939(4) 0.0367(16) Uani 1.000000 .
H18 H 0.8625(8) 0.5397(5) -0.0805(4) 0.044(2) Uiso 1.000000 R
C19 C 0.6741(8) 0.5277(5) -0.0880(4) 0.0385(17) Uani 1.000000 .
H19 H 0.6781(8) 0.4751(5) -0.0701(4) 0.046(2) Uiso 1.000000 R
C20 C 0.5577(8) 0.5661(4) -0.1086(4) 0.0336(15) Uani 1.000000 .
H20 H 0.4839(8) 0.5390(4) -0.1045(4) 0.0403(19) Uiso 1.000000 R
C21 C 0.5487(7) 0.6458(5) -0.1359(4) 0.0302(14) Uani 1.000000 .
C22 C 0.4198(8) 0.6861(5) -0.1608(4) 0.0324(16) Uani 1.000000 .
H22 H 0.4341(8) 0.7390(5) -0.1807(4) 0.0389(19) Uiso 1.000000 R
C23 C 0.3543(8) 0.7023(7) -0.1028(4) 0.050(2) Uani 1.000000 .
H23a H 0.330(6) 0.6514(7) -0.086(2) 0.075(3) Uiso 1.000000 G
H23b H 0.412(2) 0.731(4) -0.0667(16) 0.075(3) Uiso 1.000000 G
H23c H 0.280(4) 0.735(4) -0.1193(10) 0.075(3) Uiso 1.000000 G
C24 C 0.3359(8) 0.6358(6) -0.2168(4) 0.043(2) Uani 1.000000 .
H24a H 0.383(2) 0.620(4) -0.2499(19) 0.064(3) Uiso 1.000000 G
H24b H 0.308(5) 0.588(2) -0.1972(6) 0.064(3) Uiso 1.000000 G
H24c H 0.263(3) 0.6674(16) -0.239(2) 0.064(3) Uiso 1.000000 G
C25 C 0.9048(8) 0.6882(5) -0.1243(5) 0.0394(18) Uani 1.000000 .
H25 H 0.8840(8) 0.7451(5) -0.1374(5) 0.047(2) Uiso 1.000000 R
C26 C 1.0041(9) 0.6886(7) -0.0566(5) 0.055(2) Uani 1.000000 .
H26a H 0.970(3) 0.715(4) -0.0223(11) 0.083(4) Uiso 1.000000 G
H26b H 1.026(6) 0.6334(7) -0.043(2) 0.083(4) Uiso 1.000000 G
H26c H 1.079(3) 0.717(4) -0.0622(12) 0.083(4) Uiso 1.000000 G
C27 C 0.9589(8) 0.6489(6) -0.1804(4) 0.0442(19) Uani 1.000000 .
H27a H 0.976(6) 0.5923(12) -0.1700(19) 0.066(3) Uiso 1.000000 G
H27b H 0.898(3) 0.654(4) -0.2235(7) 0.066(3) Uiso 1.000000 G
H27c H 1.037(4) 0.676(3) -0.183(2) 0.066(3) Uiso 1.000000 G
C28 C 1.1242(13) 0.8787(11) -0.3123(6) 0.086(4) Uani 1.000000 .
H12a H 0.436(4) 0.939(4) -0.0538(18) 0.085(4) Uiso 1.000000 G
H12b H 0.374(7) 1.0261(8) -0.065(2) 0.085(4) Uiso 1.000000 G
H12c H 0.299(3) 0.950(4) -0.1002(7) 0.085(4) Uiso 1.000000 G
H28a H 1.046(5) 0.850(5) -0.3319(14) 0.103(5) Uiso 1.000000 R
H28b H 1.175(8) 0.928(3) -0.300(2) 0.103(5) 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
Bi1 Br1 2.6196(9) .
Bi1 Br2 2.7598(9) .
Bi1 Br3 2.6298(10) .
Bi1 Se1 2.9804(8) .
Se1 C1 1.861(8) .
Cl1 C28 1.751(14) .
Cl2 C28 1.636(15) .
N1 C1 1.352(9) .
N1 C2 1.396(8) .
N1 C16 1.450(8) .
N2 C1 1.349(9) .
N2 C3 1.382(8) .
N2 C4 1.456(9) .
C2 H2 0.9300 .
C2 C3 1.341(11) .
C3 H3 0.9300 .
C4 C5 1.368(11) .
C4 C9 1.408(10) .
C5 C6 1.415(11) .
C5 C13 1.525(11) .
C6 H6 0.9300 .
C6 C7 1.382(12) .
C7 H7 0.9300 .
C7 C8 1.362(12) .
C8 H8 0.9300 .
C8 C9 1.414(10) .
C9 C10 1.522(10) .
C10 H10 0.9800 .
C10 C11 1.544(11) .
C10 C12 1.520(11) .
C11 H11a 0.9600 .
C11 H11b 0.9600 .
C11 H11c 0.9600 .
C12 H12a 0.9600 .
C12 H12b 0.9600 .
C12 H12c 0.9600 .
C13 H13 0.9800 .
C13 C14 1.517(11) .
C13 C15 1.519(11) .
C14 H14a 0.9600 .
C14 H14b 0.9600 .
C14 H14c 0.9600 .
C15 H15a 0.9600 .
C15 H15b 0.9600 .
C15 H15c 0.9600 .
C16 C17 1.391(11) .
C16 C21 1.399(10) .
C17 C18 1.389(11) .
C17 C25 1.515(11) .
C18 H18 0.9300 .
C18 C19 1.383(12) .
C19 H19 0.9300 .
C19 C20 1.379(11) .
C20 H20 0.9300 .
C20 C21 1.411(10) .
C21 C22 1.516(11) .
C22 H22 0.9800 .
C22 C23 1.517(11) .
C22 C24 1.515(10) .
C23 H23a 0.9600 .
C23 H23b 0.9600 .
C23 H23c 0.9600 .
C24 H24a 0.9600 .
C24 H24b 0.9600 .
C24 H24c 0.9600 .
C25 H25 0.9800 .
C25 C26 1.526(13) .
C25 C27 1.524(12) .
C26 H26a 0.9600 .
C26 H26b 0.9600 .
C26 H26c 0.9600 .
C27 H27a 0.9600 .
C27 H27b 0.9600 .
C27 H27c 0.9600 .
C28 H28a 0.9700 .
C28 H28b 0.9700 .

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
Br2 Bi1 Br1 91.21(3) . .
Br3 Bi1 Br1 92.86(3) . .
Br3 Bi1 Br2 94.19(3) . .
Se1 Bi1 Br1 76.53(3) . .
Se1 Bi1 Br2 160.92(3) . .
Se1 Bi1 Br3 100.88(3) . .
C1 Se1 Bi1 111.5(2) . .
C2 N1 C1 109.9(6) . .
C16 N1 C1 124.0(5) . .
C16 N1 C2 126.0(6) . .
C3 N2 C1 110.0(6) . .
C4 N2 C1 123.1(5) . .
C4 N2 C3 126.9(6) . .
N1 C1 Se1 129.2(5) . .
N2 C1 Se1 124.8(5) . .
N2 C1 N1 105.9(6) . .
H2 C2 N1 126.8(4) . .
C3 C2 N1 106.5(6) . .
C3 C2 H2 126.8(4) . .
C2 C3 N2 107.6(6) . .
H3 C3 N2 126.2(4) . .
H3 C3 C2 126.2(4) . .
C5 C4 N2 117.7(6) . .
C9 C4 N2 117.2(6) . .
C9 C4 C5 125.1(7) . .
C6 C5 C4 116.4(7) . .
C13 C5 C4 123.9(7) . .
C13 C5 C6 119.7(7) . .
H6 C6 C5 119.9(5) . .
C7 C6 C5 120.2(7) . .
C7 C6 H6 119.9(5) . .
H7 C7 C6 119.0(5) . .
C8 C7 C6 122.0(7) . .
C8 C7 H7 119.0(5) . .
H8 C8 C7 119.8(5) . .
C9 C8 C7 120.3(7) . .
C9 C8 H8 119.8(5) . .
C8 C9 C4 115.9(7) . .
C10 C9 C4 123.3(6) . .
C10 C9 C8 120.8(7) . .
H10 C10 C9 108.0(4) . .
C11 C10 C9 110.0(7) . .
C11 C10 H10 108.0(5) . .
C12 C10 C9 111.7(6) . .
C12 C10 H10 108.0(5) . .
C12 C10 C11 111.0(7) . .
H11a C11 C10 109.5 . .
H11b C11 C10 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C10 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
H12a C12 C10 109.5 . .
H12b C12 C10 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C10 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
H13 C13 C5 106.9(4) . .
C14 C13 C5 111.5(7) . .
C14 C13 H13 106.9(5) . .
C15 C13 C5 112.3(7) . .
C15 C13 H13 106.9(6) . .
C15 C13 C14 112.1(7) . .
H14a C14 C13 109.5 . .
H14b C14 C13 109.5 . .
H14b C14 H14a 109.5 . .
H14c C14 C13 109.5 . .
H14c C14 H14a 109.5 . .
H14c C14 H14b 109.5 . .
H15a C15 C13 109.5 . .
H15b C15 C13 109.5 . .
H15b C15 H15a 109.5 . .
H15c C15 C13 109.5 . .
H15c C15 H15a 109.5 . .
H15c C15 H15b 109.5 . .
C17 C16 N1 118.6(7) . .
C21 C16 N1 117.5(6) . .
C21 C16 C17 123.9(7) . .
C18 C17 C16 117.2(7) . .
C25 C17 C16 122.3(7) . .
C25 C17 C18 120.5(7) . .
H18 C18 C17 119.4(5) . .
C19 C18 C17 121.2(7) . .
C19 C18 H18 119.4(5) . .
H19 C19 C18 119.8(5) . .
C20 C19 C18 120.4(7) . .
C20 C19 H19 119.8(4) . .
H20 C20 C19 119.5(4) . .
C21 C20 C19 121.1(7) . .
C21 C20 H20 119.5(4) . .
C20 C21 C16 116.2(7) . .
C22 C21 C16 123.2(7) . .
C22 C21 C20 120.5(7) . .
H22 C22 C21 107.6(4) . .
C23 C22 C21 112.0(6) . .
C23 C22 H22 107.6(5) . .
C24 C22 C21 110.7(7) . .
C24 C22 H22 107.6(5) . .
C24 C22 C23 111.2(7) . .
H23a C23 C22 109.5 . .
H23b C23 C22 109.5 . .
H23b C23 H23a 109.5 . .
H23c C23 C22 109.5 . .
H23c C23 H23a 109.5 . .
H23c C23 H23b 109.5 . .
H24a C24 C22 109.5 . .
H24b C24 C22 109.5 . .
H24b C24 H24a 109.5 . .
H24c C24 C22 109.5 . .
H24c C24 H24a 109.5 . .
H24c C24 H24b 109.5 . .
H25 C25 C17 107.8(4) . .
C26 C25 C17 112.8(7) . .
C26 C25 H25 107.8(5) . .
C27 C25 C17 109.9(7) . .
C27 C25 H25 107.8(5) . .
C27 C25 C26 110.5(7) . .
H26a C26 C25 109.5 . .
H26b C26 C25 109.5 . .
H26b C26 H26a 109.5 . .
H26c C26 C25 109.5 . .
H26c C26 H26a 109.5 . .
H26c C26 H26b 109.5 . .
H27a C27 C25 109.5 . .
H27b C27 C25 109.5 . .
H27b C27 H27a 109.5 . .
H27c C27 C25 109.5 . .
H27c C27 H27a 109.5 . .
H27c C27 H27b 109.5 . .
Cl2 C28 Cl1 112.6(11) . .
H28a C28 Cl1 97(4) . .
H28a C28 Cl2 97(4) . .
H28b C28 Cl1 97(3) . .
H28b C28 Cl2 97(3) . .
H28b C28 H28a 154(13) . .

####################################################################### 
# 
# 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_4a
_database_code_depnum_ccdc_archive 'CCDC 1011929'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-07-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         '0.5(C38 H40 N4 Se2)'
_chemical_formula_sum            'C19 H20 N2 Se'
_chemical_formula_weight         355.34
_chemical_oxdiff_formula         'C25 H25 N2 Se'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Se -0.79210 1.18296 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_H-M_alt        'P 1 2/n 1'
_space_group_name_Hall           '-P 2yac'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y,-z+1/2
3 -x,-y,-z
4 x-1/2,-y,z-1/2

_cell_length_a                   8.3877(14)
_cell_length_b                   7.4849(14)
_cell_length_c                   13.728(2)
_cell_angle_alpha                90
_cell_angle_beta                 98.462(15)
_cell_angle_gamma                90
_cell_volume                     852.5(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1621
_cell_measurement_temperature    150
_cell_measurement_theta_max      71.4592
_cell_measurement_theta_min      3.2544
_exptl_absorpt_coefficient_mu    2.948
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79938
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3843
_exptl_crystal_description       needle
_exptl_crystal_F_000             363.2098
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.13
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3047
_diffrn_reflns_theta_full        71.126047
_diffrn_reflns_theta_max         71.13
_diffrn_reflns_theta_min         3.25
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.944344
_diffrn_measured_fraction_theta_max 0.944344
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   27.00   52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000    0.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega  -86.00  -41.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  120.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega  -11.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  120.0000 93

#__ type_ start__ end____ width___ exp.time_
  5 omega  -12.00   49.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000    0.0000 61

#__ type_ start__ end____ width___ exp.time_
  6 omega    4.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000 -150.0000 68

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  -30.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   44.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -90.0000 51

#__ type_ start__ end____ width___ exp.time_
 11 omega   93.00  178.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -90.0000 85

#__ type_ start__ end____ width___ exp.time_
 12 omega   48.00   93.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 45

#__ type_ start__ end____ width___ exp.time_
 13 omega   47.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 41

#__ type_ start__ end____ width___ exp.time_
 14 omega   85.00  174.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   25.0000   30.0000 89

#__ type_ start__ end____ width___ exp.time_
 15 omega  -68.00   19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -57.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
 16 omega -102.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -57.0000  -30.0000 87
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0236369000
_diffrn_orient_matrix_UB_12      -0.1133015000
_diffrn_orient_matrix_UB_13      -0.0906325000
_diffrn_orient_matrix_UB_21      0.1639466000
_diffrn_orient_matrix_UB_22      -0.0655946000
_diffrn_orient_matrix_UB_23      0.0546920000
_diffrn_orient_matrix_UB_31      -0.0854125000
_diffrn_orient_matrix_UB_32      -0.1582294000
_diffrn_orient_matrix_UB_33      0.0419707000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -10
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              16
_reflns_limit_l_min              -7
_reflns_number_gt                1287
_reflns_number_total             1561
_reflns_odcompleteness_completeness 97.74
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         0.465417
_refine_diff_density_min         -0.873706
_refine_diff_density_rms         0.114703
_refine_ls_d_res_high            0.814726
_refine_ls_d_res_low             7.594127
_refine_ls_goodness_of_fit_ref   1.036298
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    16
_refine_ls_number_parameters     102
_refine_ls_number_reflns         1561
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.061601
_refine_ls_R_factor_gt           0.045226
_refine_ls_restrained_S_all      1.036298
_refine_ls_shift/su_max          0.0018
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+2.1041P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.146383
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
Se1 Se 0.250000 0.97439(10) 0.250000 0.0534(3) Uani 1.000000 S
N1 N 0.2282(5) 1.3297(5) 0.3257(3) 0.0465(9) Uani 1.000000 .
C1 C 0.250000 1.2185(9) 0.250000 0.0415(14) Uani 1.000000 S
C2 C 0.2370(8) 1.5057(6) 0.2968(4) 0.0603(14) Uani 1.000000 .
H2 H 0.2265(8) 1.6080(6) 0.3363(4) 0.0723(17) Uiso 1.000000 R
C3 C 0.1982(6) 1.2752(6) 0.4224(3) 0.0433(10) Uani 1.000000 .
C4 C 0.0396(6) 1.2630(7) 0.4393(4) 0.0522(12) Uani 1.000000 .
C5 C 0.0151(7) 1.2158(8) 0.5345(4) 0.0656(15) Uani 1.000000 .
H5 H -0.0918(7) 1.2044(8) 0.5489(4) 0.0788(19) Uiso 1.000000 R
C6 C 0.1425(9) 1.1858(9) 0.6073(4) 0.0723(17) Uani 1.000000 .
H6 H 0.1224(9) 1.1570(9) 0.6718(4) 0.087(2) Uiso 1.000000 R
C7 C 0.2993(8) 1.1965(8) 0.5886(4) 0.0625(14) Uani 1.000000 .
H7 H 0.3862(8) 1.1736(8) 0.6397(4) 0.0750(17) Uiso 1.000000 R
C8 C 0.3302(6) 1.2414(6) 0.4939(3) 0.0488(11) Uani 1.000000 .
C9 C 0.5011(6) 1.2482(8) 0.4717(4) 0.0644(15) Uani 1.000000 .
H9a H 0.5123(14) 1.167(4) 0.417(2) 0.097(2) Uiso 1.000000 G
H9b H 0.5266(17) 1.3702(14) 0.453(3) 0.097(2) Uiso 1.000000 G
H9c H 0.5754(7) 1.212(5) 0.5303(10) 0.097(2) Uiso 1.000000 G
C10 C -0.1001(7) 1.2974(9) 0.3588(4) 0.0735(17) Uani 1.000000 .
H10a H -0.103(3) 1.4244(14) 0.341(2) 0.110(3) Uiso 1.000000 G
H10b H -0.087(3) 1.226(5) 0.3007(13) 0.110(3) Uiso 1.000000 G
H10c H -0.2010(9) 1.264(6) 0.3820(13) 0.110(3) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Se1 C1 1.827(6) .
N1 C1 1.365(5) 2
N1 C2 1.381(6) .
N1 C3 1.445(5) .
C2 C2 1.334(11) 2
C2 H2 0.9500 .
C3 C4 1.387(7) .
C3 C8 1.391(7) .
C4 C5 1.397(7) .
C4 C10 1.510(8) .
C5 H5 0.9500 .
C5 C6 1.370(8) .
C6 H6 0.9500 .
C6 C7 1.379(8) .
C7 H7 0.9500 .
C7 C8 1.403(7) .
C8 C9 1.510(7) .
C9 H9a 0.9800 .
C9 H9b 0.9800 .
C9 H9c 0.9800 .
C10 H10a 0.9800 .
C10 H10b 0.9800 .
C10 H10c 0.9800 .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 N1 C1 110.1(4) . 2
C3 N1 C1 126.0(4) . 2
C3 N1 C2 123.9(4) . .
N1 C1 Se1 127.6(3) 2 .
N1 C1 Se1 127.6(3) . .
N1 C1 N1 104.8(5) . 2
C2 C2 N1 107.5(3) 2 .
H2 C2 N1 126.3(3) . .
C4 C3 N1 118.2(4) . .
C8 C3 N1 118.2(4) . .
C8 C3 C4 123.5(4) . .
C5 C4 C3 116.8(5) . .
C10 C4 C3 121.8(5) . .
C10 C4 C5 121.5(5) . .
H5 C5 C4 119.4(3) . .
C6 C5 C4 121.1(5) . .
C6 C5 H5 119.4(3) . .
H6 C6 C5 119.4(3) . .
C7 C6 C5 121.2(5) . .
C7 C6 H6 119.4(3) . .
H7 C7 C6 120.1(3) . .
C8 C7 C6 119.8(5) . .
C8 C7 H7 120.1(3) . .
C7 C8 C3 117.5(5) . .
C9 C8 C3 122.1(4) . .
C9 C8 C7 120.3(5) . .
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 C4 109.5 . .
H10b C10 C4 109.5 . .
H10b C10 H10a 109.5 . .
H10c C10 C4 109.5 . .
H10c C10 H10a 109.5 . .
H10c C10 H10b 109.5 . .

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        4a
####################################################################### 
# 
# 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 1011930'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-07-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C42 H48 Bi2 Cl6 N4 S2, 4(C H Cl3)'
_chemical_formula_sum            'C46 H52 Bi2 Cl18 N4 S2'
_chemical_formula_weight         1781.19
_chemical_oxdiff_formula         'C21 H36 N2 S Bi Cl3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Bi -3.68252 9.31182 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.33537 0.55136 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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'
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

_cell_length_a                   12.2653(8)
_cell_length_b                   17.1990(9)
_cell_length_c                   15.5570(7)
_cell_angle_alpha                90
_cell_angle_beta                 99.117(5)
_cell_angle_gamma                90
_cell_volume                     3240.3(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4772
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.7293
_cell_measurement_theta_min      3.6470
_exptl_absorpt_coefficient_mu    18.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74415
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.8255
_exptl_crystal_description       block
_exptl_crystal_F_000             1722.8694
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0569
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12843
_diffrn_reflns_theta_full        70.883503
_diffrn_reflns_theta_max         70.88
_diffrn_reflns_theta_min         3.65
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.977251
_diffrn_measured_fraction_theta_max 0.977251
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   38.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -18.00   29.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
  3 omega  -94.00  -33.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000 -180.0000 61

#__ type_ start__ end____ width___ exp.time_
  4 omega   36.00  124.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -120.0000 88

#__ type_ start__ end____ width___ exp.time_
  5 omega   44.00  109.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000   90.0000 65

#__ type_ start__ end____ width___ exp.time_
  6 omega   17.00  105.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000    0.0000 88

#__ type_ start__ end____ width___ exp.time_
  7 omega   59.00   87.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  8 omega   38.00   92.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  9 omega   66.00   93.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 10 omega   43.00  178.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000    0.0000 -150.0000 135

#__ type_ start__ end____ width___ exp.time_
 11 omega   37.00   91.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
 12 omega   37.00   93.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 56

#__ type_ start__ end____ width___ exp.time_
 13 omega   40.00   67.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 14 omega   42.00   93.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 51

#__ type_ start__ end____ width___ exp.time_
 15 omega   57.00   94.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 16 omega   86.00  113.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 17 omega   70.00  134.00   1.0000    5.5700
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -77.0000  150.0000 64
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0970398000
_diffrn_orient_matrix_UB_12      0.0060243000
_diffrn_orient_matrix_UB_13      0.0514543000
_diffrn_orient_matrix_UB_21      0.0798708000
_diffrn_orient_matrix_UB_22      -0.0142413000
_diffrn_orient_matrix_UB_23      0.0855213000
_diffrn_orient_matrix_UB_31      0.0195878000
_diffrn_orient_matrix_UB_32      0.0882251000
_diffrn_orient_matrix_UB_33      0.0102132000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -14
_reflns_limit_k_max              20
_reflns_limit_k_min              0
_reflns_limit_l_max              18
_reflns_limit_l_min              -10
_reflns_number_gt                5119
_reflns_number_total             6100
_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 1.171.35.19 (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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         7.072494
_refine_diff_density_min         -3.305245
_refine_diff_density_rms         0.427419
_refine_ls_d_res_high            0.815914
_refine_ls_d_res_low             11.456554
_refine_ls_goodness_of_fit_ref   1.045602
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    40
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6100
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.136857
_refine_ls_R_factor_gt           0.119004
_refine_ls_restrained_S_all      1.045602
_refine_ls_shift/su_max          0.0076
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1746P)²+97.2544P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.321768
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 0.93777(6) 0.11637(4) 0.53595(4) 0.0524(3) Uani 1.000000 .
C1 C 0.8099(16) 0.2893(9) 0.3987(10) 0.044(4) Uani 1.000000 .
C2 C 0.6770(15) 0.3545(11) 0.3066(11) 0.048(4) Uani 1.000000 .
H2 H 0.6406(15) 0.3932(11) 0.2690(11) 0.058(5) Uiso 1.000000 R
C3 C 0.6329(15) 0.2889(12) 0.3290(11) 0.052(4) Uani 1.000000 .
H3 H 0.5596(15) 0.2716(12) 0.3095(11) 0.062(5) Uiso 1.000000 R
C4 C 0.7029(13) 0.1747(10) 0.4282(11) 0.043(4) Uani 1.000000 .
C5 C 0.6687(15) 0.1744(12) 0.5078(12) 0.053(4) Uani 1.000000 .
C6 C 0.6500(18) 0.2443(15) 0.5579(13) 0.066(5) Uani 1.000000 .
H6a H 0.710(8) 0.281(4) 0.556(9) 0.099(8) Uiso 1.000000 G
H6b H 0.580(7) 0.268(6) 0.533(7) 0.099(8) Uiso 1.000000 G
H6c H 0.647(14) 0.230(2) 0.618(3) 0.099(8) Uiso 1.000000 G
C7 C 0.6578(15) 0.1012(13) 0.5449(13) 0.057(5) Uani 1.000000 .
H7 H 0.6400(15) 0.0989(13) 0.6021(13) 0.068(6) Uiso 1.000000 R
C8 C 0.6718(16) 0.0311(13) 0.5020(15) 0.060(5) Uani 1.000000 .
C9 C 0.661(2) -0.0457(15) 0.5430(16) 0.075(6) Uani 1.000000 .
H9a H 0.649(16) -0.086(2) 0.4978(19) 0.113(10) Uiso 1.000000 G
H9b H 0.730(6) -0.057(5) 0.583(10) 0.113(10) Uiso 1.000000 G
H9c H 0.599(10) -0.045(4) 0.575(10) 0.113(10) Uiso 1.000000 G
C10 C 0.7058(16) 0.0356(11) 0.4194(12) 0.053(4) Uani 1.000000 .
H10 H 0.7199(16) -0.0110(11) 0.3903(12) 0.063(5) Uiso 1.000000 R
C11 C 0.7194(15) 0.1084(11) 0.3789(12) 0.048(4) Uani 1.000000 .
C12 C 0.7595(19) 0.1138(12) 0.2937(12) 0.059(5) Uani 1.000000 .
H12a H 0.714(9) 0.151(7) 0.256(4) 0.088(7) Uiso 1.000000 G
H12b H 0.836(5) 0.132(9) 0.3030(16) 0.088(7) Uiso 1.000000 G
H12c H 0.755(13) 0.063(2) 0.266(5) 0.088(7) Uiso 1.000000 G
C13 C 0.8623(16) 0.4190(11) 0.3413(10) 0.047(4) Uani 1.000000 .
C14 C 0.8662(19) 0.4816(13) 0.4025(12) 0.060(5) Uani 1.000000 .
C15 C 0.935(2) 0.5430(12) 0.3889(12) 0.068(6) Uani 1.000000 .
H15 H 0.943(2) 0.5845(12) 0.4297(12) 0.081(7) Uiso 1.000000 R
C16 C 0.9902(19) 0.5471(13) 0.3216(14) 0.064(5) Uani 1.000000 .
C17 C 0.9853(19) 0.4837(12) 0.2645(13) 0.059(5) Uani 1.000000 .
H17 H 1.0262(19) 0.4856(12) 0.2176(13) 0.071(6) Uiso 1.000000 R
C18 C 0.9229(16) 0.4186(12) 0.2745(11) 0.052(4) Uani 1.000000 .
C19 C 0.9201(18) 0.3514(13) 0.2116(12) 0.058(5) Uani 1.000000 .
H19a H 0.957(12) 0.306(3) 0.242(3) 0.087(7) Uiso 1.000000 G
H19b H 0.8432(18) 0.338(6) 0.189(8) 0.087(7) Uiso 1.000000 G
H19c H 0.958(12) 0.366(3) 0.163(5) 0.087(7) Uiso 1.000000 G
C20 C 0.7986(18) 0.4775(11) 0.4742(13) 0.057(5) Uani 1.000000 .
H20a H 0.720(2) 0.474(9) 0.4493(13) 0.085(7) Uiso 1.000000 G
H20b H 0.820(9) 0.432(5) 0.510(6) 0.085(7) Uiso 1.000000 G
H20c H 0.811(10) 0.524(4) 0.510(6) 0.085(7) Uiso 1.000000 G
C21 C 1.055(3) 0.6209(14) 0.3096(18) 0.088(9) Uani 1.000000 .
H21a H 1.115(12) 0.627(7) 0.359(8) 0.133(13) Uiso 1.000000 G
H21b H 1.087(16) 0.617(6) 0.256(8) 0.133(13) Uiso 1.000000 G
H21c H 1.006(5) 0.666(2) 0.306(15) 0.133(13) Uiso 1.000000 G
C22 C 1.217(4) 0.2705(17) 0.400(4) 0.17(2) Uani 1.000000 .
H22 H 1.179(4) 0.2603(17) 0.451(4) 0.21(3) Uiso 1.000000 R
C23 C 1.082(3) 0.0128(17) 0.1589(19) 0.107(12) Uani 1.000000 .
H23 H 1.064(3) -0.0144(17) 0.2118(19) 0.128(15) Uiso 1.000000 R
Cl2 Cl 1.0103(5) 0.0228(3) 0.3894(3) 0.0689(15) Uani 1.000000 .
Cl3 Cl 1.1331(4) 0.1589(4) 0.5715(3) 0.0658(13) Uani 1.000000 .
Cl1 Cl 0.9000(4) 0.1639(3) 0.6809(3) 0.0546(10) Uani 1.000000 .
Cl4 Cl 0.9700(13) 0.0918(10) 0.1496(8) 0.184(7) Uani 1.000000 .
Cl5 Cl 1.2050(9) 0.0356(9) 0.1940(9) 0.169(6) Uani 1.000000 .
Cl6 Cl 1.0456(9) -0.0580(8) 0.0858(7) 0.145(4) Uani 1.000000 .
Cl7 Cl 1.169(2) 0.1897(12) 0.2955(16) 0.333(18) Uani 1.000000 .
Cl8 Cl 1.3606(10) 0.2490(9) 0.4222(14) 0.219(9) Uani 1.000000 .
Cl9 Cl 1.1832(8) 0.3540(6) 0.3546(7) 0.124(3) Uani 1.000000 .
N1 N 0.7877(12) 0.3566(9) 0.3484(8) 0.044(3) Uani 1.000000 .
N2 N 0.7128(11) 0.2500(9) 0.3863(9) 0.044(3) Uani 1.000000 .
S1 S 0.9325(4) 0.2687(3) 0.4595(3) 0.0503(10) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Cl2 2.693(5) 3_756
Bi1 Cl3 2.482(5) .
Bi1 Cl1 2.509(4) .
Bi1 S1 2.874(5) .
C1 N1 1.40(2) .
C1 N2 1.36(2) .
C1 S1 1.683(19) .
C2 H2 0.9500 .
C2 C3 1.32(3) .
C2 N1 1.41(2) .
C3 H3 0.9500 .
C3 N2 1.39(2) .
C4 C5 1.37(3) .
C4 C11 1.41(2) .
C4 N2 1.46(2) .
C5 C6 1.47(3) .
C5 C7 1.40(3) .
C6 H6a 0.9800 .
C6 H6b 0.9800 .
C6 H6c 0.9800 .
C7 H7 0.9500 .
C7 C8 1.40(3) .
C8 C9 1.48(3) .
C8 C10 1.41(3) .
C9 H9a 0.9800 .
C9 H9b 0.9800 .
C9 H9c 0.9800 .
C10 H10 0.9500 .
C10 C11 1.42(3) .
C11 C12 1.49(3) .
C12 H12a 0.9800 .
C12 H12b 0.9800 .
C12 H12c 0.9800 .
C13 C14 1.43(3) .
C13 C18 1.37(3) .
C13 N1 1.43(2) .
C14 C15 1.39(3) .
C14 C20 1.49(3) .
C15 H15 0.9500 .
C15 C16 1.33(3) .
C16 C17 1.40(3) .
C16 C21 1.53(3) .
C17 H17 0.9500 .
C17 C18 1.38(3) .
C18 C19 1.51(3) .
C19 H19a 0.9800 .
C19 H19b 0.9800 .
C19 H19c 0.9800 .
C20 H20a 0.9800 .
C20 H20b 0.9800 .
C20 H20c 0.9800 .
C21 H21a 0.9800 .
C21 H21b 0.9800 .
C21 H21c 0.9800 .
C22 H22 1.0000 .
C22 Cl7 2.15(6) .
C22 Cl8 1.78(5) .
C22 Cl9 1.63(4) .
C23 H23 1.0000 .
C23 Cl4 1.92(3) .
C23 Cl5 1.57(3) .
C23 Cl6 1.68(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
Cl3 Bi1 Cl2 90.66(19) . 3_756
Cl1 Bi1 Cl2 88.09(15) . 3_756
Cl1 Bi1 Cl3 90.73(15) . .
S1 Bi1 Cl2 167.75(17) . 3_756
S1 Bi1 Cl3 77.38(15) . .
S1 Bi1 Cl1 94.60(15) . .
N2 C1 N1 104.1(15) . .
S1 C1 N1 124.5(14) . .
S1 C1 N2 131.4(12) . .
C3 C2 H2 126.1(10) . .
N1 C2 H2 126.1(10) . .
N1 C2 C3 107.8(14) . .
H3 C3 C2 126.2(10) . .
N2 C3 C2 107.7(16) . .
N2 C3 H3 126.2(11) . .
C11 C4 C5 125.5(16) . .
N2 C4 C5 117.7(16) . .
N2 C4 C11 116.5(15) . .
C6 C5 C4 124.9(19) . .
C7 C5 C4 116.1(17) . .
C7 C5 C6 118.9(18) . .
H6a C6 C5 109.5 . .
H6b C6 C5 109.5 . .
H6b C6 H6a 109.5 . .
H6c C6 C5 109.5 . .
H6c C6 H6a 109.5 . .
H6c C6 H6b 109.5 . .
H7 C7 C5 118.3(12) . .
C8 C7 C5 123.3(19) . .
C8 C7 H7 118.3(12) . .
C9 C8 C7 122(2) . .
C10 C8 C7 117.5(19) . .
C10 C8 C9 120(2) . .
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 . .
H10 C10 C8 119.3(12) . .
C11 C10 C8 121.5(18) . .
C11 C10 H10 119.3(10) . .
C10 C11 C4 115.8(16) . .
C12 C11 C4 122.1(17) . .
C12 C11 C10 121.8(17) . .
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 . .
C18 C13 C14 122.8(18) . .
N1 C13 C14 117.9(16) . .
N1 C13 C18 119.1(16) . .
C15 C14 C13 115.3(18) . .
C20 C14 C13 119.8(18) . .
C20 C14 C15 124.9(18) . .
H15 C15 C14 118.1(12) . .
C16 C15 C14 124(2) . .
C16 C15 H15 118.1(13) . .
C17 C16 C15 119(2) . .
C21 C16 C15 119(2) . .
C21 C16 C17 123(2) . .
H17 C17 C16 119.0(13) . .
C18 C17 C16 122(2) . .
C18 C17 H17 119.0(11) . .
C17 C18 C13 117.3(18) . .
C19 C18 C13 122.4(18) . .
C19 C18 C17 120.3(18) . .
H19a C19 C18 109.5 . .
H19b C19 C18 109.5 . .
H19b C19 H19a 109.5 . .
H19c C19 C18 109.5 . .
H19c C19 H19a 109.5 . .
H19c C19 H19b 109.5 . .
H20a C20 C14 109.5 . .
H20b C20 C14 109.5 . .
H20b C20 H20a 109.5 . .
H20c C20 C14 109.5 . .
H20c C20 H20a 109.5 . .
H20c C20 H20b 109.5 . .
H21a C21 C16 109.5 . .
H21b C21 C16 109.5 . .
H21b C21 H21a 109.5 . .
H21c C21 C16 109.5 . .
H21c C21 H21a 109.5 . .
H21c C21 H21b 109.5 . .
Cl7 C22 H22 112.3(10) . .
Cl8 C22 H22 112.3(18) . .
Cl8 C22 Cl7 99.3(18) . .
Cl9 C22 H22 112.3(13) . .
Cl9 C22 Cl7 103(3) . .
Cl9 C22 Cl8 116.6(17) . .
Cl4 C23 H23 98.6(13) . .
Cl5 C23 H23 98.6(15) . .
Cl5 C23 Cl4 119.0(17) . .
Cl6 C23 H23 98.6(14) . .
Cl6 C23 Cl4 110.8(14) . .
Cl6 C23 Cl5 123.6(19) . .
C2 N1 C1 108.9(15) . .
C13 N1 C1 126.6(15) . .
C13 N1 C2 124.5(14) . .
C3 N2 C1 111.5(15) . .
C4 N2 C1 120.7(13) . .
C4 N2 C3 127.7(15) . .
C1 S1 Bi1 112.6(6) . .

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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 1011931'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-07-02
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C42 H48 Bi2 Br6 N4 S2, 4(C H Cl3)'
_chemical_formula_sum            'C46 H50 Bi2 Br6 Cl12 N4 S2'
_chemical_formula_weight         2045.88
_chemical_oxdiff_formula         'C21 H36 N2 S Bi Br3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Bi -3.68252 9.31182 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
S 0.33537 0.55136 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Br -0.67402 1.33011 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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

_cell_length_a                   9.9610(5)
_cell_length_b                   13.3493(6)
_cell_length_c                   14.3207(7)
_cell_angle_alpha                111.257(5)
_cell_angle_beta                 103.339(4)
_cell_angle_gamma                97.547(4)
_cell_volume                     1677.59(16)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7733
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.6762
_cell_measurement_theta_min      3.4700
_exptl_absorpt_coefficient_mu    19.615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20448
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.0249
_exptl_crystal_description       block
_exptl_crystal_F_000             961.2081
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11831
_diffrn_reflns_theta_full        70.812240
_diffrn_reflns_theta_max         70.81
_diffrn_reflns_theta_min         3.47
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.975376
_diffrn_measured_fraction_theta_max 0.975376
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00    0.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  117.0000  170.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega  -52.00   34.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000   57.0000 -120.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega -103.00  -52.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -50.0000   90.0000 51

#__ type_ start__ end____ width___ exp.time_
  4 omega -103.00  -58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000 -161.0000  -67.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega  -39.00  -14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -50.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega   33.00   70.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -57.0000  -60.0000 37

#__ type_ start__ end____ width___ exp.time_
  7 omega   77.00  121.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   90.0000 44

#__ type_ start__ end____ width___ exp.time_
  8 omega   46.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   29.00  123.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   77.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
 10 omega   37.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000   90.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   62.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   38.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
 12 omega   40.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -125.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   17.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -117.0000 -170.0000 87

#__ type_ start__ end____ width___ exp.time_
 14 omega   70.00  111.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
 15 omega   41.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 51

#__ type_ start__ end____ width___ exp.time_
 16 omega   42.00  169.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   12.0000 -180.0000 127

#__ type_ start__ end____ width___ exp.time_
 17 omega   47.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000   30.0000 41

#__ type_ start__ end____ width___ exp.time_
 18 omega   52.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -120.0000 30

#__ type_ start__ end____ width___ exp.time_
 19 omega   40.00   72.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000   60.0000 32

#__ type_ start__ end____ width___ exp.time_
 20 omega  151.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 21 omega   87.00  145.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 22 omega  109.00  135.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 23 omega   42.00   88.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   60.0000 46

#__ type_ start__ end____ width___ exp.time_
 24 omega   42.00   98.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 56

#__ type_ start__ end____ width___ exp.time_
 25 omega   40.00   66.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 26 omega   38.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000 -180.0000 49

#__ type_ start__ end____ width___ exp.time_
 27 omega   53.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -60.0000 59

#__ type_ start__ end____ width___ exp.time_
 28 omega   39.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
 29 omega   57.00  140.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -91.0000  120.0000 83

#__ type_ start__ end____ width___ exp.time_
 30 omega  143.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   63.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 31 omega   97.00  142.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000 -150.0000 45
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1270533000
_diffrn_orient_matrix_UB_12      0.0985469000
_diffrn_orient_matrix_UB_13      0.0721164000
_diffrn_orient_matrix_UB_21      -0.0148779000
_diffrn_orient_matrix_UB_22      -0.0226966000
_diffrn_orient_matrix_UB_23      0.0956610000
_diffrn_orient_matrix_UB_31      0.1020042000
_diffrn_orient_matrix_UB_32      -0.0775892000
_diffrn_orient_matrix_UB_33      -0.0173798000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -16
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                6076
_reflns_number_total             6298
_reflns_odcompleteness_completeness 99.93
_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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    
;
olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         8.039600
_refine_diff_density_min         -2.475598
_refine_diff_density_rms         0.301406
_refine_ls_d_res_high            0.816266
_refine_ls_d_res_low             12.726333
_refine_ls_goodness_of_fit_ref   1.031303
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     330
_refine_ls_number_reflns         6298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.061477
_refine_ls_R_factor_gt           0.060488
_refine_ls_restrained_S_all      1.031303
_refine_ls_shift/su_max          0.0108
_refine_ls_shift/su_mean         0.0005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1074P)²+14.5491P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.165699
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 0.49807(3) 0.15776(2) 0.48225(2) 0.02267(14) Uani 1.000000 .
Br2 Br 0.30004(9) -0.07320(8) 0.40170(8) 0.0316(2) Uani 1.000000 .
Br1 Br 0.69414(10) 0.34614(8) 0.54581(8) 0.0343(2) Uani 1.000000 .
Br3 Br 0.57061(10) 0.07423(8) 0.30933(7) 0.0324(2) Uani 1.000000 .
S1 S 0.3002(2) 0.2151(2) 0.35128(16) 0.0279(4) Uani 1.000000 .
Cl2 Cl 0.3526(4) 0.2445(3) 0.1169(3) 0.0737(10) Uani 1.000000 .
Cl5 Cl 0.7857(8) 0.4886(6) 0.1365(5) 0.135(2) Uani 1.000000 .
N1 N 0.0342(8) 0.2416(7) 0.3428(6) 0.0305(16) Uani 1.000000 .
N2 N 0.1612(7) 0.2822(6) 0.5029(6) 0.0254(15) Uani 1.000000 .
C13 C -0.0099(9) 0.2031(8) 0.2307(7) 0.0272(18) Uani 1.000000 .
C18 C 0.0145(10) 0.2794(8) 0.1864(8) 0.033(2) Uani 1.000000 .
C21 C -0.0950(11) 0.0119(9) 0.2209(9) 0.039(2) Uani 1.000000 .
C7 C 0.4936(10) 0.3077(9) 0.7559(7) 0.033(2) Uani 1.000000 .
C19 C 0.0935(14) 0.3960(9) 0.2531(9) 0.052(3) Uani 1.000000 .
C4 C 0.2744(9) 0.2930(7) 0.5908(7) 0.0242(17) Uani 1.000000 .
C5 C 0.2682(10) 0.2064(7) 0.6250(7) 0.0287(18) Uani 1.000000 .
C8 C 0.4932(10) 0.3944(8) 0.7224(7) 0.033(2) Uani 1.000000 .
C1 C 0.1653(9) 0.2468(7) 0.4025(7) 0.0246(16) Uani 1.000000 .
C15 C -0.1246(9) 0.0569(8) 0.0617(7) 0.0314(19) Uani 1.000000 .
C6 C 0.3816(11) 0.2161(8) 0.7077(7) 0.034(2) Uani 1.000000 .
C10 C 0.3851(12) 0.4796(9) 0.6019(9) 0.042(2) Uani 1.000000 .
C17 C -0.0394(11) 0.2419(9) 0.0773(8) 0.040(2) Uani 1.000000 .
C16 C -0.1079(9) 0.1298(8) 0.0135(7) 0.0307(19) Uani 1.000000 .
C11 C 0.1444(12) 0.1086(8) 0.5750(9) 0.042(2) Uani 1.000000 .
C14 C -0.0765(9) 0.0925(8) 0.1703(8) 0.0305(19) Uani 1.000000 .
Cl4 Cl 0.7553(7) 0.6488(6) 0.0522(5) 0.119(2) Uani 1.000000 .
C9 C 0.3832(10) 0.3871(8) 0.6384(7) 0.0291(18) Uani 1.000000 .
C3 C 0.0258(10) 0.2983(10) 0.5062(8) 0.038(2) Uani 1.000000 .
C2 C -0.0528(10) 0.2731(10) 0.4067(8) 0.040(2) Uani 1.000000 .
C12 C 0.6181(13) 0.3125(12) 0.8439(9) 0.057(3) Uani 1.000000 .
C20 C -0.1688(12) 0.0891(11) -0.1048(8) 0.045(3) Uani 1.000000 .
C22 C 0.4874(14) 0.1798(11) 0.0954(10) 0.054(3) Uani 1.000000 .
Cl1 Cl 0.4716(4) 0.1159(3) -0.0398(2) 0.0578(7) Uani 1.000000 .
Cl6 Cl 1.0034(5) 0.6941(4) 0.2249(3) 0.0846(12) Uani 1.000000 .
Cl3 Cl 0.6519(4) 0.2643(5) 0.1652(4) 0.0925(14) Uani 1.000000 .
C23 C 0.833(4) 0.616(2) 0.148(2) 0.20(2) Uani 1.000000 .
H15 H -0.1690(9) -0.0172(8) 0.0202(7) 0.038(2) Uiso 1.000000 R
H17 H -0.0300(11) 0.2917(9) 0.0463(8) 0.048(3) Uiso 1.000000 R
H8 H 0.5673(10) 0.4575(8) 0.7568(7) 0.040(2) Uiso 1.000000 R
H6 H 0.3818(11) 0.1595(8) 0.7310(7) 0.040(2) Uiso 1.000000 R
H21a H -0.007(3) 0.021(5) 0.271(5) 0.058(3) Uiso 1.000000 G
H21b H -0.167(6) 0.026(5) 0.256(6) 0.058(3) Uiso 1.000000 G
H21c H -0.123(8) -0.0624(9) 0.1679(12) 0.058(3) Uiso 1.000000 G
H19a H 0.049(6) 0.428(3) 0.306(5) 0.079(4) Uiso 1.000000 G
H19b H 0.190(3) 0.3980(11) 0.286(6) 0.079(4) Uiso 1.000000 G
H19c H 0.092(9) 0.437(2) 0.2103(16) 0.079(4) Uiso 1.000000 G
H10a H 0.346(8) 0.4494(9) 0.5269(11) 0.063(4) Uiso 1.000000 G
H10b H 0.330(7) 0.528(4) 0.634(5) 0.063(4) Uiso 1.000000 G
H10c H 0.4812(15) 0.521(4) 0.622(6) 0.063(4) Uiso 1.000000 G
H11a H 0.068(3) 0.128(2) 0.602(5) 0.063(4) Uiso 1.000000 G
H11b H 0.115(6) 0.087(5) 0.5004(12) 0.063(4) Uiso 1.000000 G
H11c H 0.171(3) 0.048(2) 0.590(6) 0.063(4) Uiso 1.000000 G
H3 H -0.0043(10) 0.3218(10) 0.5658(8) 0.046(3) Uiso 1.000000 R
H2 H -0.1470(10) 0.2761(10) 0.3849(8) 0.047(3) Uiso 1.000000 R
H12a H 0.662(7) 0.253(5) 0.817(2) 0.086(5) Uiso 1.000000 G
H12b H 0.686(5) 0.382(4) 0.871(6) 0.086(5) Uiso 1.000000 G
H12c H 0.584(2) 0.306(9) 0.899(4) 0.086(5) Uiso 1.000000 G
H20a H -0.165(9) 0.013(2) -0.1379(9) 0.068(4) Uiso 1.000000 G
H20b H -0.266(3) 0.095(7) -0.1220(9) 0.068(4) Uiso 1.000000 G
H20c H -0.114(6) 0.133(5) -0.1293(12) 0.068(4) Uiso 1.000000 G
H22 H 0.4779(14) 0.1205(11) 0.1202(10) 0.065(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
Bi1 Br2 3.0824(10) .
Bi1 Br2 2.9146(9) 2_656
Bi1 Br1 2.6827(9) .
Bi1 Br3 2.6330(9) .
Bi1 S1 2.778(2) .
S1 C1 1.703(9) .
Cl2 C22 1.716(13) .
Cl5 C23 1.65(2) .
N1 C13 1.433(11) .
N1 C1 1.364(11) .
N1 C2 1.395(12) .
N2 C4 1.431(11) .
N2 C1 1.354(11) .
N2 C3 1.401(11) .
C13 C18 1.405(13) .
C13 C14 1.385(14) .
C18 C19 1.487(14) .
C18 C17 1.397(14) .
C21 C14 1.514(13) .
C21 H21a 0.9600 .
C21 H21b 0.9600 .
C21 H21c 0.9600 .
C7 C8 1.405(15) .
C7 C6 1.374(14) .
C7 C12 1.527(14) .
C19 H19a 0.9600 .
C19 H19b 0.9600 .
C19 H19c 0.9600 .
C4 C5 1.409(12) .
C4 C9 1.378(13) .
C5 C6 1.389(14) .
C5 C11 1.494(13) .
C8 C9 1.391(13) .
C8 H8 0.9300 .
C15 C16 1.397(14) .
C15 C14 1.391(13) .
C15 H15 0.9300 .
C6 H6 0.9300 .
C10 C9 1.505(13) .
C10 H10a 0.9600 .
C10 H10b 0.9600 .
C10 H10c 0.9600 .
C17 C16 1.412(14) .
C17 H17 0.9300 .
C16 C20 1.518(13) .
C11 H11a 0.9600 .
C11 H11b 0.9600 .
C11 H11c 0.9600 .
Cl4 C23 1.64(2) .
C3 C2 1.351(14) .
C3 H3 0.9300 .
C2 H2 0.9300 .
C12 H12a 0.9600 .
C12 H12b 0.9600 .
C12 H12c 0.9600 .
C20 H20a 0.9600 .
C20 H20b 0.9600 .
C20 H20c 0.9600 .
C22 Cl1 1.769(12) .
C22 Cl3 1.702(14) .
C22 H22 0.9800 .
Cl6 C23 1.74(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
Br1 Bi1 Br2 173.17(3) . .
Br1 Bi1 Br2 90.64(3) . 2_656
Br3 Bi1 Br2 85.03(3) . .
Br3 Bi1 Br2 93.52(3) . 2_656
Br3 Bi1 Br1 90.08(3) . .
S1 Bi1 Br2 90.41(5) . .
S1 Bi1 Br2 173.24(5) . 2_656
S1 Bi1 Br1 93.55(5) . .
S1 Bi1 Br3 81.18(5) . .
C1 S1 Bi1 110.8(3) . .
C1 N1 C13 124.9(7) . .
C2 N1 C13 125.2(8) . .
C2 N1 C1 109.8(7) . .
C1 N2 C4 124.9(7) . .
C3 N2 C4 125.3(7) . .
C3 N2 C1 109.6(7) . .
C18 C13 N1 118.6(8) . .
C14 C13 N1 118.8(8) . .
C14 C13 C18 122.6(8) . .
C19 C18 C13 121.2(9) . .
C17 C18 C13 117.6(9) . .
C17 C18 C19 121.2(9) . .
H21a C21 C14 109.5 . .
H21b C21 C14 109.5 . .
H21b C21 H21a 109.5 . .
H21c C21 C14 109.5 . .
H21c C21 H21a 109.5 . .
H21c C21 H21b 109.5 . .
C6 C7 C8 119.8(8) . .
C12 C7 C8 121.0(10) . .
C12 C7 C6 119.2(10) . .
H19a C19 C18 109.5 . .
H19b C19 C18 109.5 . .
H19b C19 H19a 109.5 . .
H19c C19 C18 109.5 . .
H19c C19 H19a 109.5 . .
H19c C19 H19b 109.5 . .
C5 C4 N2 118.0(8) . .
C9 C4 N2 118.9(8) . .
C9 C4 C5 123.1(8) . .
C6 C5 C4 117.3(8) . .
C11 C5 C4 121.5(9) . .
C11 C5 C6 121.3(9) . .
C9 C8 C7 120.8(9) . .
H8 C8 C7 119.6(5) . .
H8 C8 C9 119.6(6) . .
N1 C1 S1 123.0(6) . .
N2 C1 S1 130.7(6) . .
N2 C1 N1 106.3(7) . .
C14 C15 C16 121.5(9) . .
H15 C15 C16 119.2(5) . .
H15 C15 C14 119.2(6) . .
C5 C6 C7 121.3(9) . .
H6 C6 C7 119.3(6) . .
H6 C6 C5 119.3(5) . .
H10a C10 C9 109.5 . .
H10b C10 C9 109.5 . .
H10b C10 H10a 109.5 . .
H10c C10 C9 109.5 . .
H10c C10 H10a 109.5 . .
H10c C10 H10b 109.5 . .
C16 C17 C18 121.1(9) . .
H17 C17 C18 119.5(6) . .
H17 C17 C16 119.5(6) . .
C17 C16 C15 118.7(9) . .
C20 C16 C15 120.0(9) . .
C20 C16 C17 121.3(9) . .
H11a C11 C5 109.5 . .
H11b C11 C5 109.5 . .
H11b C11 H11a 109.5 . .
H11c C11 C5 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
C21 C14 C13 121.0(9) . .
C15 C14 C13 118.4(9) . .
C15 C14 C21 120.7(9) . .
C8 C9 C4 117.7(9) . .
C10 C9 C4 122.0(8) . .
C10 C9 C8 120.3(9) . .
C2 C3 N2 107.2(8) . .
H3 C3 N2 126.4(5) . .
H3 C3 C2 126.4(6) . .
C3 C2 N1 107.0(8) . .
H2 C2 N1 126.5(5) . .
H2 C2 C3 126.5(6) . .
H12a C12 C7 109.5 . .
H12b C12 C7 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C7 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
H20a C20 C16 109.5 . .
H20b C20 C16 109.5 . .
H20b C20 H20a 109.5 . .
H20c C20 C16 109.5 . .
H20c C20 H20a 109.5 . .
H20c C20 H20b 109.5 . .
Cl1 C22 Cl2 112.1(7) . .
Cl3 C22 Cl2 113.2(8) . .
Cl3 C22 Cl1 110.9(7) . .
H22 C22 Cl2 106.7(5) . .
H22 C22 Cl1 106.7(5) . .
H22 C22 Cl3 106.7(5) . .
Cl4 C23 Cl5 118.8(14) . .
Cl6 C23 Cl5 118.7(14) . .
Cl6 C23 Cl4 117.1(19) . .

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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 1011932'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-06-03
_audit_creation_method           
;
  Olex2 1.1
  (compiled Nov  1 2011 20:42:30, GUI svn.r3906)
;
_chemical_formula_moiety         'C42 H48 Bi2 Cl6 N4 Se2, 4(C H2 Cl2)'
_chemical_formula_sum            'C46 H56 Bi2 Cl14 N4 Se2'
_chemical_formula_weight         1737.20
_chemical_oxdiff_formula         'C21 H36 N2 Se Bi Cl3'
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C 0.01920 0.00962 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Cl 0.36843 0.69943 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Bi -3.68252 9.31182 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
N 0.03256 0.01839 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
Se -0.79210 1.18296 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'

_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

_cell_length_a                   15.9721(6)
_cell_length_b                   10.8271(4)
_cell_length_c                   18.3916(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.510(3)
_cell_angle_gamma                90
_cell_volume                     3153.19(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6261
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      70.5991
_cell_measurement_theta_min      3.4467
_exptl_absorpt_coefficient_mu    17.875
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31219
_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            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.8296
_exptl_crystal_description       block
_exptl_crystal_F_000             1659.2918
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0437
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14171
_diffrn_reflns_theta_full        70.710824
_diffrn_reflns_theta_max         70.71
_diffrn_reflns_theta_min         3.45
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.979071
_diffrn_measured_fraction_theta_max 0.979071
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   22.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 40

#__ type_ start__ end____ width___ exp.time_
  2 omega   35.00   65.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   57.0000  150.0000 30

#__ type_ start__ end____ width___ exp.time_
  3 omega -102.00  -53.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -77.0000   60.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega   31.00  121.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   66.0000   75.0000 90

#__ type_ start__ end____ width___ exp.time_
  5 omega   17.00  102.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   19.0000 -150.0000 85

#__ type_ start__ end____ width___ exp.time_
  6 omega   70.00  123.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -164.0000   72.0000 53

#__ type_ start__ end____ width___ exp.time_
  7 omega   42.00   68.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
  8 omega   84.00  118.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000 -150.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega   92.00  178.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000   30.0000 86

#__ type_ start__ end____ width___ exp.time_
 10 omega  113.00  140.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 11 omega   55.00  105.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  150.0000 50

#__ type_ start__ end____ width___ exp.time_
 12 omega   41.00   90.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
 13 omega   37.00   91.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 54

#__ type_ start__ end____ width___ exp.time_
 14 omega   45.00  124.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -63.0000  -60.0000 79

#__ type_ start__ end____ width___ exp.time_
 15 omega   36.00   86.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000 -150.0000 50

#__ type_ start__ end____ width___ exp.time_
 16 omega  100.00  165.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000   38.0000  -30.0000 65

#__ type_ start__ end____ width___ exp.time_
 17 omega   69.00  103.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -120.0000 34

#__ type_ start__ end____ width___ exp.time_
 18 omega   42.00   70.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 19 omega  -74.00  -25.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  164.0000  -72.0000 49

#__ type_ start__ end____ width___ exp.time_
 20 omega -101.00  -73.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 21 omega  -17.00   76.00   1.0000    1.9200
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -38.0000   60.0000 93
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0947544000
_diffrn_orient_matrix_UB_12      0.0101314000
_diffrn_orient_matrix_UB_13      -0.0075437000
_diffrn_orient_matrix_UB_21      0.0221450000
_diffrn_orient_matrix_UB_22      -0.0208636000
_diffrn_orient_matrix_UB_23      0.0831653000
_diffrn_orient_matrix_UB_31      0.0035889000
_diffrn_orient_matrix_UB_32      -0.1402473000
_diffrn_orient_matrix_UB_33      -0.0129944000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              19
_reflns_limit_h_min              -19
_reflns_limit_k_max              13
_reflns_limit_k_min              0
_reflns_limit_l_max              22
_reflns_limit_l_min              0
_reflns_number_gt                5031
_reflns_number_total             5941
_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 1.171.35.19 (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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_refine_diff_density_max         6.335816
_refine_diff_density_min         -2.269692
_refine_diff_density_rms         0.270022
_refine_ls_d_res_high            0.816771
_refine_ls_d_res_low             9.309559
_refine_ls_goodness_of_fit_ref   1.040703
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     299
_refine_ls_number_reflns         5941
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.063470
_refine_ls_R_factor_gt           0.053101
_refine_ls_restrained_S_all      1.040703
_refine_ls_shift/su_max          3.9901
_refine_ls_shift/su_mean         0.0146
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²+33.6989P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.161189
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 0.410073(19) 0.64677(3) 0.015091(16) 0.02681(14) Uani 1.000000 .
Se1 Se 0.25782(6) 0.65644(10) 0.08458(6) 0.0350(3) Uani 1.000000 .
C22 C 0.2416(14) 0.3126(19) 0.0952(8) 0.087(5) Uani 1.000000 .
H22a H 0.294(2) 0.276(10) 0.081(3) 0.105(6) Uiso 1.000000 R
H22b H 0.1881(18) 0.342(11) 0.111(3) 0.105(6) Uiso 1.000000 R
Cl2 Cl 0.47475(13) 0.4058(2) 0.08037(12) 0.0352(5) Uani 1.000000 .
Cl3 Cl 0.30865(13) 0.5092(2) -0.06022(11) 0.0320(5) Uani 1.000000 .
Cl1 Cl 0.36148(16) 0.8277(2) -0.06606(13) 0.0397(5) Uani 1.000000 .
C4 C 0.1324(6) 0.7288(10) 0.2038(6) 0.037(2) Uani 1.000000 .
C3 C 0.3380(6) 0.8500(9) 0.2709(5) 0.032(2) Uani 1.000000 .
H3 H 0.3789(6) 0.8920(9) 0.3042(5) 0.039(2) Uiso 1.000000 R
N2 N 0.2202(5) 0.7663(8) 0.2179(4) 0.0315(17) Uani 1.000000 .
N1 N 0.3507(4) 0.7967(8) 0.2042(4) 0.0290(16) Uani 1.000000 .
C2 C 0.2570(6) 0.8302(9) 0.2787(5) 0.034(2) Uani 1.000000 .
H2 H 0.2296(6) 0.8558(9) 0.3190(5) 0.041(3) Uiso 1.000000 R
C1 C 0.2782(6) 0.7450(9) 0.1724(5) 0.0308(19) Uani 1.000000 .
C11 C -0.1274(8) 0.6219(16) 0.1639(10) 0.081(5) Uani 1.000000 .
H11a H -0.1317(10) 0.5317(17) 0.166(7) 0.121(8) Uiso 1.000000 G
H11b H -0.1588(17) 0.658(9) 0.201(4) 0.121(8) Uiso 1.000000 G
H11c H -0.151(2) 0.651(10) 0.115(3) 0.121(8) Uiso 1.000000 G
C7 C -0.0355(7) 0.6596(12) 0.1794(7) 0.052(3) Uani 1.000000 .
C9 C 0.0750(6) 0.8098(11) 0.1657(6) 0.041(2) Uani 1.000000 .
C5 C 0.1092(6) 0.6166(11) 0.2309(6) 0.043(2) Uani 1.000000 .
C12 C 0.1749(8) 0.5312(12) 0.2716(8) 0.062(4) Uani 1.000000 .
H12a H 0.222(3) 0.521(7) 0.243(3) 0.093(5) Uiso 1.000000 G
H12b H 0.196(5) 0.567(5) 0.320(2) 0.093(5) Uiso 1.000000 G
H12c H 0.1493(19) 0.450(3) 0.278(5) 0.093(5) Uiso 1.000000 G
C8 C -0.0096(7) 0.7728(12) 0.1543(7) 0.053(3) Uani 1.000000 .
H8 H -0.0505(7) 0.8263(12) 0.1288(7) 0.064(4) Uiso 1.000000 R
C10 C 0.1034(8) 0.9292(12) 0.1351(8) 0.064(4) Uani 1.000000 .
H10a H 0.084(6) 0.9986(13) 0.163(4) 0.096(5) Uiso 1.000000 G
H10b H 0.1652(8) 0.930(4) 0.139(5) 0.096(5) Uiso 1.000000 G
H10c H 0.079(5) 0.936(5) 0.0834(17) 0.096(5) Uiso 1.000000 G
C6 C 0.0243(7) 0.5833(12) 0.2178(7) 0.050(3) Uani 1.000000 .
H6 H 0.0070(7) 0.5064(12) 0.2357(7) 0.060(3) Uiso 1.000000 R
Cl5 Cl 0.1837(3) 0.1947(5) 0.0448(3) 0.0936(13) Uani 1.000000 .
Cl4 Cl 0.2738(5) 0.2652(6) 0.1846(3) 0.145(3) Uani 1.000000 .
C23 C 0.063(3) 0.745(6) -0.044(3) 0.29(2) Uiso 1.000000 .
H23a H 0.091(16) 0.684(6) -0.009(10) 0.35(3) Uiso 1.000000 R
H23b H 0.025(13) 0.73(2) -0.008(10) 0.35(3) Uiso 1.000000 R
Cl7 Cl 0.0407(4) 0.7158(7) -0.1190(4) 0.1273(19) Uiso 1.000000 .
Cl6 Cl 0.1149(8) 0.9259(13) -0.0531(7) 0.238(5) Uiso 1.000000 .
C16 C 0.5809(5) 0.8101(9) 0.1173(5) 0.0315(19) Uani 1.000000 .
C15 C 0.5183(6) 0.8987(9) 0.0975(5) 0.0307(19) Uani 1.000000 .
C14 C 0.4412(5) 0.8949(9) 0.1248(5) 0.0279(18) Uani 1.000000 .
C17 C 0.5643(5) 0.7150(9) 0.1648(5) 0.032(2) Uani 1.000000 .
C13 C 0.4285(5) 0.7989(8) 0.1731(4) 0.0249(17) Uani 1.000000 .
C20 C 0.3760(6) 0.9919(9) 0.1044(5) 0.035(2) Uani 1.000000 .
C19 C 0.4711(7) 0.6075(10) 0.2459(6) 0.040(2) Uani 1.000000 .
C18 C 0.4886(6) 0.7080(9) 0.1933(5) 0.0311(19) Uani 1.000000 .
C21 C 0.6656(7) 0.8192(12) 0.0873(7) 0.048(3) Uani 1.000000 .
H17 H 0.6061(5) 0.6536(9) 0.1777(5) 0.038(2) Uiso 1.000000 R
H15 H 0.5287(6) 0.9629(9) 0.0647(5) 0.037(2) Uiso 1.000000 R
H20a H 0.4016(12) 1.061(3) 0.081(4) 0.052(3) Uiso 1.000000 G
H20b H 0.330(2) 0.957(2) 0.070(3) 0.052(3) Uiso 1.000000 G
H20c H 0.354(3) 1.021(5) 0.1486(7) 0.052(3) Uiso 1.000000 G
H19a H 0.519(2) 0.551(4) 0.253(3) 0.060(3) Uiso 1.000000 G
H19b H 0.462(5) 0.6444(12) 0.2929(15) 0.060(3) Uiso 1.000000 G
H19c H 0.420(3) 0.562(5) 0.226(2) 0.060(3) Uiso 1.000000 G
H21a H 0.6582(13) 0.795(8) 0.0355(14) 0.073(4) Uiso 1.000000 G
H21b H 0.686(3) 0.904(2) 0.092(4) 0.073(4) Uiso 1.000000 G
H21c H 0.7065(17) 0.764(6) 0.115(3) 0.073(4) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 Se1 2.8931(10) .
Bi1 Cl2 2.763(2) 3_665
Bi1 Cl2 2.998(2) .
Bi1 Cl3 2.485(2) .
Bi1 Cl1 2.523(2) .
Se1 C1 1.870(9) .
C22 H22a 0.9900 .
C22 H22b 0.9900 .
C22 Cl5 1.77(2) .
C22 Cl4 1.734(15) .
C4 N2 1.451(11) .
C4 C9 1.390(14) .
C4 C5 1.382(16) .
C3 H3 0.9500 .
C3 N1 1.394(12) .
C3 C2 1.339(14) .
N2 C2 1.379(11) .
N2 C1 1.346(11) .
N1 C1 1.349(11) .
N1 C13 1.434(11) .
C2 H2 0.9500 .
C11 H11a 0.9800 .
C11 H11b 0.9800 .
C11 H11c 0.9800 .
C11 C7 1.513(15) .
C7 C8 1.391(18) .
C7 C6 1.384(17) .
C9 C8 1.399(14) .
C9 C10 1.504(17) .
C5 C12 1.520(15) .
C5 C6 1.393(15) .
C12 H12a 0.9800 .
C12 H12b 0.9800 .
C12 H12c 0.9800 .
C8 H8 0.9500 .
C10 H10a 0.9800 .
C10 H10b 0.9800 .
C10 H10c 0.9800 .
C6 H6 0.9500 .
C23 H23a 0.9900 .
C23 H23b 0.9900 .
C23 Cl7 1.41(6) .
C23 Cl6 2.14(6) .
C16 C15 1.399(13) .
C16 C17 1.398(14) .
C16 C21 1.529(14) .
C15 C14 1.390(12) .
C15 H15 0.9500 .
C14 C13 1.400(13) .
C14 C20 1.491(13) .
C17 C18 1.383(13) .
C17 H17 0.9500 .
C13 C18 1.390(13) .
C20 H20a 0.9800 .
C20 H20b 0.9800 .
C20 H20c 0.9800 .
C19 C18 1.506(13) .
C19 H19a 0.9800 .
C19 H19b 0.9800 .
C19 H19c 0.9800 .
C21 H21a 0.9800 .
C21 H21b 0.9800 .
C21 H21c 0.9800 .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
Cl2 Bi1 Se1 162.94(5) 3_665 .
Cl2 Bi1 Se1 96.90(5) . .
Cl3 Bi1 Se1 75.14(5) . .
Cl3 Bi1 Cl2 87.82(7) . 3_665
Cl3 Bi1 Cl2 82.36(7) . .
Cl1 Bi1 Se1 91.26(6) . .
Cl1 Bi1 Cl2 87.88(8) . 3_665
Cl1 Bi1 Cl2 167.35(7) . .
Cl1 Bi1 Cl3 90.45(8) . .
C1 Se1 Bi1 109.8(3) . .
H22b C22 H22a 175(15) . .
Cl5 C22 H22a 89(4) . .
Cl5 C22 H22b 89(4) . .
Cl4 C22 H22a 89(4) . .
Cl4 C22 H22b 89(4) . .
Cl4 C22 Cl5 110.7(11) . .
C9 C4 N2 118.2(9) . .
C5 C4 N2 118.7(9) . .
C5 C4 C9 123.1(9) . .
N1 C3 H3 126.8(5) . .
C2 C3 H3 126.8(6) . .
C2 C3 N1 106.4(8) . .
C2 N2 C4 125.8(8) . .
C1 N2 C4 124.6(8) . .
C1 N2 C2 109.6(7) . .
C1 N1 C3 109.7(7) . .
C13 N1 C3 125.2(7) . .
C13 N1 C1 125.1(7) . .
N2 C2 C3 108.0(8) . .
H2 C2 C3 126.0(6) . .
H2 C2 N2 126.0(5) . .
N2 C1 Se1 124.7(7) . .
N1 C1 Se1 129.0(7) . .
N1 C1 N2 106.3(7) . .
H11b C11 H11a 109.5 . .
H11c C11 H11a 109.5 . .
H11c C11 H11b 109.5 . .
C7 C11 H11a 109.5 . .
C7 C11 H11b 109.5 . .
C7 C11 H11c 109.5 . .
C8 C7 C11 119.9(12) . .
C6 C7 C11 121.5(12) . .
C6 C7 C8 118.6(10) . .
C8 C9 C4 117.1(10) . .
C10 C9 C4 121.4(9) . .
C10 C9 C8 121.5(10) . .
C12 C5 C4 120.8(9) . .
C6 C5 C4 117.8(10) . .
C6 C5 C12 121.4(11) . .
H12a C12 C5 109.5 . .
H12b C12 C5 109.5 . .
H12b C12 H12a 109.5 . .
H12c C12 C5 109.5 . .
H12c C12 H12a 109.5 . .
H12c C12 H12b 109.5 . .
C9 C8 C7 121.8(11) . .
H8 C8 C7 119.1(7) . .
H8 C8 C9 119.1(7) . .
H10a C10 C9 109.5 . .
H10b C10 C9 109.5 . .
H10b C10 H10a 109.5 . .
H10c C10 C9 109.5 . .
H10c C10 H10a 109.5 . .
H10c C10 H10b 109.5 . .
C5 C6 C7 121.6(11) . .
H6 C6 C7 119.2(7) . .
H6 C6 C5 119.2(7) . .
H23b C23 H23a 70(40) . .
Cl7 C23 H23a 121(9) . .
Cl7 C23 H23b 121(9) . .
Cl6 C23 H23a 121(8) . .
Cl6 C23 H23b 121(8) . .
Cl6 C23 Cl7 100(4) . .
C17 C16 C15 118.7(8) . .
C21 C16 C15 119.9(9) . .
C21 C16 C17 121.4(9) . .
C14 C15 C16 121.6(9) . .
H15 C15 C16 119.2(5) . .
H15 C15 C14 119.2(5) . .
C13 C14 C15 117.3(8) . .
C20 C14 C15 120.8(8) . .
C20 C14 C13 121.9(8) . .
C18 C17 C16 121.6(9) . .
H17 C17 C16 119.2(5) . .
H17 C17 C18 119.2(6) . .
C14 C13 N1 118.0(8) . .
C18 C13 N1 119.0(8) . .
C18 C13 C14 122.9(8) . .
H20a C20 C14 109.5 . .
H20b C20 C14 109.5 . .
H20b C20 H20a 109.5 . .
H20c C20 C14 109.5 . .
H20c C20 H20a 109.5 . .
H20c C20 H20b 109.5 . .
H19a C19 C18 109.5 . .
H19b C19 C18 109.5 . .
H19b C19 H19a 109.5 . .
H19c C19 C18 109.5 . .
H19c C19 H19a 109.5 . .
H19c C19 H19b 109.5 . .
C13 C18 C17 117.9(9) . .
C19 C18 C17 121.9(9) . .
C19 C18 C13 120.2(8) . .
H21a C21 C16 109.5 . .
H21b C21 C16 109.5 . .
H21b C21 H21a 109.5 . .
H21c C21 C16 109.5 . .
H21c C21 H21a 109.5 . .
H21c C21 H21b 109.5 . .

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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 1011933'
_audit_update_record             
;
2014-07-03 deposited with the CCDC.
2015-01-22 downloaded from the CCDC.
;
_audit_creation_date             2014-05-14
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.11.01 svn.r2039, GUI svn.r3906)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C42 H48 Bi2 Br6 N4 Se2'
_chemical_formula_sum            'C42 H48 Bi2 Br6 N4 Se2'
_chemical_formula_weight         1664.18
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C21 H36 N2 Se Bi Br3'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0111 8.9310 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 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'

_cell_length_a                   9.5278(2)
_cell_length_b                   16.1998(4)
_cell_length_c                   16.2869(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.199(2)
_cell_angle_gamma                90.00
_cell_volume                     2488.15(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5117
_cell_measurement_temperature    150
_cell_measurement_theta_max      70.5703
_cell_measurement_theta_min      3.8652
_exptl_absorpt_coefficient_mu    21.293
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.35381
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.221
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1544
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10803
_diffrn_reflns_theta_full        70.71
_diffrn_reflns_theta_max         70.71
_diffrn_reflns_theta_min         3.87
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 16.1293
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -54.00  -13.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000   60.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -39.00  -12.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega -107.00  -80.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -69.00  -42.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -91.00  -62.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -33.5000  -63.0000   60.0000 29

#__ type_ start__ end____ width___ exp.time_
  6 omega   36.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000   60.0000 70

#__ type_ start__ end____ width___ exp.time_
  7 omega   54.00  106.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000 -123.0000  -64.0000 52

#__ type_ start__ end____ width___ exp.time_
  8 omega   20.00   82.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
  9 omega  -15.00   19.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000  -77.0000  150.0000 34

#__ type_ start__ end____ width___ exp.time_
 10 omega   36.00  120.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       54.0000   57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
 11 omega   59.00   92.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
 12 omega   89.00  177.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   50.0000  -60.0000 88

#__ type_ start__ end____ width___ exp.time_
 13 omega   74.00  112.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000 -111.0000 -150.0000 38

#__ type_ start__ end____ width___ exp.time_
 14 omega   50.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 15 omega   77.00  104.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -50.0000 -180.0000 27

#__ type_ start__ end____ width___ exp.time_
 16 omega  134.00  169.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 17 omega   37.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -25.0000  -60.0000 47

#__ type_ start__ end____ width___ exp.time_
 18 omega  101.00  128.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  111.0000    0.0000 27

#__ type_ start__ end____ width___ exp.time_
 19 omega   48.00   74.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  -38.0000   30.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   86.00  164.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000   77.0000   30.0000 78

#__ type_ start__ end____ width___ exp.time_
 21 omega   64.00  149.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      108.0000  178.0000 -150.0000 85
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0293409000
_diffrn_orient_matrix_UB_12      0.0865284000
_diffrn_orient_matrix_UB_13      0.0381939000
_diffrn_orient_matrix_UB_21      -0.0296390000
_diffrn_orient_matrix_UB_22      0.0388052000
_diffrn_orient_matrix_UB_23      -0.0871057000
_diffrn_orient_matrix_UB_31      -0.1576927000
_diffrn_orient_matrix_UB_32      0.0086745000
_diffrn_orient_matrix_UB_33      0.0094123000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_diffrn_source_current           n/a
_diffrn_source_voltage           n/a
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                4223
_reflns_number_total             4715
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     >2sigma(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    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.920
_refine_diff_density_min         -2.282
_refine_diff_density_rms         0.221
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4715
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0406
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0586P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1005
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.01489(2) 0.359374(13) 0.017806(13) 0.02313(10) Uani 1 1 d . . .
Br1 Br 0.22067(8) 0.25999(5) 0.09569(5) 0.0463(2) Uani 1 1 d . . .
Br2 Br 0.17596(8) 0.50660(4) 0.07327(4) 0.03169(16) Uani 1 1 d . . .
Br3 Br 0.13846(9) 0.34855(4) -0.11523(5) 0.03838(19) Uani 1 1 d . . .
C1 C -0.2948(6) 0.1963(3) -0.0109(4) 0.0253(12) Uani 1 1 d . . .
C2 C -0.4335(7) 0.1796(4) 0.0878(4) 0.0355(15) Uani 1 1 d . . .
H2 H -0.4735 0.1872 0.1375 0.043 Uiso 1 1 calc R . .
C3 C -0.4736(7) 0.1245(5) 0.0287(4) 0.0356(16) Uani 1 1 d . . .
H3 H -0.5474 0.0850 0.0287 0.043 Uiso 1 1 calc R . .
C4 C -0.4011(6) 0.0831(4) -0.1056(4) 0.0257(12) Uani 1 1 d . . .
C5 C -0.3097(7) 0.0152(4) -0.1064(4) 0.0260(12) Uani 1 1 d . . .
C6 C -0.3364(7) -0.0391(4) -0.1722(4) 0.0282(13) Uani 1 1 d . . .
H6 H -0.2755 -0.0852 -0.1746 0.034 Uiso 1 1 calc R . .
C7 C -0.4509(7) -0.0280(4) -0.2357(4) 0.0288(13) Uani 1 1 d . . .
C8 C -0.5362(7) 0.0408(4) -0.2329(4) 0.0330(14) Uani 1 1 d . . .
H8 H -0.6128 0.0494 -0.2762 0.040 Uiso 1 1 calc R . .
C9 C -0.5131(7) 0.0978(4) -0.1685(4) 0.0324(14) Uani 1 1 d . . .
C10 C -0.6092(9) 0.1718(5) -0.1658(5) 0.051(2) Uani 1 1 d . . .
H10A H -0.6739 0.1620 -0.1251 0.076 Uiso 1 1 calc R . .
H10B H -0.6643 0.1804 -0.2207 0.076 Uiso 1 1 calc R . .
H10C H -0.5517 0.2209 -0.1498 0.076 Uiso 1 1 calc R . .
C11 C -0.1899(8) -0.0008(4) -0.0363(4) 0.0348(15) Uani 1 1 d . . .
H11A H -0.1140 0.0395 -0.0390 0.052 Uiso 1 1 calc R . .
H11B H -0.1527 -0.0567 -0.0416 0.052 Uiso 1 1 calc R . .
H11C H -0.2255 0.0044 0.0170 0.052 Uiso 1 1 calc R . .
C12 C -0.4799(8) -0.0909(4) -0.3038(4) 0.0385(16) Uani 1 1 d . . .
H12A H -0.4704 -0.0650 -0.3571 0.058 Uiso 1 1 calc R . .
H12B H -0.5764 -0.1124 -0.3054 0.058 Uiso 1 1 calc R . .
H12C H -0.4118 -0.1363 -0.2933 0.058 Uiso 1 1 calc R . .
C13 C -0.2402(7) 0.2845(4) 0.1149(3) 0.0256(13) Uani 1 1 d . . .
C14 C -0.1248(7) 0.2557(4) 0.1692(4) 0.0280(13) Uani 1 1 d . . .
C15 C -0.0466(7) 0.3135(4) 0.2199(4) 0.0327(14) Uani 1 1 d . . .
H15 H 0.0329 0.2955 0.2576 0.039 Uiso 1 1 calc R . .
C16 C -0.0813(7) 0.3961(4) 0.2169(4) 0.0290(13) Uani 1 1 d . . .
C17 C -0.1991(7) 0.4216(4) 0.1623(4) 0.0271(13) Uani 1 1 d . . .
H17 H -0.2233 0.4786 0.1600 0.032 Uiso 1 1 calc R . .
C18 C -0.2828(7) 0.3668(4) 0.1108(4) 0.0286(14) Uani 1 1 d . . .
C19 C -0.4128(7) 0.3937(4) 0.0544(4) 0.0354(15) Uani 1 1 d . . .
H19A H -0.4124 0.3693 -0.0007 0.053 Uiso 1 1 calc R . .
H19B H -0.4136 0.4540 0.0498 0.053 Uiso 1 1 calc R . .
H19C H -0.4974 0.3753 0.0771 0.053 Uiso 1 1 calc R . .
C20 C -0.0842(8) 0.1651(4) 0.1740(4) 0.0380(16) Uani 1 1 d . . .
H20A H 0.0094 0.1589 0.2072 0.057 Uiso 1 1 calc R . .
H20B H -0.0812 0.1438 0.1180 0.057 Uiso 1 1 calc R . .
H20C H -0.1545 0.1341 0.2000 0.057 Uiso 1 1 calc R . .
C21 C 0.0046(8) 0.4576(4) 0.2722(4) 0.0368(15) Uani 1 1 d . . .
H21A H 0.0408 0.4314 0.3253 0.055 Uiso 1 1 calc R . .
H21B H -0.0553 0.5047 0.2820 0.055 Uiso 1 1 calc R . .
H21C H 0.0844 0.4768 0.2454 0.055 Uiso 1 1 calc R . .
N1 N -0.3223(5) 0.2238(3) 0.0633(3) 0.0250(10) Uani 1 1 d . . .
N2 N -0.3885(6) 0.1348(3) -0.0328(3) 0.0285(12) Uani 1 1 d . . .
Se1 Se -0.15808(8) 0.23157(4) -0.07451(4) 0.03183(17) Uani 1 1 d . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 Br1 2.7084(8) . ?
Bi1 Br2 3.0744(7) 3_565 ?
Bi1 Br2 2.9092(7) . ?
Bi1 Br3 2.6152(7) . ?
Bi1 Se1 2.9251(7) . ?
Br2 Bi1 3.0744(7) 3_565 ?
C1 N1 1.348(7) . ?
C1 N2 1.351(7) . ?
C1 Se1 1.866(6) . ?
C2 C3 1.328(10) . ?
C2 N1 1.384(8) . ?
C3 N2 1.386(8) . ?
C4 C5 1.405(8) . ?
C4 C9 1.390(9) . ?
C4 N2 1.443(7) . ?
C5 C6 1.381(8) . ?
C5 C11 1.517(8) . ?
C6 C7 1.403(9) . ?
C7 C8 1.385(9) . ?
C7 C12 1.502(8) . ?
C8 C9 1.391(9) . ?
C9 C10 1.513(9) . ?
C13 C14 1.390(9) . ?
C13 C18 1.392(8) . ?
C13 N1 1.448(7) . ?
C14 C15 1.392(9) . ?
C14 C20 1.517(8) . ?
C15 C16 1.378(9) . ?
C16 C17 1.392(9) . ?
C16 C21 1.506(8) . ?
C17 C18 1.391(9) . ?
C18 C19 1.498(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Br1 Bi1 Br2 91.57(2) . . ?
Br1 Bi1 Br2 169.94(2) . 3_565 ?
Br1 Bi1 Se1 97.88(2) . . ?
Br2 Bi1 Br2 79.65(2) . 3_565 ?
Br2 Bi1 Se1 166.76(2) . . ?
Br3 Bi1 Br1 88.10(3) . . ?
Br3 Bi1 Br2 91.85(2) . . ?
Br3 Bi1 Br2 87.30(2) . 3_565 ?
Br3 Bi1 Se1 79.27(2) . . ?
Se1 Bi1 Br2 90.05(2) . 3_565 ?
Bi1 Br2 Bi1 100.35(2) . 3_565 ?
N1 C1 N2 105.9(5) . . ?
N1 C1 Se1 129.6(4) . . ?
N2 C1 Se1 124.5(4) . . ?
C3 C2 N1 107.0(5) . . ?
C2 C3 N2 107.7(6) . . ?
C5 C4 N2 118.9(6) . . ?
C9 C4 C5 122.6(6) . . ?
C9 C4 N2 118.1(6) . . ?
C4 C5 C11 121.8(5) . . ?
C6 C5 C4 117.4(6) . . ?
C6 C5 C11 120.7(6) . . ?
C5 C6 C7 121.9(6) . . ?
C6 C7 C12 120.0(6) . . ?
C8 C7 C6 118.5(6) . . ?
C8 C7 C12 121.6(6) . . ?
C7 C8 C9 121.9(6) . . ?
C4 C9 C8 117.7(6) . . ?
C4 C9 C10 121.2(6) . . ?
C8 C9 C10 121.1(6) . . ?
C14 C13 C18 123.4(6) . . ?
C14 C13 N1 117.0(5) . . ?
C18 C13 N1 119.6(6) . . ?
C13 C14 C15 117.4(6) . . ?
C13 C14 C20 122.1(6) . . ?
C15 C14 C20 120.6(6) . . ?
C16 C15 C14 121.7(6) . . ?
C15 C16 C17 118.7(6) . . ?
C15 C16 C21 120.9(6) . . ?
C17 C16 C21 120.4(6) . . ?
C18 C17 C16 122.4(6) . . ?
C13 C18 C19 121.1(6) . . ?
C17 C18 C13 116.4(6) . . ?
C17 C18 C19 122.5(6) . . ?
C1 N1 C2 110.0(5) . . ?
C1 N1 C13 125.9(5) . . ?
C2 N1 C13 123.8(5) . . ?
C1 N2 C3 109.3(5) . . ?
C1 N2 C4 128.3(5) . . ?
C3 N2 C4 122.3(5) . . ?
C1 Se1 Bi1 108.54(19) . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
