# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 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_yodme

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H33 Bi O4'
_chemical_formula_sum            'C36 H33 Bi O4'
_chemical_formula_weight         738.60

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   20.8600(11)
_cell_length_b                   9.7446(4)
_cell_length_c                   15.9050(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.932(3)
_cell_angle_gamma                90.00
_cell_volume                     3231.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    37.741
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      27.60

_exptl_crystal_description       rhombus
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    5.492
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.311
_exptl_absorpt_correction_T_max  0.490
_exptl_absorpt_process_details   'SADDABS (Bruker 2005)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(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  'Bruker X8 Apex KAPPA CCD'
_diffrn_measurement_method       '0.5 deg frames in phi and omega'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            37741
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0122
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         27.60
_reflns_number_total             3738
_reflns_number_gt                3335
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2 v2.0 (Bruker Axs 2005)'
_computing_cell_refinement       'Bruker Apex2 v2.0 (Bruker Axs 2005)'
_computing_data_reduction        'Bruker Apex2 v2.0 (Bruker Axs 2005)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-seed (Barbour, 2001)'
_computing_publication_material  'CIFTAB (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0337P)²+3.5036P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0192
_refine_ls_R_factor_gt           0.0147
_refine_ls_wR_factor_ref         0.0688
_refine_ls_wR_factor_gt          0.0491
_refine_ls_goodness_of_fit_ref   1.410
_refine_ls_restrained_S_all      1.410
_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 0.0000 0.246701(11) 0.2500 0.01376(7) Uani 1 2 d S . .
O1 O 0.08505(9) 0.45787(19) 0.21843(12) 0.0198(4) Uani 1 1 d . . .
O2 O 0.10478(12) 0.23422(19) 0.21332(17) 0.0211(5) Uani 1 1 d . . .
C11 C -0.05957(14) 0.4105(3) 0.09437(17) 0.0235(6) Uani 1 1 d . . .
H11 H -0.0728 0.4758 0.1346 0.028 Uiso 1 1 calc R . .
C1 C 0.12112(13) 0.3608(3) 0.20222(16) 0.0176(5) Uani 1 1 d . . .
C10 C -0.02506(13) 0.2969(3) 0.11870(16) 0.0167(5) Uani 1 1 d . . .
C14 C -0.0201(2) 0.2194(4) -0.0232(2) 0.0348(8) Uani 1 1 d . . .
H14 H -0.0063 0.1548 -0.0635 0.042 Uiso 1 1 calc R . .
C7 C 0.22403(18) 0.2753(4) 0.1457(3) 0.0296(7) Uani 1 1 d . . .
H7 H 0.2097 0.1841 0.1549 0.036 Uiso 1 1 calc R . .
C3 C 0.20698(14) 0.5190(3) 0.15562(18) 0.0250(6) Uani 1 1 d . . .
H3 H 0.1809 0.5940 0.1713 0.030 Uiso 1 1 calc R . .
C2 C 0.18584(13) 0.3852(3) 0.16756(17) 0.0217(6) Uani 1 1 d . . .
C13 C -0.05556(16) 0.3326(3) -0.04892(18) 0.0281(7) Uani 1 1 d . . .
H13 H -0.0667 0.3449 -0.1068 0.034 Uiso 1 1 calc R . .
C15 C -0.00457(17) 0.1999(3) 0.06131(19) 0.0294(7) Uani 1 1 d . . .
H15 H 0.0195 0.1221 0.0797 0.035 Uiso 1 1 calc R . .
C12 C -0.07481(16) 0.4277(3) 0.00936(18) 0.0298(7) Uani 1 1 d . . .
H12 H -0.0987 0.5058 -0.0089 0.036 Uiso 1 1 calc R . .
C6 C 0.28304(17) 0.2978(5) 0.1104(2) 0.0385(8) Uani 1 1 d . . .
C4 C 0.26632(15) 0.5433(4) 0.12075(19) 0.0350(8) Uani 1 1 d . . .
C5 C 0.30296(16) 0.4306(5) 0.0985(2) 0.0415(9) Uani 1 1 d . . .
H5 H 0.3433 0.4460 0.0742 0.050 Uiso 1 1 calc R . .
C8 C 0.2897(2) 0.6878(5) 0.1081(3) 0.0503(11) Uani 1 1 d . . .
H8A H 0.3188 0.7137 0.1551 0.075 Uiso 1 1 calc R . .
H8B H 0.2530 0.7506 0.1056 0.075 Uiso 1 1 calc R . .
H8C H 0.3125 0.6932 0.0553 0.075 Uiso 1 1 calc R . .
C9 C 0.32327(19) 0.1768(6) 0.0853(3) 0.0556(12) Uani 1 1 d . . .
H9A H 0.3244 0.1087 0.1307 0.083 Uiso 1 1 calc R . .
H9B H 0.3670 0.2078 0.0749 0.083 Uiso 1 1 calc R . .
H9C H 0.3046 0.1353 0.0340 0.083 Uiso 1 1 calc R . .
C19 C 0.0000 -0.2638(4) 0.2500 0.0234(10) Uani 1 2 d S . .
H19 H 0.0000 -0.3613 0.2500 0.028 Uiso 1 2 calc SR . .
C16 C 0.0000 0.0203(4) 0.2500 0.0168(7) Uani 1 2 d S . .
C21 C 0.05768(14) -0.0502(3) 0.25702(17) 0.0212(6) Uani 1 1 d . . .
H21 H 0.0971 -0.0014 0.2618 0.025 Uiso 1 1 calc R . .
C20 C 0.05730(15) -0.1928(3) 0.25694(18) 0.0238(6) Uani 1 1 d . . .
H20 H 0.0966 -0.2417 0.2617 0.029 Uiso 1 1 calc R . .


_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 C10 2.191(3) . ?
Bi1 C10 2.191(3) 2 ?
Bi1 C16 2.206(3) . ?
Bi1 O2 2.284(3) 2 ?
Bi1 O2 2.284(3) . ?
Bi1 O1 2.7737(19) . ?
O1 C1 1.241(3) . ?
O2 C1 1.293(3) . ?
C11 C10 1.369(4) . ?
C11 C12 1.389(4) . ?
C11 H11 0.9500 . ?
C1 C2 1.494(4) . ?
C10 C15 1.391(4) . ?
C14 C13 1.383(5) . ?
C14 C15 1.384(5) . ?
C14 H14 0.9500 . ?
C7 C2 1.386(4) . ?
C7 C6 1.387(6) . ?
C7 H7 0.9500 . ?
C3 C2 1.391(4) . ?
C3 C4 1.394(4) . ?
C3 H3 0.9500 . ?
C13 C12 1.380(4) . ?
C13 H13 0.9500 . ?
C15 H15 0.9500 . ?
C12 H12 0.9500 . ?
C6 C5 1.375(6) . ?
C6 C9 1.509(6) . ?
C4 C5 1.390(5) . ?
C4 C8 1.506(5) . ?
C5 H5 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C19 C20 1.382(4) . ?
C19 C20 1.382(4) 2 ?
C19 H19 0.9500 . ?
C16 C21 1.387(3) . ?
C16 C21 1.387(3) 2 ?
C21 C20 1.389(4) . ?
C21 H21 0.9500 . ?
C20 H20 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 Bi1 C10 154.19(15) . 2 ?
C10 Bi1 C16 102.91(7) . . ?
C10 Bi1 C16 102.91(7) 2 . ?
C10 Bi1 O2 93.20(10) . 2 ?
C10 Bi1 O2 88.17(10) 2 2 ?
C16 Bi1 O2 86.95(5) . 2 ?
C10 Bi1 O2 88.17(10) . . ?
C10 Bi1 O2 93.20(10) 2 . ?
C16 Bi1 O2 86.95(5) . . ?
O2 Bi1 O2 173.89(9) 2 . ?
C10 Bi1 O1 78.19(8) . . ?
C10 Bi1 O1 82.72(8) 2 . ?
C16 Bi1 O1 137.89(4) . . ?
O2 Bi1 O1 135.16(6) 2 . ?
O2 Bi1 O1 50.95(6) . . ?
C1 O1 Bi1 82.42(16) . . ?
C1 O2 Bi1 104.06(18) . . ?
C10 C11 C12 118.3(3) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
O1 C1 O2 122.3(3) . . ?
O1 C1 C2 121.1(2) . . ?
O2 C1 C2 116.6(2) . . ?
C11 C10 C15 122.3(3) . . ?
C11 C10 Bi1 123.8(2) . . ?
C15 C10 Bi1 113.9(2) . . ?
C13 C14 C15 120.1(3) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C2 C7 C6 120.3(4) . . ?
C2 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C2 C3 C4 120.2(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C7 C2 C3 120.1(3) . . ?
C7 C2 C1 120.3(3) . . ?
C3 C2 C1 119.6(3) . . ?
C12 C13 C14 120.1(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C14 C15 C10 118.5(3) . . ?
C14 C15 H15 120.8 . . ?
C10 C15 H15 120.8 . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C5 C6 C7 118.7(4) . . ?
C5 C6 C9 121.7(4) . . ?
C7 C6 C9 119.5(5) . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 C8 121.4(3) . . ?
C3 C4 C8 120.5(4) . . ?
C6 C5 C4 122.5(3) . . ?
C6 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
C4 C8 H8A 109.5 . . ?
C4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C20 C19 C20 119.9(4) . 2 ?
C20 C19 H19 120.0 . . ?
C20 C19 H19 120.0 2 . ?
C21 C16 C21 120.6(3) . 2 ?
C21 C16 Bi1 119.70(17) . . ?
C21 C16 Bi1 119.70(17) 2 . ?
C16 C21 C20 119.4(3) . . ?
C16 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C19 C20 C21 120.4(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.583
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.232
_database_code_depnum_ccdc_archive 'CCDC 978095'
#######################################################################
#
#                 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_vb78-yc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H29 Bi O6'
_chemical_formula_sum            'C34 H29 Bi O6'
_chemical_formula_weight         742.55

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.028 10.608 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   15.413(3)
_cell_length_b                   9.4312(19)
_cell_length_c                   19.920(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.62(3)
_cell_angle_gamma                90.00
_cell_volume                     2894.6(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    22811
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.704
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1456
_exptl_absorpt_coefficient_mu    6.136
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7914
_exptl_absorpt_correction_T_max  0.9412
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 210r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22123
_diffrn_reflns_av_R_equivalents  0.0702
_diffrn_reflns_av_sigmaI/netI    0.0412
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         27.20
_reflns_number_total             3205
_reflns_number_gt                3181
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_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. 

 The data is a merge of two synchrotron data sets collected on the same crystal sample
 at different orientations inorder to get satisfactory data.

 Atom C18 sits on a two fold symmerty axis and to avoid an unusually shaped
 elipsoid was modelled with approximate isotropic behaviour.

;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0223P)²+9.1015P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     188
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0231
_refine_ls_R_factor_gt           0.0230
_refine_ls_wR_factor_ref         0.0563
_refine_ls_wR_factor_gt          0.0563
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.045
_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 0.0000 0.113889(12) 0.7500 0.01194(6) Uani 1 2 d S . .
O1 O 0.04857(14) 0.3215(2) 0.66345(10) 0.0204(4) Uani 1 1 d . . .
O2 O 0.05370(15) 0.0908(2) 0.64489(11) 0.0189(4) Uani 1 1 d . . .
O3 O 0.11955(16) 0.0039(2) 0.53229(11) 0.0256(5) Uani 1 1 d . . .
C1 C 0.06588(17) 0.2198(3) 0.62586(13) 0.0163(5) Uani 1 1 d . . .
C2 C 0.10016(17) 0.2480(3) 0.55769(13) 0.0169(5) Uani 1 1 d . . .
C3 C 0.1068(2) 0.3894(3) 0.53823(18) 0.0220(6) Uani 1 1 d . . .
H3 H 0.0890 0.4613 0.5683 0.026 Uiso 1 1 calc R . .
C4 C 0.1384(2) 0.4284(4) 0.47654(16) 0.0259(6) Uani 1 1 d . . .
H4 H 0.1413 0.5254 0.4639 0.031 Uiso 1 1 calc R . .
C5 C 0.1658(2) 0.3221(4) 0.43351(15) 0.0254(6) Uani 1 1 d . . .
H5 H 0.1894 0.3473 0.3916 0.031 Uiso 1 1 calc R . .
C6 C 0.15919(19) 0.1814(3) 0.45062(15) 0.0223(6) Uani 1 1 d . . .
H6 H 0.1769 0.1106 0.4200 0.027 Uiso 1 1 calc R . .
C7 C 0.1266(2) 0.1412(3) 0.51283(15) 0.0191(5) Uani 1 1 d . . .
C8 C 0.1336(3) -0.1026(3) 0.4828(2) 0.0326(8) Uani 1 1 d . . .
H8A H 0.0967 -0.0835 0.4430 0.049 Uiso 1 1 calc R . .
H8B H 0.1191 -0.1958 0.5012 0.049 Uiso 1 1 calc R . .
H8C H 0.1947 -0.1017 0.4704 0.049 Uiso 1 1 calc R . .
C9 C -0.12948(17) 0.1705(3) 0.70900(13) 0.0161(5) Uani 1 1 d . . .
C10 C -0.14867(19) 0.2982(3) 0.67780(14) 0.0191(5) Uani 1 1 d . . .
H10 H -0.1057 0.3697 0.6741 0.023 Uiso 1 1 calc R . .
C11 C -0.23281(19) 0.3195(3) 0.65184(15) 0.0217(6) Uani 1 1 d . . .
H11 H -0.2476 0.4066 0.6305 0.026 Uiso 1 1 calc R . .
C12 C -0.29492(19) 0.2137(4) 0.65707(16) 0.0252(6) Uani 1 1 d . . .
H12 H -0.3517 0.2286 0.6387 0.030 Uiso 1 1 calc R . .
C13 C -0.2747(2) 0.0864(4) 0.68898(19) 0.0272(6) Uani 1 1 d . . .
H13 H -0.3178 0.0150 0.6929 0.033 Uiso 1 1 calc R . .
C14 C -0.19114(19) 0.0642(3) 0.71511(15) 0.0219(6) Uani 1 1 d . . .
H14 H -0.1764 -0.0226 0.7368 0.026 Uiso 1 1 calc R . .
C15 C 0.0000 -0.1194(4) 0.7500 0.0166(8) Uani 1 2 d S . .
C16 C -0.01242(18) -0.1920(3) 0.68990(13) 0.0164(5) Uani 1 1 d . . .
H16 H -0.0208 -0.1417 0.6489 0.020 Uiso 1 1 calc R . .
C17 C -0.01250(18) -0.3399(3) 0.69045(15) 0.0192(5) Uani 1 1 d . . .
H17 H -0.0213 -0.3900 0.6494 0.023 Uiso 1 1 calc R . .
C18 C 0.0000 -0.4157(4) 0.7500 0.0090(6) Uani 1 2 d SU . .
H18 H 0.0000 -0.5164 0.7500 0.011 Uiso 1 2 calc SR . .


_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 C15 2.200(3) . ?
Bi1 C9 2.201(3) . ?
Bi1 C9 2.201(3) 2_556 ?
Bi1 O2 2.284(2) 2_556 ?
Bi1 O2 2.284(2) . ?
Bi1 O1 2.728(2) 2_556 ?
Bi1 O1 2.728(2) . ?
O1 C1 1.250(3) . ?
O2 C1 1.290(3) . ?
O3 C7 1.357(4) . ?
O3 C8 1.428(4) . ?
C1 C2 1.495(4) . ?
C2 C3 1.394(4) . ?
C2 C7 1.414(4) . ?
C3 C4 1.385(4) . ?
C4 C5 1.392(5) . ?
C5 C6 1.375(4) . ?
C6 C7 1.403(4) . ?
C9 C10 1.383(4) . ?
C9 C14 1.389(4) . ?
C10 C11 1.397(4) . ?
C11 C12 1.388(4) . ?
C12 C13 1.390(5) . ?
C13 C14 1.392(4) . ?
C15 C16 1.388(3) . ?
C15 C16 1.388(3) 2_556 ?
C16 C17 1.395(4) . ?
C17 C18 1.393(3) . ?
C18 C17 1.394(3) 2_556 ?

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
C15 Bi1 C9 104.03(7) . . ?
C15 Bi1 C9 104.03(7) . 2_556 ?
C9 Bi1 C9 151.93(14) . 2_556 ?
C15 Bi1 O2 84.52(5) . 2_556 ?
C9 Bi1 O2 90.86(9) . 2_556 ?
C9 Bi1 O2 91.80(9) 2_556 2_556 ?
C15 Bi1 O2 84.52(5) . . ?
C9 Bi1 O2 91.80(9) . . ?
C9 Bi1 O2 90.86(9) 2_556 . ?
O2 Bi1 O2 169.04(10) 2_556 . ?
C15 Bi1 O1 135.88(4) . 2_556 ?
C9 Bi1 O1 78.36(8) . 2_556 ?
C9 Bi1 O1 81.58(9) 2_556 2_556 ?
O2 Bi1 O1 51.38(7) 2_556 2_556 ?
O2 Bi1 O1 139.57(7) . 2_556 ?
C15 Bi1 O1 135.88(4) . . ?
C9 Bi1 O1 81.58(9) . . ?
C9 Bi1 O1 78.36(9) 2_556 . ?
O2 Bi1 O1 139.57(7) 2_556 . ?
O2 Bi1 O1 51.39(7) . . ?
O1 Bi1 O1 88.25(9) 2_556 . ?
C1 O1 Bi1 83.97(16) . . ?
C1 O2 Bi1 103.81(16) . . ?
C7 O3 C8 117.4(3) . . ?
O1 C1 O2 120.8(2) . . ?
O1 C1 C2 119.7(2) . . ?
O2 C1 C2 119.5(2) . . ?
C3 C2 C7 118.8(3) . . ?
C3 C2 C1 116.9(3) . . ?
C7 C2 C1 124.3(3) . . ?
C4 C3 C2 122.1(3) . . ?
C3 C4 C5 118.4(3) . . ?
C6 C5 C4 121.1(3) . . ?
C5 C6 C7 120.7(3) . . ?
O3 C7 C6 122.9(3) . . ?
O3 C7 C2 118.2(3) . . ?
C6 C7 C2 118.9(3) . . ?
C10 C9 C14 122.0(3) . . ?
C10 C9 Bi1 123.9(2) . . ?
C14 C9 Bi1 114.1(2) . . ?
C9 C10 C11 118.4(3) . . ?
C12 C11 C10 120.3(3) . . ?
C11 C12 C13 120.6(3) . . ?
C12 C13 C14 119.6(3) . . ?
C9 C14 C13 119.1(3) . . ?
C16 C15 C16 120.9(3) . 2_556 ?
C16 C15 Bi1 119.57(17) . . ?
C16 C15 Bi1 119.57(17) 2_556 . ?
C15 C16 C17 119.1(3) . . ?
C18 C17 C16 121.3(3) . . ?
C17 C18 C17 118.3(3) . 2_556 ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.20
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.890
_refine_diff_density_min         -2.027
_refine_diff_density_rms         0.131
_database_code_depnum_ccdc_archive 'CCDC 978096'
#######################################################################
#
#                 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_vb73-yc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C36 H33 Bi O6'
_chemical_formula_sum            'C36 H33 Bi O6'
_chemical_formula_weight         770.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.028 10.608 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   19.838(4)
_cell_length_b                   9.6450(19)
_cell_length_c                   15.899(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.27(3)
_cell_angle_gamma                90.00
_cell_volume                     3042.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    31429
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.683
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
_exptl_absorpt_coefficient_mu    5.842
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8442
_exptl_absorpt_correction_T_max  0.8921
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX2 beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 315r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            29667
_diffrn_reflns_av_R_equivalents  0.0501
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.35
_diffrn_reflns_theta_max         29.61
_reflns_number_total             4067
_reflns_number_gt                3885
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_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. 

 Due to hardware constraints (synchrotron radiation source) the reported 
 diffraction measured fraction theta full is slightly low.  
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0398P)²+9.5531P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4067
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0268
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0676
_refine_ls_wR_factor_gt          0.0655
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_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 0.0000 0.256511(10) 0.2500 0.01336(6) Uani 1 2 d S . .
O1 O -0.11019(11) 0.2715(2) 0.21186(16) 0.0195(4) Uani 1 1 d . . .
O2 O -0.09565(9) 0.04295(19) 0.21096(12) 0.0188(4) Uani 1 1 d . . .
O3 O -0.21281(10) 0.3675(2) 0.12638(14) 0.0237(4) Uani 1 1 d . . .
C1 C -0.13107(12) 0.1464(3) 0.19677(16) 0.0153(4) Uani 1 1 d . . .
C2 C -0.20078(13) 0.1295(3) 0.16156(17) 0.0173(5) Uani 1 1 d . . .
C3 C -0.22837(13) -0.0043(3) 0.16265(18) 0.0208(5) Uani 1 1 d . . .
H3 H -0.2024 -0.0784 0.1851 0.025 Uiso 1 1 calc R . .
C4 C -0.29263(14) -0.0315(3) 0.1318(2) 0.0268(6) Uani 1 1 d . . .
H4 H -0.3107 -0.1226 0.1342 0.032 Uiso 1 1 calc R . .
C5 C -0.32997(14) 0.0762(3) 0.0976(2) 0.0270(6) Uani 1 1 d . . .
H5 H -0.3737 0.0584 0.0756 0.032 Uiso 1 1 calc R . .
C6 C -0.30419(14) 0.2094(3) 0.0951(2) 0.0243(5) Uani 1 1 d . . .
H6 H -0.3303 0.2819 0.0709 0.029 Uiso 1 1 calc R . .
C7 C -0.24007(17) 0.2384(3) 0.1277(2) 0.0206(6) Uani 1 1 d . . .
C8 C -0.25373(14) 0.4793(3) 0.0959(2) 0.0260(6) Uani 1 1 d . . .
H8A H -0.2959 0.4858 0.1286 0.031 Uiso 1 1 calc R . .
H8B H -0.2655 0.4645 0.0360 0.031 Uiso 1 1 calc R . .
C9 C -0.21267(18) 0.6103(3) 0.1060(2) 0.0351(7) Uani 1 1 d . . .
H9A H -0.2028 0.6255 0.1658 0.053 Uiso 1 1 calc R . .
H9B H -0.2382 0.6893 0.0838 0.053 Uiso 1 1 calc R . .
H9C H -0.1703 0.6011 0.0751 0.053 Uiso 1 1 calc R . .
C10 C 0.0000 0.4851(3) 0.2500 0.0156(6) Uani 1 2 d S . .
C11 C -0.06089(13) 0.5567(3) 0.24368(17) 0.0183(5) Uani 1 1 d . . .
H11 H -0.1022 0.5075 0.2384 0.022 Uiso 1 1 calc R . .
C12 C -0.06053(14) 0.7005(3) 0.24525(17) 0.0200(5) Uani 1 1 d . . .
H12 H -0.1020 0.7497 0.2431 0.024 Uiso 1 1 calc R . .
C13 C 0.0000 0.7739(4) 0.2500 0.0198(7) Uani 1 2 d S . .
H13 H 0.0000 0.8724 0.2500 0.024 Uiso 1 2 calc SR . .
C14 C 0.02589(12) 0.1977(3) 0.12053(16) 0.0164(4) Uani 1 1 d . . .
C15 C 0.00331(16) 0.2911(3) 0.05980(19) 0.0248(6) Uani 1 1 d . . .
H15 H -0.0234 0.3688 0.0751 0.030 Uiso 1 1 calc R . .
C16 C 0.0208(2) 0.2681(3) -0.0238(3) 0.0303(7) Uani 1 1 d . . .
H16 H 0.0059 0.3302 -0.0664 0.036 Uiso 1 1 calc R . .
C17 C 0.06013(14) 0.1537(3) -0.04475(18) 0.0227(5) Uani 1 1 d . . .
H17 H 0.0727 0.1389 -0.1016 0.027 Uiso 1 1 calc R . .
C18 C 0.08098(14) 0.0614(3) 0.01689(18) 0.0220(5) Uani 1 1 d . . .
H18 H 0.1070 -0.0173 0.0017 0.026 Uiso 1 1 calc R . .
C19 C 0.06422(13) 0.0826(3) 0.10080(17) 0.0200(5) Uani 1 1 d . . .
H19 H 0.0787 0.0198 0.1433 0.024 Uiso 1 1 calc R . .


_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 C14 2.198(3) . ?
Bi1 C14 2.198(3) 2 ?
Bi1 C10 2.204(3) . ?
Bi1 O1 2.270(2) 2 ?
Bi1 O1 2.270(2) . ?
O1 C1 1.298(3) . ?
O2 C1 1.240(3) . ?
O3 C7 1.357(3) . ?
O3 C8 1.433(3) . ?
C1 C2 1.498(3) . ?
C2 C3 1.401(4) . ?
C2 C7 1.413(4) . ?
C3 C4 1.389(4) . ?
C4 C5 1.386(4) . ?
C5 C6 1.383(4) . ?
C6 C7 1.400(4) . ?
C8 C9 1.511(4) . ?
C10 C11 1.395(3) 2 ?
C10 C11 1.395(3) . ?
C11 C12 1.388(3) . ?
C12 C13 1.395(3) . ?
C13 C12 1.395(3) 2 ?
C14 C19 1.383(3) . ?
C14 C15 1.393(4) . ?
C15 C16 1.393(5) . ?
C16 C17 1.393(4) . ?
C17 C18 1.386(4) . ?
C18 C19 1.391(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 Bi1 C14 150.12(13) . 2 ?
C14 Bi1 C10 104.94(6) . . ?
C14 Bi1 C10 104.94(6) 2 . ?
C14 Bi1 O1 92.15(9) . 2 ?
C14 Bi1 O1 89.72(9) 2 2 ?
C10 Bi1 O1 86.36(5) . 2 ?
C14 Bi1 O1 89.72(9) . . ?
C14 Bi1 O1 92.15(9) 2 . ?
C10 Bi1 O1 86.36(5) . . ?
O1 Bi1 O1 172.72(10) 2 . ?
C1 O1 Bi1 107.24(16) . . ?
C7 O3 C8 118.1(2) . . ?
O2 C1 O1 122.3(2) . . ?
O2 C1 C2 120.1(2) . . ?
O1 C1 C2 117.6(2) . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 117.1(2) . . ?
C7 C2 C1 124.6(2) . . ?
C4 C3 C2 121.9(3) . . ?
C5 C4 C3 119.0(3) . . ?
C6 C5 C4 120.7(3) . . ?
C5 C6 C7 120.7(3) . . ?
O3 C7 C6 122.6(3) . . ?
O3 C7 C2 118.0(3) . . ?
C6 C7 C2 119.4(3) . . ?
O3 C8 C9 106.8(2) . . ?
C11 C10 C11 120.6(3) 2 . ?
C11 C10 Bi1 119.68(16) 2 . ?
C11 C10 Bi1 119.68(16) . . ?
C12 C11 C10 119.3(2) . . ?
C11 C12 C13 120.8(3) . . ?
C12 C13 C12 119.1(4) . 2 ?
C19 C14 C15 122.5(3) . . ?
C19 C14 Bi1 123.41(19) . . ?
C15 C14 Bi1 113.98(19) . . ?
C14 C15 C16 118.5(3) . . ?
C17 C16 C15 119.8(3) . . ?
C18 C17 C16 120.4(3) . . ?
C17 C18 C19 120.8(2) . . ?
C14 C19 C18 118.0(2) . . ?

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         1.594
_refine_diff_density_min         -1.498
_refine_diff_density_rms         0.134
_database_code_depnum_ccdc_archive 'CCDC 978097'
#######################################################################
#
#                 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_vb39-yc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H23 Bi N2 O8'
_chemical_formula_sum            'C32 H23 Bi N2 O8'
_chemical_formula_weight         772.50

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.1077 10.2566 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'F d d 2'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   13.4495(7)
_cell_length_b                   19.5188(13)
_cell_length_c                   21.4053(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5619.3(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2022
_cell_measurement_theta_min      2.0663
_cell_measurement_theta_max      29.2775

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.826
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3008
_exptl_absorpt_coefficient_mu    6.333
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.1439
_exptl_absorpt_correction_T_max  0.3640
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Ruby, Gemini ultra'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3813
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0496
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.07
_diffrn_reflns_theta_max         29.34
_reflns_number_total             2377
_reflns_number_gt                2162
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIF-TAB

_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.

 The highest residual electron density peak is found 0.913 Angstrongs from 
 Bi1. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.023(7)
_refine_ls_number_reflns         2377
_refine_ls_number_parameters     196
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0184
_refine_ls_wR_factor_ref         0.0418
_refine_ls_wR_factor_gt          0.0389
_refine_ls_goodness_of_fit_ref   0.849
_refine_ls_restrained_S_all      0.849
_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 0.5000 0.0000 0.47748(3) 0.01585(6) Uani 1 2 d S . .
O1 O -0.1493(2) 0.10375(17) 0.36133(16) 0.0347(8) Uani 1 1 d . . .
O2 O 0.3410(2) 0.03938(16) 0.48590(13) 0.0229(7) Uani 1 1 d . . .
O3 O -0.1583(2) 0.1111(2) 0.46217(16) 0.0373(9) Uani 1 1 d . . .
O4 O 0.3553(2) 0.03593(16) 0.38244(14) 0.0236(7) Uani 1 1 d . . .
N12 N -0.1113(3) 0.1028(2) 0.4138(2) 0.0283(9) Uani 1 1 d . . .
C1 C 0.3051(3) 0.0454(2) 0.4302(2) 0.0194(9) Uani 1 1 d . . .
C2 C 0.1960(3) 0.0636(2) 0.4256(2) 0.0187(9) Uani 1 1 d . . .
C3 C 0.1508(4) 0.0708(2) 0.3678(2) 0.0240(11) Uani 1 1 d . . .
H3 H 0.1888 0.0657 0.3307 0.029 Uiso 1 1 calc R . .
C4 C 0.0507(3) 0.0852(2) 0.3642(2) 0.0259(11) Uani 1 1 d . . .
H4 H 0.0191 0.0907 0.3248 0.031 Uiso 1 1 calc R . .
C5 C -0.0022(3) 0.0915(2) 0.4182(2) 0.0217(10) Uani 1 1 d . . .
C6 C 0.0404(3) 0.0865(2) 0.4764(3) 0.0244(9) Uani 1 1 d . . .
H6 H 0.0021 0.0930 0.5132 0.029 Uiso 1 1 calc R . .
C7 C 0.1402(3) 0.0719(2) 0.4797(3) 0.0222(10) Uani 1 1 d . . .
H7 H 0.1713 0.0674 0.5193 0.027 Uiso 1 1 calc R . .
C8 C 0.5550(3) 0.0984(2) 0.4440(2) 0.0200(10) Uani 1 1 d . . .
C9 C 0.5572(3) 0.1147(2) 0.3806(2) 0.0220(10) Uani 1 1 d . . .
H9 H 0.5350 0.0828 0.3501 0.026 Uiso 1 1 calc R . .
C10 C 0.5928(4) 0.1792(2) 0.3629(2) 0.0259(11) Uani 1 1 d . . .
H10 H 0.5938 0.1920 0.3201 0.031 Uiso 1 1 calc R . .
C11 C 0.6265(4) 0.2240(2) 0.4080(3) 0.0322(12) Uani 1 1 d . . .
H11 H 0.6515 0.2674 0.3956 0.039 Uiso 1 1 calc R . .
C12 C 0.6247(3) 0.2073(2) 0.4709(3) 0.0291(11) Uani 1 1 d . . .
H12 H 0.6481 0.2391 0.5012 0.035 Uiso 1 1 calc R . .
C13 C 0.5885(3) 0.1438(2) 0.4894(2) 0.0236(10) Uani 1 1 d . . .
H13 H 0.5867 0.1316 0.5324 0.028 Uiso 1 1 calc R . .
C14 C 0.5000 0.0000 0.5802(3) 0.0190(13) Uani 1 2 d S . .
C15 C 0.4112(4) -0.0078(2) 0.6124(2) 0.0251(10) Uani 1 1 d . . .
H15 H 0.3506 -0.0129 0.5902 0.030 Uiso 1 1 calc R . .
C16 C 0.4113(4) -0.0083(2) 0.6777(2) 0.0317(12) Uani 1 1 d . . .
H16 H 0.3508 -0.0142 0.6999 0.038 Uiso 1 1 calc R . .
C17 C 0.5000 0.0000 0.7100(3) 0.0347(18) Uani 1 2 d S . .
H17 H 0.5000 0.0000 0.7543 0.042 Uiso 1 2 calc SR . .


_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 C8 2.180(4) 2_655 ?
Bi1 C8 2.180(4) . ?
Bi1 C14 2.198(6) . ?
Bi1 O2 2.280(3) . ?
Bi1 O2 2.280(3) 2_655 ?
O1 N12 1.235(5) . ?
O2 C1 1.292(5) . ?
O3 N12 1.223(5) . ?
O4 C1 1.238(5) . ?
N12 C5 1.486(5) . ?
C1 C2 1.514(6) . ?
C2 C3 1.385(6) . ?
C2 C7 1.390(7) . ?
C3 C4 1.378(7) . ?
C4 C5 1.363(7) . ?
C5 C6 1.375(7) . ?
C6 C7 1.373(6) . ?
C8 C13 1.391(6) . ?
C8 C9 1.394(6) . ?
C9 C10 1.399(6) . ?
C10 C11 1.380(7) . ?
C11 C12 1.386(7) . ?
C12 C13 1.390(6) . ?
C14 C15 1.388(6) . ?
C14 C15 1.388(6) 2_655 ?
C15 C16 1.397(7) . ?
C16 C17 1.387(7) . ?
C17 C16 1.387(7) 2_655 ?

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
C8 Bi1 C8 141.6(2) 2_655 . ?
C8 Bi1 C14 109.21(11) 2_655 . ?
C8 Bi1 C14 109.21(11) . . ?
C8 Bi1 O2 90.29(13) 2_655 . ?
C8 Bi1 O2 92.69(13) . . ?
C14 Bi1 O2 85.47(7) . . ?
C8 Bi1 O2 92.69(13) 2_655 2_655 ?
C8 Bi1 O2 90.29(13) . 2_655 ?
C14 Bi1 O2 85.47(7) . 2_655 ?
O2 Bi1 O2 170.93(14) . 2_655 ?
C1 O2 Bi1 107.9(3) . . ?
O3 N12 O1 123.7(4) . . ?
O3 N12 C5 118.4(4) . . ?
O1 N12 C5 117.9(4) . . ?
O4 C1 O2 123.0(4) . . ?
O4 C1 C2 120.6(4) . . ?
O2 C1 C2 116.3(4) . . ?
C3 C2 C7 119.7(4) . . ?
C3 C2 C1 120.5(4) . . ?
C7 C2 C1 119.8(4) . . ?
C4 C3 C2 120.0(5) . . ?
C5 C4 C3 118.7(4) . . ?
C4 C5 C6 123.0(4) . . ?
C4 C5 N12 118.4(4) . . ?
C6 C5 N12 118.6(4) . . ?
C7 C6 C5 118.0(5) . . ?
C6 C7 C2 120.5(5) . . ?
C13 C8 C9 122.0(4) . . ?
C13 C8 Bi1 116.2(3) . . ?
C9 C8 Bi1 121.9(3) . . ?
C8 C9 C10 118.4(4) . . ?
C11 C10 C9 119.6(5) . . ?
C10 C11 C12 121.7(5) . . ?
C11 C12 C13 119.5(4) . . ?
C12 C13 C8 118.8(4) . . ?
C15 C14 C15 120.3(6) . 2_655 ?
C15 C14 Bi1 119.9(3) . . ?
C15 C14 Bi1 119.9(3) 2_655 . ?
C14 C15 C16 119.8(5) . . ?
C17 C16 C15 119.8(5) . . ?
C16 C17 C16 120.3(7) . 2_655 ?

_diffrn_measured_fraction_theta_max 0.838
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.913
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.091
_database_code_depnum_ccdc_archive 'CCDC 978098'
#######################################################################
#
#                 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_vb53-yc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H23 Bi Cl2 O6, C4 H8 O'
_chemical_formula_sum            'C36 H31 Bi Cl2 O7'
_chemical_formula_weight         855.49

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'
O O 0.0106 0.0060 '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 -4.028 10.608 '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                   9.1640(18)
_cell_length_b                   11.027(2)
_cell_length_c                   17.058(3)
_cell_angle_alpha                103.21(3)
_cell_angle_beta                 90.76(3)
_cell_angle_gamma                100.90(3)
_cell_volume                     1645.0(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27775
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.727
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    5.571
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8507
_exptl_absorpt_correction_T_max  0.8967
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 210r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27996
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0262
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.23
_diffrn_reflns_theta_max         28.74
_reflns_number_total             7377
_reflns_number_gt                7274
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_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. 

 Due to hardware constraints (synchrotorn radiation and fixed phi) diffraction
 measured fraction theta full is low.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0092P)²+4.1320P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7377
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0232
_refine_ls_R_factor_gt           0.0229
_refine_ls_wR_factor_ref         0.0552
_refine_ls_wR_factor_gt          0.0551
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.710174(10) 0.553813(9) 0.735898(6) 0.01458(4) Uani 1 1 d . . .
Cl1 Cl 1.01603(11) 0.01322(8) 0.82845(5) 0.03500(18) Uani 1 1 d . . .
Cl2 Cl 0.49802(10) 1.18731(7) 0.85835(5) 0.03079(17) Uani 1 1 d . . .
O1 O 0.7803(2) 0.37134(19) 0.74968(13) 0.0214(4) Uani 1 1 d . . .
O2 O 0.7426(2) 0.3255(2) 0.61610(13) 0.0212(4) Uani 1 1 d . . .
O3 O 0.7942(3) 0.1116(2) 0.52979(13) 0.0267(5) Uani 1 1 d . . .
H3 H 0.7647 0.1808 0.5381 0.032 Uiso 1 1 calc R . .
O4 O 0.6478(2) 0.74752(19) 0.74791(12) 0.0201(4) Uani 1 1 d . . .
O5 O 0.6136(2) 0.69493(19) 0.61388(12) 0.0205(4) Uani 1 1 d . . .
O6 O 0.5051(3) 0.8428(2) 0.54163(12) 0.0233(4) Uani 1 1 d . . .
H6 H 0.5422 0.7803 0.5457 0.028 Uiso 1 1 calc R . .
O7 O 0.7476(3) 0.3298(2) 1.09584(16) 0.0337(5) Uani 1 1 d . . .
C1 C 0.7813(3) 0.2973(3) 0.67870(17) 0.0172(5) Uani 1 1 d . . .
C2 C 0.8372(3) 0.1786(2) 0.67510(17) 0.0166(5) Uani 1 1 d . . .
C3 C 0.8436(3) 0.0936(3) 0.60051(17) 0.0189(5) Uani 1 1 d . . .
C4 C 0.9061(3) -0.0136(3) 0.59728(18) 0.0220(6) Uani 1 1 d . . .
H4 H 0.9111 -0.0706 0.5468 0.026 Uiso 1 1 calc R . .
C5 C 0.9602(3) -0.0371(3) 0.6665(2) 0.0233(6) Uani 1 1 d . . .
H5 H 1.0038 -0.1094 0.6642 0.028 Uiso 1 1 calc R . .
C6 C 0.9505(3) 0.0466(3) 0.74063(18) 0.0218(6) Uani 1 1 d . . .
C7 C 0.8909(3) 0.1524(3) 0.74544(17) 0.0189(5) Uani 1 1 d . . .
H7 H 0.8859 0.2081 0.7964 0.023 Uiso 1 1 calc R . .
C8 C 0.6069(3) 0.7704(2) 0.68034(16) 0.0174(5) Uani 1 1 d . . .
C9 C 0.5551(3) 0.8903(3) 0.68512(16) 0.0172(5) Uani 1 1 d . . .
C10 C 0.5523(3) 0.9737(3) 0.76048(16) 0.0179(5) Uani 1 1 d . . .
H10 H 0.5874 0.9547 0.8081 0.022 Uiso 1 1 calc R . .
C11 C 0.4986(3) 1.0831(3) 0.76497(18) 0.0204(5) Uani 1 1 d . . .
C12 C 0.4450(3) 1.1118(3) 0.69579(19) 0.0230(6) Uani 1 1 d . . .
H12 H 0.4062 1.1869 0.6999 0.028 Uiso 1 1 calc R . .
C13 C 0.4486(3) 1.0310(3) 0.62174(18) 0.0227(6) Uani 1 1 d . . .
H13 H 0.4130 1.0507 0.5745 0.027 Uiso 1 1 calc R . .
C14 C 0.5044(3) 0.9201(3) 0.61568(16) 0.0178(5) Uani 1 1 d . . .
C15 C 0.4810(3) 0.4609(3) 0.69406(18) 0.0192(5) Uani 1 1 d . . .
C16 C 0.3789(4) 0.4595(3) 0.7534(2) 0.0260(6) Uani 1 1 d . . .
H16 H 0.4087 0.4964 0.8086 0.031 Uiso 1 1 calc R . .
C17 C 0.2306(4) 0.4021(3) 0.7292(2) 0.0322(7) Uani 1 1 d . . .
H17 H 0.1577 0.4000 0.7682 0.039 Uiso 1 1 calc R . .
C18 C 0.1905(4) 0.3487(4) 0.6490(2) 0.0348(8) Uani 1 1 d . . .
H18 H 0.0897 0.3093 0.6333 0.042 Uiso 1 1 calc R . .
C19 C 0.2946(3) 0.3513(3) 0.5905(2) 0.0283(7) Uani 1 1 d . . .
H19 H 0.2649 0.3144 0.5353 0.034 Uiso 1 1 calc R . .
C20 C 0.4427(3) 0.4085(3) 0.61337(19) 0.0233(6) Uani 1 1 d . . .
H20 H 0.5154 0.4114 0.5743 0.028 Uiso 1 1 calc R . .
C21 C 0.7365(3) 0.6121(3) 0.86802(16) 0.0179(5) Uani 1 1 d . . .
C22 C 0.7727(3) 0.7410(3) 0.90544(18) 0.0211(5) Uani 1 1 d . . .
H22 H 0.7865 0.8033 0.8744 0.025 Uiso 1 1 calc R . .
C23 C 0.7883(4) 0.7765(3) 0.98910(18) 0.0251(6) Uani 1 1 d . . .
H23 H 0.8139 0.8640 1.0156 0.030 Uiso 1 1 calc R . .
C24 C 0.7669(4) 0.6862(3) 1.03432(18) 0.0273(6) Uani 1 1 d . . .
H24 H 0.7781 0.7119 1.0915 0.033 Uiso 1 1 calc R . .
C25 C 0.7294(4) 0.5586(3) 0.9968(2) 0.0322(7) Uani 1 1 d . . .
H25 H 0.7132 0.4968 1.0281 0.039 Uiso 1 1 calc R . .
C26 C 0.7151(4) 0.5203(3) 0.91270(19) 0.0274(6) Uani 1 1 d . . .
H26 H 0.6912 0.4326 0.8865 0.033 Uiso 1 1 calc R . .
C27 C 0.9161(3) 0.6122(3) 0.67936(17) 0.0177(5) Uani 1 1 d . . .
C28 C 1.0429(3) 0.6566(3) 0.72995(19) 0.0254(6) Uani 1 1 d . . .
H28 H 1.0393 0.6610 0.7861 0.031 Uiso 1 1 calc R . .
C29 C 1.1775(4) 0.6952(4) 0.6959(2) 0.0326(7) Uani 1 1 d . . .
H29 H 1.2669 0.7254 0.7292 0.039 Uiso 1 1 calc R . .
C30 C 1.1802(4) 0.6894(3) 0.6141(2) 0.0293(7) Uani 1 1 d . . .
H30 H 1.2715 0.7161 0.5915 0.035 Uiso 1 1 calc R . .
C31 C 1.0507(4) 0.6449(3) 0.56494(19) 0.0263(6) Uani 1 1 d . . .
H31 H 1.0535 0.6413 0.5088 0.032 Uiso 1 1 calc R . .
C32 C 0.9163(3) 0.6055(3) 0.59743(17) 0.0212(6) Uani 1 1 d . . .
H32 H 0.8270 0.5747 0.5641 0.025 Uiso 1 1 calc R . .
C33 C 0.6189(4) 0.2307(4) 1.0900(2) 0.0334(7) Uani 1 1 d . . .
H33A H 0.5489 0.2299 1.0451 0.040 Uiso 1 1 calc R . .
H33B H 0.5667 0.2419 1.1408 0.040 Uiso 1 1 calc R . .
C34 C 0.6797(5) 0.1090(4) 1.0743(3) 0.0427(9) Uani 1 1 d . . .
H34A H 0.6047 0.0358 1.0441 0.051 Uiso 1 1 calc R . .
H34B H 0.7113 0.0907 1.1254 0.051 Uiso 1 1 calc R . .
C35 C 0.8120(5) 0.1381(4) 1.0242(3) 0.0418(9) Uani 1 1 d . . .
H35A H 0.7890 0.0928 0.9669 0.050 Uiso 1 1 calc R . .
H35B H 0.9005 0.1128 1.0446 0.050 Uiso 1 1 calc R . .
C36 C 0.8389(4) 0.2816(4) 1.0334(2) 0.0341(7) Uani 1 1 d . . .
H36A H 0.9451 0.3199 1.0483 0.041 Uiso 1 1 calc R . .
H36B H 0.8112 0.3017 0.9822 0.041 Uiso 1 1 calc R . .


_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 C27 2.186(3) . ?
Bi1 C15 2.187(3) . ?
Bi1 C21 2.194(3) . ?
Bi1 O4 2.279(2) . ?
Bi1 O1 2.284(2) . ?
Cl1 C6 1.747(3) . ?
Cl2 C11 1.739(3) . ?
O1 C1 1.298(3) . ?
O2 C1 1.243(4) . ?
O3 C3 1.352(4) . ?
O4 C8 1.300(3) . ?
O5 C8 1.254(3) . ?
O6 C14 1.354(3) . ?
O7 C36 1.432(4) . ?
O7 C33 1.433(4) . ?
C1 C2 1.482(4) . ?
C2 C7 1.401(4) . ?
C2 C3 1.407(4) . ?
C3 C4 1.399(4) . ?
C4 C5 1.372(5) . ?
C5 C6 1.399(4) . ?
C6 C7 1.366(4) . ?
C8 C9 1.472(4) . ?
C9 C14 1.396(4) . ?
C9 C10 1.403(4) . ?
C10 C11 1.374(4) . ?
C11 C12 1.396(4) . ?
C12 C13 1.374(4) . ?
C13 C14 1.395(4) . ?
C15 C20 1.378(4) . ?
C15 C16 1.388(4) . ?
C16 C17 1.399(5) . ?
C17 C18 1.375(5) . ?
C18 C19 1.391(5) . ?
C19 C20 1.394(4) . ?
C21 C26 1.388(4) . ?
C21 C22 1.392(4) . ?
C22 C23 1.389(4) . ?
C23 C24 1.381(5) . ?
C24 C25 1.381(5) . ?
C25 C26 1.396(4) . ?
C27 C28 1.378(4) . ?
C27 C32 1.383(4) . ?
C28 C29 1.405(4) . ?
C29 C30 1.382(5) . ?
C30 C31 1.385(5) . ?
C31 C32 1.392(4) . ?
C33 C34 1.518(6) . ?
C34 C35 1.520(5) . ?
C35 C36 1.525(6) . ?

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
C27 Bi1 C15 136.09(11) . . ?
C27 Bi1 C21 112.11(11) . . ?
C15 Bi1 C21 111.70(11) . . ?
C27 Bi1 O4 91.90(9) . . ?
C15 Bi1 O4 90.01(10) . . ?
C21 Bi1 O4 83.62(10) . . ?
C27 Bi1 O1 91.67(9) . . ?
C15 Bi1 O1 94.48(10) . . ?
C21 Bi1 O1 85.58(10) . . ?
O4 Bi1 O1 169.19(7) . . ?
C1 O1 Bi1 108.99(18) . . ?
C8 O4 Bi1 114.73(17) . . ?
C36 O7 C33 105.2(3) . . ?
O2 C1 O1 122.3(3) . . ?
O2 C1 C2 121.0(2) . . ?
O1 C1 C2 116.7(3) . . ?
C7 C2 C3 119.0(3) . . ?
C7 C2 C1 120.5(2) . . ?
C3 C2 C1 120.4(3) . . ?
O3 C3 C4 117.2(3) . . ?
O3 C3 C2 122.9(3) . . ?
C4 C3 C2 119.9(3) . . ?
C5 C4 C3 120.4(3) . . ?
C4 C5 C6 119.3(3) . . ?
C7 C6 C5 121.5(3) . . ?
C7 C6 Cl1 119.8(2) . . ?
C5 C6 Cl1 118.7(2) . . ?
C6 C7 C2 119.9(3) . . ?
O5 C8 O4 121.5(3) . . ?
O5 C8 C9 121.4(3) . . ?
O4 C8 C9 117.1(2) . . ?
C14 C9 C10 119.6(3) . . ?
C14 C9 C8 120.7(2) . . ?
C10 C9 C8 119.7(3) . . ?
C11 C10 C9 119.5(3) . . ?
C10 C11 C12 121.0(3) . . ?
C10 C11 Cl2 119.3(2) . . ?
C12 C11 Cl2 119.7(2) . . ?
C13 C12 C11 119.7(3) . . ?
C12 C13 C14 120.2(3) . . ?
O6 C14 C13 118.3(3) . . ?
O6 C14 C9 121.7(3) . . ?
C13 C14 C9 120.0(3) . . ?
C20 C15 C16 123.1(3) . . ?
C20 C15 Bi1 121.1(2) . . ?
C16 C15 Bi1 115.9(2) . . ?
C15 C16 C17 117.8(3) . . ?
C18 C17 C16 120.0(3) . . ?
C17 C18 C19 121.3(3) . . ?
C18 C19 C20 119.6(3) . . ?
C15 C20 C19 118.3(3) . . ?
C26 C21 C22 121.3(3) . . ?
C26 C21 Bi1 119.5(2) . . ?
C22 C21 Bi1 119.2(2) . . ?
C23 C22 C21 118.6(3) . . ?
C24 C23 C22 120.8(3) . . ?
C25 C24 C23 120.3(3) . . ?
C24 C25 C26 120.0(3) . . ?
C21 C26 C25 119.1(3) . . ?
C28 C27 C32 122.8(3) . . ?
C28 C27 Bi1 116.3(2) . . ?
C32 C27 Bi1 120.9(2) . . ?
C27 C28 C29 118.0(3) . . ?
C30 C29 C28 120.2(3) . . ?
C29 C30 C31 120.5(3) . . ?
C30 C31 C32 120.2(3) . . ?
C27 C32 C31 118.4(3) . . ?
O7 C33 C34 104.7(3) . . ?
C33 C34 C35 102.9(3) . . ?
C34 C35 C36 104.8(3) . . ?
O7 C36 C35 106.6(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O6 H6 O5 0.84 1.84 2.582(3) 146.6 .
O3 H3 O2 0.84 1.87 2.609(3) 145.2 .

_diffrn_measured_fraction_theta_max 0.864
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.904
_refine_diff_density_max         0.895
_refine_diff_density_min         -1.895
_refine_diff_density_rms         0.098
_database_code_depnum_ccdc_archive 'CCDC 978099'
#######################################################################
#
#                 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_vb57-yc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H23 Bi Br2 O6, C4 H10 O'
_chemical_formula_sum            'C36 H33 Bi Br2 O7'
_chemical_formula_weight         946.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.382 2.466 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.028 10.608 '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                   8.7860(18)
_cell_length_b                   11.096(2)
_cell_length_c                   18.289(4)
_cell_angle_alpha                103.99(3)
_cell_angle_beta                 96.10(3)
_cell_angle_gamma                98.63(3)
_cell_volume                     1691.5(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3526
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.858
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             916
_exptl_absorpt_coefficient_mu    7.622
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.7502
_exptl_absorpt_correction_T_max  0.8036
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX2 beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 315r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            32646
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         29.63
_reflns_number_total             8514
_reflns_number_gt                8159
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_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. 

 Due to hardware constraints (synchrotorn radiation and fixed phi) diffraction
 measured fraction theta full is low.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0308P)²+4.1197P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8514
_refine_ls_number_parameters     419
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0774
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.915344(13) 0.633133(11) 0.722388(6) 0.01692(5) Uani 1 1 d . . .
Br1 Br 0.67860(6) 1.27339(4) 0.83392(2) 0.03442(10) Uani 1 1 d . . .
Br2 Br 1.25174(5) 0.11774(4) 0.85392(2) 0.03399(9) Uani 1 1 d . . .
O1 O 0.8506(3) 0.8278(3) 0.73328(15) 0.0230(5) Uani 1 1 d . . .
O2 O 0.8075(3) 0.7667(3) 0.60615(15) 0.0250(5) Uani 1 1 d . . .
O3 O 0.6974(4) 0.9152(3) 0.53121(15) 0.0290(6) Uani 1 1 d . . .
H3A H 0.7387 0.8537 0.5366 0.035 Uiso 1 1 calc R . .
O4 O 0.9918(3) 0.4535(3) 0.74099(14) 0.0230(5) Uani 1 1 d . . .
O5 O 0.9494(3) 0.3910(3) 0.61431(14) 0.0224(5) Uani 1 1 d . . .
O6 O 1.0160(4) 0.1767(3) 0.54542(15) 0.0280(6) Uani 1 1 d . . .
H6A H 0.9846 0.2456 0.5496 0.034 Uiso 1 1 calc R . .
C1 C 0.8074(4) 0.8466(3) 0.6675(2) 0.0209(6) Uani 1 1 d . . .
C2 C 0.7517(4) 0.9667(3) 0.66844(19) 0.0204(6) Uani 1 1 d . . .
C3 C 0.7466(4) 1.0523(3) 0.7382(2) 0.0222(6) Uani 1 1 d . . .
H3 H 0.7852 1.0362 0.7848 0.027 Uiso 1 1 calc R . .
C4 C 0.6856(4) 1.1592(3) 0.7390(2) 0.0231(7) Uani 1 1 d . . .
C5 C 0.6267(5) 1.1847(4) 0.6717(2) 0.0268(7) Uani 1 1 d . . .
H5 H 0.5831 1.2585 0.6734 0.032 Uiso 1 1 calc R . .
C6 C 0.6321(5) 1.1021(4) 0.6024(2) 0.0264(7) Uani 1 1 d . . .
H6 H 0.5927 1.1195 0.5563 0.032 Uiso 1 1 calc R . .
C7 C 0.6958(4) 0.9924(4) 0.5999(2) 0.0227(7) Uani 1 1 d . . .
C8 C 0.9930(4) 0.3723(3) 0.67752(19) 0.0199(6) Uani 1 1 d . . .
C9 C 1.0534(4) 0.2556(3) 0.68202(19) 0.0193(6) Uani 1 1 d . . .
C10 C 1.1086(4) 0.2398(3) 0.7533(2) 0.0216(6) Uani 1 1 d . . .
H10 H 1.1014 0.3007 0.7987 0.026 Uiso 1 1 calc R . .
C11 C 1.1730(4) 0.1360(4) 0.7570(2) 0.0223(7) Uani 1 1 d . . .
C12 C 1.1831(5) 0.0440(4) 0.6909(2) 0.0271(7) Uani 1 1 d . . .
H12 H 1.2286 -0.0272 0.6944 0.032 Uiso 1 1 calc R . .
C13 C 1.1265(5) 0.0578(4) 0.6207(2) 0.0259(7) Uani 1 1 d . . .
H13 H 1.1299 -0.0056 0.5758 0.031 Uiso 1 1 calc R . .
C14 C 1.0641(4) 0.1644(3) 0.61538(19) 0.0208(6) Uani 1 1 d . . .
C15 C 0.6773(4) 0.5365(3) 0.67667(19) 0.0197(6) Uani 1 1 d . . .
C16 C 0.5714(5) 0.5285(4) 0.7276(2) 0.0243(7) Uani 1 1 d . . .
H16 H 0.6025 0.5647 0.7807 0.029 Uiso 1 1 calc R . .
C17 C 0.4201(4) 0.4668(4) 0.6991(2) 0.0268(7) Uani 1 1 d . . .
H17 H 0.3459 0.4615 0.7329 0.032 Uiso 1 1 calc R . .
C18 C 0.3761(4) 0.4125(4) 0.6214(2) 0.0266(7) Uani 1 1 d . . .
H18 H 0.2725 0.3690 0.6024 0.032 Uiso 1 1 calc R . .
C19 C 0.4832(4) 0.4218(4) 0.5713(2) 0.0256(7) Uani 1 1 d . . .
H19 H 0.4522 0.3852 0.5181 0.031 Uiso 1 1 calc R . .
C20 C 0.6356(4) 0.4846(4) 0.5986(2) 0.0239(7) Uani 1 1 d . . .
H20 H 0.7093 0.4918 0.5647 0.029 Uiso 1 1 calc R . .
C21 C 1.1220(4) 0.6833(3) 0.67173(19) 0.0194(6) Uani 1 1 d . . .
C22 C 1.1116(4) 0.6733(4) 0.5940(2) 0.0237(7) Uani 1 1 d . . .
H22 H 1.0152 0.6415 0.5612 0.028 Uiso 1 1 calc R . .
C23 C 1.2465(4) 0.7110(4) 0.5657(2) 0.0250(7) Uani 1 1 d . . .
H23 H 1.2423 0.7053 0.5128 0.030 Uiso 1 1 calc R . .
C24 C 1.3873(4) 0.7570(4) 0.6139(2) 0.0257(7) Uani 1 1 d . . .
H24 H 1.4783 0.7838 0.5941 0.031 Uiso 1 1 calc R . .
C25 C 1.3950(4) 0.7637(4) 0.6903(2) 0.0251(7) Uani 1 1 d . . .
H25 H 1.4920 0.7938 0.7228 0.030 Uiso 1 1 calc R . .
C26 C 1.2614(4) 0.7267(4) 0.7207(2) 0.0231(7) Uani 1 1 d . . .
H26 H 1.2663 0.7313 0.7735 0.028 Uiso 1 1 calc R . .
C27 C 0.9636(4) 0.6966(4) 0.8469(2) 0.0231(7) Uani 1 1 d . . .
C28 C 0.9287(5) 0.6124(4) 0.8912(2) 0.0315(8) Uani 1 1 d . . .
H28 H 0.8823 0.5268 0.8679 0.038 Uiso 1 1 calc R . .
C29 C 0.9636(6) 0.6567(5) 0.9700(3) 0.0409(11) Uani 1 1 d . . .
H29 H 0.9389 0.6015 1.0012 0.049 Uiso 1 1 calc R . .
C30 C 1.0342(6) 0.7815(5) 1.0034(2) 0.0425(11) Uani 1 1 d . . .
H30 H 1.0587 0.8111 1.0573 0.051 Uiso 1 1 calc R . .
C31 C 1.0693(6) 0.8630(5) 0.9584(3) 0.0414(11) Uani 1 1 d . . .
H31 H 1.1193 0.9479 0.9813 0.050 Uiso 1 1 calc R . .
C32 C 1.0315(5) 0.8207(4) 0.8801(2) 0.0324(8) Uani 1 1 d . . .
H32 H 1.0523 0.8772 0.8492 0.039 Uiso 1 1 calc R . .
C34 C 0.6039(6) 0.9142(5) 0.8863(3) 0.0420(10) Uani 1 1 d . . .
H34A H 0.6677 0.8720 0.8510 0.063 Uiso 1 1 calc R . .
H34B H 0.6616 0.9980 0.9147 0.063 Uiso 1 1 calc R . .
H34C H 0.5074 0.9230 0.8576 0.063 Uiso 1 1 calc R . .
O7 O 0.4790(4) 0.7182(3) 0.90043(17) 0.0379(7) Uani 1 1 d . . .
C33 C 0.5655(8) 0.8369(6) 0.9411(3) 0.0530(14) Uani 1 1 d . . .
H33A H 0.6627 0.8263 0.9696 0.064 Uiso 1 1 calc R . .
H33B H 0.5044 0.8807 0.9782 0.064 Uiso 1 1 calc R . .
C36 C 0.3411(7) 0.5174(6) 0.9038(3) 0.0475(12) Uani 1 1 d . . .
H36A H 0.2587 0.5273 0.8663 0.071 Uiso 1 1 calc R . .
H36B H 0.2948 0.4705 0.9374 0.071 Uiso 1 1 calc R . .
H36C H 0.4144 0.4710 0.8773 0.071 Uiso 1 1 calc R . .
C35 C 0.4250(8) 0.6442(6) 0.9498(3) 0.0525(14) Uani 1 1 d . . .
H35A H 0.3543 0.6875 0.9813 0.063 Uiso 1 1 calc R . .
H35B H 0.5145 0.6348 0.9843 0.063 Uiso 1 1 calc R . .


_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 C15 2.178(4) . ?
Bi1 C21 2.184(3) . ?
Bi1 C27 2.188(4) . ?
Bi1 O1 2.283(3) . ?
Bi1 O4 2.285(3) . ?
Br1 C4 1.899(4) . ?
Br2 C11 1.903(3) . ?
O1 C1 1.297(4) . ?
O2 C1 1.251(5) . ?
O3 C7 1.342(5) . ?
O4 C8 1.288(4) . ?
O5 C8 1.253(4) . ?
O6 C14 1.349(4) . ?
C1 C2 1.484(5) . ?
C2 C3 1.404(5) . ?
C2 C7 1.406(5) . ?
C3 C4 1.371(5) . ?
C4 C5 1.392(5) . ?
C5 C6 1.384(6) . ?
C6 C7 1.407(5) . ?
C8 C9 1.488(5) . ?
C9 C10 1.402(4) . ?
C9 C14 1.405(5) . ?
C10 C11 1.370(5) . ?
C11 C12 1.401(5) . ?
C12 C13 1.378(5) . ?
C13 C14 1.396(5) . ?
C15 C20 1.390(5) . ?
C15 C16 1.393(5) . ?
C16 C17 1.384(6) . ?
C17 C18 1.391(6) . ?
C18 C19 1.391(5) . ?
C19 C20 1.392(5) . ?
C21 C26 1.384(5) . ?
C21 C22 1.391(5) . ?
C22 C23 1.390(5) . ?
C23 C24 1.389(5) . ?
C24 C25 1.375(5) . ?
C25 C26 1.400(5) . ?
C27 C32 1.376(6) . ?
C27 C28 1.399(5) . ?
C28 C29 1.391(6) . ?
C29 C30 1.388(8) . ?
C30 C31 1.386(8) . ?
C31 C32 1.381(6) . ?
C34 C33 1.501(7) . ?
O7 C33 1.405(7) . ?
O7 C35 1.430(6) . ?
C36 C35 1.489(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
C15 Bi1 C21 134.35(13) . . ?
C15 Bi1 C27 114.54(14) . . ?
C21 Bi1 C27 111.11(14) . . ?
C15 Bi1 O1 92.58(11) . . ?
C21 Bi1 O1 92.24(11) . . ?
C27 Bi1 O1 83.53(12) . . ?
C15 Bi1 O4 92.88(11) . . ?
C21 Bi1 O4 92.39(11) . . ?
C27 Bi1 O4 83.43(12) . . ?
O1 Bi1 O4 166.96(9) . . ?
C1 O1 Bi1 112.3(2) . . ?
C8 O4 Bi1 111.9(2) . . ?
O2 C1 O1 122.3(3) . . ?
O2 C1 C2 121.1(3) . . ?
O1 C1 C2 116.6(3) . . ?
C3 C2 C7 119.6(3) . . ?
C3 C2 C1 119.9(3) . . ?
C7 C2 C1 120.4(3) . . ?
C4 C3 C2 119.8(3) . . ?
C3 C4 C5 121.4(3) . . ?
C3 C4 Br1 119.2(3) . . ?
C5 C4 Br1 119.4(3) . . ?
C6 C5 C4 119.7(3) . . ?
C5 C6 C7 120.1(3) . . ?
O3 C7 C2 122.8(3) . . ?
O3 C7 C6 117.7(3) . . ?
C2 C7 C6 119.4(3) . . ?
O5 C8 O4 122.2(3) . . ?
O5 C8 C9 120.8(3) . . ?
O4 C8 C9 117.0(3) . . ?
C10 C9 C14 119.5(3) . . ?
C10 C9 C8 119.7(3) . . ?
C14 C9 C8 120.6(3) . . ?
C11 C10 C9 119.5(3) . . ?
C10 C11 C12 121.4(3) . . ?
C10 C11 Br2 119.1(3) . . ?
C12 C11 Br2 119.6(3) . . ?
C13 C12 C11 119.4(3) . . ?
C12 C13 C14 120.3(3) . . ?
O6 C14 C13 118.3(3) . . ?
O6 C14 C9 121.8(3) . . ?
C13 C14 C9 119.8(3) . . ?
C20 C15 C16 122.1(4) . . ?
C20 C15 Bi1 119.7(3) . . ?
C16 C15 Bi1 118.2(3) . . ?
C17 C16 C15 118.6(3) . . ?
C16 C17 C18 120.4(3) . . ?
C17 C18 C19 120.3(4) . . ?
C18 C19 C20 120.3(4) . . ?
C15 C20 C19 118.4(3) . . ?
C26 C21 C22 122.3(3) . . ?
C26 C21 Bi1 116.8(2) . . ?
C22 C21 Bi1 120.9(3) . . ?
C23 C22 C21 118.1(3) . . ?
C24 C23 C22 120.7(3) . . ?
C25 C24 C23 120.1(3) . . ?
C24 C25 C26 120.7(4) . . ?
C21 C26 C25 118.1(3) . . ?
C32 C27 C28 121.1(4) . . ?
C32 C27 Bi1 118.2(3) . . ?
C28 C27 Bi1 120.7(3) . . ?
C29 C28 C27 118.6(4) . . ?
C30 C29 C28 120.2(4) . . ?
C31 C30 C29 120.3(4) . . ?
C32 C31 C30 120.0(5) . . ?
C27 C32 C31 119.8(4) . . ?
C33 O7 C35 112.2(4) . . ?
O7 C33 C34 109.3(4) . . ?
O7 C35 C36 109.9(4) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3A O2 0.84 1.88 2.611(4) 145.2 .
O6 H6A O5 0.84 1.85 2.590(4) 146.9 .

_diffrn_measured_fraction_theta_max 0.891
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.904
_refine_diff_density_max         1.746
_refine_diff_density_min         -1.313
_refine_diff_density_rms         0.133
_database_code_depnum_ccdc_archive 'CCDC 978100'
#######################################################################
#
#                 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_vb52-yc

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C44 H29 Bi F4 O6'
_chemical_formula_sum            'C44 H29 Bi F4 O6'
_chemical_formula_weight         938.65

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.028 10.608 '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/c

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

_cell_length_a                   11.139(2)
_cell_length_b                   9.972(2)
_cell_length_c                   16.079(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.81(3)
_cell_angle_gamma                90.00
_cell_volume                     1773.4(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3507
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.758
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920
_exptl_absorpt_coefficient_mu    5.044
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.8237
_exptl_absorpt_correction_T_max  0.9058
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 210r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            30400
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.84
_diffrn_reflns_theta_max         28.75
_reflns_number_total             4442
_reflns_number_gt                4316
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_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. 
 The diflunisal ligand F1, F2,O1-3, C11-23 was modelled with F1 and C19 and 
 C20 as disordered over two positions, with occupancies fixed at 
 0.6:0.4 after trial refinement.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0947P)²+11.2232P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4442
_refine_ls_number_parameters     278
_refine_ls_number_restraints     30
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1434
_refine_ls_wR_factor_gt          0.1405
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.036
_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
Bi01 Bi 0.5000 -0.24015(3) 1.2500 0.02446(12) Uani 1 2 d S . .
F1 F 0.1069(13) 0.0614(17) 1.3585(11) 0.091(5) Uani 0.50 1 d P A 1
F1' F 0.0455(19) 0.048(2) 1.3072(13) 0.122(6) Uani 0.50 1 d PU B 2
F2 F -0.2251(7) 0.2890(9) 1.4432(6) 0.090(2) Uani 1 1 d . . .
O1 O 0.3055(5) -0.2293(5) 1.2747(4) 0.0388(11) Uani 1 1 d . . .
O2 O 0.3114(5) -0.4514(6) 1.2784(3) 0.0493(12) Uani 1 1 d . . .
O3 O 0.1277(6) -0.5797(6) 1.3298(5) 0.0592(16) Uani 1 1 d . . .
H30 H 0.1923 -0.5713 1.3081 0.071 Uiso 1 1 calc R . .
C1 C 0.5000 -0.0173(10) 1.2500 0.0380(19) Uani 1 2 d S . .
C2 C 0.3907(7) 0.0510(8) 1.2427(5) 0.0483(16) Uani 1 1 d . . .
H2 H 0.3163 0.0034 1.2378 0.058 Uiso 1 1 calc R . .
C3 C 0.3922(8) 0.1925(9) 1.2427(5) 0.0542(19) Uani 1 1 d . . .
H3 H 0.3182 0.2409 1.2375 0.065 Uiso 1 1 calc R . .
C4 C 0.5000 0.2606(9) 1.2500 0.045(3) Uani 1 2 d S . .
H4 H 0.5000 0.3559 1.2500 0.054 Uiso 1 2 calc SR . .
C5 C 0.4534(6) -0.3004(8) 1.1184(4) 0.0400(14) Uani 1 1 d . . .
C6 C 0.4950(8) -0.2167(10) 1.0637(5) 0.0485(17) Uani 1 1 d . . .
H6 H 0.5460 -0.1438 1.0826 0.058 Uiso 1 1 calc R . .
C7 C 0.4619(11) -0.2384(8) 0.9779(5) 0.051(2) Uani 1 1 d . . .
H7 H 0.4843 -0.1755 0.9382 0.061 Uiso 1 1 calc R . .
C8 C 0.3988(8) -0.3476(11) 0.9520(5) 0.059(2) Uani 1 1 d . . .
H8 H 0.3831 -0.3658 0.8937 0.071 Uiso 1 1 calc R . .
C9 C 0.3551(7) -0.4365(9) 1.0099(5) 0.0538(19) Uani 1 1 d . . .
H9 H 0.3064 -0.5112 0.9908 0.065 Uiso 1 1 calc R . .
C10 C 0.3843(6) -0.4132(8) 1.0956(4) 0.0441(15) Uani 1 1 d . . .
H10 H 0.3580 -0.4719 1.1363 0.053 Uiso 1 1 calc R . .
C11 C 0.2601(6) -0.3411(8) 1.2909(4) 0.0397(14) Uani 1 1 d . . .
C12 C 0.1438(6) -0.3388(7) 1.3272(4) 0.0376(13) Uani 1 1 d . . .
C13 C 0.0853(7) -0.4597(9) 1.3457(5) 0.0495(17) Uani 1 1 d . . .
C14 C -0.0224(9) -0.4497(10) 1.3822(7) 0.066(3) Uani 1 1 d . . .
H14 H -0.0639 -0.5287 1.3951 0.080 Uiso 1 1 calc R . .
C15 C -0.0677(9) -0.3277(11) 1.3991(7) 0.067(3) Uani 1 1 d . . .
H15 H -0.1398 -0.3245 1.4252 0.081 Uiso 1 1 calc R . .
C16 C -0.0141(7) -0.2069(9) 1.3801(5) 0.0442(15) Uani 1 1 d . . .
C17 C 0.0938(6) -0.2188(8) 1.3445(4) 0.0378(13) Uani 1 1 d . . .
H17 H 0.1345 -0.1391 1.3317 0.045 Uiso 1 1 calc R . .
C18 C -0.0681(7) -0.0750(9) 1.3966(5) 0.0481(17) Uani 1 1 d . . .
C19 C -0.0125(18) 0.046(2) 1.3854(13) 0.057(4) Uani 0.50 1 d PU A 1
C19' C -0.0489(17) 0.042(2) 1.3514(12) 0.054(4) Uani 0.50 1 d PU B 2
C20 C -0.0662(19) 0.171(2) 1.4002(14) 0.060(5) Uani 0.50 1 d PU A 1
H20 H -0.0250 0.2517 1.3909 0.072 Uiso 0.50 1 calc PR A 1
C20' C -0.093(2) 0.171(2) 1.3636(15) 0.065(5) Uani 0.50 1 d PU B 2
H20' H -0.0721 0.2479 1.3335 0.079 Uiso 0.50 1 calc PR B 2
C21 C -0.1743(8) 0.1741(11) 1.4270(7) 0.062(2) Uani 1 1 d . . .
C22 C -0.2181(9) 0.0602(14) 1.4591(8) 0.085(4) Uani 1 1 d . A .
H22 H -0.2844 0.0644 1.4911 0.102 Uiso 1 1 calc R . .
C23 C -0.1642(8) -0.0637(12) 1.4444(7) 0.074(3) Uani 1 1 d . A .
H23 H -0.1944 -0.1425 1.4678 0.089 Uiso 1 1 calc R . .


_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
Bi01 C5 2.201(7) . ?
Bi01 C5 2.201(7) 2_657 ?
Bi01 C1 2.222(10) . ?
Bi01 O1 2.252(5) . ?
Bi01 O1 2.252(5) 2_657 ?
F1 C19 1.45(2) . ?
F1' C19' 1.34(3) . ?
F2 C21 1.317(12) . ?
O1 C11 1.264(9) . ?
O2 C11 1.266(9) . ?
O3 C13 1.322(11) . ?
C1 C2 1.388(9) 2_657 ?
C1 C2 1.388(9) . ?
C2 C3 1.412(12) . ?
C3 C4 1.372(10) . ?
C4 C3 1.372(10) 2_657 ?
C5 C6 1.335(12) . ?
C5 C10 1.388(10) . ?
C6 C7 1.402(11) . ?
C7 C8 1.335(13) . ?
C8 C9 1.414(12) . ?
C9 C10 1.397(10) . ?
C11 C12 1.483(9) . ?
C12 C17 1.362(11) . ?
C12 C13 1.419(10) . ?
C13 C14 1.400(12) . ?
C14 C15 1.356(14) . ?
C15 C16 1.395(13) . ?
C16 C17 1.397(10) . ?
C16 C18 1.483(12) . ?
C18 C19 1.37(2) . ?
C18 C23 1.395(11) . ?
C18 C19' 1.41(2) . ?
C19 C20 1.42(3) . ?
C19' C20' 1.40(3) . ?
C20 C21 1.33(2) . ?
C20' C21 1.44(2) . ?
C21 C22 1.362(17) . ?
C22 C23 1.405(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 Bi01 C5 148.3(4) . 2_657 ?
C5 Bi01 C1 105.8(2) . . ?
C5 Bi01 C1 105.8(2) 2_657 . ?
C5 Bi01 O1 93.5(2) . . ?
C5 Bi01 O1 88.0(2) 2_657 . ?
C1 Bi01 O1 87.24(13) . . ?
C5 Bi01 O1 88.0(2) . 2_657 ?
C5 Bi01 O1 93.5(2) 2_657 2_657 ?
C1 Bi01 O1 87.24(14) . 2_657 ?
O1 Bi01 O1 174.5(3) . 2_657 ?
C11 O1 Bi01 114.2(5) . . ?
C2 C1 C2 121.2(10) 2_657 . ?
C2 C1 Bi01 119.4(5) 2_657 . ?
C2 C1 Bi01 119.4(5) . . ?
C1 C2 C3 118.7(8) . . ?
C4 C3 C2 120.3(8) . . ?
C3 C4 C3 120.7(10) . 2_657 ?
C6 C5 C10 123.9(7) . . ?
C6 C5 Bi01 113.7(6) . . ?
C10 C5 Bi01 122.4(5) . . ?
C5 C6 C7 118.7(8) . . ?
C8 C7 C6 120.0(8) . . ?
C7 C8 C9 121.0(8) . . ?
C10 C9 C8 119.2(8) . . ?
C5 C10 C9 116.9(7) . . ?
O1 C11 O2 122.3(7) . . ?
O1 C11 C12 117.2(6) . . ?
O2 C11 C12 120.5(7) . . ?
C17 C12 C13 119.7(7) . . ?
C17 C12 C11 119.4(6) . . ?
C13 C12 C11 120.9(7) . . ?
O3 C13 C14 119.3(8) . . ?
O3 C13 C12 123.0(7) . . ?
C14 C13 C12 117.7(8) . . ?
C15 C14 C13 120.4(8) . . ?
C14 C15 C16 123.4(8) . . ?
C15 C16 C17 115.4(9) . . ?
C15 C16 C18 122.3(7) . . ?
C17 C16 C18 122.4(8) . . ?
C12 C17 C16 123.4(8) . . ?
C19 C18 C23 112.9(11) . . ?
C23 C18 C19' 113.0(11) . . ?
C19 C18 C16 123.6(10) . . ?
C23 C18 C16 121.6(9) . . ?
C19' C18 C16 123.7(10) . . ?
C18 C19 C20 122.9(17) . . ?
C18 C19 F1 125.2(16) . . ?
C20 C19 F1 111.9(18) . . ?
F1' C19' C20' 110.2(19) . . ?
F1' C19' C18 119.3(17) . . ?
C20' C19' C18 127.8(17) . . ?
C21 C20 C19 119.7(19) . . ?
C19' C20' C21 112.4(19) . . ?
F2 C21 C20 121.0(14) . . ?
F2 C21 C22 118.0(10) . . ?
C20 C21 C22 118.7(13) . . ?
F2 C21 C20' 118.6(14) . . ?
C22 C21 C20' 122.2(13) . . ?
C21 C22 C23 119.4(9) . . ?
C18 C23 C22 122.3(11) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H30 O2 0.84 1.89 2.629(9) 146.1 .

_diffrn_measured_fraction_theta_max 0.964
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         4.561
_refine_diff_density_min         -2.687
_refine_diff_density_rms         0.208
_database_code_depnum_ccdc_archive 'CCDC 978101'
#######################################################################
#
#                 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_vb86-yc1

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H35 Bi Cl2 N2 O4, C2 H6 O S'
_chemical_formula_sum            'C48 H41 Bi Cl2 N2 O5 S'
_chemical_formula_weight         1037.77

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'
O O 0.0106 0.0060 '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 -4.028 10.608 '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                   11.180(2)
_cell_length_b                   12.750(3)
_cell_length_c                   16.190(3)
_cell_angle_alpha                79.78(3)
_cell_angle_beta                 71.76(3)
_cell_angle_gamma                84.42(3)
_cell_volume                     2154.9(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    42090
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1032
_exptl_absorpt_coefficient_mu    4.313
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9187
_exptl_absorpt_correction_T_max  0.9581
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 beamline, Australian Synchrotron'
_diffrn_radiation_monochromator  silicon
_diffrn_measurement_device_type  'ADSC Quantum 210r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            42087
_diffrn_reflns_av_R_equivalents  0.1895
_diffrn_reflns_av_sigmaI/netI    0.1418
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.34
_diffrn_reflns_theta_max         27.20
_reflns_number_total             9486
_reflns_number_gt                8137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB

_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. 

 The final data collection is a merge of two seperate data collections of
 the same crystal at different angles.

 The highest residual electron density peak of 8.48 is found 0.846 Angstrongs 
 from Bi1.
 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1178P)²+2.8926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9486
_refine_ls_number_parameters     536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1098
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1772
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.135919(17) 0.790342(15) 0.123885(12) 0.02034(11) Uani 1 1 d . . .
Cl1 Cl 0.04028(19) 1.25809(16) 0.50140(12) 0.0387(4) Uani 1 1 d . . .
Cl2 Cl 0.39378(19) 0.62687(18) 0.63603(12) 0.0422(4) Uani 1 1 d . . .
S1 S 0.7081(2) 0.66456(17) 0.75070(17) 0.0455(5) Uani 1 1 d . . .
O1 O -0.0586(5) 0.8705(4) 0.1476(4) 0.0287(11) Uani 1 1 d . . .
O2 O -0.0076(4) 0.8792(4) 0.2678(3) 0.0258(9) Uani 1 1 d . . .
O3 O 0.3329(5) 0.7046(5) 0.0893(3) 0.0304(11) Uani 1 1 d . . .
O4 O 0.2975(4) 0.7278(4) 0.2275(3) 0.0240(9) Uani 1 1 d . . .
O5 O 0.6680(7) 0.7604(5) 0.6971(5) 0.0506(15) Uani 1 1 d . . .
N1 N -0.1599(5) 0.9933(5) 0.3854(4) 0.0294(12) Uani 1 1 d . . .
N2 N 0.4800(5) 0.6641(5) 0.3021(4) 0.0294(12) Uani 1 1 d . . .
C1 C -0.0848(6) 0.8997(5) 0.2247(4) 0.0238(12) Uani 1 1 d . . .
C2 C -0.2073(6) 0.9575(5) 0.2569(4) 0.0241(12) Uani 1 1 d . . .
C3 C -0.2919(7) 0.9666(6) 0.2084(5) 0.0316(15) Uani 1 1 d . . .
H3 H -0.2704 0.9324 0.1577 0.038 Uiso 1 1 calc R . .
C4 C -0.4052(7) 1.0230(8) 0.2311(5) 0.0432(19) Uani 1 1 d . . .
H4 H -0.4616 1.0276 0.1972 0.052 Uiso 1 1 calc R . .
C5 C -0.4359(7) 1.0741(7) 0.3062(5) 0.0404(18) Uani 1 1 d . . .
H5 H -0.5125 1.1157 0.3218 0.048 Uiso 1 1 calc R . .
C6 C -0.3566(6) 1.0641(6) 0.3559(5) 0.0331(15) Uani 1 1 d . . .
H6 H -0.3803 1.0977 0.4070 0.040 Uiso 1 1 calc R . .
C7 C -0.2401(6) 1.0055(5) 0.3345(4) 0.0252(12) Uani 1 1 d . . .
C8 C -0.1681(6) 1.0542(5) 0.4523(4) 0.0262(13) Uani 1 1 d . . .
C9 C -0.2721(7) 1.0459(6) 0.5282(5) 0.0334(15) Uani 1 1 d . . .
H9 H -0.3379 1.0005 0.5345 0.040 Uiso 1 1 calc R . .
C10 C -0.2787(7) 1.1042(6) 0.5940(5) 0.0379(17) Uani 1 1 d . . .
H10 H -0.3505 1.1000 0.6448 0.046 Uiso 1 1 calc R . .
C11 C -0.1824(7) 1.1679(6) 0.5867(5) 0.0325(15) Uani 1 1 d . . .
H11 H -0.1857 1.2070 0.6323 0.039 Uiso 1 1 calc R . .
C12 C -0.0799(6) 1.1734(5) 0.5105(4) 0.0253(12) Uani 1 1 d . . .
C13 C -0.0682(6) 1.1188(5) 0.4418(4) 0.0249(12) Uani 1 1 d . . .
C14 C 0.0450(7) 1.1265(6) 0.3612(5) 0.0313(15) Uani 1 1 d . . .
H14A H 0.0524 1.2006 0.3315 0.047 Uiso 1 1 calc R . .
H14B H 0.0354 1.0808 0.3212 0.047 Uiso 1 1 calc R . .
H14C H 0.1211 1.1030 0.3785 0.047 Uiso 1 1 calc R . .
C15 C 0.3697(6) 0.6979(5) 0.1579(4) 0.0243(12) Uani 1 1 d . . .
C16 C 0.5008(6) 0.6558(6) 0.1493(4) 0.0304(14) Uani 1 1 d . . .
C17 C 0.5724(7) 0.6262(7) 0.0690(5) 0.0398(18) Uani 1 1 d . . .
H17 H 0.5354 0.6343 0.0227 0.048 Uiso 1 1 calc R . .
C18 C 0.6941(8) 0.5859(9) 0.0540(6) 0.052(2) Uani 1 1 d . . .
H18 H 0.7417 0.5678 -0.0019 0.062 Uiso 1 1 calc R . .
C19 C 0.7461(8) 0.5722(9) 0.1238(7) 0.053(3) Uani 1 1 d . . .
H19 H 0.8301 0.5439 0.1153 0.064 Uiso 1 1 calc R . .
C20 C 0.6770(7) 0.5990(7) 0.2047(5) 0.0382(17) Uani 1 1 d . . .
H20 H 0.7148 0.5889 0.2507 0.046 Uiso 1 1 calc R . .
C21 C 0.5527(6) 0.6407(6) 0.2206(4) 0.0287(13) Uani 1 1 d . . .
C22 C 0.5237(7) 0.6775(5) 0.3729(5) 0.0296(14) Uani 1 1 d . . .
C23 C 0.6337(8) 0.7288(6) 0.3582(6) 0.0373(16) Uani 1 1 d . . .
H23 H 0.6849 0.7509 0.2996 0.045 Uiso 1 1 calc R . .
C24 C 0.6697(8) 0.7481(7) 0.4283(6) 0.0415(18) Uani 1 1 d . . .
H24 H 0.7465 0.7816 0.4178 0.050 Uiso 1 1 calc R . .
C25 C 0.5947(8) 0.7190(6) 0.5129(6) 0.0371(16) Uani 1 1 d . . .
H25 H 0.6175 0.7346 0.5611 0.045 Uiso 1 1 calc R . .
C26 C 0.4857(7) 0.6667(5) 0.5274(5) 0.0300(14) Uani 1 1 d . . .
C27 C 0.4461(6) 0.6444(5) 0.4598(4) 0.0239(12) Uani 1 1 d . . .
C28 C 0.3279(6) 0.5849(6) 0.4782(5) 0.0288(13) Uani 1 1 d . . .
H28A H 0.3233 0.5262 0.5270 0.043 Uiso 1 1 calc R . .
H28B H 0.3298 0.5561 0.4255 0.043 Uiso 1 1 calc R . .
H28C H 0.2540 0.6337 0.4938 0.043 Uiso 1 1 calc R . .
C29 C 0.2322(6) 0.9380(5) 0.1091(4) 0.0257(12) Uani 1 1 d . . .
C30 C 0.2826(10) 0.9871(9) 0.0224(6) 0.054(2) Uani 1 1 d . . .
H30 H 0.2716 0.9590 -0.0252 0.064 Uiso 1 1 calc R . .
C31 C 0.3486(14) 1.0772(11) 0.0077(7) 0.079(4) Uani 1 1 d . . .
H31 H 0.3874 1.1104 -0.0509 0.095 Uiso 1 1 calc R . .
C32 C 0.3592(11) 1.1204(8) 0.0784(7) 0.057(3) Uani 1 1 d . . .
H32 H 0.4037 1.1836 0.0678 0.068 Uiso 1 1 calc R . .
C33 C 0.3053(7) 1.0718(6) 0.1631(5) 0.0351(15) Uani 1 1 d . . .
H33 H 0.3117 1.1020 0.2111 0.042 Uiso 1 1 calc R . .
C34 C 0.2421(6) 0.9794(6) 0.1791(5) 0.0288(13) Uani 1 1 d . . .
H34 H 0.2059 0.9449 0.2377 0.035 Uiso 1 1 calc R . .
C35 C 0.1315(6) 0.7784(5) -0.0096(4) 0.0249(12) Uani 1 1 d . . .
C36 C 0.0262(9) 0.8177(8) -0.0346(6) 0.045(2) Uani 1 1 d . . .
H36 H -0.0455 0.8460 0.0060 0.054 Uiso 1 1 calc R . .
C37 C 0.0273(10) 0.8150(9) -0.1207(6) 0.053(2) Uani 1 1 d . . .
H37 H -0.0436 0.8439 -0.1389 0.063 Uiso 1 1 calc R . .
C38 C 0.1276(9) 0.7721(6) -0.1791(5) 0.0380(18) Uani 1 1 d . . .
H38 H 0.1270 0.7712 -0.2375 0.046 Uiso 1 1 calc R . .
C39 C 0.2285(11) 0.7306(9) -0.1525(6) 0.060(3) Uani 1 1 d . . .
H39 H 0.2978 0.6983 -0.1922 0.071 Uiso 1 1 calc R . .
C40 C 0.2319(10) 0.7345(9) -0.0686(6) 0.055(3) Uani 1 1 d . . .
H40 H 0.3041 0.7067 -0.0516 0.066 Uiso 1 1 calc R . .
C41 C 0.0558(6) 0.6429(5) 0.2075(5) 0.0250(12) Uani 1 1 d . . .
C42 C -0.0003(7) 0.6346(6) 0.2965(5) 0.0327(14) Uani 1 1 d . . .
H42 H -0.0036 0.6934 0.3261 0.039 Uiso 1 1 calc R . .
C43 C -0.0524(8) 0.5382(6) 0.3434(6) 0.0413(17) Uani 1 1 d . . .
H43 H -0.0916 0.5310 0.4052 0.050 Uiso 1 1 calc R . .
C44 C -0.0467(7) 0.4534(6) 0.2991(6) 0.0406(17) Uani 1 1 d . . .
H44 H -0.0845 0.3887 0.3306 0.049 Uiso 1 1 calc R . .
C45 C 0.0130(8) 0.4617(6) 0.2105(6) 0.0385(17) Uani 1 1 d . . .
H45 H 0.0198 0.4019 0.1815 0.046 Uiso 1 1 calc R . .
C46 C 0.0641(7) 0.5578(6) 0.1626(5) 0.0314(14) Uani 1 1 d . . .
H46 H 0.1035 0.5649 0.1008 0.038 Uiso 1 1 calc R . .
C47 C 0.5697(16) 0.6182(12) 0.8342(8) 0.095(5) Uani 1 1 d . . .
H47A H 0.5328 0.6739 0.8705 0.143 Uiso 1 1 calc R . .
H47B H 0.5913 0.5543 0.8712 0.143 Uiso 1 1 calc R . .
H47C H 0.5087 0.6009 0.8070 0.143 Uiso 1 1 calc R . .
C48 C 0.7277(8) 0.5576(6) 0.6901(6) 0.0437(19) Uani 1 1 d . . .
H48A H 0.6540 0.5565 0.6698 0.066 Uiso 1 1 calc R . .
H48B H 0.7365 0.4900 0.7278 0.066 Uiso 1 1 calc R . .
H48C H 0.8035 0.5672 0.6391 0.066 Uiso 1 1 calc R . .


_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 C41 2.199(7) . ?
Bi1 C29 2.198(7) . ?
Bi1 C35 2.210(6) . ?
Bi1 O1 2.260(5) . ?
Bi1 O3 2.310(5) . ?
Bi1 O2 2.745(5) . ?
Bi1 O4 2.803(4) . ?
Cl1 C12 1.759(7) . ?
Cl2 C26 1.750(8) . ?
S1 O5 1.486(6) . ?
S1 C48 1.776(9) . ?
S1 C47 1.776(14) . ?
O1 C1 1.304(8) . ?
O2 C1 1.252(8) . ?
O3 C15 1.287(8) . ?
O4 C15 1.261(8) . ?
N1 C7 1.377(8) . ?
N1 C8 1.416(8) . ?
N2 C21 1.383(9) . ?
N2 C22 1.421(9) . ?
C1 C2 1.479(8) . ?
C2 C3 1.392(9) . ?
C2 C7 1.424(9) . ?
C3 C4 1.372(10) . ?
C4 C5 1.412(12) . ?
C5 C6 1.357(11) . ?
C6 C7 1.413(9) . ?
C8 C9 1.399(9) . ?
C8 C13 1.402(10) . ?
C9 C10 1.383(10) . ?
C10 C11 1.375(12) . ?
C11 C12 1.394(10) . ?
C12 C13 1.380(9) . ?
C13 C14 1.503(9) . ?
C15 C16 1.484(8) . ?
C16 C17 1.391(10) . ?
C16 C21 1.424(9) . ?
C17 C18 1.369(11) . ?
C18 C19 1.403(13) . ?
C19 C20 1.379(13) . ?
C20 C21 1.401(9) . ?
C22 C23 1.384(10) . ?
C22 C27 1.416(10) . ?
C23 C24 1.384(11) . ?
C24 C25 1.370(13) . ?
C25 C26 1.381(11) . ?
C26 C27 1.382(9) . ?
C27 C28 1.510(9) . ?
C29 C34 1.371(9) . ?
C29 C30 1.393(11) . ?
C30 C31 1.371(14) . ?
C31 C32 1.396(14) . ?
C32 C33 1.372(13) . ?
C33 C34 1.376(11) . ?
C35 C40 1.371(11) . ?
C35 C36 1.383(10) . ?
C36 C37 1.396(10) . ?
C37 C38 1.361(13) . ?
C38 C39 1.359(12) . ?
C39 C40 1.381(11) . ?
C41 C42 1.369(10) . ?
C41 C46 1.390(9) . ?
C42 C43 1.398(11) . ?
C43 C44 1.386(12) . ?
C44 C45 1.369(13) . ?
C45 C46 1.397(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C41 Bi1 C29 148.8(2) . . ?
C41 Bi1 C35 105.6(2) . . ?
C29 Bi1 C35 105.4(2) . . ?
C41 Bi1 O1 90.6(2) . . ?
C29 Bi1 O1 94.9(2) . . ?
C35 Bi1 O1 87.6(2) . . ?
C41 Bi1 O3 89.7(2) . . ?
C29 Bi1 O3 87.3(2) . . ?
C35 Bi1 O3 87.8(2) . . ?
O1 Bi1 O3 175.26(15) . . ?
C41 Bi1 O2 82.2(2) . . ?
C29 Bi1 O2 77.5(2) . . ?
C35 Bi1 O2 138.76(19) . . ?
O1 Bi1 O2 51.47(16) . . ?
O3 Bi1 O2 133.24(16) . . ?
C41 Bi1 O4 76.54(19) . . ?
C29 Bi1 O4 77.72(19) . . ?
C35 Bi1 O4 138.02(19) . . ?
O1 Bi1 O4 134.36(16) . . ?
O3 Bi1 O4 50.24(15) . . ?
O2 Bi1 O4 83.19(13) . . ?
O5 S1 C48 106.5(4) . . ?
O5 S1 C47 106.4(7) . . ?
C48 S1 C47 95.9(5) . . ?
C1 O1 Bi1 104.8(4) . . ?
C1 O2 Bi1 83.4(4) . . ?
C15 O3 Bi1 105.6(4) . . ?
C15 O4 Bi1 83.1(3) . . ?
C7 N1 C8 125.1(5) . . ?
C21 N2 C22 126.8(6) . . ?
O2 C1 O1 120.3(5) . . ?
O2 C1 C2 122.9(6) . . ?
O1 C1 C2 116.8(5) . . ?
C3 C2 C7 119.4(6) . . ?
C3 C2 C1 118.4(6) . . ?
C7 C2 C1 122.2(6) . . ?
C4 C3 C2 122.3(7) . . ?
C3 C4 C5 118.5(7) . . ?
C6 C5 C4 120.4(6) . . ?
C5 C6 C7 122.3(7) . . ?
N1 C7 C6 122.8(6) . . ?
N1 C7 C2 120.1(5) . . ?
C6 C7 C2 117.2(6) . . ?
C9 C8 C13 121.5(6) . . ?
C9 C8 N1 120.0(7) . . ?
C13 C8 N1 118.6(6) . . ?
C10 C9 C8 119.7(7) . . ?
C11 C10 C9 120.7(7) . . ?
C10 C11 C12 117.9(7) . . ?
C13 C12 C11 124.4(7) . . ?
C13 C12 Cl1 118.5(5) . . ?
C11 C12 Cl1 117.1(5) . . ?
C12 C13 C8 115.8(6) . . ?
C12 C13 C14 122.4(7) . . ?
C8 C13 C14 121.8(6) . . ?
O4 C15 O3 120.9(6) . . ?
O4 C15 C16 122.8(6) . . ?
O3 C15 C16 116.4(6) . . ?
C17 C16 C21 119.6(6) . . ?
C17 C16 C15 117.9(6) . . ?
C21 C16 C15 122.4(6) . . ?
C18 C17 C16 122.8(8) . . ?
C17 C18 C19 117.8(8) . . ?
C20 C19 C18 121.0(7) . . ?
C19 C20 C21 121.7(7) . . ?
N2 C21 C20 122.7(6) . . ?
N2 C21 C16 120.2(6) . . ?
C20 C21 C16 117.1(6) . . ?
C23 C22 C27 120.6(7) . . ?
C23 C22 N2 121.3(7) . . ?
C27 C22 N2 117.9(6) . . ?
C22 C23 C24 120.3(8) . . ?
C25 C24 C23 120.1(7) . . ?
C24 C25 C26 119.3(7) . . ?
C25 C26 C27 122.9(7) . . ?
C25 C26 Cl2 118.5(6) . . ?
C27 C26 Cl2 118.6(6) . . ?
C26 C27 C22 116.7(7) . . ?
C26 C27 C28 121.4(6) . . ?
C22 C27 C28 121.8(6) . . ?
C34 C29 C30 122.1(7) . . ?
C34 C29 Bi1 123.1(5) . . ?
C30 C29 Bi1 114.8(5) . . ?
C31 C30 C29 118.1(8) . . ?
C30 C31 C32 120.4(10) . . ?
C33 C32 C31 120.1(9) . . ?
C32 C33 C34 120.4(7) . . ?
C29 C34 C33 118.9(7) . . ?
C40 C35 C36 119.5(7) . . ?
C40 C35 Bi1 121.3(5) . . ?
C36 C35 Bi1 119.2(5) . . ?
C35 C36 C37 118.6(7) . . ?
C38 C37 C36 121.6(8) . . ?
C39 C38 C37 118.9(7) . . ?
C38 C39 C40 121.0(8) . . ?
C35 C40 C39 120.3(8) . . ?
C42 C41 C46 121.9(7) . . ?
C42 C41 Bi1 123.4(5) . . ?
C46 C41 Bi1 114.6(5) . . ?
C41 C42 C43 119.0(7) . . ?
C44 C43 C42 119.7(8) . . ?
C45 C44 C43 120.7(8) . . ?
C44 C45 C46 120.3(7) . . ?
C41 C46 C45 118.3(7) . . ?

_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         8.482
_refine_diff_density_min         -10.508
_refine_diff_density_rms         0.427
_database_code_depnum_ccdc_archive 'CCDC 978102'
