# Electronic Supplementary Material (ESI) for Dalton Transactions
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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data_jd2_89_new2

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H46 Bi Cl3 N2 O'
_chemical_formula_weight         778.03

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P2(1)/n

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

_cell_length_a                   12.334(3)
_cell_length_b                   15.235(3)
_cell_length_c                   19.277(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.87(3)
_cell_angle_gamma                90.00
_cell_volume                     3516.9(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6282
_cell_measurement_theta_min      3.0650
_cell_measurement_theta_max      27.8130

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    5.265
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3528
_exptl_absorpt_correction_T_max  0.7095
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_exptl_special_details           
; 
  The atom C1 was refined using the ISOR command
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27630
_diffrn_reflns_av_R_equivalents  0.1238
_diffrn_reflns_av_sigmaI/netI    0.1636
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.22
_diffrn_reflns_theta_max         24.71
_reflns_number_total             5972
_reflns_number_gt                3062
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELXP

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0302P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5972
_refine_ls_number_parameters     343
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0690
_refine_ls_goodness_of_fit_ref   0.814
_refine_ls_restrained_S_all      0.814
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.14173(3) 0.53397(2) 0.087667(17) 0.03273(11) Uani 1 1 d . . .
Cl2 Cl 0.00131(17) 0.62601(14) -0.01614(11) 0.0419(6) Uani 1 1 d . . .
N2 N 0.3134(5) 0.7172(4) 0.1144(3) 0.0314(17) Uani 1 1 d . . .
N1 N 0.2005(5) 0.7135(4) 0.1851(4) 0.0340(17) Uani 1 1 d . . .
C26 C 0.4744(7) 0.6504(6) 0.0831(5) 0.037(2) Uani 1 1 d . . .
C2 C 0.2627(7) 0.7885(6) 0.2003(5) 0.042(2) Uani 1 1 d . . .
H2A H 0.2568 0.8310 0.2353 0.050 Uiso 1 1 calc R . .
C21 C 0.3774(7) 0.6989(5) 0.0621(4) 0.034(2) Uani 1 1 d . . .
C1 C 0.2302(6) 0.6697(5) 0.1315(4) 0.030(2) Uani 1 1 d U . .
C22 C 0.3398(8) 0.7385(6) -0.0053(5) 0.043(2) Uani 1 1 d . . .
C25 C 0.5382(9) 0.6403(7) 0.0341(7) 0.062(3) Uani 1 1 d . . .
H25A H 0.6046 0.6062 0.0459 0.074 Uiso 1 1 calc R . .
C11 C 0.1203(7) 0.6845(5) 0.2230(5) 0.036(2) Uani 1 1 d . . .
C23 C 0.4103(11) 0.7251(7) -0.0516(5) 0.064(3) Uani 1 1 d . . .
H23A H 0.3899 0.7491 -0.0984 0.077 Uiso 1 1 calc R . .
C3 C 0.3329(7) 0.7917(5) 0.1576(5) 0.039(2) Uani 1 1 d . . .
H3A H 0.3863 0.8364 0.1568 0.047 Uiso 1 1 calc R . .
C24 C 0.5060(11) 0.6793(8) -0.0317(8) 0.075(4) Uani 1 1 d . . .
H24A H 0.5526 0.6738 -0.0642 0.091 Uiso 1 1 calc R . .
Cl1 Cl 0.29356(19) 0.45487(17) 0.18553(12) 0.0636(7) Uani 1 1 d . . .
Cl3 Cl 0.25403(18) 0.51044(15) 0.00109(12) 0.0509(7) Uani 1 1 d . . .
C403 C 0.5617(8) 0.5173(7) 0.1544(6) 0.081(4) Uani 1 1 d . . .
H40A H 0.5085 0.4796 0.1217 0.121 Uiso 1 1 calc R . .
H40B H 0.5780 0.4919 0.2026 0.121 Uiso 1 1 calc R . .
H40C H 0.6310 0.5216 0.1382 0.121 Uiso 1 1 calc R . .
C402 C 0.5119(7) 0.6077(6) 0.1559(5) 0.044(2) Uani 1 1 d . . .
H40D H 0.4440 0.6009 0.1752 0.052 Uiso 1 1 calc R . .
C16 C 0.0084(8) 0.7036(6) 0.1957(6) 0.051(3) Uani 1 1 d . . .
C302 C 0.2370(8) 0.7936(7) -0.0252(5) 0.059(3) Uani 1 1 d . . .
H30A H 0.1894 0.7799 0.0087 0.071 Uiso 1 1 calc R . .
C15 C -0.0663(9) 0.6779(8) 0.2368(8) 0.077(4) Uani 1 1 d . . .
H15A H -0.1437 0.6901 0.2202 0.093 Uiso 1 1 calc R . .
O1 O 0.5706(5) 0.9132(4) 0.1863(3) 0.0515(17) Uani 1 1 d . . .
C504 C 0.5322(9) 0.9318(7) 0.3012(5) 0.073(3) Uani 1 1 d . . .
H50A H 0.5673 0.9402 0.3521 0.109 Uiso 1 1 calc R . .
H50B H 0.4880 0.8776 0.2950 0.109 Uiso 1 1 calc R . .
H50C H 0.4833 0.9817 0.2835 0.109 Uiso 1 1 calc R . .
C503 C 0.6208(8) 0.9253(6) 0.2602(5) 0.058(3) Uani 1 1 d . . .
H50D H 0.6663 0.9795 0.2670 0.069 Uiso 1 1 calc R . .
H50E H 0.6708 0.8752 0.2782 0.069 Uiso 1 1 calc R . .
C203 C -0.1499(8) 0.7313(8) 0.0863(6) 0.093(4) Uani 1 1 d . . .
H20A H -0.1739 0.7676 0.0434 0.139 Uiso 1 1 calc R . .
H20B H -0.2026 0.7384 0.1167 0.139 Uiso 1 1 calc R . .
H20C H -0.1479 0.6695 0.0724 0.139 Uiso 1 1 calc R . .
C12 C 0.1610(10) 0.6434(6) 0.2896(6) 0.059(3) Uani 1 1 d . . .
C14 C -0.0283(13) 0.6353(8) 0.3005(8) 0.087(4) Uani 1 1 d . . .
H14A H -0.0801 0.6168 0.3269 0.105 Uiso 1 1 calc R . .
C201 C -0.0299(8) 0.8571(7) 0.1493(6) 0.082(4) Uani 1 1 d . . .
H20D H -0.0555 0.8934 0.1065 0.123 Uiso 1 1 calc R . .
H20E H 0.0467 0.8736 0.1734 0.123 Uiso 1 1 calc R . .
H20F H -0.0790 0.8663 0.1818 0.123 Uiso 1 1 calc R . .
C502 C 0.5919(9) 0.8985(7) 0.0679(5) 0.074(3) Uani 1 1 d . . .
H50F H 0.6469 0.8975 0.0388 0.112 Uiso 1 1 calc R . .
H50G H 0.5393 0.9469 0.0522 0.112 Uiso 1 1 calc R . .
H50H H 0.5511 0.8428 0.0625 0.112 Uiso 1 1 calc R . .
C103 C 0.3122(10) 0.5426(7) 0.3626(5) 0.099(4) Uani 1 1 d . . .
H10A H 0.2866 0.4943 0.3290 0.149 Uiso 1 1 calc R . .
H10B H 0.2746 0.5391 0.4018 0.149 Uiso 1 1 calc R . .
H10C H 0.3931 0.5380 0.3817 0.149 Uiso 1 1 calc R . .
C501 C 0.6508(8) 0.9115(7) 0.1453(5) 0.062(3) Uani 1 1 d . . .
H50I H 0.7043 0.8630 0.1615 0.075 Uiso 1 1 calc R . .
H50J H 0.6930 0.9674 0.1511 0.075 Uiso 1 1 calc R . .
C13 C 0.0833(14) 0.6188(7) 0.3269(6) 0.088(4) Uani 1 1 d . . .
H13A H 0.1076 0.5901 0.3717 0.105 Uiso 1 1 calc R . .
C303 C 0.1682(9) 0.7744(8) -0.1016(5) 0.099(4) Uani 1 1 d . . .
H30B H 0.1491 0.7119 -0.1060 0.149 Uiso 1 1 calc R . .
H30C H 0.2123 0.7897 -0.1360 0.149 Uiso 1 1 calc R . .
H30D H 0.0996 0.8094 -0.1114 0.149 Uiso 1 1 calc R . .
C102 C 0.2847(10) 0.6302(7) 0.3238(5) 0.070(3) Uani 1 1 d . . .
H10D H 0.3262 0.6332 0.2852 0.085 Uiso 1 1 calc R . .
C202 C -0.0327(8) 0.7600(8) 0.1277(6) 0.068(3) Uani 1 1 d . . .
H20G H 0.0200 0.7515 0.0961 0.082 Uiso 1 1 calc R . .
C401 C 0.5927(9) 0.6679(7) 0.2075(5) 0.080(4) Uani 1 1 d . . .
H40E H 0.6160 0.6394 0.2543 0.120 Uiso 1 1 calc R . .
H40F H 0.5553 0.7235 0.2125 0.120 Uiso 1 1 calc R . .
H40G H 0.6584 0.6794 0.1887 0.120 Uiso 1 1 calc R . .
C301 C 0.2646(9) 0.8919(7) -0.0193(7) 0.099(4) Uani 1 1 d . . .
H30E H 0.3079 0.9052 0.0292 0.148 Uiso 1 1 calc R . .
H30F H 0.1951 0.9259 -0.0296 0.148 Uiso 1 1 calc R . .
H30G H 0.3084 0.9074 -0.0537 0.148 Uiso 1 1 calc R . .
C101 C 0.3253(10) 0.7061(7) 0.3762(6) 0.103(5) Uani 1 1 d . . .
H10E H 0.3079 0.7622 0.3511 0.155 Uiso 1 1 calc R . .
H10F H 0.4061 0.7013 0.3954 0.155 Uiso 1 1 calc R . .
H10G H 0.2876 0.7031 0.4155 0.155 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.03108(17) 0.02904(17) 0.03710(17) -0.0027(2) 0.00625(11) -0.0041(2)
Cl2 0.0400(13) 0.0338(14) 0.0480(14) -0.0035(11) 0.0027(11) -0.0007(10)
N2 0.023(4) 0.026(4) 0.045(4) -0.006(4) 0.009(3) -0.007(3)
N1 0.018(4) 0.032(5) 0.052(5) -0.009(4) 0.009(3) 0.003(3)
C26 0.024(5) 0.042(6) 0.051(6) -0.022(5) 0.019(5) -0.009(4)
C2 0.038(6) 0.035(6) 0.058(6) -0.015(5) 0.021(5) -0.003(5)
C21 0.027(5) 0.038(6) 0.043(6) -0.015(5) 0.021(4) -0.015(4)
C1 0.028(5) 0.028(5) 0.041(5) 0.011(4) 0.022(4) 0.016(4)
C22 0.054(7) 0.034(6) 0.040(6) 0.003(5) 0.007(5) -0.017(5)
C25 0.070(8) 0.047(7) 0.079(8) -0.015(7) 0.037(7) -0.003(6)
C11 0.030(6) 0.035(5) 0.047(6) -0.012(5) 0.014(5) -0.021(4)
C23 0.097(10) 0.061(8) 0.039(6) -0.013(6) 0.023(7) -0.040(7)
C3 0.029(5) 0.027(5) 0.067(6) -0.009(5) 0.023(5) -0.006(4)
C24 0.090(10) 0.056(8) 0.100(11) -0.033(8) 0.062(9) -0.028(7)
Cl1 0.0541(15) 0.0538(17) 0.0727(15) 0.0296(15) -0.0051(12) -0.0082(14)
Cl3 0.0380(13) 0.0555(17) 0.0623(14) -0.0210(12) 0.0182(11) -0.0034(11)
C403 0.064(7) 0.066(8) 0.104(8) -0.018(7) 0.006(6) 0.032(6)
C402 0.030(5) 0.046(6) 0.059(6) -0.017(5) 0.018(5) -0.008(5)
C16 0.039(6) 0.049(7) 0.077(8) -0.039(6) 0.035(6) -0.013(5)
C302 0.053(7) 0.070(8) 0.045(6) 0.012(5) -0.006(5) -0.023(6)
C15 0.056(8) 0.070(9) 0.120(11) -0.048(8) 0.046(8) -0.021(7)
O1 0.039(4) 0.056(4) 0.061(4) -0.008(3) 0.015(3) -0.002(3)
C504 0.075(8) 0.077(9) 0.069(7) 0.012(6) 0.023(6) 0.008(6)
C503 0.040(6) 0.066(7) 0.062(7) -0.004(5) 0.002(5) -0.002(5)
C203 0.031(6) 0.127(11) 0.114(10) -0.066(9) 0.006(6) -0.002(7)
C12 0.100(9) 0.030(6) 0.064(8) -0.019(6) 0.054(7) -0.027(6)
C14 0.109(12) 0.073(10) 0.102(11) -0.036(9) 0.071(10) -0.036(9)
C201 0.045(7) 0.074(9) 0.116(10) -0.028(7) -0.004(6) 0.004(6)
C502 0.089(8) 0.073(8) 0.074(8) -0.015(6) 0.046(6) -0.015(7)
C103 0.152(11) 0.064(8) 0.067(7) 0.020(7) -0.004(7) 0.000(9)
C501 0.050(7) 0.063(7) 0.085(8) -0.004(6) 0.039(6) -0.013(6)
C13 0.147(13) 0.062(8) 0.067(8) -0.024(7) 0.052(9) -0.040(9)
C303 0.091(9) 0.119(11) 0.073(8) 0.029(8) -0.007(7) -0.031(8)
C102 0.089(9) 0.057(8) 0.056(7) 0.000(6) 0.001(6) -0.009(7)
C202 0.042(7) 0.085(9) 0.082(8) -0.029(7) 0.023(6) 0.010(6)
C401 0.085(8) 0.082(9) 0.062(7) -0.010(6) -0.005(6) -0.010(7)
C301 0.090(9) 0.057(8) 0.139(11) 0.015(8) 0.007(8) 0.005(7)
C101 0.108(10) 0.089(9) 0.088(9) -0.025(8) -0.027(8) -0.007(8)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.395(8) . ?
Bi1 Cl3 2.437(2) . ?
Bi1 Cl1 2.612(2) . ?
Bi1 Cl2 2.703(2) . ?
N2 C1 1.359(9) . ?
N2 C3 1.394(9) . ?
N2 C21 1.449(10) . ?
N1 C1 1.354(9) . ?
N1 C2 1.368(10) . ?
N1 C11 1.433(10) . ?
C26 C25 1.375(12) . ?
C26 C21 1.382(11) . ?
C26 C402 1.515(11) . ?
C2 C3 1.330(11) . ?
C2 H2A 0.9500 . ?
C21 C22 1.406(11) . ?
C22 C23 1.403(13) . ?
C22 C302 1.492(12) . ?
C25 C24 1.371(14) . ?
C25 H25A 0.9500 . ?
C11 C16 1.386(11) . ?
C11 C12 1.408(12) . ?
C23 C24 1.345(14) . ?
C23 H23A 0.9500 . ?
C3 H3A 0.9500 . ?
C24 H24A 0.9500 . ?
C403 C402 1.512(11) . ?
C403 H40A 0.9800 . ?
C403 H40B 0.9800 . ?
C403 H40C 0.9800 . ?
C402 C401 1.532(11) . ?
C402 H40D 1.0000 . ?
C16 C15 1.407(14) . ?
C16 C202 1.548(14) . ?
C302 C301 1.534(13) . ?
C302 C303 1.542(12) . ?
C302 H30A 1.0000 . ?
C15 C14 1.368(15) . ?
C15 H15A 0.9500 . ?
O1 C501 1.407(10) . ?
O1 C503 1.421(9) . ?
C504 C503 1.499(12) . ?
C504 H50A 0.9800 . ?
C504 H50B 0.9800 . ?
C504 H50C 0.9800 . ?
C503 H50D 0.9900 . ?
C503 H50E 0.9900 . ?
C203 C202 1.538(12) . ?
C203 H20A 0.9800 . ?
C203 H20B 0.9800 . ?
C203 H20C 0.9800 . ?
C12 C13 1.381(14) . ?
C12 C102 1.523(13) . ?
C14 C13 1.371(16) . ?
C14 H14A 0.9500 . ?
C201 C202 1.534(13) . ?
C201 H20D 0.9800 . ?
C201 H20E 0.9800 . ?
C201 H20F 0.9800 . ?
C502 C501 1.508(12) . ?
C502 H50F 0.9800 . ?
C502 H50G 0.9800 . ?
C502 H50H 0.9800 . ?
C103 C102 1.528(13) . ?
C103 H10A 0.9800 . ?
C103 H10B 0.9800 . ?
C103 H10C 0.9800 . ?
C501 H50I 0.9900 . ?
C501 H50J 0.9900 . ?
C13 H13A 0.9500 . ?
C303 H30B 0.9800 . ?
C303 H30C 0.9800 . ?
C303 H30D 0.9800 . ?
C102 C101 1.537(12) . ?
C102 H10D 1.0000 . ?
C202 H20G 1.0000 . ?
C401 H40E 0.9800 . ?
C401 H40F 0.9800 . ?
C401 H40G 0.9800 . ?
C301 H30E 0.9800 . ?
C301 H30F 0.9800 . ?
C301 H30G 0.9800 . ?
C101 H10E 0.9800 . ?
C101 H10F 0.9800 . ?
C101 H10G 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 Cl3 94.7(2) . . ?
C1 Bi1 Cl1 87.50(18) . . ?
Cl3 Bi1 Cl1 90.00(8) . . ?
C1 Bi1 Cl2 88.29(18) . . ?
Cl3 Bi1 Cl2 86.44(7) . . ?
Cl1 Bi1 Cl2 174.24(7) . . ?
C1 N2 C3 108.8(7) . . ?
C1 N2 C21 129.3(7) . . ?
C3 N2 C21 121.8(6) . . ?
C1 N1 C2 109.6(7) . . ?
C1 N1 C11 125.7(7) . . ?
C2 N1 C11 124.7(7) . . ?
C25 C26 C21 117.2(9) . . ?
C25 C26 C402 119.3(9) . . ?
C21 C26 C402 123.5(8) . . ?
C3 C2 N1 108.3(8) . . ?
C3 C2 H2A 125.8 . . ?
N1 C2 H2A 125.8 . . ?
C26 C21 C22 124.8(8) . . ?
C26 C21 N2 118.5(8) . . ?
C22 C21 N2 116.5(8) . . ?
N1 C1 N2 106.2(7) . . ?
N1 C1 Bi1 120.8(6) . . ?
N2 C1 Bi1 133.0(6) . . ?
C23 C22 C21 114.1(9) . . ?
C23 C22 C302 122.4(9) . . ?
C21 C22 C302 123.4(9) . . ?
C24 C25 C26 120.1(11) . . ?
C24 C25 H25A 120.0 . . ?
C26 C25 H25A 120.0 . . ?
C16 C11 C12 123.0(9) . . ?
C16 C11 N1 119.2(8) . . ?
C12 C11 N1 117.6(8) . . ?
C24 C23 C22 122.0(11) . . ?
C24 C23 H23A 119.0 . . ?
C22 C23 H23A 119.0 . . ?
C2 C3 N2 107.1(7) . . ?
C2 C3 H3A 126.5 . . ?
N2 C3 H3A 126.5 . . ?
C23 C24 C25 121.8(12) . . ?
C23 C24 H24A 119.1 . . ?
C25 C24 H24A 119.1 . . ?
C402 C403 H40A 109.5 . . ?
C402 C403 H40B 109.5 . . ?
H40A C403 H40B 109.5 . . ?
C402 C403 H40C 109.5 . . ?
H40A C403 H40C 109.5 . . ?
H40B C403 H40C 109.5 . . ?
C403 C402 C26 114.2(8) . . ?
C403 C402 C401 110.7(8) . . ?
C26 C402 C401 110.5(7) . . ?
C403 C402 H40D 107.0 . . ?
C26 C402 H40D 107.0 . . ?
C401 C402 H40D 107.0 . . ?
C11 C16 C15 117.1(10) . . ?
C11 C16 C202 122.2(9) . . ?
C15 C16 C202 120.4(10) . . ?
C22 C302 C301 111.8(8) . . ?
C22 C302 C303 112.2(9) . . ?
C301 C302 C303 108.5(9) . . ?
C22 C302 H30A 108.1 . . ?
C301 C302 H30A 108.1 . . ?
C303 C302 H30A 108.1 . . ?
C14 C15 C16 120.5(12) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C501 O1 C503 111.7(7) . . ?
C503 C504 H50A 109.5 . . ?
C503 C504 H50B 109.5 . . ?
H50A C504 H50B 109.5 . . ?
C503 C504 H50C 109.5 . . ?
H50A C504 H50C 109.5 . . ?
H50B C504 H50C 109.5 . . ?
O1 C503 C504 109.9(8) . . ?
O1 C503 H50D 109.7 . . ?
C504 C503 H50D 109.7 . . ?
O1 C503 H50E 109.7 . . ?
C504 C503 H50E 109.7 . . ?
H50D C503 H50E 108.2 . . ?
C202 C203 H20A 109.5 . . ?
C202 C203 H20B 109.5 . . ?
H20A C203 H20B 109.5 . . ?
C202 C203 H20C 109.5 . . ?
H20A C203 H20C 109.5 . . ?
H20B C203 H20C 109.5 . . ?
C13 C12 C11 117.1(11) . . ?
C13 C12 C102 119.2(11) . . ?
C11 C12 C102 123.6(9) . . ?
C15 C14 C13 121.2(13) . . ?
C15 C14 H14A 119.4 . . ?
C13 C14 H14A 119.4 . . ?
C202 C201 H20D 109.5 . . ?
C202 C201 H20E 109.5 . . ?
H20D C201 H20E 109.5 . . ?
C202 C201 H20F 109.5 . . ?
H20D C201 H20F 109.5 . . ?
H20E C201 H20F 109.5 . . ?
C501 C502 H50F 109.5 . . ?
C501 C502 H50G 109.5 . . ?
H50F C502 H50G 109.5 . . ?
C501 C502 H50H 109.5 . . ?
H50F C502 H50H 109.5 . . ?
H50G C502 H50H 109.5 . . ?
C102 C103 H10A 109.5 . . ?
C102 C103 H10B 109.5 . . ?
H10A C103 H10B 109.5 . . ?
C102 C103 H10C 109.5 . . ?
H10A C103 H10C 109.5 . . ?
H10B C103 H10C 109.5 . . ?
O1 C501 C502 108.8(8) . . ?
O1 C501 H50I 109.9 . . ?
C502 C501 H50I 109.9 . . ?
O1 C501 H50J 109.9 . . ?
C502 C501 H50J 109.9 . . ?
H50I C501 H50J 108.3 . . ?
C14 C13 C12 121.2(13) . . ?
C14 C13 H13A 119.4 . . ?
C12 C13 H13A 119.4 . . ?
C302 C303 H30B 109.5 . . ?
C302 C303 H30C 109.5 . . ?
H30B C303 H30C 109.5 . . ?
C302 C303 H30D 109.5 . . ?
H30B C303 H30D 109.5 . . ?
H30C C303 H30D 109.5 . . ?
C12 C102 C103 114.1(9) . . ?
C12 C102 C101 108.6(9) . . ?
C103 C102 C101 109.7(8) . . ?
C12 C102 H10D 108.1 . . ?
C103 C102 H10D 108.1 . . ?
C101 C102 H10D 108.1 . . ?
C201 C202 C203 111.9(8) . . ?
C201 C202 C16 108.9(8) . . ?
C203 C202 C16 111.0(9) . . ?
C201 C202 H20G 108.3 . . ?
C203 C202 H20G 108.3 . . ?
C16 C202 H20G 108.3 . . ?
C402 C401 H40E 109.5 . . ?
C402 C401 H40F 109.5 . . ?
H40E C401 H40F 109.5 . . ?
C402 C401 H40G 109.5 . . ?
H40E C401 H40G 109.5 . . ?
H40F C401 H40G 109.5 . . ?
C302 C301 H30E 109.5 . . ?
C302 C301 H30F 109.5 . . ?
H30E C301 H30F 109.5 . . ?
C302 C301 H30G 109.5 . . ?
H30E C301 H30G 109.5 . . ?
H30F C301 H30G 109.5 . . ?
C102 C101 H10E 109.5 . . ?
C102 C101 H10F 109.5 . . ?
H10E C101 H10F 109.5 . . ?
C102 C101 H10G 109.5 . . ?
H10E C101 H10G 109.5 . . ?
H10F C101 H10G 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 N1 C2 C3 -1.1(10) . . . . ?
C11 N1 C2 C3 176.1(7) . . . . ?
C25 C26 C21 C22 -0.2(12) . . . . ?
C402 C26 C21 C22 -179.3(7) . . . . ?
C25 C26 C21 N2 -174.7(7) . . . . ?
C402 C26 C21 N2 6.2(11) . . . . ?
C1 N2 C21 C26 -89.4(10) . . . . ?
C3 N2 C21 C26 89.6(9) . . . . ?
C1 N2 C21 C22 95.7(10) . . . . ?
C3 N2 C21 C22 -85.4(9) . . . . ?
C2 N1 C1 N2 1.3(8) . . . . ?
C11 N1 C1 N2 -175.8(7) . . . . ?
C2 N1 C1 Bi1 -180.0(5) . . . . ?
C11 N1 C1 Bi1 2.9(10) . . . . ?
C3 N2 C1 N1 -1.0(8) . . . . ?
C21 N2 C1 N1 178.1(7) . . . . ?
C3 N2 C1 Bi1 -179.5(6) . . . . ?
C21 N2 C1 Bi1 -0.4(12) . . . . ?
Cl3 Bi1 C1 N1 -178.2(5) . . . . ?
Cl1 Bi1 C1 N1 -88.4(5) . . . . ?
Cl2 Bi1 C1 N1 95.5(5) . . . . ?
Cl3 Bi1 C1 N2 0.1(7) . . . . ?
Cl1 Bi1 C1 N2 89.9(7) . . . . ?
Cl2 Bi1 C1 N2 -86.2(7) . . . . ?
C26 C21 C22 C23 -0.1(12) . . . . ?
N2 C21 C22 C23 174.5(7) . . . . ?
C26 C21 C22 C302 -177.3(8) . . . . ?
N2 C21 C22 C302 -2.7(11) . . . . ?
C21 C26 C25 C24 1.5(13) . . . . ?
C402 C26 C25 C24 -179.3(8) . . . . ?
C1 N1 C11 C16 -86.5(10) . . . . ?
C2 N1 C11 C16 96.7(9) . . . . ?
C1 N1 C11 C12 98.3(9) . . . . ?
C2 N1 C11 C12 -78.4(10) . . . . ?
C21 C22 C23 C24 -1.0(13) . . . . ?
C302 C22 C23 C24 176.3(9) . . . . ?
N1 C2 C3 N2 0.4(10) . . . . ?
C1 N2 C3 C2 0.4(9) . . . . ?
C21 N2 C3 C2 -178.8(7) . . . . ?
C22 C23 C24 C25 2.4(16) . . . . ?
C26 C25 C24 C23 -2.7(15) . . . . ?
C25 C26 C402 C403 -39.0(11) . . . . ?
C21 C26 C402 C403 140.1(8) . . . . ?
C25 C26 C402 C401 86.6(10) . . . . ?
C21 C26 C402 C401 -94.3(10) . . . . ?
C12 C11 C16 C15 -1.8(13) . . . . ?
N1 C11 C16 C15 -176.6(7) . . . . ?
C12 C11 C16 C202 171.4(8) . . . . ?
N1 C11 C16 C202 -3.5(12) . . . . ?
C23 C22 C302 C301 -77.5(11) . . . . ?
C21 C22 C302 C301 99.5(11) . . . . ?
C23 C22 C302 C303 44.7(12) . . . . ?
C21 C22 C302 C303 -138.3(9) . . . . ?
C11 C16 C15 C14 -0.4(14) . . . . ?
C202 C16 C15 C14 -173.7(10) . . . . ?
C501 O1 C503 C504 176.8(8) . . . . ?
C16 C11 C12 C13 2.5(13) . . . . ?
N1 C11 C12 C13 177.5(8) . . . . ?
C16 C11 C12 C102 -173.5(8) . . . . ?
N1 C11 C12 C102 1.4(13) . . . . ?
C16 C15 C14 C13 1.9(17) . . . . ?
C503 O1 C501 C502 180.0(8) . . . . ?
C15 C14 C13 C12 -1.1(18) . . . . ?
C11 C12 C13 C14 -1.1(15) . . . . ?
C102 C12 C13 C14 175.2(10) . . . . ?
C13 C12 C102 C103 42.3(13) . . . . ?
C11 C12 C102 C103 -141.7(9) . . . . ?
C13 C12 C102 C101 -80.4(12) . . . . ?
C11 C12 C102 C101 95.6(11) . . . . ?
C11 C16 C202 C201 -88.0(10) . . . . ?
C15 C16 C202 C201 84.9(11) . . . . ?
C11 C16 C202 C203 148.4(8) . . . . ?
C15 C16 C202 C203 -38.7(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.71
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.671
_refine_diff_density_min         -0.782
_refine_diff_density_rms         0.136
_database_code_depnum_ccdc_archive 'CCDC 942985'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_rc1_38

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H28 Bi Cl2 F3 N2 O4 S'
_chemical_formula_weight         681.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4153(19)
_cell_length_b                   10.538(2)
_cell_length_c                   12.433(3)
_cell_angle_alpha                102.25(3)
_cell_angle_beta                 92.74(3)
_cell_angle_gamma                95.89(3)
_cell_volume                     1196.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3663
_cell_measurement_theta_min      2.8669
_cell_measurement_theta_max      29.2933

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.892
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             660
_exptl_absorpt_coefficient_mu    7.728
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2482
_exptl_absorpt_correction_T_max  0.3902
_exptl_absorpt_process_details   'CrysAlisPro, Agilent Technologies'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9400
_diffrn_reflns_av_R_equivalents  0.0761
_diffrn_reflns_av_sigmaI/netI    0.0837
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.87
_diffrn_reflns_theta_max         25.03
_reflns_number_total             4231
_reflns_number_gt                3525
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    SHELXP
_computing_publication_material  SHELXP

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0590P)^2^+6.1438P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4231
_refine_ls_number_parameters     262
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0556
_refine_ls_wR_factor_ref         0.1303
_refine_ls_wR_factor_gt          0.1202
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.50282(4) 0.65173(4) 0.19981(3) 0.02594(15) Uani 1 1 d . . .
Cl1 Cl 0.3524(3) 0.8375(3) 0.2349(2) 0.0392(7) Uani 1 1 d . . .
Cl2 Cl 0.3057(3) 0.4953(3) 0.2426(3) 0.0404(7) Uani 1 1 d . . .
S1 S 0.6688(3) 0.3623(2) 0.1120(2) 0.0280(6) Uani 1 1 d . . .
F13 F 0.8798(9) 0.2803(8) -0.0005(6) 0.060(2) Uani 1 1 d . . .
F18 F 0.9217(9) 0.4779(8) 0.0948(6) 0.064(2) Uani 1 1 d . . .
F23 F 0.9231(9) 0.3182(8) 0.1757(7) 0.066(2) Uani 1 1 d . . .
O2 O 0.6935(9) 0.8202(7) 0.1339(6) 0.0364(18) Uani 1 1 d . . .
O1 O 0.6667(8) 0.4583(7) 0.2137(6) 0.0347(18) Uani 1 1 d . . .
O3 O 0.6200(11) 0.2333(7) 0.1171(8) 0.060(3) Uani 1 1 d . . .
N1 N 0.7420(9) 0.7328(8) 0.4166(6) 0.0238(18) Uani 1 1 d . . .
N2 N 0.5324(9) 0.7430(8) 0.4791(7) 0.0269(19) Uani 1 1 d . . .
C40 C 0.8593(14) 0.3595(12) 0.0934(9) 0.040(3) Uani 1 1 d . . .
C101 C 0.725(2) 0.9495(14) 0.0037(14) 0.081(6) Uani 1 1 d . . .
H10A H 0.6440 0.9434 -0.0518 0.098 Uiso 1 1 calc R . .
H10B H 0.7863 1.0327 0.0076 0.098 Uiso 1 1 calc R . .
C103 C 0.8048(19) 0.8430(13) -0.0273(12) 0.066(5) Uani 1 1 d . . .
H10C H 0.9083 0.8742 -0.0204 0.079 Uiso 1 1 calc R . .
H10D H 0.7777 0.7980 -0.1050 0.079 Uiso 1 1 calc R . .
C105 C 0.3282(15) 0.8681(14) 0.5336(11) 0.057(4) Uani 1 1 d . . .
H10E H 0.3694 0.9339 0.4953 0.086 Uiso 1 1 calc R . .
H10F H 0.3618 0.8930 0.6118 0.086 Uiso 1 1 calc R . .
H10G H 0.2236 0.8628 0.5265 0.086 Uiso 1 1 calc R . .
C107 C 0.3194(15) 0.6240(15) 0.5356(11) 0.056(4) Uani 1 1 d . . .
H10H H 0.3529 0.5425 0.4974 0.084 Uiso 1 1 calc R . .
H10I H 0.2145 0.6143 0.5304 0.084 Uiso 1 1 calc R . .
H10J H 0.3550 0.6439 0.6134 0.084 Uiso 1 1 calc R . .
C108 C 0.9560(12) 0.6254(11) 0.3563(9) 0.036(3) Uani 1 1 d . . .
H10K H 0.9000 0.5411 0.3542 0.054 Uiso 1 1 calc R . .
H10L H 1.0094 0.6563 0.4283 0.054 Uiso 1 1 calc R . .
H10M H 1.0232 0.6150 0.2981 0.054 Uiso 1 1 calc R . .
C109 C 0.7740(14) 0.7514(11) 0.0467(10) 0.042(3) Uani 1 1 d . . .
H10N H 0.7167 0.6700 0.0057 0.051 Uiso 1 1 calc R . .
H10O H 0.8641 0.7288 0.0782 0.051 Uiso 1 1 calc R . .
C110 C 0.9327(14) 0.8559(12) 0.3399(10) 0.045(3) Uani 1 1 d . . .
H11A H 0.8625 0.9143 0.3263 0.068 Uiso 1 1 calc R . .
H11B H 1.0009 0.8490 0.2823 0.068 Uiso 1 1 calc R . .
H11C H 0.9842 0.8913 0.4121 0.068 Uiso 1 1 calc R . .
C113 C 0.6711(15) 0.9467(11) 0.1107(10) 0.042(3) Uani 1 1 d . . .
H11D H 0.5680 0.9579 0.1095 0.051 Uiso 1 1 calc R . .
H11E H 0.7233 1.0180 0.1682 0.051 Uiso 1 1 calc R . .
C115 C 0.3749(12) 0.7349(10) 0.4823(9) 0.031(2) Uani 1 1 d . . .
H11F H 0.3343 0.7115 0.4039 0.037 Uiso 1 1 calc R . .
C116 C 0.8569(12) 0.7231(10) 0.3382(8) 0.030(2) Uani 1 1 d . . .
H11G H 0.8085 0.6899 0.2626 0.036 Uiso 1 1 calc R . .
C1 C 0.6010(12) 0.7174(10) 0.3849(9) 0.028(2) Uani 1 1 d . . .
C201 C 0.9022(13) 0.7867(14) 0.5979(10) 0.049(3) Uani 1 1 d . . .
H20A H 0.8852 0.8081 0.6765 0.074 Uiso 1 1 calc R . .
H20B H 0.9644 0.8585 0.5797 0.074 Uiso 1 1 calc R . .
H20C H 0.9485 0.7063 0.5815 0.074 Uiso 1 1 calc R . .
C204 C 0.5958(14) 0.8052(11) 0.6876(9) 0.040(3) Uani 1 1 d . . .
H20D H 0.6856 0.8240 0.7343 0.059 Uiso 1 1 calc R . .
H20E H 0.5376 0.7306 0.7050 0.059 Uiso 1 1 calc R . .
H20F H 0.5431 0.8819 0.7012 0.059 Uiso 1 1 calc R . .
C205 C 0.7615(12) 0.7671(10) 0.5301(9) 0.031(2) Uani 1 1 d . . .
C206 C 0.6280(12) 0.7734(9) 0.5696(8) 0.029(2) Uani 1 1 d . . .
O4 O 0.6153(10) 0.4068(9) 0.0173(6) 0.052(2) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Bi1 0.0309(3) 0.0205(2) 0.0276(2) 0.00670(15) 0.00088(15) 0.00606(16)
Cl1 0.0500(19) 0.0306(14) 0.0440(16) 0.0143(12) 0.0091(13) 0.0213(13)
Cl2 0.0309(16) 0.0252(13) 0.0627(19) 0.0045(12) 0.0057(13) 0.0015(12)
S1 0.0313(16) 0.0200(12) 0.0338(14) 0.0049(10) 0.0047(11) 0.0095(11)
F13 0.052(5) 0.068(5) 0.058(5) -0.005(4) 0.021(4) 0.023(4)
F18 0.055(5) 0.060(5) 0.069(5) 0.003(4) 0.020(4) -0.009(4)
F23 0.056(5) 0.079(6) 0.070(5) 0.019(4) -0.007(4) 0.040(5)
O2 0.040(5) 0.027(4) 0.046(5) 0.013(3) 0.010(4) 0.010(4)
O1 0.035(5) 0.028(4) 0.041(4) 0.002(3) 0.011(3) 0.013(3)
O3 0.066(7) 0.021(4) 0.095(7) 0.008(4) 0.037(5) 0.008(4)
N1 0.019(5) 0.030(5) 0.023(4) 0.007(3) 0.001(3) 0.003(4)
N2 0.026(5) 0.021(4) 0.035(5) 0.008(4) 0.003(4) 0.006(4)
C40 0.044(8) 0.039(7) 0.036(7) 0.007(5) 0.006(5) 0.010(6)
C101 0.131(17) 0.047(9) 0.087(12) 0.039(8) 0.048(11) 0.043(10)
C103 0.103(14) 0.054(8) 0.063(9) 0.034(7) 0.042(9) 0.050(9)
C105 0.042(8) 0.065(9) 0.060(9) -0.008(7) 0.008(6) 0.028(7)
C107 0.038(8) 0.078(10) 0.062(9) 0.044(8) 0.004(6) -0.004(7)
C108 0.021(6) 0.040(7) 0.046(7) 0.000(5) 0.001(5) 0.013(5)
C109 0.043(8) 0.034(6) 0.056(8) 0.010(5) 0.016(6) 0.026(6)
C110 0.046(8) 0.046(7) 0.040(7) 0.006(5) 0.003(6) -0.006(6)
C113 0.060(9) 0.029(6) 0.045(7) 0.014(5) 0.009(6) 0.026(6)
C115 0.030(6) 0.034(6) 0.031(6) 0.012(5) 0.003(4) 0.010(5)
C116 0.025(6) 0.033(6) 0.031(6) 0.002(4) 0.003(4) 0.004(5)
C1 0.026(6) 0.022(5) 0.038(6) 0.007(4) 0.004(5) 0.008(5)
C201 0.036(8) 0.069(9) 0.040(7) 0.010(6) -0.002(5) 0.000(7)
C204 0.054(8) 0.033(6) 0.031(6) 0.005(5) 0.002(5) 0.011(6)
C205 0.034(7) 0.025(5) 0.037(6) 0.014(5) -0.003(5) 0.004(5)
C206 0.042(7) 0.021(5) 0.024(5) 0.006(4) 0.004(5) 0.004(5)
O4 0.061(6) 0.057(6) 0.034(5) 0.000(4) -0.015(4) 0.018(5)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C1 2.371(10) . ?
Bi1 Cl2 2.506(3) . ?
Bi1 Cl1 2.508(3) . ?
Bi1 O2 2.673(7) . ?
Bi1 O1 2.708(7) . ?
S1 O3 1.405(8) . ?
S1 O1 1.444(7) . ?
S1 O4 1.445(8) . ?
S1 C40 1.823(13) . ?
F13 C40 1.318(13) . ?
F18 C40 1.320(14) . ?
F23 C40 1.335(14) . ?
O2 C113 1.456(12) . ?
O2 C109 1.461(13) . ?
N1 C1 1.350(13) . ?
N1 C205 1.379(13) . ?
N1 C116 1.487(13) . ?
N2 C1 1.355(13) . ?
N2 C206 1.368(13) . ?
N2 C115 1.479(14) . ?
C101 C103 1.412(19) . ?
C101 C113 1.452(18) . ?
C101 H10A 0.9900 . ?
C101 H10B 0.9900 . ?
C103 C109 1.485(17) . ?
C103 H10C 0.9900 . ?
C103 H10D 0.9900 . ?
C105 C115 1.532(16) . ?
C105 H10E 0.9800 . ?
C105 H10F 0.9800 . ?
C105 H10G 0.9800 . ?
C107 C115 1.521(16) . ?
C107 H10H 0.9800 . ?
C107 H10I 0.9800 . ?
C107 H10J 0.9800 . ?
C108 C116 1.502(15) . ?
C108 H10K 0.9800 . ?
C108 H10L 0.9800 . ?
C108 H10M 0.9800 . ?
C109 H10N 0.9900 . ?
C109 H10O 0.9900 . ?
C110 C116 1.500(15) . ?
C110 H11A 0.9800 . ?
C110 H11B 0.9800 . ?
C110 H11C 0.9800 . ?
C113 H11D 0.9900 . ?
C113 H11E 0.9900 . ?
C115 H11F 1.0000 . ?
C116 H11G 1.0000 . ?
C201 C205 1.508(16) . ?
C201 H20A 0.9800 . ?
C201 H20B 0.9800 . ?
C201 H20C 0.9800 . ?
C204 C206 1.486(14) . ?
C204 H20D 0.9800 . ?
C204 H20E 0.9800 . ?
C204 H20F 0.9800 . ?
C205 C206 1.374(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 Cl2 94.2(3) . . ?
C1 Bi1 Cl1 89.2(3) . . ?
Cl2 Bi1 Cl1 92.06(10) . . ?
C1 Bi1 O2 91.8(3) . . ?
Cl2 Bi1 O2 173.38(18) . . ?
Cl1 Bi1 O2 85.26(18) . . ?
C1 Bi1 O1 78.4(3) . . ?
Cl2 Bi1 O1 83.86(17) . . ?
Cl1 Bi1 O1 166.62(16) . . ?
O2 Bi1 O1 100.1(2) . . ?
O3 S1 O1 115.2(5) . . ?
O3 S1 O4 116.3(6) . . ?
O1 S1 O4 112.4(5) . . ?
O3 S1 C40 104.2(6) . . ?
O1 S1 C40 103.1(5) . . ?
O4 S1 C40 103.6(6) . . ?
C113 O2 C109 108.4(8) . . ?
C113 O2 Bi1 127.6(7) . . ?
C109 O2 Bi1 110.5(6) . . ?
S1 O1 Bi1 114.5(4) . . ?
C1 N1 C205 109.9(9) . . ?
C1 N1 C116 123.8(8) . . ?
C205 N1 C116 126.2(9) . . ?
C1 N2 C206 110.8(9) . . ?
C1 N2 C115 124.0(8) . . ?
C206 N2 C115 125.2(9) . . ?
F13 C40 F18 109.4(10) . . ?
F13 C40 F23 108.5(10) . . ?
F18 C40 F23 107.2(10) . . ?
F13 C40 S1 110.7(8) . . ?
F18 C40 S1 110.7(9) . . ?
F23 C40 S1 110.1(8) . . ?
C103 C101 C113 108.7(12) . . ?
C103 C101 H10A 109.9 . . ?
C113 C101 H10A 109.9 . . ?
C103 C101 H10B 109.9 . . ?
C113 C101 H10B 109.9 . . ?
H10A C101 H10B 108.3 . . ?
C101 C103 C109 108.2(11) . . ?
C101 C103 H10C 110.1 . . ?
C109 C103 H10C 110.1 . . ?
C101 C103 H10D 110.1 . . ?
C109 C103 H10D 110.1 . . ?
H10C C103 H10D 108.4 . . ?
C115 C105 H10E 109.5 . . ?
C115 C105 H10F 109.5 . . ?
H10E C105 H10F 109.5 . . ?
C115 C105 H10G 109.5 . . ?
H10E C105 H10G 109.5 . . ?
H10F C105 H10G 109.5 . . ?
C115 C107 H10H 109.5 . . ?
C115 C107 H10I 109.5 . . ?
H10H C107 H10I 109.5 . . ?
C115 C107 H10J 109.5 . . ?
H10H C107 H10J 109.5 . . ?
H10I C107 H10J 109.5 . . ?
C116 C108 H10K 109.5 . . ?
C116 C108 H10L 109.5 . . ?
H10K C108 H10L 109.5 . . ?
C116 C108 H10M 109.5 . . ?
H10K C108 H10M 109.5 . . ?
H10L C108 H10M 109.5 . . ?
O2 C109 C103 105.9(9) . . ?
O2 C109 H10N 110.6 . . ?
C103 C109 H10N 110.6 . . ?
O2 C109 H10O 110.6 . . ?
C103 C109 H10O 110.6 . . ?
H10N C109 H10O 108.7 . . ?
C116 C110 H11A 109.5 . . ?
C116 C110 H11B 109.5 . . ?
H11A C110 H11B 109.5 . . ?
C116 C110 H11C 109.5 . . ?
H11A C110 H11C 109.5 . . ?
H11B C110 H11C 109.5 . . ?
C101 C113 O2 107.1(10) . . ?
C101 C113 H11D 110.3 . . ?
O2 C113 H11D 110.3 . . ?
C101 C113 H11E 110.3 . . ?
O2 C113 H11E 110.3 . . ?
H11D C113 H11E 108.6 . . ?
N2 C115 C107 110.5(9) . . ?
N2 C115 C105 111.0(9) . . ?
C107 C115 C105 114.7(11) . . ?
N2 C115 H11F 106.7 . . ?
C107 C115 H11F 106.7 . . ?
C105 C115 H11F 106.7 . . ?
N1 C116 C110 110.5(9) . . ?
N1 C116 C108 112.2(9) . . ?
C110 C116 C108 113.6(10) . . ?
N1 C116 H11G 106.7 . . ?
C110 C116 H11G 106.7 . . ?
C108 C116 H11G 106.7 . . ?
N1 C1 N2 106.0(8) . . ?
N1 C1 Bi1 125.0(7) . . ?
N2 C1 Bi1 129.0(7) . . ?
C205 C201 H20A 109.5 . . ?
C205 C201 H20B 109.5 . . ?
H20A C201 H20B 109.5 . . ?
C205 C201 H20C 109.5 . . ?
H20A C201 H20C 109.5 . . ?
H20B C201 H20C 109.5 . . ?
C206 C204 H20D 109.5 . . ?
C206 C204 H20E 109.5 . . ?
H20D C204 H20E 109.5 . . ?
C206 C204 H20F 109.5 . . ?
H20D C204 H20F 109.5 . . ?
H20E C204 H20F 109.5 . . ?
C206 C205 N1 107.1(9) . . ?
C206 C205 C201 126.5(10) . . ?
N1 C205 C201 126.3(10) . . ?
N2 C206 C205 106.2(9) . . ?
N2 C206 C204 127.5(11) . . ?
C205 C206 C204 126.3(10) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 Bi1 O2 C113 -101.7(8) . . . . ?
Cl2 Bi1 O2 C113 53.7(19) . . . . ?
Cl1 Bi1 O2 C113 -12.6(8) . . . . ?
O1 Bi1 O2 C113 179.8(8) . . . . ?
C1 Bi1 O2 C109 123.0(7) . . . . ?
Cl2 Bi1 O2 C109 -81.7(17) . . . . ?
Cl1 Bi1 O2 C109 -147.9(7) . . . . ?
O1 Bi1 O2 C109 44.4(7) . . . . ?
O3 S1 O1 Bi1 -120.6(6) . . . . ?
O4 S1 O1 Bi1 15.7(6) . . . . ?
C40 S1 O1 Bi1 126.6(5) . . . . ?
C1 Bi1 O1 S1 -177.4(5) . . . . ?
Cl2 Bi1 O1 S1 87.0(4) . . . . ?
Cl1 Bi1 O1 S1 159.8(5) . . . . ?
O2 Bi1 O1 S1 -87.6(4) . . . . ?
O3 S1 C40 F13 62.8(10) . . . . ?
O1 S1 C40 F13 -176.6(8) . . . . ?
O4 S1 C40 F13 -59.3(9) . . . . ?
O3 S1 C40 F18 -175.7(8) . . . . ?
O1 S1 C40 F18 -55.1(9) . . . . ?
O4 S1 C40 F18 62.2(9) . . . . ?
O3 S1 C40 F23 -57.2(9) . . . . ?
O1 S1 C40 F23 63.4(9) . . . . ?
O4 S1 C40 F23 -179.3(8) . . . . ?
C113 C101 C103 C109 14(2) . . . . ?
C113 O2 C109 C103 2.4(14) . . . . ?
Bi1 O2 C109 C103 146.4(10) . . . . ?
C101 C103 C109 O2 -9.9(19) . . . . ?
C103 C101 C113 O2 -12(2) . . . . ?
C109 O2 C113 C101 5.8(15) . . . . ?
Bi1 O2 C113 C101 -130.3(12) . . . . ?
C1 N2 C115 C107 113.4(11) . . . . ?
C206 N2 C115 C107 -64.8(13) . . . . ?
C1 N2 C115 C105 -118.1(11) . . . . ?
C206 N2 C115 C105 63.7(13) . . . . ?
C1 N1 C116 C110 106.7(11) . . . . ?
C205 N1 C116 C110 -68.5(13) . . . . ?
C1 N1 C116 C108 -125.4(10) . . . . ?
C205 N1 C116 C108 59.3(13) . . . . ?
C205 N1 C1 N2 0.4(11) . . . . ?
C116 N1 C1 N2 -175.5(8) . . . . ?
C205 N1 C1 Bi1 -177.8(7) . . . . ?
C116 N1 C1 Bi1 6.2(13) . . . . ?
C206 N2 C1 N1 -0.4(11) . . . . ?
C115 N2 C1 N1 -178.8(8) . . . . ?
C206 N2 C1 Bi1 177.7(7) . . . . ?
C115 N2 C1 Bi1 -0.7(14) . . . . ?
Cl2 Bi1 C1 N1 136.5(8) . . . . ?
Cl1 Bi1 C1 N1 -131.5(8) . . . . ?
O2 Bi1 C1 N1 -46.3(8) . . . . ?
O1 Bi1 C1 N1 53.6(8) . . . . ?
Cl2 Bi1 C1 N2 -41.3(9) . . . . ?
Cl1 Bi1 C1 N2 50.7(9) . . . . ?
O2 Bi1 C1 N2 135.9(9) . . . . ?
O1 Bi1 C1 N2 -124.2(9) . . . . ?
C1 N1 C205 C206 -0.2(11) . . . . ?
C116 N1 C205 C206 175.6(9) . . . . ?
C1 N1 C205 C201 176.8(10) . . . . ?
C116 N1 C205 C201 -7.4(16) . . . . ?
C1 N2 C206 C205 0.3(11) . . . . ?
C115 N2 C206 C205 178.6(9) . . . . ?
C1 N2 C206 C204 -178.9(10) . . . . ?
C115 N2 C206 C204 -0.5(16) . . . . ?
N1 C205 C206 N2 0.0(11) . . . . ?
C201 C205 C206 N2 -177.1(10) . . . . ?
N1 C205 C206 C204 179.1(10) . . . . ?
C201 C205 C206 C204 2.1(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.892
_refine_diff_density_min         -2.147
_refine_diff_density_rms         0.232
_database_code_depnum_ccdc_archive 'CCDC 963493'