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

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

data_yo_10a
_database_code_depnum_ccdc_archive 'CCDC 1420787'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C47 H35 Bi F4 O6, C4 H10 O'
_chemical_formula_sum            'C51 H45 Bi F4 O7'
_chemical_formula_weight         1054.85

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 -4.1077 10.2566 '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                   12.2901(3)
_cell_length_b                   12.4486(3)
_cell_length_c                   15.1716(4)
_cell_angle_alpha                76.296(2)
_cell_angle_beta                 76.185(2)
_cell_angle_gamma                84.494(2)
_cell_volume                     2187.95(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    17399
_cell_measurement_theta_min      1.9433
_cell_measurement_theta_max      32.4676

_exptl_crystal_description       Rhombic
_exptl_crystal_colour            Colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1052
_exptl_absorpt_coefficient_mu    4.100
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3727
_exptl_absorpt_correction_T_max  0.4944
_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      123(2)
_diffrn_radiation_wavelength     0.7107
_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 10.3389
_diffrn_reflns_number            56966
_diffrn_reflns_av_R_equivalents  0.0449
_diffrn_reflns_av_sigmaI/netI    0.0451
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         32.54
_reflns_number_total             14625
_reflns_number_gt                12889
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_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)+(0.0179P)²+1.0953P] 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         14625
_refine_ls_number_parameters     575
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0355
_refine_ls_R_factor_gt           0.0265
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0503
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.002
_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 0.728467(6) 0.799468(6) 0.573929(5) 0.01292(2) Uani 1 1 d . . .
F1 F 0.83528(13) 0.94874(15) -0.03503(12) 0.0400(4) Uani 1 1 d . . .
O1 O 0.70960(13) 0.88572(12) 0.42667(11) 0.0182(3) Uani 1 1 d . . .
C1 C 0.90085(17) 0.74424(17) 0.51248(15) 0.0165(4) Uani 1 1 d . . .
F2 F 0.50551(15) 0.80551(16) -0.05106(12) 0.0476(5) Uani 1 1 d . . .
O2 O 0.83476(14) 1.00170(13) 0.42954(12) 0.0233(3) Uani 1 1 d . . .
C2 C 0.92312(19) 0.66414(18) 0.45976(17) 0.0204(4) Uani 1 1 d . . .
F3 F 0.60494(14) 0.67641(16) 1.30750(12) 0.0449(4) Uani 1 1 d . . .
O3 O 0.91935(16) 1.14246(15) 0.28265(13) 0.0299(4) Uani 1 1 d . . .
H3 H 0.9107 1.1074 0.3383 0.036 Uiso 1 1 calc R . .
C3 C 1.0362(2) 0.6346(2) 0.42964(18) 0.0261(5) Uani 1 1 d . . .
H3A H 1.0556 0.5793 0.3942 0.031 Uiso 1 1 calc R . .
F4 F 0.81717(12) 0.66021(13) 1.01028(11) 0.0337(4) Uani 1 1 d . . .
O4 O 0.73664(13) 0.69628(12) 0.71791(11) 0.0178(3) Uani 1 1 d . . .
C4 C 1.1204(2) 0.6837(2) 0.45017(19) 0.0275(5) Uani 1 1 d . . .
H4 H 1.1964 0.6605 0.4302 0.033 Uiso 1 1 calc R . .
O5 O 0.74252(14) 0.54940(13) 0.65692(12) 0.0231(3) Uani 1 1 d . . .
C5 C 1.0949(2) 0.7662(2) 0.49952(18) 0.0267(5) Uani 1 1 d . . .
H5 H 1.1533 0.8011 0.5119 0.032 Uiso 1 1 calc R . .
O6 O 0.72630(16) 0.35541(13) 0.76228(13) 0.0275(4) Uani 1 1 d . . .
H6 H 0.7316 0.4036 0.7124 0.033 Uiso 1 1 calc R . .
C6 C 0.98417(19) 0.79778(19) 0.53093(17) 0.0215(5) Uani 1 1 d . . .
H6A H 0.9655 0.8550 0.5645 0.026 Uiso 1 1 calc R . .
O7 O 0.97966(16) 0.61740(15) 1.19557(15) 0.0352(4) Uani 1 1 d . . .
C7 C 0.8340(2) 0.6131(2) 0.43218(19) 0.0267(5) Uani 1 1 d . . .
H7A H 0.7810 0.5769 0.4882 0.040 Uiso 1 1 calc R . .
H7B H 0.8689 0.5583 0.3960 0.040 Uiso 1 1 calc R . .
H7C H 0.7940 0.6709 0.3943 0.040 Uiso 1 1 calc R . .
C8 C 0.56046(17) 0.73622(16) 0.58872(16) 0.0161(4) Uani 1 1 d . . .
C9 C 0.54720(19) 0.68797(18) 0.51810(16) 0.0197(4) Uani 1 1 d . . .
H9 H 0.6082 0.6827 0.4671 0.024 Uiso 1 1 calc R . .
C10 C 0.4439(2) 0.6477(2) 0.52304(18) 0.0258(5) Uani 1 1 d . . .
H10 H 0.4342 0.6132 0.4761 0.031 Uiso 1 1 calc R . .
C11 C 0.3550(2) 0.6582(2) 0.59683(19) 0.0272(5) Uani 1 1 d . . .
H11 H 0.2841 0.6312 0.6002 0.033 Uiso 1 1 calc R . .
C12 C 0.36950(19) 0.70745(19) 0.66512(18) 0.0245(5) Uani 1 1 d . . .
H12 H 0.3073 0.7148 0.7146 0.029 Uiso 1 1 calc R . .
C13 C 0.47290(18) 0.74725(17) 0.66425(16) 0.0184(4) Uani 1 1 d . . .
C14 C 0.4823(2) 0.7969(2) 0.74303(17) 0.0244(5) Uani 1 1 d . . .
H14A H 0.5314 0.7490 0.7795 0.037 Uiso 1 1 calc R . .
H14B H 0.4077 0.8039 0.7831 0.037 Uiso 1 1 calc R . .
H14C H 0.5138 0.8702 0.7180 0.037 Uiso 1 1 calc R . .
C15 C 0.73245(18) 0.93859(17) 0.64013(15) 0.0178(4) Uani 1 1 d . . .
C16 C 0.66236(19) 1.03256(17) 0.62677(17) 0.0205(4) Uani 1 1 d . . .
C17 C 0.6735(2) 1.11507(19) 0.67249(19) 0.0269(5) Uani 1 1 d . . .
H17 H 0.6254 1.1796 0.6668 0.032 Uiso 1 1 calc R . .
C18 C 0.7518(2) 1.1051(2) 0.72521(19) 0.0282(5) Uani 1 1 d . . .
H18 H 0.7588 1.1636 0.7537 0.034 Uiso 1 1 calc R . .
C19 C 0.8210(2) 1.01040(19) 0.73743(17) 0.0245(5) Uani 1 1 d . . .
H19 H 0.8752 1.0040 0.7740 0.029 Uiso 1 1 calc R . .
C20 C 0.81054(19) 0.92537(18) 0.69592(16) 0.0205(4) Uani 1 1 d . . .
H20 H 0.8556 0.8591 0.7052 0.025 Uiso 1 1 calc R . .
C21 C 0.5793(2) 1.04826(19) 0.56681(19) 0.0263(5) Uani 1 1 d . . .
H21A H 0.6115 1.0928 0.5051 0.039 Uiso 1 1 calc R . .
H21B H 0.5111 1.0863 0.5953 0.039 Uiso 1 1 calc R . .
H21C H 0.5606 0.9759 0.5607 0.039 Uiso 1 1 calc R . .
C22 C 0.77747(18) 0.96424(17) 0.38667(15) 0.0171(4) Uani 1 1 d . . .
C23 C 0.78706(18) 1.00970(17) 0.28562(16) 0.0169(4) Uani 1 1 d . . .
C24 C 0.85932(19) 1.09637(18) 0.23847(17) 0.0217(5) Uani 1 1 d . . .
C25 C 0.8705(2) 1.1364(2) 0.14325(18) 0.0277(5) Uani 1 1 d . . .
H25 H 0.9185 1.1956 0.1113 0.033 Uiso 1 1 calc R . .
C26 C 0.8122(2) 1.0905(2) 0.09489(18) 0.0270(5) Uani 1 1 d . . .
H26 H 0.8210 1.1182 0.0297 0.032 Uiso 1 1 calc R . .
C27 C 0.74002(19) 1.00334(19) 0.14037(17) 0.0208(4) Uani 1 1 d . . .
C28 C 0.72874(18) 0.96481(17) 0.23524(16) 0.0173(4) Uani 1 1 d . . .
H28 H 0.6800 0.9062 0.2670 0.021 Uiso 1 1 calc R . .
C29 C 0.6777(2) 0.9532(2) 0.08853(17) 0.0235(5) Uani 1 1 d . . .
C30 C 0.7262(2) 0.9276(2) 0.00325(17) 0.0263(5) Uani 1 1 d . . .
C31 C 0.6706(2) 0.8784(2) -0.04490(18) 0.0305(6) Uani 1 1 d . . .
H31 H 0.7063 0.8631 -0.1037 0.037 Uiso 1 1 calc R . .
C32 C 0.5614(2) 0.8527(2) -0.00385(19) 0.0336(6) Uani 1 1 d . . .
C33 C 0.5074(2) 0.8739(3) 0.08086(19) 0.0350(6) Uani 1 1 d . . .
H33 H 0.4319 0.8541 0.1079 0.042 Uiso 1 1 calc R . .
C34 C 0.5661(2) 0.9250(2) 0.12602(18) 0.0275(5) Uani 1 1 d . . .
H34 H 0.5293 0.9414 0.1842 0.033 Uiso 1 1 calc R . .
C35 C 0.73415(17) 0.59174(17) 0.72575(15) 0.0163(4) Uani 1 1 d . . .
C36 C 0.71664(17) 0.52052(17) 0.82083(16) 0.0169(4) Uani 1 1 d . . .
C37 C 0.71196(19) 0.40552(18) 0.83426(17) 0.0202(4) Uani 1 1 d . . .
C38 C 0.6905(2) 0.34035(18) 0.92374(18) 0.0256(5) Uani 1 1 d . . .
H38 H 0.6871 0.2624 0.9330 0.031 Uiso 1 1 calc R . .
C39 C 0.6741(2) 0.38812(19) 0.99928(18) 0.0251(5) Uani 1 1 d . . .
H39 H 0.6594 0.3424 1.0602 0.030 Uiso 1 1 calc R . .
C40 C 0.67872(18) 0.50264(18) 0.98819(16) 0.0196(4) Uani 1 1 d . . .
C41 C 0.70045(17) 0.56708(17) 0.89870(16) 0.0172(4) Uani 1 1 d . . .
H41 H 0.7045 0.6449 0.8898 0.021 Uiso 1 1 calc R . .
C42 C 0.65885(19) 0.55019(19) 1.07184(16) 0.0205(4) Uani 1 1 d . . .
C43 C 0.5696(2) 0.5176(2) 1.14697(18) 0.0256(5) Uani 1 1 d . . .
H43 H 0.5201 0.4654 1.1434 0.031 Uiso 1 1 calc R . .
C44 C 0.5505(2) 0.5587(2) 1.22674(18) 0.0292(5) Uani 1 1 d . . .
H44 H 0.4890 0.5357 1.2773 0.035 Uiso 1 1 calc R . .
C45 C 0.6228(2) 0.6331(2) 1.23033(18) 0.0301(6) Uani 1 1 d . . .
C46 C 0.7134(2) 0.6680(2) 1.15976(19) 0.0304(6) Uani 1 1 d . . .
H46 H 0.7636 0.7187 1.1647 0.036 Uiso 1 1 calc R . .
C47 C 0.7282(2) 0.6259(2) 1.08114(17) 0.0245(5) Uani 1 1 d . . .
C48 C 0.9990(3) 0.8069(2) 1.1863(3) 0.0500(9) Uani 1 1 d . . .
H48A H 0.9221 0.8104 1.2233 0.075 Uiso 1 1 calc R . .
H48B H 1.0163 0.8785 1.1434 0.075 Uiso 1 1 calc R . .
H48C H 1.0513 0.7892 1.2278 0.075 Uiso 1 1 calc R . .
C49 C 1.0100(2) 0.7193(2) 1.1321(2) 0.0358(6) Uani 1 1 d . . .
H49A H 0.9602 0.7384 1.0876 0.043 Uiso 1 1 calc R . .
H49B H 1.0882 0.7131 1.0965 0.043 Uiso 1 1 calc R . .
C50 C 0.9959(2) 0.5263(2) 1.1521(2) 0.0409(7) Uani 1 1 d . . .
H50A H 1.0753 0.5197 1.1191 0.049 Uiso 1 1 calc R . .
H50B H 0.9484 0.5371 1.1062 0.049 Uiso 1 1 calc R . .
C51 C 0.9649(4) 0.4240(3) 1.2258(4) 0.0767(14) Uani 1 1 d . . .
H51A H 1.0102 0.4156 1.2723 0.115 Uiso 1 1 calc R . .
H51B H 0.9789 0.3595 1.1975 0.115 Uiso 1 1 calc R . .
H51C H 0.8853 0.4297 1.2559 0.115 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 2.208(2) . ?
Bi1 C1 2.216(2) . ?
Bi1 C8 2.223(2) . ?
Bi1 O4 2.2764(15) . ?
Bi1 O1 2.2936(15) . ?
Bi1 O5 3.0740(16) . ?
Bi1 O2 3.0813(17) . ?
F1 C30 1.351(3) . ?
O1 C22 1.286(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.389(3) . ?
F2 C32 1.357(3) . ?
O2 C22 1.250(3) . ?
C2 C3 1.398(3) . ?
C2 C7 1.502(3) . ?
F3 C45 1.365(3) . ?
O3 C24 1.350(3) . ?
C3 C4 1.381(3) . ?
F4 C47 1.358(3) . ?
O4 C35 1.281(2) . ?
C4 C5 1.380(3) . ?
O5 C35 1.256(3) . ?
C5 C6 1.383(3) . ?
O6 C37 1.350(3) . ?
O7 C50 1.417(3) . ?
O7 C49 1.419(3) . ?
C8 C9 1.394(3) . ?
C8 C13 1.395(3) . ?
C9 C10 1.388(3) . ?
C10 C11 1.386(4) . ?
C11 C12 1.375(3) . ?
C12 C13 1.404(3) . ?
C13 C14 1.501(3) . ?
C15 C16 1.389(3) . ?
C15 C20 1.399(3) . ?
C16 C17 1.402(3) . ?
C16 C21 1.493(3) . ?
C17 C18 1.371(4) . ?
C18 C19 1.388(3) . ?
C19 C20 1.384(3) . ?
C22 C23 1.483(3) . ?
C23 C28 1.397(3) . ?
C23 C24 1.407(3) . ?
C24 C25 1.390(3) . ?
C25 C26 1.381(3) . ?
C26 C27 1.406(3) . ?
C27 C28 1.383(3) . ?
C27 C29 1.486(3) . ?
C29 C30 1.386(3) . ?
C29 C34 1.398(3) . ?
C30 C31 1.381(3) . ?
C31 C32 1.371(4) . ?
C32 C33 1.372(4) . ?
C33 C34 1.388(3) . ?
C35 C36 1.482(3) . ?
C36 C41 1.400(3) . ?
C36 C37 1.402(3) . ?
C37 C38 1.385(3) . ?
C38 C39 1.378(3) . ?
C39 C40 1.400(3) . ?
C40 C41 1.382(3) . ?
C40 C42 1.484(3) . ?
C42 C47 1.382(3) . ?
C42 C43 1.392(3) . ?
C43 C44 1.384(3) . ?
C44 C45 1.362(4) . ?
C45 C46 1.371(4) . ?
C46 C47 1.380(3) . ?
C48 C49 1.492(4) . ?
C50 C51 1.494(5) . ?

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 C1 110.62(8) . . ?
C15 Bi1 C8 116.29(8) . . ?
C1 Bi1 C8 132.94(8) . . ?
C15 Bi1 O4 82.86(7) . . ?
C1 Bi1 O4 92.24(7) . . ?
C8 Bi1 O4 90.07(7) . . ?
C15 Bi1 O1 103.38(7) . . ?
C1 Bi1 O1 88.48(7) . . ?
C8 Bi1 O1 84.37(7) . . ?
O4 Bi1 O1 173.02(5) . . ?
C15 Bi1 O5 129.01(7) . . ?
C1 Bi1 O5 74.95(6) . . ?
C8 Bi1 O5 73.25(6) . . ?
O4 Bi1 O5 46.22(5) . . ?
O1 Bi1 O5 127.60(5) . . ?
C15 Bi1 O2 68.98(6) . . ?
C1 Bi1 O2 73.79(6) . . ?
C8 Bi1 O2 126.52(6) . . ?
O4 Bi1 O2 140.68(5) . . ?
O1 Bi1 O2 46.02(5) . . ?
O5 Bi1 O2 148.19(4) . . ?
C22 O1 Bi1 113.86(13) . . ?
C6 C1 C2 123.3(2) . . ?
C6 C1 Bi1 113.75(15) . . ?
C2 C1 Bi1 122.97(16) . . ?
C22 O2 Bi1 76.82(13) . . ?
C1 C2 C3 116.1(2) . . ?
C1 C2 C7 123.7(2) . . ?
C3 C2 C7 120.2(2) . . ?
C4 C3 C2 121.6(2) . . ?
C35 O4 Bi1 114.24(13) . . ?
C5 C4 C3 120.5(2) . . ?
C35 O5 Bi1 76.45(12) . . ?
C4 C5 C6 119.8(2) . . ?
C5 C6 C1 118.6(2) . . ?
C50 O7 C49 113.1(2) . . ?
C9 C8 C13 122.4(2) . . ?
C9 C8 Bi1 116.61(16) . . ?
C13 C8 Bi1 120.96(15) . . ?
C10 C9 C8 119.3(2) . . ?
C11 C10 C9 119.7(2) . . ?
C12 C11 C10 120.1(2) . . ?
C11 C12 C13 122.3(2) . . ?
C8 C13 C12 116.2(2) . . ?
C8 C13 C14 124.9(2) . . ?
C12 C13 C14 118.9(2) . . ?
C16 C15 C20 122.6(2) . . ?
C16 C15 Bi1 122.08(16) . . ?
C20 C15 Bi1 115.29(15) . . ?
C15 C16 C17 116.5(2) . . ?
C15 C16 C21 123.2(2) . . ?
C17 C16 C21 120.3(2) . . ?
C18 C17 C16 121.8(2) . . ?
C17 C18 C19 120.6(2) . . ?
C20 C19 C18 119.5(2) . . ?
C19 C20 C15 118.9(2) . . ?
O2 C22 O1 122.5(2) . . ?
O2 C22 C23 120.1(2) . . ?
O1 C22 C23 117.45(18) . . ?
C28 C23 C24 119.1(2) . . ?
C28 C23 C22 121.0(2) . . ?
C24 C23 C22 119.86(19) . . ?
O3 C24 C25 118.2(2) . . ?
O3 C24 C23 122.1(2) . . ?
C25 C24 C23 119.6(2) . . ?
C26 C25 C24 120.2(2) . . ?
C25 C26 C27 121.2(2) . . ?
C28 C27 C26 118.1(2) . . ?
C28 C27 C29 120.5(2) . . ?
C26 C27 C29 121.4(2) . . ?
C27 C28 C23 121.8(2) . . ?
C30 C29 C34 116.1(2) . . ?
C30 C29 C27 123.0(2) . . ?
C34 C29 C27 120.9(2) . . ?
F1 C30 C31 117.1(2) . . ?
F1 C30 C29 119.0(2) . . ?
C31 C30 C29 123.9(2) . . ?
C32 C31 C30 116.9(2) . . ?
F2 C32 C31 117.4(2) . . ?
F2 C32 C33 119.6(2) . . ?
C31 C32 C33 123.0(2) . . ?
C32 C33 C34 118.1(2) . . ?
C33 C34 C29 122.1(2) . . ?
O5 C35 O4 122.5(2) . . ?
O5 C35 C36 120.00(19) . . ?
O4 C35 C36 117.46(19) . . ?
C41 C36 C37 119.0(2) . . ?
C41 C36 C35 120.67(18) . . ?
C37 C36 C35 120.28(19) . . ?
O6 C37 C38 118.3(2) . . ?
O6 C37 C36 122.0(2) . . ?
C38 C37 C36 119.7(2) . . ?
C39 C38 C37 120.2(2) . . ?
C38 C39 C40 121.4(2) . . ?
C41 C40 C39 118.0(2) . . ?
C41 C40 C42 122.6(2) . . ?
C39 C40 C42 119.3(2) . . ?
C40 C41 C36 121.6(2) . . ?
C47 C42 C43 116.3(2) . . ?
C47 C42 C40 122.7(2) . . ?
C43 C42 C40 120.9(2) . . ?
C44 C43 C42 122.2(2) . . ?
C45 C44 C43 117.8(2) . . ?
C44 C45 F3 119.1(2) . . ?
C44 C45 C46 123.4(2) . . ?
F3 C45 C46 117.5(2) . . ?
C45 C46 C47 116.7(2) . . ?
F4 C47 C46 117.4(2) . . ?
F4 C47 C42 119.0(2) . . ?
C46 C47 C42 123.6(2) . . ?
O7 C49 C48 108.3(3) . . ?
O7 C50 C51 108.2(3) . . ?

_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.732
_refine_diff_density_min         -1.011
_refine_diff_density_rms         0.129
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yo_18
_database_code_depnum_ccdc_archive 'CCDC 1420788'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H45 Bi O11'
_chemical_formula_weight         898.73

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Bi Bi -4.0280 10.6080 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   15.636(3)
_cell_length_b                   15.607(3)
_cell_length_c                   30.709(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     7494(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    123455
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_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    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3600
_exptl_absorpt_coefficient_mu    4.765
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9107
_exptl_absorpt_correction_T_max  0.9539
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71080
_diffrn_radiation_type           synchrotron
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            123455
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.33
_diffrn_reflns_theta_max         27.90
_reflns_number_total             8933
_reflns_number_gt                8296
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_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. 

 The two water molecules were refined anistropically with a DFIX restraint 
 of 0.84 applied to the O-H distances and DANG of 1.38 applied to the H-O-H
 angles.

 The carbons C21 & C21' occupy two positions with occupancies refined to be
 0.67:0.33.
;

_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)+(0.0330P)²+29.1010P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         8933
_refine_ls_number_parameters     492
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0331
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0846
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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 0.009076(8) 0.375799(8) 0.159784(4) 0.01357(5) Uani 1 1 d . . .
O1 O -0.09900(16) 0.27997(15) 0.16667(8) 0.0167(5) Uani 1 1 d . . .
C1 C -0.0619(2) 0.4528(2) 0.20700(11) 0.0155(6) Uani 1 1 d . . .
C19' C 0.0453(3) 0.3924(3) 0.01693(14) 0.0308(9) Uani 0.330(11) 1 d P A 2
O2 O -0.01186(15) 0.18587(17) 0.13586(10) 0.0211(6) Uani 1 1 d . . .
C2 C -0.1502(2) 0.4522(2) 0.20917(12) 0.0180(7) Uani 1 1 d . . .
H2 H -0.1828 0.4203 0.1887 0.022 Uiso 1 1 calc R . .
O3 O -0.38962(16) 0.18067(16) 0.12221(10) 0.0233(6) Uani 1 1 d . . .
H3 H -0.4280 0.1435 0.1191 0.028 Uiso 1 1 calc R . .
C3 C -0.1909(2) 0.4995(2) 0.24218(12) 0.0205(7) Uani 1 1 d . . .
O4 O -0.21896(17) -0.07095(15) 0.11781(11) 0.0258(6) Uani 1 1 d . . .
H4A H -0.1704 -0.0887 0.1253 0.031 Uiso 1 1 calc R . .
C4 C -0.1408(3) 0.5422(3) 0.27254(14) 0.0293(9) Uani 1 1 d . . .
H4 H -0.1678 0.5729 0.2955 0.035 Uiso 1 1 calc R . .
O5 O 0.01971(15) 0.57003(17) 0.12094(10) 0.0207(5) Uani 1 1 d . . .
C5 C -0.0523(3) 0.5411(3) 0.27018(15) 0.0346(10) Uani 1 1 d . . .
H5 H -0.0194 0.5708 0.2913 0.042 Uiso 1 1 calc R . .
O6 O 0.11070(15) 0.47574(15) 0.15000(8) 0.0164(5) Uani 1 1 d . . .
C6 C -0.0117(2) 0.4965(3) 0.23692(15) 0.0284(9) Uani 1 1 d . . .
H6 H 0.0489 0.4959 0.2347 0.034 Uiso 1 1 calc R . .
O7 O 0.23163(18) 0.81581(16) 0.08517(10) 0.0245(6) Uani 1 1 d . . .
H7 H 0.1830 0.8357 0.0908 0.029 Uiso 1 1 calc R . .
C7 C -0.2873(3) 0.5035(3) 0.24437(14) 0.0279(8) Uani 1 1 d . . .
H7A H -0.3055 0.5061 0.2749 0.042 Uiso 1 1 calc R . .
H7B H -0.3115 0.4522 0.2307 0.042 Uiso 1 1 calc R . .
H7C H -0.3075 0.5546 0.2290 0.042 Uiso 1 1 calc R . .
O8 O 0.40026(15) 0.56823(15) 0.11252(9) 0.0194(5) Uani 1 1 d . . .
H8 H 0.4385 0.6055 0.1158 0.023 Uiso 1 1 calc R . .
C8 C 0.1074(2) 0.3110(2) 0.19855(11) 0.0170(6) Uani 1 1 d . . .
O9 O 0.4553(4) 0.3848(2) 0.00717(13) 0.0602(12) Uani 1 1 d . . .
C9 C 0.0807(3) 0.2729(3) 0.23678(13) 0.0268(8) Uani 1 1 d . . .
H9 H 0.0217 0.2680 0.2437 0.032 Uiso 1 1 calc R . .
O10 O 0.42309(18) 0.39593(16) 0.09328(9) 0.0219(5) Uani 1 1 d D . .
H10A H 0.417(3) 0.4456(16) 0.1017(14) 0.033 Uiso 1 1 d D . .
H10B H 0.433(3) 0.395(3) 0.0662(7) 0.033 Uiso 1 1 d D . .
C10 C 0.1436(3) 0.2417(3) 0.26498(14) 0.0353(10) Uani 1 1 d . . .
H10 H 0.1275 0.2156 0.2917 0.042 Uiso 1 1 calc R . .
O11 O -0.0725(2) -0.14509(18) 0.14082(12) 0.0313(7) Uani 1 1 d D . .
H11B H -0.082(3) -0.1947(18) 0.1318(17) 0.047 Uiso 1 1 d D . .
H11A H -0.025(2) -0.127(3) 0.132(2) 0.047 Uiso 1 1 d D . .
C11 C 0.2301(3) 0.2486(3) 0.25411(15) 0.0337(10) Uani 1 1 d . . .
H11 H 0.2722 0.2274 0.2736 0.040 Uiso 1 1 calc R . .
C12 C 0.2551(2) 0.2857(2) 0.21568(13) 0.0234(8) Uani 1 1 d . . .
C13 C 0.1929(2) 0.3187(2) 0.18743(12) 0.0180(7) Uani 1 1 d . . .
H13 H 0.2092 0.3460 0.1610 0.022 Uiso 1 1 calc R . .
C14 C 0.3493(3) 0.2932(3) 0.20449(16) 0.0356(10) Uani 1 1 d . . .
H14A H 0.3794 0.3220 0.2283 0.053 Uiso 1 1 calc R . .
H14B H 0.3558 0.3265 0.1777 0.053 Uiso 1 1 calc R . .
H14C H 0.3734 0.2358 0.2003 0.053 Uiso 1 1 calc R . .
C15 C -0.0099(2) 0.3741(2) 0.08874(13) 0.0198(7) Uani 1 1 d . A .
C16 C -0.0913(3) 0.3586(2) 0.07288(13) 0.0234(8) Uani 1 1 d . . .
H16 H -0.1372 0.3467 0.0922 0.028 Uiso 1 1 calc R A 1
C17 C -0.1044(3) 0.3609(3) 0.02798(14) 0.0316(9) Uani 0.670(11) 1 d P A 1
C17' C -0.1044(3) 0.3609(3) 0.02798(14) 0.0316(9) Uani 0.330(11) 1 d P A 2
H17' H -0.1597 0.3504 0.0162 0.038 Uiso 0.330(11) 1 calc PR A 2
C18 C -0.0354(4) 0.3788(3) 0.00043(15) 0.0368(11) Uani 1 1 d . . .
H18 H -0.0444 0.3815 -0.0301 0.044 Uiso 1 1 calc R A 1
C19 C 0.0453(3) 0.3924(3) 0.01693(14) 0.0308(9) Uani 0.670(11) 1 d P A 1
H19 H 0.0915 0.4035 -0.0024 0.037 Uiso 0.670(11) 1 calc PR A 1
C20 C 0.0598(3) 0.3901(2) 0.06175(13) 0.0235(8) Uani 1 1 d . . .
H20 H 0.1153 0.3992 0.0734 0.028 Uiso 1 1 calc R A 1
C21 C -0.1880(4) 0.3442(5) 0.0097(2) 0.0393(19) Uani 0.670(11) 1 d P A 1
H21A H -0.1976 0.3822 -0.0153 0.059 Uiso 0.670(11) 1 calc PR A 1
H21B H -0.2319 0.3548 0.0318 0.059 Uiso 0.670(11) 1 calc PR A 1
H21C H -0.1911 0.2844 0.0001 0.059 Uiso 0.670(11) 1 calc PR A 1
C21' C 0.1082(11) 0.4103(10) -0.0152(4) 0.041(4) Uani 0.330(11) 1 d P A 2
H21D H 0.1352 0.3566 -0.0245 0.062 Uiso 0.330(11) 1 calc PR A 2
H21E H 0.1517 0.4485 -0.0029 0.062 Uiso 0.330(11) 1 calc PR A 2
H21F H 0.0811 0.4380 -0.0403 0.062 Uiso 0.330(11) 1 calc PR A 2
C22 C -0.0841(2) 0.2076(2) 0.14730(11) 0.0151(6) Uani 1 1 d . . .
C23 C -0.1614(2) 0.1530(2) 0.13835(11) 0.0155(6) Uani 1 1 d . . .
C24 C -0.1511(2) 0.0653(2) 0.13267(12) 0.0169(6) Uani 1 1 d . . .
H24 H -0.0963 0.0396 0.1353 0.020 Uiso 1 1 calc R . .
C25 C -0.2227(2) 0.0161(2) 0.12306(12) 0.0183(7) Uani 1 1 d . . .
C26 C -0.3031(2) 0.0532(2) 0.11876(12) 0.0176(7) Uani 1 1 d . . .
H26 H -0.3514 0.0190 0.1117 0.021 Uiso 1 1 calc R . .
C27 C -0.3118(2) 0.1414(2) 0.12501(12) 0.0168(7) Uani 1 1 d . . .
C28 C -0.2413(2) 0.1919(2) 0.13473(12) 0.0163(6) Uani 1 1 d . . .
H28 H -0.2474 0.2519 0.1388 0.020 Uiso 1 1 calc R . .
C29 C 0.0928(2) 0.5464(2) 0.12988(11) 0.0155(6) Uani 1 1 d . . .
C30 C 0.1702(2) 0.5981(2) 0.11766(11) 0.0124(6) Uani 1 1 d . . .
C31 C 0.2505(2) 0.5596(2) 0.11981(11) 0.0152(6) Uani 1 1 d . . .
H31 H 0.2559 0.5012 0.1281 0.018 Uiso 1 1 calc R . .
C32 C 0.3222(2) 0.6074(2) 0.10980(11) 0.0137(6) Uani 1 1 d . . .
C33 C 0.3151(2) 0.6931(2) 0.09783(12) 0.0161(6) Uani 1 1 d . . .
H33 H 0.3646 0.7256 0.0909 0.019 Uiso 1 1 calc R . .
C34 C 0.2341(2) 0.7306(2) 0.09610(12) 0.0172(7) Uani 1 1 d . . .
C35 C 0.1611(2) 0.6838(2) 0.10547(11) 0.0159(6) Uani 1 1 d . . .
H35 H 0.1061 0.7094 0.1036 0.019 Uiso 1 1 calc R . .
C36 C 0.5867(5) 0.3184(5) 0.0239(2) 0.072(2) Uani 1 1 d . . .
H36A H 0.6037 0.3679 0.0415 0.108 Uiso 1 1 calc R . .
H36B H 0.6377 0.2913 0.0115 0.108 Uiso 1 1 calc R . .
H36C H 0.5564 0.2770 0.0423 0.108 Uiso 1 1 calc R . .
C37 C 0.5311(5) 0.3461(4) -0.0108(2) 0.0623(18) Uani 1 1 d . . .
H37A H 0.5614 0.3881 -0.0294 0.075 Uiso 1 1 calc R . .
H37B H 0.5150 0.2964 -0.0291 0.075 Uiso 1 1 calc R . .
C38 C 0.3987(7) 0.4139(5) -0.02475(19) 0.084(3) Uani 1 1 d . . .
H38A H 0.3837 0.3661 -0.0445 0.101 Uiso 1 1 calc R . .
H38B H 0.4264 0.4594 -0.0422 0.101 Uiso 1 1 calc R . .
C39 C 0.3179(6) 0.4489(5) -0.0037(2) 0.086(3) Uani 1 1 d . . .
H39A H 0.2886 0.4028 0.0120 0.129 Uiso 1 1 calc R . .
H39B H 0.2800 0.4719 -0.0263 0.129 Uiso 1 1 calc R . .
H39C H 0.3330 0.4947 0.0167 0.129 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 C1 2.186(3) . ?
Bi1 C8 2.191(3) . ?
Bi1 C15 2.202(4) . ?
Bi1 O6 2.247(2) . ?
Bi1 O1 2.267(2) . ?
Bi1 O2 3.071(3) . ?
Bi1 O5 3.262(3) . ?
O1 C22 1.297(4) . ?
C1 C2 1.382(5) . ?
C1 C6 1.388(5) . ?
C19' C18 1.377(8) . ?
C19' C20 1.396(6) . ?
C19' C21' 1.419(13) . ?
O2 C22 1.230(4) . ?
C2 C3 1.407(5) . ?
O3 C27 1.366(4) . ?
C3 C4 1.388(6) . ?
C3 C7 1.510(5) . ?
O4 C25 1.369(4) . ?
C4 C5 1.386(6) . ?
O5 C29 1.232(4) . ?
C5 C6 1.390(6) . ?
O6 C29 1.294(4) . ?
O7 C34 1.372(4) . ?
O8 C32 1.368(4) . ?
C8 C9 1.381(5) . ?
C8 C13 1.386(5) . ?
O9 C38 1.397(9) . ?
O9 C37 1.439(9) . ?
C9 C10 1.398(6) . ?
C10 C11 1.397(7) . ?
C11 C12 1.371(6) . ?
C12 C13 1.402(5) . ?
C12 C14 1.516(6) . ?
C15 C16 1.384(5) . ?
C15 C20 1.392(6) . ?
C16 C17 1.395(6) . ?
C17 C18 1.400(7) . ?
C17 C21 1.445(8) . ?
C22 C23 1.505(5) . ?
C23 C24 1.389(5) . ?
C23 C28 1.393(5) . ?
C24 C25 1.389(5) . ?
C25 C26 1.391(5) . ?
C26 C27 1.397(5) . ?
C27 C28 1.388(5) . ?
C29 C30 1.503(4) . ?
C30 C31 1.393(4) . ?
C30 C35 1.397(4) . ?
C31 C32 1.380(5) . ?
C32 C33 1.391(4) . ?
C33 C34 1.395(5) . ?
C34 C35 1.386(5) . ?
C36 C37 1.441(10) . ?
C38 C39 1.521(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 C8 104.44(13) . . ?
C1 Bi1 C15 126.55(13) . . ?
C8 Bi1 C15 128.84(13) . . ?
C1 Bi1 O6 93.80(11) . . ?
C8 Bi1 O6 84.09(11) . . ?
C15 Bi1 O6 88.35(12) . . ?
C1 Bi1 O1 85.54(11) . . ?
C8 Bi1 O1 99.65(11) . . ?
C15 Bi1 O1 89.09(12) . . ?
O6 Bi1 O1 176.25(9) . . ?
C1 Bi1 O2 129.42(10) . . ?
C8 Bi1 O2 76.07(10) . . ?
C15 Bi1 O2 74.75(11) . . ?
O6 Bi1 O2 135.51(8) . . ?
O1 Bi1 O2 46.05(8) . . ?
C1 Bi1 O5 75.98(10) . . ?
C8 Bi1 O5 126.29(10) . . ?
C15 Bi1 O5 69.86(10) . . ?
O6 Bi1 O5 43.11(8) . . ?
O1 Bi1 O5 133.27(8) . . ?
O2 Bi1 O5 144.57(8) . . ?
C22 O1 Bi1 113.4(2) . . ?
C2 C1 C6 122.4(3) . . ?
C2 C1 Bi1 122.4(3) . . ?
C6 C1 Bi1 115.0(3) . . ?
C18 C19' C20 120.5(4) . . ?
C18 C19' C21' 114.2(8) . . ?
C20 C19' C21' 125.3(8) . . ?
C22 O2 Bi1 76.30(19) . . ?
C1 C2 C3 118.9(3) . . ?
C4 C3 C2 118.7(3) . . ?
C4 C3 C7 120.9(3) . . ?
C2 C3 C7 120.3(4) . . ?
C5 C4 C3 121.5(4) . . ?
C29 O5 Bi1 71.8(2) . . ?
C4 C5 C6 120.1(4) . . ?
C29 O6 Bi1 120.1(2) . . ?
C1 C6 C5 118.3(4) . . ?
C9 C8 C13 122.6(3) . . ?
C9 C8 Bi1 116.7(3) . . ?
C13 C8 Bi1 120.2(3) . . ?
C38 O9 C37 112.9(5) . . ?
C8 C9 C10 117.7(4) . . ?
C11 C10 C9 120.4(4) . . ?
C12 C11 C10 121.0(4) . . ?
C11 C12 C13 119.3(4) . . ?
C11 C12 C14 120.3(4) . . ?
C13 C12 C14 120.3(4) . . ?
C8 C13 C12 119.0(4) . . ?
C16 C15 C20 122.8(4) . . ?
C16 C15 Bi1 118.3(3) . . ?
C20 C15 Bi1 118.8(3) . . ?
C15 C16 C17 118.7(4) . . ?
C16 C17 C18 119.3(4) . . ?
C16 C17 C21 120.9(5) . . ?
C18 C17 C21 119.9(5) . . ?
C19' C18 C17 121.0(4) . . ?
C15 C20 C19' 117.7(4) . . ?
O2 C22 O1 122.4(3) . . ?
O2 C22 C23 122.0(3) . . ?
O1 C22 C23 115.6(3) . . ?
C24 C23 C28 121.5(3) . . ?
C24 C23 C22 119.2(3) . . ?
C28 C23 C22 119.2(3) . . ?
C23 C24 C25 118.6(3) . . ?
O4 C25 C24 122.7(3) . . ?
O4 C25 C26 116.1(3) . . ?
C24 C25 C26 121.2(3) . . ?
C25 C26 C27 119.0(3) . . ?
O3 C27 C28 117.8(3) . . ?
O3 C27 C26 121.4(3) . . ?
C28 C27 C26 120.8(3) . . ?
C27 C28 C23 118.8(3) . . ?
O5 C29 O6 124.2(3) . . ?
O5 C29 C30 122.1(3) . . ?
O6 C29 C30 113.7(3) . . ?
C31 C30 C35 121.2(3) . . ?
C31 C30 C29 118.9(3) . . ?
C35 C30 C29 119.9(3) . . ?
C32 C31 C30 119.2(3) . . ?
O8 C32 C31 118.0(3) . . ?
O8 C32 C33 121.1(3) . . ?
C31 C32 C33 120.9(3) . . ?
C32 C33 C34 119.1(3) . . ?
O7 C34 C35 122.6(3) . . ?
O7 C34 C33 116.2(3) . . ?
C35 C34 C33 121.2(3) . . ?
C34 C35 C30 118.4(3) . . ?
O9 C37 C36 109.9(5) . . ?
O9 C38 C39 110.2(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.90
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.083
_refine_diff_density_min         -2.248
_refine_diff_density_rms         0.140
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yo_08
_database_code_depnum_ccdc_archive 'CCDC 1420789'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H39 Bi O6'
_chemical_formula_sum            'C39 H39 Bi O6'
_chemical_formula_weight         812.68

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           Orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   9.1878(4)
_cell_length_b                   18.7150(10)
_cell_length_c                   19.9856(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3436.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5462
_cell_measurement_theta_min      2.2122
_cell_measurement_theta_max      32.3315

_exptl_crystal_description       cubic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.571
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    5.176
_exptl_absorpt_correction_type   Analytical
_exptl_absorpt_correction_T_min  0.3058
_exptl_absorpt_correction_T_max  0.6256
_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)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.7107
_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 10.3389
_diffrn_reflns_number            20817
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0717
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.2122
_diffrn_reflns_theta_max         32.3315
_reflns_number_total             10969
_reflns_number_gt                9720
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET)
(compiled Aug  3 2011,13:03:54)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_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)+(0.0170P)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   -0.047(5)
_refine_ls_number_reflns         10969
_refine_ls_number_parameters     420
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0685
_refine_ls_wR_factor_gt          0.0639
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.002
_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 0.527952(16) 0.532468(8) 0.778474(8) 0.01343(4) Uani 1 1 d . . .
C8 C 0.3067(4) 0.5390(3) 0.8206(2) 0.0157(8) Uani 1 1 d . . .
C11 C 0.0325(5) 0.5405(3) 0.8753(2) 0.0271(10) Uani 1 1 d . . .
H11 H -0.0614 0.5407 0.8951 0.033 Uiso 1 1 calc R . .
C9 C 0.2333(4) 0.6030(2) 0.8252(2) 0.0167(9) Uani 1 1 d . . .
H9 H 0.2771 0.6459 0.8097 0.020 Uiso 1 1 calc R . .
C10 C 0.0939(5) 0.6042(3) 0.8529(2) 0.0220(10) Uani 1 1 d . . .
C13 C 0.2464(5) 0.4749(3) 0.8407(2) 0.0234(10) Uani 1 1 d . . .
H13 H 0.2975 0.4311 0.8356 0.028 Uiso 1 1 calc R . .
C12 C 0.1076(5) 0.4768(3) 0.8687(3) 0.0298(12) Uani 1 1 d . . .
H12 H 0.0638 0.4337 0.8836 0.036 Uiso 1 1 calc R . .
O5 O 0.4307(3) 0.49242(15) 0.67899(16) 0.0198(7) Uani 1 1 d . . .
O4 O 0.3759(3) 0.60768(17) 0.68368(16) 0.0213(7) Uani 1 1 d . . .
C32 C 0.2666(4) 0.5399(3) 0.5970(2) 0.0208(9) Uani 1 1 d . . .
C31 C 0.3639(4) 0.5485(2) 0.6570(2) 0.0188(9) Uani 1 1 d . . .
C15 C 0.5990(4) 0.4206(2) 0.7943(2) 0.0164(9) Uani 1 1 d . . .
C20 C 0.5593(5) 0.3684(2) 0.7475(3) 0.0246(11) Uani 1 1 d . . .
H20 H 0.5048 0.3812 0.7089 0.029 Uiso 1 1 calc R . .
C16 C 0.6778(5) 0.4008(2) 0.8510(2) 0.0202(9) Uani 1 1 d . . .
H16 H 0.7055 0.4362 0.8826 0.024 Uiso 1 1 calc R . .
C14 C 0.0101(5) 0.6736(3) 0.8568(3) 0.0348(13) Uani 1 1 d . . .
H14A H 0.0717 0.7128 0.8410 0.052 Uiso 1 1 calc R . .
H14B H -0.0188 0.6825 0.9032 0.052 Uiso 1 1 calc R . .
H14C H -0.0770 0.6703 0.8286 0.052 Uiso 1 1 calc R . .
O1 O 0.5391(3) 0.65997(14) 0.83991(16) 0.0194(6) Uani 1 1 d . . .
O2 O 0.6371(3) 0.56085(16) 0.87910(16) 0.0174(7) Uani 1 1 d . . .
C33 C 0.1768(5) 0.4807(3) 0.5877(3) 0.0254(11) Uani 1 1 d . . .
C37 C 0.2594(5) 0.5965(3) 0.5514(3) 0.0288(11) Uani 1 1 d . . .
H37 H 0.3199 0.6372 0.5574 0.035 Uiso 1 1 calc R . .
C35 C 0.0768(6) 0.5349(4) 0.4892(3) 0.0443(15) Uani 1 1 d . . .
H35 H 0.0112 0.5335 0.4524 0.053 Uiso 1 1 calc R . .
C22 C 0.6129(4) 0.6285(2) 0.8833(2) 0.0171(9) Uani 1 1 d . . .
C19 C 0.6000(6) 0.2979(2) 0.7578(3) 0.0304(12) Uani 1 1 d . . .
H19 H 0.5753 0.2626 0.7257 0.036 Uiso 1 1 calc R . .
C34 C 0.0820(5) 0.4790(4) 0.5323(3) 0.0406(15) Uani 1 1 d . . .
H34 H 0.0216 0.4386 0.5251 0.049 Uiso 1 1 calc R . .
C17 C 0.7169(5) 0.3291(3) 0.8621(3) 0.0256(11) Uani 1 1 d . . .
C6 C 0.8382(4) 0.5463(2) 0.7261(3) 0.0233(10) Uani 1 1 d . . .
H6 H 0.8442 0.4998 0.7451 0.028 Uiso 1 1 calc R . .
C1 C 0.7094(4) 0.5853(2) 0.7269(3) 0.0172(8) Uani 1 1 d . . .
C24 C 0.7475(5) 0.6408(3) 0.9958(3) 0.0201(9) Uani 1 1 d . . .
C28 C 0.6642(5) 0.7450(3) 0.9366(3) 0.0257(11) Uani 1 1 d . . .
H28 H 0.6161 0.7656 0.8992 0.031 Uiso 1 1 calc R . .
C23 C 0.6757(5) 0.6705(2) 0.9404(2) 0.0185(9) Uani 1 1 d . . .
C2 C 0.6965(5) 0.6528(2) 0.6991(2) 0.0247(11) Uani 1 1 d . . .
H2 H 0.6069 0.6781 0.7011 0.030 Uiso 1 1 calc R . .
C25 C 0.8056(5) 0.6864(3) 1.0456(3) 0.0309(12) Uani 1 1 d . . .
H25 H 0.8543 0.6668 1.0833 0.037 Uiso 1 1 calc R . .
C36 C 0.1652(6) 0.5938(4) 0.4978(3) 0.0420(15) Uani 1 1 d . . .
H36 H 0.1611 0.6323 0.4669 0.050 Uiso 1 1 calc R . .
C18 C 0.6770(5) 0.2787(3) 0.8152(3) 0.0313(13) Uani 1 1 d . . .
H18 H 0.7025 0.2301 0.8220 0.038 Uiso 1 1 calc R . .
O3 O 0.7608(3) 0.56848(16) 0.99940(17) 0.0216(7) Uani 1 1 d . . .
C29 C 0.8402(5) 0.5376(3) 1.0541(2) 0.0273(10) Uani 1 1 d . . .
H29A H 0.7941 0.5503 1.0973 0.033 Uiso 1 1 calc R . .
H29B H 0.9419 0.5551 1.0544 0.033 Uiso 1 1 calc R . .
O6 O 0.1797(4) 0.4290(2) 0.6350(2) 0.0396(10) Uani 1 1 d . . .
C5 C 0.9581(6) 0.5788(3) 0.6961(3) 0.0339(12) Uani 1 1 d . . .
H5 H 1.0487 0.5543 0.6955 0.041 Uiso 1 1 calc R . .
C30 C 0.8362(5) 0.4577(3) 1.0434(3) 0.0304(12) Uani 1 1 d . . .
H30A H 0.7349 0.4419 1.0396 0.046 Uiso 1 1 calc R . .
H30B H 0.8824 0.4337 1.0814 0.046 Uiso 1 1 calc R . .
H30C H 0.8888 0.4457 1.0022 0.046 Uiso 1 1 calc R . .
C4 C 0.9489(5) 0.6452(3) 0.6674(3) 0.0355(13) Uani 1 1 d . . .
H4 H 1.0324 0.6657 0.6469 0.043 Uiso 1 1 calc R . .
C26 C 0.7910(5) 0.7594(3) 1.0389(3) 0.0361(14) Uani 1 1 d . . .
H26 H 0.8308 0.7898 1.0723 0.043 Uiso 1 1 calc R . .
C3 C 0.8184(6) 0.6830(3) 0.6680(3) 0.0351(13) Uani 1 1 d . . .
C38 C 0.0519(7) 0.3839(3) 0.6421(3) 0.0524(18) Uani 1 1 d . . .
H38A H 0.0500 0.3470 0.6066 0.063 Uiso 1 1 calc R . .
H38B H -0.0380 0.4128 0.6389 0.063 Uiso 1 1 calc R . .
C27 C 0.7203(6) 0.7895(3) 0.9851(3) 0.0320(13) Uani 1 1 d . . .
H27 H 0.7103 0.8399 0.9815 0.038 Uiso 1 1 calc R . .
C21 C 0.7959(6) 0.3086(3) 0.9250(3) 0.0378(14) Uani 1 1 d . . .
H21A H 0.8186 0.2575 0.9239 0.057 Uiso 1 1 calc R . .
H21B H 0.7342 0.3189 0.9638 0.057 Uiso 1 1 calc R . .
H21C H 0.8864 0.3361 0.9283 0.057 Uiso 1 1 calc R . .
C39 C 0.0626(8) 0.3499(4) 0.7090(4) 0.076(3) Uani 1 1 d . . .
H39A H 0.1473 0.3181 0.7101 0.114 Uiso 1 1 calc R . .
H39B H -0.0259 0.3221 0.7178 0.114 Uiso 1 1 calc R . .
H39C H 0.0733 0.3869 0.7433 0.114 Uiso 1 1 calc R . .
C7 C 0.8049(7) 0.7553(3) 0.6352(4) 0.055(2) Uani 1 1 d . . .
H7A H 0.7132 0.7777 0.6488 0.083 Uiso 1 1 calc R . .
H7B H 0.8061 0.7495 0.5864 0.083 Uiso 1 1 calc R . .
H7C H 0.8866 0.7855 0.6489 0.083 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 C1 2.195(4) . ?
Bi1 C8 2.203(4) . ?
Bi1 C15 2.216(4) . ?
Bi1 O5 2.305(3) . ?
Bi1 O2 2.309(3) . ?
Bi1 O1 2.686(3) . ?
Bi1 O4 2.743(3) . ?
C8 C9 1.378(6) . ?
C8 C13 1.381(6) . ?
C11 C12 1.382(7) . ?
C11 C10 1.393(7) . ?
C9 C10 1.395(6) . ?
C10 C14 1.512(6) . ?
C13 C12 1.393(6) . ?
O5 C31 1.292(5) . ?
O4 C31 1.234(5) . ?
C32 C33 1.393(6) . ?
C32 C37 1.399(7) . ?
C32 C31 1.505(6) . ?
C15 C16 1.396(6) . ?
C15 C20 1.400(6) . ?
C20 C19 1.386(6) . ?
C16 C17 1.406(6) . ?
O1 C22 1.248(5) . ?
O2 C22 1.288(5) . ?
C33 O6 1.354(6) . ?
C33 C34 1.410(7) . ?
C37 C36 1.378(7) . ?
C35 C34 1.356(9) . ?
C35 C36 1.380(9) . ?
C22 C23 1.501(6) . ?
C19 C18 1.394(8) . ?
C17 C18 1.379(7) . ?
C17 C21 1.501(7) . ?
C6 C1 1.390(6) . ?
C6 C5 1.394(6) . ?
C1 C2 1.387(6) . ?
C24 O3 1.361(5) . ?
C24 C23 1.403(7) . ?
C24 C25 1.414(7) . ?
C28 C27 1.377(7) . ?
C28 C23 1.401(6) . ?
C2 C3 1.400(7) . ?
C25 C26 1.381(7) . ?
O3 C29 1.436(5) . ?
C29 C30 1.511(7) . ?
O6 C38 1.454(6) . ?
C5 C4 1.372(7) . ?
C4 C3 1.392(7) . ?
C26 C27 1.377(8) . ?
C3 C7 1.508(8) . ?
C38 C39 1.484(9) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 Bi1 C8 148.79(16) . . ?
C1 Bi1 C15 105.57(15) . . ?
C8 Bi1 C15 105.63(16) . . ?
C1 Bi1 O5 92.06(14) . . ?
C8 Bi1 O5 89.41(13) . . ?
C15 Bi1 O5 85.97(14) . . ?
C1 Bi1 O2 88.59(15) . . ?
C8 Bi1 O2 93.18(13) . . ?
C15 Bi1 O2 88.03(14) . . ?
O5 Bi1 O2 173.91(10) . . ?
C1 Bi1 O1 77.62(13) . . ?
C8 Bi1 O1 79.14(14) . . ?
C15 Bi1 O1 139.76(13) . . ?
O5 Bi1 O1 134.27(10) . . ?
O2 Bi1 O1 51.75(10) . . ?
C1 Bi1 O4 80.32(14) . . ?
C8 Bi1 O4 76.43(13) . . ?
C15 Bi1 O4 137.16(13) . . ?
O5 Bi1 O4 51.21(10) . . ?
O2 Bi1 O4 134.81(10) . . ?
O1 Bi1 O4 83.07(9) . . ?
C9 C8 C13 122.6(4) . . ?
C9 C8 Bi1 121.7(3) . . ?
C13 C8 Bi1 115.7(3) . . ?
C12 C11 C10 120.3(4) . . ?
C8 C9 C10 119.4(4) . . ?
C11 C10 C9 119.0(4) . . ?
C11 C10 C14 120.8(4) . . ?
C9 C10 C14 120.1(4) . . ?
C8 C13 C12 117.5(5) . . ?
C11 C12 C13 121.2(5) . . ?
C31 O5 Bi1 102.3(3) . . ?
C31 O4 Bi1 83.2(3) . . ?
C33 C32 C37 119.1(4) . . ?
C33 C32 C31 122.8(4) . . ?
C37 C32 C31 117.9(4) . . ?
O4 C31 O5 122.7(4) . . ?
O4 C31 C32 119.5(4) . . ?
O5 C31 C32 117.8(4) . . ?
C16 C15 C20 119.5(4) . . ?
C16 C15 Bi1 121.3(3) . . ?
C20 C15 Bi1 119.2(3) . . ?
C19 C20 C15 119.6(5) . . ?
C15 C16 C17 120.9(4) . . ?
C22 O1 Bi1 85.4(2) . . ?
C22 O2 Bi1 102.0(3) . . ?
O6 C33 C32 117.6(4) . . ?
O6 C33 C34 123.0(5) . . ?
C32 C33 C34 119.2(5) . . ?
C36 C37 C32 120.6(6) . . ?
C34 C35 C36 121.0(5) . . ?
O1 C22 O2 120.8(4) . . ?
O1 C22 C23 119.3(4) . . ?
O2 C22 C23 119.8(4) . . ?
C20 C19 C18 120.3(5) . . ?
C35 C34 C33 120.3(5) . . ?
C18 C17 C16 118.5(5) . . ?
C18 C17 C21 121.5(5) . . ?
C16 C17 C21 119.9(5) . . ?
C1 C6 C5 116.7(4) . . ?
C2 C1 C6 123.2(4) . . ?
C2 C1 Bi1 122.2(3) . . ?
C6 C1 Bi1 114.6(3) . . ?
O3 C24 C23 118.5(4) . . ?
O3 C24 C25 121.9(5) . . ?
C23 C24 C25 119.6(5) . . ?
C27 C28 C23 122.4(5) . . ?
C28 C23 C24 118.1(4) . . ?
C28 C23 C22 116.8(4) . . ?
C24 C23 C22 125.0(4) . . ?
C1 C2 C3 118.5(4) . . ?
C26 C25 C24 119.5(5) . . ?
C37 C36 C35 119.8(6) . . ?
C17 C18 C19 121.2(4) . . ?
C24 O3 C29 119.1(4) . . ?
O3 C29 C30 106.1(4) . . ?
C33 O6 C38 117.9(4) . . ?
C4 C5 C6 121.7(5) . . ?
C5 C4 C3 120.7(5) . . ?
C27 C26 C25 121.8(5) . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 C7 121.5(5) . . ?
C2 C3 C7 119.3(5) . . ?
O6 C38 C39 106.5(5) . . ?
C26 C27 C28 118.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.917
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.780
_refine_diff_density_min         -1.248
_refine_diff_density_rms         0.147
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yo_04
_database_code_depnum_ccdc_archive 'CCDC 1420790'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29 Bi N2 O8'
_chemical_formula_sum            'C35 H29 Bi N2 O8'
_chemical_formula_weight         814.58

# start Validation Reply Form
_vrf_PLAT230_yo_04               
;
PROBLEM: Hirshfeld Test Diff for    N2     --  C33     ..        6.5 su    
RESPONSE:The thermal ellipsoids of N2 & O7-O8 are relatively large, possibly 
indicating that these might be disordered but was not successfully modelled. 
Please see .cif for more details.
;
# end Validation Reply Form

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           Monoclinic
_symmetry_space_group_name_H-M   C2

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

_cell_length_a                   17.8158(13)
_cell_length_b                   14.7358(6)
_cell_length_c                   15.0730(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 125.227(10)
_cell_angle_gamma                90.00
_cell_volume                     3232.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    7543
_cell_measurement_theta_min      1.9628
_cell_measurement_theta_max      29.3045

_exptl_crystal_description       Cubic
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1600
_exptl_absorpt_coefficient_mu    5.509
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4054
_exptl_absorpt_correction_T_max  0.6088
_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      123(2)
_diffrn_radiation_wavelength     0.7107
_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 10.3389
_diffrn_reflns_number            15330
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0615
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.97
_diffrn_reflns_theta_max         29.37
_reflns_number_total             7286
_reflns_number_gt                6490
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_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. 


 The thermal ellipsoids of N2 & O7-O8 are relatively large, possibly indicating
 that these might be disordered. The bond distances of C33-N2 are larger than 
 anticipated, with 1.515, as compared to the aromatic carbon-nitrogen bond 
 distance of 1.48. However, they could not be modelled.
;

_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   -0.038(4)
_refine_ls_number_reflns         7286
_refine_ls_number_parameters     418
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0281
_refine_ls_wR_factor_ref         0.0444
_refine_ls_wR_factor_gt          0.0417
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_restrained_S_all      0.910
_refine_ls_shift/su_max          0.002
_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 0.132230(9) 0.52128(2) 0.837971(9) 0.02455(4) Uani 1 1 d . . .
O1 O 0.12177(17) 0.5260(4) 1.01902(18) 0.0308(6) Uani 1 1 d . . .
O2 O 0.11312(19) 0.6418(2) 0.9188(2) 0.0292(7) Uani 1 1 d . . .
C28 C 0.1224(3) 0.7679(3) 1.0611(3) 0.0252(10) Uani 1 1 d . . .
H28 H 0.1178 0.7890 0.9986 0.030 Uiso 1 1 calc R . .
C27 C 0.1311(3) 0.8292(3) 1.1356(3) 0.0266(10) Uani 1 1 d . . .
H27 H 0.1335 0.8925 1.1259 0.032 Uiso 1 1 calc R . .
O6 O 0.1485(3) 0.4200(3) 0.7363(3) 0.0303(10) Uani 1 1 d . . .
N1 N 0.1519(3) 0.8603(3) 1.3087(3) 0.0348(10) Uani 1 1 d . . .
C26 C 0.1361(3) 0.7961(3) 1.2254(3) 0.0257(10) Uani 1 1 d . . .
C1 C 0.2740(3) 0.5065(5) 0.9821(3) 0.0271(14) Uani 1 1 d . . .
O4 O 0.1758(2) 0.9381(3) 1.3069(3) 0.0430(9) Uani 1 1 d . . .
O3 O 0.1407(3) 0.8336(3) 1.3768(3) 0.0576(11) Uani 1 1 d . . .
C25 C 0.1305(3) 0.7056(4) 1.2402(3) 0.0284(11) Uani 1 1 d . . .
H25 H 0.1316 0.6850 1.3007 0.034 Uiso 1 1 calc R . .
C23 C 0.1203(3) 0.6754(3) 1.0772(3) 0.0240(10) Uani 1 1 d . . .
C22 C 0.1168(3) 0.6078(3) 1.0004(3) 0.0261(10) Uani 1 1 d . . .
C24 C 0.1232(3) 0.6443(3) 1.1660(3) 0.0269(10) Uani 1 1 d . . .
H24 H 0.1202 0.5811 1.1758 0.032 Uiso 1 1 calc R . .
O5 O 0.1474(2) 0.3251(2) 0.8512(2) 0.0318(8) Uani 1 1 d . . .
C15 C -0.0067(3) 0.4697(3) 0.7640(3) 0.0278(10) Uani 1 1 d . . .
C20 C -0.0329(3) 0.4238(3) 0.8214(3) 0.0303(11) Uani 1 1 d . . .
H20 H 0.0109 0.4136 0.8970 0.036 Uiso 1 1 calc R . .
C18 C -0.1828(3) 0.4069(4) 0.6609(4) 0.0496(14) Uani 1 1 d . . .
H18 H -0.2440 0.3851 0.6243 0.059 Uiso 1 1 calc R . .
C19 C -0.1220(3) 0.3921(4) 0.7710(4) 0.0369(13) Uani 1 1 d . . .
C17 C -0.1570(4) 0.4528(4) 0.6024(4) 0.0564(16) Uani 1 1 d . . .
H17 H -0.2005 0.4617 0.5265 0.068 Uiso 1 1 calc R . .
C8 C 0.1302(4) 0.6247(5) 0.7309(5) 0.0264(15) Uani 1 1 d . . .
C11 C 0.1285(4) 0.7495(5) 0.5966(5) 0.0313(16) Uani 1 1 d . . .
H11 H 0.1260 0.7923 0.5478 0.038 Uiso 1 1 calc R . .
C21 C -0.1517(4) 0.3431(4) 0.8330(4) 0.0484(15) Uani 1 1 d . . .
H21A H -0.2086 0.3703 0.8167 0.073 Uiso 1 1 calc R . .
H21B H -0.1035 0.3480 0.9110 0.073 Uiso 1 1 calc R . .
H21C H -0.1624 0.2790 0.8117 0.073 Uiso 1 1 calc R . .
C13 C 0.1816(3) 0.6091(3) 0.6893(3) 0.0295(11) Uani 1 1 d . . .
H13 H 0.2166 0.5550 0.7067 0.035 Uiso 1 1 calc R . .
C12 C 0.1806(3) 0.6745(3) 0.6216(3) 0.0323(11) Uani 1 1 d . . .
C9 C 0.0787(3) 0.7025(3) 0.7074(3) 0.0326(11) Uani 1 1 d . . .
H9 H 0.0445 0.7120 0.7369 0.039 Uiso 1 1 calc R . .
C10 C 0.0782(3) 0.7670(3) 0.6389(4) 0.0375(12) Uani 1 1 d . . .
H10 H 0.0442 0.8217 0.6217 0.045 Uiso 1 1 calc R . .
C14 C 0.2384(3) 0.6616(4) 0.5785(4) 0.0457(14) Uani 1 1 d . . .
H14A H 0.2681 0.6019 0.6007 0.069 Uiso 1 1 calc R . .
H14B H 0.2855 0.7090 0.6078 0.069 Uiso 1 1 calc R . .
H14C H 0.1991 0.6654 0.4990 0.069 Uiso 1 1 calc R . .
C29 C 0.1456(3) 0.3398(3) 0.7693(4) 0.0295(11) Uani 1 1 d . . .
C16 C -0.0683(3) 0.4858(3) 0.6535(3) 0.0431(13) Uani 1 1 d . . .
H16 H -0.0503 0.5184 0.6142 0.052 Uiso 1 1 calc R . .
C34 C 0.1147(3) 0.2066(4) 0.5348(3) 0.0334(12) Uani 1 1 d . . .
H34 H 0.1061 0.2169 0.4672 0.040 Uiso 1 1 calc R . .
C30 C 0.1374(3) 0.2623(3) 0.6997(3) 0.0266(10) Uani 1 1 d . . .
C31 C 0.1403(3) 0.1737(3) 0.7314(3) 0.0302(11) Uani 1 1 d . . .
H31 H 0.1501 0.1623 0.7994 0.036 Uiso 1 1 calc R . .
C35 C 0.1256(4) 0.2774(5) 0.6001(5) 0.0288(16) Uani 1 1 d . . .
H35 H 0.1253 0.3379 0.5778 0.035 Uiso 1 1 calc R . .
C32 C 0.1294(3) 0.1010(3) 0.6667(3) 0.0326(11) Uani 1 1 d . . .
H32 H 0.1307 0.0402 0.6884 0.039 Uiso 1 1 calc R . .
C33 C 0.1166(3) 0.1203(4) 0.5701(4) 0.0326(13) Uani 1 1 d . . .
N2 N 0.1014(3) 0.0412(4) 0.4971(4) 0.044(2) Uani 1 1 d . . .
O8 O 0.0942(2) 0.0607(3) 0.4142(3) 0.0617(12) Uani 1 1 d . . .
O7 O 0.0950(3) -0.0333(3) 0.5263(4) 0.0588(13) Uani 1 1 d . . .
C4 C 0.4497(3) 0.5026(5) 1.1617(4) 0.046(2) Uani 1 1 d . . .
H4 H 0.5111 0.5004 1.2249 0.055 Uiso 1 1 calc R . .
C5 C 0.4220(3) 0.5776(4) 1.0948(4) 0.0403(13) Uani 1 1 d . . .
C2 C 0.3020(3) 0.4315(4) 1.0490(3) 0.0360(12) Uani 1 1 d . . .
H2 H 0.2615 0.3824 1.0332 0.043 Uiso 1 1 calc R . .
C6 C 0.3308(3) 0.5789(4) 1.0022(3) 0.0363(12) Uani 1 1 d . . .
H6 H 0.3086 0.6292 0.9538 0.044 Uiso 1 1 calc R . .
C3 C 0.3922(4) 0.4312(4) 1.1406(4) 0.0472(14) Uani 1 1 d . . .
H3 H 0.4143 0.3810 1.1891 0.057 Uiso 1 1 calc R . .
C7 C 0.4844(4) 0.6559(5) 1.1211(4) 0.0671(19) Uani 1 1 d . . .
H7A H 0.4855 0.6951 1.1743 0.101 Uiso 1 1 calc R . .
H7B H 0.4623 0.6905 1.0548 0.101 Uiso 1 1 calc R . .
H7C H 0.5466 0.6335 1.1515 0.101 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 2.182(4) . ?
Bi1 C1 2.195(4) . ?
Bi1 C8 2.205(7) . ?
Bi1 O6 2.274(4) . ?
Bi1 O2 2.287(3) . ?
Bi1 O1 2.841(2) . ?
Bi1 O5 2.899(3) . ?
O1 C22 1.229(7) . ?
O2 C22 1.294(5) . ?
C28 C27 1.379(6) . ?
C28 C23 1.389(6) . ?
C27 C26 1.391(5) . ?
O6 C29 1.294(6) . ?
N1 O3 1.219(5) . ?
N1 O4 1.228(5) . ?
N1 C26 1.464(5) . ?
C26 C25 1.365(6) . ?
C1 C6 1.380(7) . ?
C1 C2 1.381(7) . ?
C25 C24 1.385(6) . ?
C23 C24 1.386(6) . ?
C23 C22 1.500(6) . ?
O5 C29 1.237(5) . ?
C15 C20 1.375(6) . ?
C15 C16 1.387(5) . ?
C20 C19 1.388(6) . ?
C18 C19 1.379(7) . ?
C18 C17 1.383(7) . ?
C19 C21 1.496(7) . ?
C17 C16 1.388(7) . ?
C8 C9 1.380(8) . ?
C8 C13 1.397(7) . ?
C11 C12 1.350(8) . ?
C11 C10 1.392(8) . ?
C13 C12 1.397(6) . ?
C12 C14 1.514(6) . ?
C9 C10 1.399(6) . ?
C29 C30 1.500(6) . ?
C34 C35 1.369(8) . ?
C34 C33 1.371(7) . ?
C30 C31 1.381(6) . ?
C30 C35 1.409(7) . ?
C31 C32 1.385(6) . ?
C32 C33 1.368(6) . ?
C33 N2 1.515(7) . ?
N2 O7 1.212(8) . ?
N2 O8 1.216(5) . ?
C4 C3 1.373(8) . ?
C4 C5 1.380(8) . ?
C5 C6 1.404(6) . ?
C5 C7 1.489(7) . ?
C2 C3 1.389(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
C15 Bi1 C1 142.15(18) . . ?
C15 Bi1 C8 109.37(19) . . ?
C1 Bi1 C8 108.5(2) . . ?
C15 Bi1 O6 88.53(15) . . ?
C1 Bi1 O6 94.63(17) . . ?
C8 Bi1 O6 85.15(13) . . ?
C15 Bi1 O2 93.99(13) . . ?
C1 Bi1 O2 89.42(16) . . ?
C8 Bi1 O2 84.73(19) . . ?
O6 Bi1 O2 169.84(14) . . ?
C15 Bi1 O1 79.42(12) . . ?
C1 Bi1 O1 74.18(10) . . ?
C8 Bi1 O1 134.7(2) . . ?
O6 Bi1 O1 140.16(17) . . ?
O2 Bi1 O1 49.98(14) . . ?
C15 Bi1 O5 73.80(13) . . ?
C1 Bi1 O5 79.88(19) . . ?
C8 Bi1 O5 134.54(17) . . ?
O6 Bi1 O5 49.39(13) . . ?
O2 Bi1 O5 140.71(9) . . ?
O1 Bi1 O5 90.78(14) . . ?
C22 O1 Bi1 80.8(3) . . ?
C22 O2 Bi1 105.3(3) . . ?
C27 C28 C23 120.2(4) . . ?
C28 C27 C26 118.5(4) . . ?
C29 O6 Bi1 107.0(3) . . ?
O3 N1 O4 123.2(4) . . ?
O3 N1 C26 118.0(4) . . ?
O4 N1 C26 118.8(4) . . ?
C25 C26 C27 122.1(4) . . ?
C25 C26 N1 119.2(4) . . ?
C27 C26 N1 118.7(4) . . ?
C6 C1 C2 123.3(4) . . ?
C6 C1 Bi1 114.8(4) . . ?
C2 C1 Bi1 121.8(4) . . ?
C26 C25 C24 119.1(4) . . ?
C24 C23 C28 120.2(4) . . ?
C24 C23 C22 119.1(4) . . ?
C28 C23 C22 120.7(4) . . ?
O1 C22 O2 123.6(4) . . ?
O1 C22 C23 120.6(4) . . ?
O2 C22 C23 115.7(4) . . ?
C25 C24 C23 119.9(5) . . ?
C29 O5 Bi1 79.0(3) . . ?
C20 C15 C16 121.3(4) . . ?
C20 C15 Bi1 123.1(3) . . ?
C16 C15 Bi1 115.6(3) . . ?
C15 C20 C19 121.2(4) . . ?
C19 C18 C17 121.7(5) . . ?
C18 C19 C20 117.5(5) . . ?
C18 C19 C21 120.8(5) . . ?
C20 C19 C21 121.7(5) . . ?
C18 C17 C16 120.5(5) . . ?
C9 C8 C13 122.2(6) . . ?
C9 C8 Bi1 119.4(4) . . ?
C13 C8 Bi1 118.4(4) . . ?
C12 C11 C10 123.0(6) . . ?
C12 C13 C8 118.6(5) . . ?
C11 C12 C13 119.1(5) . . ?
C11 C12 C14 120.8(5) . . ?
C13 C12 C14 120.1(4) . . ?
C8 C9 C10 118.3(5) . . ?
C11 C10 C9 118.7(5) . . ?
O5 C29 O6 124.0(5) . . ?
O5 C29 C30 120.1(4) . . ?
O6 C29 C30 115.9(4) . . ?
C15 C16 C17 117.7(5) . . ?
C35 C34 C33 117.8(5) . . ?
C31 C30 C35 118.2(5) . . ?
C31 C30 C29 120.6(4) . . ?
C35 C30 C29 121.2(5) . . ?
C30 C31 C32 121.6(4) . . ?
C34 C35 C30 121.1(6) . . ?
C33 C32 C31 117.3(5) . . ?
C32 C33 C34 123.9(4) . . ?
C32 C33 N2 117.6(5) . . ?
C34 C33 N2 118.6(5) . . ?
O7 N2 O8 127.6(5) . . ?
O7 N2 C33 116.7(5) . . ?
O8 N2 C33 115.7(6) . . ?
C3 C4 C5 122.7(4) . . ?
C4 C5 C6 117.4(5) . . ?
C4 C5 C7 121.8(5) . . ?
C6 C5 C7 120.8(5) . . ?
C1 C2 C3 116.9(5) . . ?
C1 C6 C5 119.2(5) . . ?
C4 C3 C2 120.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.902
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.885
_refine_diff_density_min         -0.995
_refine_diff_density_rms         0.100
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yo_13
_database_code_depnum_ccdc_archive 'CCDC 1420791'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29 Bi Cl2 O6'
_chemical_formula_sum            'C35 H29 Bi Cl2 O6'
_chemical_formula_weight         825.46

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 -4.1077 10.2566 '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                   9.0562(4)
_cell_length_b                   11.5012(5)
_cell_length_c                   16.2432(7)
_cell_angle_alpha                107.263(4)
_cell_angle_beta                 90.519(4)
_cell_angle_gamma                99.342(4)
_cell_volume                     1591.26(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    5137
_cell_measurement_theta_min      1.9396
_cell_measurement_theta_max      29.1583

_exptl_crystal_description       rhombic
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.723
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    5.753
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.1298
_exptl_absorpt_correction_T_max  0.5969
_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      123(2)
_diffrn_radiation_wavelength     0.7107
_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 10.3389
_diffrn_reflns_number            24451
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0776
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         29.22
_reflns_number_total             7585
_reflns_number_gt                6057
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_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.

 Structure was solved by Patterson methods. 

 The carboxylate ligand 04-06, C9-14, C12 was refined as disordered over two 
 positions with occupencies fixed at 0.5. Equivalent bond distances between two 
 disorder components were restrained to be the same (SADI). An ISOR restraint
 was applied to C9 & C9'.

 In the disordered carboxylate ligand, the phenolic hydrogen atoms H6 & H6' 
 were located in the difference Fourier map & were refined with the O-H 
 distance restrained to 0.88 and Uiso(H) = 1.5 x Ueq(O).   
;

_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)+(0.0265P)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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7585
_refine_ls_number_parameters     482
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.0769
_refine_ls_wR_factor_gt          0.0672
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.036
_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 0.861815(19) 0.733855(18) 0.713049(12) 0.02193(7) Uani 1 1 d . . .
Cl1 Cl 0.62014(14) 1.35835(13) 0.77614(9) 0.0363(3) Uani 1 1 d . . .
O1 O 0.7997(3) 0.9288(3) 0.7393(2) 0.0252(8) Uani 1 1 d . . .
C1 C 0.8448(5) 0.9898(5) 0.8184(3) 0.0229(11) Uani 1 1 d . . .
H3 H 0.959(7) 1.072(3) 0.952(4) 0.07(2) Uiso 1 1 d D . .
Cl2 Cl 0.8997(5) 0.0583(3) 0.5392(2) 0.0645(10) Uani 0.50 1 d PD A 1
O2 O 0.9081(4) 0.9407(3) 0.8653(2) 0.0291(8) Uani 1 1 d . . .
C2 C 0.8233(5) 1.1199(4) 0.8527(3) 0.0216(10) Uani 1 1 d . . .
Cl2' Cl 1.2163(3) 0.1546(3) 0.78248(18) 0.0398(7) Uani 0.50 1 d PD B 2
O3 O 0.9671(5) 1.1486(4) 0.9858(2) 0.0420(10) Uani 1 1 d D . .
C3 C 0.8885(6) 1.1942(5) 0.9344(3) 0.0299(12) Uani 1 1 d . . .
O4 O 0.8968(4) 0.5332(3) 0.6718(2) 0.0280(8) Uani 1 1 d . . .
C4 C 0.8738(6) 1.3176(5) 0.9639(3) 0.0356(13) Uani 1 1 d . . .
H4 H 0.9200 1.3677 1.0184 0.043 Uiso 1 1 calc R . .
O5 O 1.0093(4) 0.5807(3) 0.8031(2) 0.0337(9) Uani 1 1 d . . .
C5 C 0.7933(6) 1.3688(5) 0.9155(3) 0.0325(13) Uani 1 1 d . . .
H5 H 0.7839 1.4535 0.9360 0.039 Uiso 1 1 calc R . .
O6 O 1.1468(8) 0.4395(7) 0.8570(5) 0.0345(17) Uani 0.50 1 d PD A 1
H6 H 1.104(12) 0.505(7) 0.862(8) 0.052 Uiso 0.50 1 d PD C 1
C6 C 0.7262(5) 1.2939(5) 0.8363(3) 0.0267(11) Uani 1 1 d . . .
O6' O 0.8051(8) 0.3082(7) 0.5705(5) 0.0357(18) Uani 0.50 1 d PD B 2
H6' H 0.785(13) 0.375(6) 0.608(6) 0.053 Uiso 0.50 1 d PD D 2
C7 C 0.7413(5) 1.1720(4) 0.8047(3) 0.0218(10) Uani 1 1 d . . .
H7 H 0.6955 1.1231 0.7498 0.026 Uiso 1 1 calc R . .
C8 C 0.9651(5) 0.5049(5) 0.7324(3) 0.0275(12) Uani 1 1 d D . .
C9 C 1.008(2) 0.3816(12) 0.7219(11) 0.024(4) Uani 0.50 1 d PDU A 1
C9' C 0.9757(18) 0.3689(11) 0.6992(11) 0.016(3) Uani 0.50 1 d PDU B 2
C10 C 1.0919(19) 0.3561(14) 0.7822(8) 0.022(3) Uani 0.50 1 d PD A 1
C10' C 0.901(2) 0.285(2) 0.6270(15) 0.028(5) Uani 0.50 1 d PD B 2
C11 C 1.1290(16) 0.2359(13) 0.7643(9) 0.030(3) Uani 0.50 1 d PD A 1
H11 H 1.1917 0.2167 0.8039 0.037 Uiso 0.50 1 calc PR A 1
C11' C 0.9209(14) 0.1589(12) 0.6001(8) 0.025(3) Uani 0.50 1 d PD B 2
H11' H 0.8694 0.1023 0.5491 0.029 Uiso 0.50 1 calc PR B 2
C12 C 1.0716(18) 0.1475(13) 0.6877(11) 0.037(5) Uani 0.50 1 d PD A 1
H12 H 1.0981 0.0677 0.6740 0.044 Uiso 0.50 1 calc PR A 1
C12' C 1.0184(14) 0.1200(14) 0.6504(9) 0.027(3) Uani 0.50 1 d PD B 2
H12' H 1.0296 0.0357 0.6354 0.032 Uiso 0.50 1 calc PR B 2
C13 C 0.9773(17) 0.1728(13) 0.6313(8) 0.030(3) Uani 0.50 1 d PD A 1
C13' C 1.0973(16) 0.2052(15) 0.7216(10) 0.026(4) Uani 0.50 1 d PD B 2
C14 C 0.950(2) 0.2880(19) 0.6431(15) 0.031(4) Uani 0.50 1 d PD A 1
H14 H 0.8939 0.3069 0.6005 0.037 Uiso 0.50 1 calc PR A 1
C14' C 1.076(2) 0.3242(15) 0.7476(8) 0.024(3) Uani 0.50 1 d PD B 2
H14' H 1.1274 0.3795 0.7990 0.029 Uiso 0.50 1 calc PR B 2
C15 C 0.7736(5) 0.6939(5) 0.5775(3) 0.0263(11) Uani 1 1 d . . .
C16 C 0.7067(6) 0.7821(5) 0.5550(3) 0.0323(12) Uani 1 1 d . . .
H16 H 0.6989 0.8580 0.5972 0.039 Uiso 1 1 calc R . .
C17 C 0.6504(6) 0.7575(5) 0.4689(3) 0.0324(13) Uani 1 1 d . . .
C18 C 0.6654(6) 0.6461(6) 0.4094(3) 0.0382(14) Uani 1 1 d . . .
H18 H 0.6278 0.6283 0.3514 0.046 Uiso 1 1 calc R . .
C19 C 0.7331(7) 0.5608(6) 0.4323(4) 0.0448(15) Uani 1 1 d . . .
H19 H 0.7423 0.4852 0.3902 0.054 Uiso 1 1 calc R . .
C20 C 0.7886(6) 0.5846(6) 0.5171(3) 0.0397(14) Uani 1 1 d . . .
H20 H 0.8363 0.5260 0.5330 0.048 Uiso 1 1 calc R . .
C21 C 0.5799(7) 0.8516(6) 0.4427(4) 0.0489(16) Uani 1 1 d . . .
H21A H 0.6167 0.8579 0.3874 0.073 Uiso 1 1 calc R . .
H21B H 0.6063 0.9321 0.4869 0.073 Uiso 1 1 calc R . .
H21C H 0.4707 0.8262 0.4368 0.073 Uiso 1 1 calc R . .
C22 C 1.1030(5) 0.8026(4) 0.7201(3) 0.0229(11) Uani 1 1 d . . .
C23 C 1.1873(5) 0.8478(5) 0.7979(3) 0.0269(11) Uani 1 1 d . . .
H23 H 1.1417 0.8477 0.8503 0.032 Uiso 1 1 calc R . .
C24 C 1.3397(5) 0.8936(5) 0.7989(4) 0.0306(12) Uani 1 1 d . . .
C25 C 1.4022(6) 0.8902(5) 0.7202(4) 0.0380(14) Uani 1 1 d . . .
H25 H 1.5058 0.9218 0.7197 0.046 Uiso 1 1 calc R . .
C26 C 1.3171(6) 0.8420(5) 0.6429(4) 0.0369(14) Uani 1 1 d . . .
H26 H 1.3631 0.8388 0.5901 0.044 Uiso 1 1 calc R . .
C27 C 1.1637(5) 0.7980(5) 0.6420(3) 0.0291(12) Uani 1 1 d . . .
H27 H 1.1035 0.7660 0.5894 0.035 Uiso 1 1 calc R . .
C28 C 1.4344(6) 0.9449(5) 0.8831(4) 0.0402(14) Uani 1 1 d . . .
H28A H 1.3723 0.9367 0.9309 0.060 Uiso 1 1 calc R . .
H28B H 1.4751 1.0323 0.8921 0.060 Uiso 1 1 calc R . .
H28C H 1.5170 0.8988 0.8809 0.060 Uiso 1 1 calc R . .
C29 C 0.6852(5) 0.6872(4) 0.7935(3) 0.0227(11) Uani 1 1 d . . .
C30 C 0.7137(5) 0.7014(5) 0.8804(3) 0.0273(11) Uani 1 1 d . . .
H30 H 0.8122 0.7322 0.9065 0.033 Uiso 1 1 calc R . .
C31 C 0.5964(6) 0.6701(5) 0.9291(3) 0.0312(12) Uani 1 1 d . . .
C32 C 0.4520(6) 0.6264(5) 0.8883(3) 0.0331(13) Uani 1 1 d . . .
H32 H 0.3706 0.6058 0.9208 0.040 Uiso 1 1 calc R . .
C33 C 0.4265(6) 0.6128(5) 0.8012(3) 0.0329(13) Uani 1 1 d . . .
H33 H 0.3281 0.5829 0.7748 0.039 Uiso 1 1 calc R . .
C34 C 0.5432(5) 0.6425(5) 0.7525(3) 0.0279(12) Uani 1 1 d . . .
H34 H 0.5266 0.6325 0.6928 0.033 Uiso 1 1 calc R . .
C35 C 0.6231(7) 0.6857(6) 1.0236(4) 0.0469(16) Uani 1 1 d . . .
H35A H 0.5623 0.7439 1.0574 0.070 Uiso 1 1 calc R . .
H35B H 0.7294 0.7178 1.0410 0.070 Uiso 1 1 calc R . .
H35C H 0.5950 0.6055 1.0341 0.070 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 C29 2.176(4) . ?
Bi1 C22 2.189(4) . ?
Bi1 C15 2.224(5) . ?
Bi1 O4 2.280(3) . ?
Bi1 O1 2.318(3) . ?
Bi1 O2 2.849(3) . ?
Bi1 O5 3.047(3) . ?
Cl1 C6 1.752(5) . ?
O1 C1 1.293(6) . ?
C1 O2 1.257(6) . ?
C1 C2 1.479(7) . ?
Cl2 C13 1.726(13) . ?
C2 C7 1.390(6) . ?
C2 C3 1.411(7) . ?
Cl2' C13' 1.734(13) . ?
O3 C3 1.359(6) . ?
C3 C4 1.386(7) . ?
O4 C8 1.305(6) . ?
C4 C5 1.378(7) . ?
O5 C8 1.234(6) . ?
C5 C6 1.388(7) . ?
O6 C10 1.336(13) . ?
C6 C7 1.374(7) . ?
O6' C10' 1.368(15) . ?
C8 C9 1.490(13) . ?
C8 C9' 1.515(12) . ?
C9 C10 1.36(2) . ?
C9 C14 1.43(2) . ?
C9' C10' 1.37(2) . ?
C9' C14' 1.44(2) . ?
C10 C11 1.42(2) . ?
C10' C11' 1.43(2) . ?
C11 C12 1.384(15) . ?
C11' C12' 1.407(14) . ?
C12 C13 1.371(18) . ?
C12' C13' 1.375(16) . ?
C13 C14 1.35(2) . ?
C13' C14' 1.36(2) . ?
C15 C20 1.373(7) . ?
C15 C16 1.395(7) . ?
C16 C17 1.415(7) . ?
C17 C18 1.384(8) . ?
C17 C21 1.500(8) . ?
C18 C19 1.374(8) . ?
C19 C20 1.394(7) . ?
C22 C27 1.377(6) . ?
C22 C23 1.384(7) . ?
C23 C24 1.393(7) . ?
C24 C25 1.396(7) . ?
C24 C28 1.513(7) . ?
C25 C26 1.381(8) . ?
C26 C27 1.397(7) . ?
C29 C30 1.388(7) . ?
C29 C34 1.389(7) . ?
C30 C31 1.394(7) . ?
C31 C32 1.405(7) . ?
C31 C35 1.505(7) . ?
C32 C33 1.389(7) . ?
C33 C34 1.385(7) . ?

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
C29 Bi1 C22 140.70(19) . . ?
C29 Bi1 C15 111.05(18) . . ?
C22 Bi1 C15 108.20(18) . . ?
C29 Bi1 O4 89.31(15) . . ?
C22 Bi1 O4 92.08(15) . . ?
C15 Bi1 O4 85.35(16) . . ?
C29 Bi1 O1 90.03(14) . . ?
C22 Bi1 O1 93.58(15) . . ?
C15 Bi1 O1 87.29(15) . . ?
O4 Bi1 O1 171.83(12) . . ?
C29 Bi1 O2 76.55(15) . . ?
C22 Bi1 O2 76.35(14) . . ?
C15 Bi1 O2 136.76(15) . . ?
O4 Bi1 O2 137.88(11) . . ?
O1 Bi1 O2 49.58(10) . . ?
C29 Bi1 O5 78.66(14) . . ?
C22 Bi1 O5 74.03(14) . . ?
C15 Bi1 O5 131.84(15) . . ?
O4 Bi1 O5 46.81(11) . . ?
O1 Bi1 O5 140.81(11) . . ?
O2 Bi1 O5 91.23(10) . . ?
C1 O1 Bi1 106.8(3) . . ?
O2 C1 O1 121.0(4) . . ?
O2 C1 C2 120.2(4) . . ?
O1 C1 C2 118.8(4) . . ?
C1 O2 Bi1 82.6(3) . . ?
C7 C2 C3 118.7(4) . . ?
C7 C2 C1 120.9(4) . . ?
C3 C2 C1 120.4(4) . . ?
O3 C3 C4 118.3(5) . . ?
O3 C3 C2 121.9(5) . . ?
C4 C3 C2 119.8(5) . . ?
C8 O4 Bi1 112.7(3) . . ?
C5 C4 C3 121.1(5) . . ?
C8 O5 Bi1 77.6(3) . . ?
C4 C5 C6 118.6(5) . . ?
C7 C6 C5 121.6(5) . . ?
C7 C6 Cl1 119.9(4) . . ?
C5 C6 Cl1 118.5(4) . . ?
C6 C7 C2 120.2(5) . . ?
O5 C8 O4 122.8(5) . . ?
O5 C8 C9 112.9(7) . . ?
O4 C8 C9 124.1(7) . . ?
O5 C8 C9' 129.3(8) . . ?
O4 C8 C9' 107.9(7) . . ?
C9 C8 C9' 16.8(9) . . ?
C10 C9 C14 121.2(12) . . ?
C10 C9 C8 123.9(11) . . ?
C14 C9 C8 114.9(12) . . ?
C10' C9' C14' 117.0(11) . . ?
C10' C9' C8 126.0(12) . . ?
C14' C9' C8 117.0(12) . . ?
O6 C10 C9 123.5(14) . . ?
O6 C10 C11 117.4(14) . . ?
C9 C10 C11 119.0(11) . . ?
C9' C10' O6' 126.6(16) . . ?
C9' C10' C11' 121.7(13) . . ?
O6' C10' C11' 111.6(15) . . ?
C12 C11 C10 118.3(13) . . ?
C12' C11' C10' 118.9(12) . . ?
C13 C12 C11 121.4(13) . . ?
C13' C12' C11' 119.4(12) . . ?
C14 C13 C12 121.3(14) . . ?
C14 C13 Cl2 118.2(13) . . ?
C12 C13 Cl2 120.3(11) . . ?
C14' C13' C12' 121.4(14) . . ?
C14' C13' Cl2' 120.1(12) . . ?
C12' C13' Cl2' 118.4(11) . . ?
C13 C14 C9 118.2(16) . . ?
C13' C14' C9' 121.6(12) . . ?
C20 C15 C16 121.2(5) . . ?
C20 C15 Bi1 119.8(4) . . ?
C16 C15 Bi1 119.1(4) . . ?
C15 C16 C17 119.4(5) . . ?
C18 C17 C16 118.3(5) . . ?
C18 C17 C21 121.2(5) . . ?
C16 C17 C21 120.5(5) . . ?
C19 C18 C17 121.5(5) . . ?
C18 C19 C20 120.3(5) . . ?
C15 C20 C19 119.2(5) . . ?
C27 C22 C23 122.8(4) . . ?
C27 C22 Bi1 115.2(4) . . ?
C23 C22 Bi1 121.9(3) . . ?
C22 C23 C24 119.5(5) . . ?
C23 C24 C25 118.1(5) . . ?
C23 C24 C28 120.7(5) . . ?
C25 C24 C28 121.2(5) . . ?
C26 C25 C24 121.6(5) . . ?
C25 C26 C27 120.3(5) . . ?
C22 C27 C26 117.6(5) . . ?
C30 C29 C34 122.5(4) . . ?
C30 C29 Bi1 121.7(4) . . ?
C34 C29 Bi1 115.8(3) . . ?
C29 C30 C31 119.4(5) . . ?
C30 C31 C32 118.5(5) . . ?
C30 C31 C35 120.7(5) . . ?
C32 C31 C35 120.8(5) . . ?
C33 C32 C31 121.0(5) . . ?
C34 C33 C32 120.6(5) . . ?
C33 C34 C29 118.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.877
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.983
_refine_diff_density_min         -1.302
_refine_diff_density_rms         0.181
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yo_20
_database_code_depnum_ccdc_archive 'CCDC 1420792'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C49 H43 Bi Cl2 N2 O4'
_chemical_formula_sum            'C49 H43 Bi Cl2 N2 O4'
_chemical_formula_weight         1003.73

# start Validation Reply Form
_vrf_PLAT029_yo_20               
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.934 Note  
RESPONSE: Structure was collected at the MX1 beamline at the Australian 
synchrotron. A full 365 Phi scan was run however data completeness was 
still low due to hardware constraints. Please see .cif for more details
;
# end Validation Reply Form

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 -4.0280 10.6080 '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'

_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                   9.0480(18)
_cell_length_b                   11.217(2)
_cell_length_c                   20.912(4)
_cell_angle_alpha                101.82(3)
_cell_angle_beta                 90.76(3)
_cell_angle_gamma                90.17(3)
_cell_volume                     2077.2(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    35459
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       cubic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.02
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    4.421
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.9168
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_process_details   'XDS (Kabsch, 1993)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71080
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_source         'MX1 Beamline Australian Synchrotron'
_diffrn_radiation_monochromator  'Silicon Double Crystal'
_diffrn_measurement_device_type  'ADSC Quantum 210r'
_diffrn_measurement_method       'Phi Scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            35459
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0323
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         27.91
_reflns_number_total             9060
_reflns_number_gt                8299
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BluIce (McPhillips, 2002)'
_computing_cell_refinement       'XDS (Kabsch, 1993)'
_computing_data_reduction        'XDS (Kabsch, 1993)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_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. 

 Structure was collected at the MX1 beamline at the synchrotron. 
 A full 365 Phi scan was run however data completeness was still low due to 
 hardware constraints.

 The structure refined to 0.0398, the data parameter ratio is greater than 10,
 and there are no other indications of errors in the structure.
;

_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)+(0.0719P)²+2.4368P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9060
_refine_ls_number_parameters     530
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0398
_refine_ls_wR_factor_ref         0.1027
_refine_ls_wR_factor_gt          0.1003
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.002
_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 0.661488(16) 0.708038(13) 0.649144(7) 0.01522(6) Uani 1 1 d . . .
Cl1 Cl 0.71842(18) 1.15697(14) 1.10782(7) 0.0420(3) Uani 1 1 d . . .
O1 O 0.7472(4) 0.9068(3) 0.66800(16) 0.0204(6) Uani 1 1 d . . .
N1 N 0.6194(5) 1.0661(4) 0.8587(2) 0.0249(8) Uani 1 1 d . . .
C1 C 0.4289(5) 0.7614(4) 0.6422(2) 0.0192(8) Uani 1 1 d . . .
Cl2 Cl 0.23376(15) 0.51862(12) 0.99572(6) 0.0330(3) Uani 1 1 d . . .
O2 O 0.6408(3) 0.8814(3) 0.75958(16) 0.0204(6) Uani 1 1 d . . .
N2 N 0.3899(4) 0.3671(3) 0.7598(2) 0.0212(8) Uani 1 1 d . . .
C2 C 0.3479(5) 0.8167(4) 0.6963(2) 0.0196(8) Uani 1 1 d . . .
H2 H 0.3898 0.8282 0.7390 0.024 Uiso 1 1 calc R . .
O3 O 0.5974(4) 0.5091(3) 0.61500(17) 0.0215(7) Uani 1 1 d . . .
C3 C 0.2041(5) 0.8549(4) 0.6868(2) 0.0214(9) Uani 1 1 d . . .
O4 O 0.5138(4) 0.5480(3) 0.71613(16) 0.0213(6) Uani 1 1 d . . .
C4 C 0.1450(5) 0.8338(4) 0.6236(2) 0.0233(9) Uani 1 1 d . . .
H4 H 0.0469 0.8590 0.6167 0.028 Uiso 1 1 calc R . .
C5 C 0.2269(6) 0.7766(5) 0.5706(3) 0.0275(10) Uani 1 1 d . . .
H5 H 0.1840 0.7627 0.5280 0.033 Uiso 1 1 calc R . .
C6 C 0.3715(5) 0.7394(4) 0.5792(2) 0.0238(9) Uani 1 1 d . . .
H6 H 0.4284 0.7004 0.5431 0.029 Uiso 1 1 calc R . .
C7 C 0.1135(5) 0.9156(5) 0.7444(3) 0.0276(10) Uani 1 1 d . . .
H7A H 0.0432 0.9718 0.7305 0.041 Uiso 1 1 calc R . .
H7B H 0.1792 0.9608 0.7786 0.041 Uiso 1 1 calc R . .
H7C H 0.0593 0.8534 0.7616 0.041 Uiso 1 1 calc R . .
C8 C 0.7527(5) 0.6916(4) 0.5488(2) 0.0194(9) Uani 1 1 d . . .
C9 C 0.7937(5) 0.7940(4) 0.5269(2) 0.0223(9) Uani 1 1 d . . .
H9 H 0.7847 0.8722 0.5545 0.027 Uiso 1 1 calc R . .
C10 C 0.8495(5) 0.7828(5) 0.4630(2) 0.0231(9) Uani 1 1 d . . .
C11 C 0.8593(6) 0.6674(5) 0.4244(3) 0.0294(11) Uani 1 1 d . . .
H11 H 0.8968 0.6581 0.3814 0.035 Uiso 1 1 calc R . .
C12 C 0.8158(7) 0.5654(5) 0.4468(3) 0.0341(12) Uani 1 1 d . . .
H12 H 0.8235 0.4872 0.4192 0.041 Uiso 1 1 calc R . .
C13 C 0.7608(6) 0.5763(4) 0.5097(3) 0.0279(10) Uani 1 1 d . . .
H13 H 0.7298 0.5066 0.5253 0.034 Uiso 1 1 calc R . .
C14 C 0.8976(6) 0.8915(5) 0.4375(3) 0.0316(11) Uani 1 1 d . . .
H14A H 1.0046 0.9029 0.4439 0.047 Uiso 1 1 calc R . .
H14B H 0.8467 0.9640 0.4611 0.047 Uiso 1 1 calc R . .
H14C H 0.8730 0.8791 0.3908 0.047 Uiso 1 1 calc R . .
C15 C 0.8350(5) 0.6546(4) 0.7123(2) 0.0180(8) Uani 1 1 d . . .
C16 C 0.8189(5) 0.6685(4) 0.7789(2) 0.0212(9) Uani 1 1 d . . .
H16 H 0.7287 0.6980 0.7988 0.025 Uiso 1 1 calc R . .
C17 C 0.9358(5) 0.6389(4) 0.8171(2) 0.0232(9) Uani 1 1 d . . .
C18 C 1.0644(5) 0.5941(4) 0.7852(3) 0.0242(10) Uani 1 1 d . . .
H18 H 1.1454 0.5744 0.8104 0.029 Uiso 1 1 calc R . .
C19 C 1.0782(5) 0.5772(4) 0.7184(3) 0.0255(10) Uani 1 1 d . . .
H19 H 1.1669 0.5449 0.6982 0.031 Uiso 1 1 calc R . .
C20 C 0.9619(5) 0.6076(4) 0.6807(2) 0.0224(9) Uani 1 1 d . . .
H20 H 0.9694 0.5963 0.6346 0.027 Uiso 1 1 calc R . .
C21 C 0.9229(6) 0.6568(6) 0.8894(3) 0.0328(12) Uani 1 1 d . . .
H21A H 1.0028 0.6131 0.9067 0.049 Uiso 1 1 calc R . .
H21B H 0.8273 0.6253 0.9002 0.049 Uiso 1 1 calc R . .
H21C H 0.9303 0.7439 0.9090 0.049 Uiso 1 1 calc R . .
C22 C 0.7050(4) 0.9497(4) 0.7276(2) 0.0169(8) Uani 1 1 d . . .
C23 C 0.7311(5) 1.0811(4) 0.7555(2) 0.0185(8) Uani 1 1 d . . .
C24 C 0.7971(5) 1.1535(4) 0.7170(2) 0.0221(9) Uani 1 1 d . . .
H24 H 0.8303 1.1167 0.6746 0.026 Uiso 1 1 calc R . .
C25 C 0.8153(5) 1.2773(5) 0.7389(3) 0.0254(10) Uani 1 1 d . . .
H25 H 0.8592 1.3255 0.7117 0.031 Uiso 1 1 calc R . .
C26 C 0.7690(5) 1.3306(4) 0.8009(3) 0.0253(10) Uani 1 1 d . . .
H26 H 0.7815 1.4159 0.8162 0.030 Uiso 1 1 calc R . .
C27 C 0.7048(5) 1.2619(4) 0.8410(3) 0.0229(9) Uani 1 1 d . . .
H27 H 0.6739 1.3002 0.8835 0.028 Uiso 1 1 calc R . .
C28 C 0.6846(5) 1.1347(4) 0.8191(2) 0.0179(8) Uani 1 1 d . . .
C29 C 0.5702(5) 1.1139(4) 0.9235(2) 0.0222(9) Uani 1 1 d . . .
C30 C 0.6668(6) 1.1160(4) 0.9769(3) 0.0259(10) Uani 1 1 d . . .
C31 C 0.6068(6) 1.1524(4) 1.0386(3) 0.0270(10) Uani 1 1 d . . .
C32 C 0.4609(6) 1.1851(4) 1.0488(2) 0.0263(10) Uani 1 1 d . . .
H32 H 0.4238 1.2072 1.0919 0.032 Uiso 1 1 calc R . .
C33 C 0.3691(6) 1.1850(5) 0.9951(3) 0.0288(11) Uani 1 1 d . . .
H33 H 0.2689 1.2095 1.0011 0.035 Uiso 1 1 calc R . .
C34 C 0.4242(6) 1.1492(4) 0.9328(3) 0.0266(10) Uani 1 1 d . . .
H34 H 0.3614 1.1488 0.8961 0.032 Uiso 1 1 calc R . .
C35 C 0.8257(6) 1.0795(6) 0.9670(3) 0.0381(13) Uani 1 1 d . . .
H35A H 0.8898 1.1472 0.9880 0.057 Uiso 1 1 calc R . .
H35B H 0.8461 1.0588 0.9202 0.057 Uiso 1 1 calc R . .
H35C H 0.8450 1.0085 0.9865 0.057 Uiso 1 1 calc R . .
C36 C 0.5371(5) 0.4742(4) 0.6642(2) 0.0181(8) Uani 1 1 d . . .
C37 C 0.5021(5) 0.3411(4) 0.6544(2) 0.0190(8) Uani 1 1 d . . .
C38 C 0.5471(5) 0.2654(4) 0.5967(2) 0.0232(9) Uani 1 1 d . . .
H38 H 0.5946 0.3002 0.5646 0.028 Uiso 1 1 calc R . .
C39 C 0.5246(6) 0.1408(5) 0.5849(3) 0.0274(10) Uani 1 1 d . . .
H39 H 0.5549 0.0907 0.5449 0.033 Uiso 1 1 calc R . .
C40 C 0.4565(5) 0.0898(4) 0.6326(3) 0.0251(10) Uani 1 1 d . . .
H40 H 0.4411 0.0042 0.6252 0.030 Uiso 1 1 calc R . .
C41 C 0.4115(5) 0.1622(4) 0.6904(2) 0.0218(9) Uani 1 1 d . . .
H41 H 0.3673 0.1256 0.7226 0.026 Uiso 1 1 calc R . .
C42 C 0.4301(5) 0.2897(4) 0.7023(2) 0.0176(8) Uani 1 1 d . . .
C43 C 0.2997(5) 0.3468(4) 0.8100(2) 0.0202(9) Uani 1 1 d . . .
C44 C 0.3204(5) 0.4272(4) 0.8712(2) 0.0218(9) Uani 1 1 d . . .
C45 C 0.2207(5) 0.4166(5) 0.9202(2) 0.0251(10) Uani 1 1 d . . .
C46 C 0.1088(5) 0.3305(5) 0.9129(3) 0.0278(10) Uani 1 1 d . . .
H46 H 0.0443 0.3259 0.9478 0.033 Uiso 1 1 calc R . .
C47 C 0.0939(5) 0.2512(5) 0.8530(3) 0.0260(10) Uani 1 1 d . . .
H47 H 0.0195 0.1898 0.8468 0.031 Uiso 1 1 calc R . .
C48 C 0.1870(5) 0.2604(4) 0.8017(3) 0.0237(9) Uani 1 1 d . . .
H48 H 0.1731 0.2071 0.7604 0.028 Uiso 1 1 calc R . .
C49 C 0.4404(6) 0.5214(5) 0.8813(3) 0.0262(10) Uani 1 1 d . . .
H49A H 0.4119 0.5883 0.8602 0.039 Uiso 1 1 calc R . .
H49B H 0.5321 0.4848 0.8623 0.039 Uiso 1 1 calc R . .
H49C H 0.4557 0.5528 0.9283 0.039 Uiso 1 1 calc R . .
H1' H 0.6012 0.9787 0.8394 0.043(19) Uiso 1 1 d R . .
H2' H 0.4311 0.4464 0.7625 0.043(19) Uiso 1 1 d 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 2.200(4) . ?
Bi1 C1 2.201(4) . ?
Bi1 C8 2.238(5) . ?
Bi1 O3 2.270(3) . ?
Bi1 O1 2.313(3) . ?
Bi1 O2 2.706(3) . ?
Bi1 O4 2.835(3) . ?
Cl1 C31 1.747(5) . ?
O1 C22 1.304(6) . ?
N1 C28 1.378(6) . ?
N1 C29 1.430(6) . ?
C1 C6 1.385(7) . ?
C1 C2 1.392(7) . ?
Cl2 C45 1.752(5) . ?
O2 C22 1.261(6) . ?
N2 C42 1.386(6) . ?
N2 C43 1.392(6) . ?
C2 C3 1.395(6) . ?
O3 C36 1.300(5) . ?
C3 C4 1.392(7) . ?
C3 C7 1.511(7) . ?
O4 C36 1.243(6) . ?
C4 C5 1.387(7) . ?
C5 C6 1.395(7) . ?
C8 C9 1.373(6) . ?
C8 C13 1.384(7) . ?
C9 C10 1.415(7) . ?
C10 C11 1.382(7) . ?
C10 C14 1.495(7) . ?
C11 C12 1.380(8) . ?
C12 C13 1.394(8) . ?
C15 C16 1.380(7) . ?
C15 C20 1.383(6) . ?
C16 C17 1.398(6) . ?
C17 C18 1.391(7) . ?
C17 C21 1.492(7) . ?
C18 C19 1.379(7) . ?
C19 C20 1.392(7) . ?
C22 C23 1.487(6) . ?
C23 C24 1.394(6) . ?
C23 C28 1.413(7) . ?
C24 C25 1.379(7) . ?
C25 C26 1.384(7) . ?
C26 C27 1.381(7) . ?
C27 C28 1.417(6) . ?
C29 C34 1.384(7) . ?
C29 C30 1.404(7) . ?
C30 C31 1.389(8) . ?
C30 C35 1.502(7) . ?
C31 C32 1.379(8) . ?
C32 C33 1.389(7) . ?
C33 C34 1.381(8) . ?
C36 C37 1.498(6) . ?
C37 C38 1.393(7) . ?
C37 C42 1.417(6) . ?
C38 C39 1.382(7) . ?
C39 C40 1.397(7) . ?
C40 C41 1.377(7) . ?
C41 C42 1.410(6) . ?
C43 C48 1.389(7) . ?
C43 C44 1.416(7) . ?
C44 C45 1.397(7) . ?
C44 C49 1.495(7) . ?
C45 C46 1.383(7) . ?
C46 C47 1.386(8) . ?
C47 C48 1.393(7) . ?

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 C1 145.70(17) . . ?
C15 Bi1 C8 108.23(17) . . ?
C1 Bi1 C8 105.92(17) . . ?
C15 Bi1 O3 89.61(14) . . ?
C1 Bi1 O3 90.29(15) . . ?
C8 Bi1 O3 85.01(15) . . ?
C15 Bi1 O1 92.07(14) . . ?
C1 Bi1 O1 93.50(14) . . ?
C8 Bi1 O1 85.72(15) . . ?
O3 Bi1 O1 170.63(12) . . ?
C15 Bi1 O2 77.46(14) . . ?
C1 Bi1 O2 79.60(14) . . ?
C8 Bi1 O2 137.61(14) . . ?
O3 Bi1 O2 137.38(11) . . ?
O1 Bi1 O2 51.89(11) . . ?
C15 Bi1 O4 76.23(13) . . ?
C1 Bi1 O4 77.63(14) . . ?
C8 Bi1 O4 134.91(14) . . ?
O3 Bi1 O4 49.91(11) . . ?
O1 Bi1 O4 139.37(11) . . ?
O2 Bi1 O4 87.48(10) . . ?
C22 O1 Bi1 102.5(3) . . ?
C28 N1 C29 124.3(4) . . ?
C6 C1 C2 122.8(4) . . ?
C6 C1 Bi1 114.3(3) . . ?
C2 C1 Bi1 122.9(3) . . ?
C22 O2 Bi1 85.3(3) . . ?
C42 N2 C43 130.5(4) . . ?
C1 C2 C3 119.0(4) . . ?
C36 O3 Bi1 107.1(3) . . ?
C4 C3 C2 118.9(4) . . ?
C4 C3 C7 120.8(4) . . ?
C2 C3 C7 120.2(4) . . ?
C36 O4 Bi1 81.8(2) . . ?
C5 C4 C3 121.1(4) . . ?
C4 C5 C6 120.7(5) . . ?
C1 C6 C5 117.5(5) . . ?
C9 C8 C13 122.0(5) . . ?
C9 C8 Bi1 120.2(4) . . ?
C13 C8 Bi1 117.8(3) . . ?
C8 C9 C10 119.8(5) . . ?
C11 C10 C9 118.1(5) . . ?
C11 C10 C14 120.3(5) . . ?
C9 C10 C14 121.6(5) . . ?
C12 C11 C10 121.4(5) . . ?
C11 C12 C13 120.5(5) . . ?
C8 C13 C12 118.2(5) . . ?
C16 C15 C20 122.4(4) . . ?
C16 C15 Bi1 122.2(3) . . ?
C20 C15 Bi1 115.4(3) . . ?
C15 C16 C17 119.7(4) . . ?
C18 C17 C16 117.7(5) . . ?
C18 C17 C21 121.5(4) . . ?
C16 C17 C21 120.8(5) . . ?
C19 C18 C17 122.3(4) . . ?
C18 C19 C20 119.9(5) . . ?
C15 C20 C19 118.0(5) . . ?
O2 C22 O1 120.3(4) . . ?
O2 C22 C23 121.6(4) . . ?
O1 C22 C23 118.1(4) . . ?
C24 C23 C28 119.6(4) . . ?
C24 C23 C22 119.1(4) . . ?
C28 C23 C22 121.3(4) . . ?
C25 C24 C23 121.5(5) . . ?
C24 C25 C26 119.2(5) . . ?
C27 C26 C25 121.1(5) . . ?
C26 C27 C28 120.4(5) . . ?
N1 C28 C23 121.2(4) . . ?
N1 C28 C27 120.6(4) . . ?
C23 C28 C27 118.2(4) . . ?
C34 C29 C30 121.1(5) . . ?
C34 C29 N1 119.0(5) . . ?
C30 C29 N1 119.7(4) . . ?
C31 C30 C29 116.4(5) . . ?
C31 C30 C35 122.4(5) . . ?
C29 C30 C35 121.3(5) . . ?
C32 C31 C30 123.4(5) . . ?
C32 C31 Cl1 117.0(4) . . ?
C30 C31 Cl1 119.6(4) . . ?
C31 C32 C33 118.8(5) . . ?
C34 C33 C32 119.6(5) . . ?
C33 C34 C29 120.7(5) . . ?
O4 C36 O3 121.0(4) . . ?
O4 C36 C37 123.2(4) . . ?
O3 C36 C37 115.7(4) . . ?
C38 C37 C42 119.4(4) . . ?
C38 C37 C36 118.0(4) . . ?
C42 C37 C36 122.6(4) . . ?
C39 C38 C37 121.7(5) . . ?
C38 C39 C40 118.9(5) . . ?
C41 C40 C39 120.7(4) . . ?
C40 C41 C42 120.9(4) . . ?
N2 C42 C41 123.7(4) . . ?
N2 C42 C37 118.0(4) . . ?
C41 C42 C37 118.2(4) . . ?
C48 C43 N2 123.9(4) . . ?
C48 C43 C44 119.9(4) . . ?
N2 C43 C44 116.0(4) . . ?
C45 C44 C43 116.9(4) . . ?
C45 C44 C49 122.1(5) . . ?
C43 C44 C49 121.0(4) . . ?
C46 C45 C44 123.9(5) . . ?
C46 C45 Cl2 116.8(4) . . ?
C44 C45 Cl2 119.2(4) . . ?
C45 C46 C47 117.7(5) . . ?
C46 C47 C48 120.7(5) . . ?
C43 C48 C47 120.8(5) . . ?

_diffrn_measured_fraction_theta_max 0.915
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.934
_refine_diff_density_max         0.900
_refine_diff_density_min         -3.437
_refine_diff_density_rms         0.181
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb108-yc
_database_code_depnum_ccdc_archive 'CCDC 1420793'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H35 Bi O6'
_chemical_formula_sum            'C37 H35 Bi O6'
_chemical_formula_weight         784.63

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   P21/c

_vrf_PLAT029_vb108-yc            
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.949 Note  
RESPONSE: The structure was collected at the MX1 beamline at the synchrotron
A full 365 Phi scan was ran however completness was still low due to deterioration
of the crystal in the beam. See Cif for further details
;

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

_cell_length_a                   10.960(2)
_cell_length_b                   15.975(3)
_cell_length_c                   17.886(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.79(3)
_cell_angle_gamma                90.00
_cell_volume                     3130.1(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    58996
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.04
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.665
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1552
_exptl_absorpt_coefficient_mu    5.679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8047
_exptl_absorpt_correction_T_max  0.9454
_exptl_absorpt_process_details   
'SADABS: Sheldrick Acta Cryst. A51, (1995) 33-38'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71080
_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            58996
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0245
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         31.55
_reflns_number_total             7976
_reflns_number_gt                6820
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XSeed
_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 crystal was collected at the MX1 beanline at the synchrotron. A full 365 phi
scan was completed however completness was still low due to deterioration of the 
crystal in the beam. 

There appears to be no other indications that there is anything else wrong 
with the data apart from low completness. All other analytical data 
(NMR and microanalysis) support the composition of the complex.
 
;

_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)+(0.0712P)²+0.5915P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0130(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7976
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0943
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_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 0.683561(10) 0.312401(7) 0.162855(7) 0.02147(7) Uani 1 1 d . . .
O1 O 0.8243(2) 0.24182(15) 0.09911(14) 0.0275(5) Uani 1 1 d . . .
O2 O 0.9424(2) 0.26707(18) 0.19995(15) 0.0322(6) Uani 1 1 d . . .
O3 O 0.9153(2) 0.16309(17) -0.01244(15) 0.0272(5) Uani 1 1 d . . .
O4 O 0.5233(2) 0.38307(16) 0.20787(14) 0.0269(5) Uani 1 1 d . . .
O5 O 0.6530(2) 0.39876(17) 0.30400(15) 0.0292(5) Uani 1 1 d . . .
O6 O 0.2933(2) 0.41612(17) 0.22841(16) 0.0327(6) Uani 1 1 d . . .
C1 C 0.9263(3) 0.2355(2) 0.1373(2) 0.0239(6) Uani 1 1 d . . .
C2 C 1.0264(3) 0.1870(2) 0.1014(2) 0.0247(7) Uani 1 1 d . . .
C3 C 1.0166(3) 0.1517(2) 0.0286(2) 0.0245(7) Uani 1 1 d . . .
C4 C 1.1170(3) 0.1061(2) 0.0030(2) 0.0293(7) Uani 1 1 d . . .
H4 H 1.1132 0.0825 -0.0458 0.035 Uiso 1 1 calc R . .
C5 C 1.2213(3) 0.0949(3) 0.0477(2) 0.0359(9) Uani 1 1 d . . .
H5 H 1.2875 0.0634 0.0293 0.043 Uiso 1 1 calc R . .
C6 C 1.2304(3) 0.1291(3) 0.1189(2) 0.0346(8) Uani 1 1 d . . .
H6 H 1.3019 0.1210 0.1495 0.042 Uiso 1 1 calc R . .
C7 C 1.1334(4) 0.1750(2) 0.1447(2) 0.0293(8) Uani 1 1 d . . .
H7 H 1.1396 0.1992 0.1932 0.035 Uiso 1 1 calc R . .
C8 C 0.9072(4) 0.1260(3) -0.0857(2) 0.0349(8) Uani 1 1 d . . .
H8A H 0.9703 0.1499 -0.1169 0.052 Uiso 1 1 calc R . .
H8B H 0.8265 0.1374 -0.1086 0.052 Uiso 1 1 calc R . .
H8C H 0.9192 0.0654 -0.0815 0.052 Uiso 1 1 calc R . .
C9 C 0.5506(3) 0.4093(2) 0.2744(2) 0.0239(6) Uani 1 1 d . . .
C10 C 0.4526(3) 0.4542(2) 0.3152(2) 0.0245(7) Uani 1 1 d . . .
C11 C 0.3295(3) 0.4600(2) 0.2912(2) 0.0266(7) Uani 1 1 d . . .
C12 C 0.2503(4) 0.5086(3) 0.3321(2) 0.0348(9) Uani 1 1 d . . .
H12 H 0.1670 0.5129 0.3162 0.042 Uiso 1 1 calc R . .
C13 C 0.2902(4) 0.5503(2) 0.3948(2) 0.0379(9) Uani 1 1 d . . .
H13 H 0.2347 0.5843 0.4210 0.045 Uiso 1 1 calc R . .
C14 C 0.4103(4) 0.5440(2) 0.4208(2) 0.0369(9) Uani 1 1 d . . .
H14 H 0.4372 0.5722 0.4651 0.044 Uiso 1 1 calc R . .
C15 C 0.4898(4) 0.4959(2) 0.3808(2) 0.0283(7) Uani 1 1 d . . .
H15 H 0.5722 0.4908 0.3983 0.034 Uiso 1 1 calc R . .
C16 C 0.1660(4) 0.4166(3) 0.2073(3) 0.0462(11) Uani 1 1 d . . .
H16A H 0.1194 0.3901 0.2467 0.069 Uiso 1 1 calc R . .
H16B H 0.1534 0.3856 0.1604 0.069 Uiso 1 1 calc R . .
H16C H 0.1384 0.4745 0.2004 0.069 Uiso 1 1 calc R . .
C17 C 0.7853(3) 0.4278(2) 0.1411(2) 0.0251(7) Uani 1 1 d . . .
C18 C 0.8308(3) 0.4821(2) 0.1956(2) 0.0314(8) Uani 1 1 d . . .
H18 H 0.8213 0.4705 0.2472 0.038 Uiso 1 1 calc R . .
C19 C 0.8911(3) 0.5543(2) 0.1726(2) 0.0338(8) Uani 1 1 d . . .
H19 H 0.9234 0.5916 0.2095 0.041 Uiso 1 1 calc R . .
C20 C 0.9055(3) 0.5733(2) 0.0977(2) 0.0335(8) Uani 1 1 d . . .
C21 C 0.8574(4) 0.5176(3) 0.0446(2) 0.0390(9) Uani 1 1 d . . .
H21 H 0.8660 0.5291 -0.0071 0.047 Uiso 1 1 calc R . .
C22 C 0.7967(4) 0.4452(3) 0.0661(2) 0.0358(8) Uani 1 1 d . . .
H22 H 0.7635 0.4080 0.0293 0.043 Uiso 1 1 calc R . .
C23 C 0.9695(4) 0.6522(3) 0.0739(3) 0.0414(10) Uani 1 1 d . . .
H23A H 0.9091 0.6924 0.0541 0.062 Uiso 1 1 calc R . .
H23B H 1.0274 0.6388 0.0350 0.062 Uiso 1 1 calc R . .
H23C H 1.0135 0.6768 0.1171 0.062 Uiso 1 1 calc R . .
C24 C 0.5605(3) 0.2864(2) 0.0657(2) 0.0230(6) Uani 1 1 d . . .
C25 C 0.4363(4) 0.3056(2) 0.0696(2) 0.0278(7) Uani 1 1 d . . .
H25 H 0.4049 0.3295 0.1137 0.033 Uiso 1 1 calc R . .
C26 C 0.3593(3) 0.2892(2) 0.0080(2) 0.0299(7) Uani 1 1 d . . .
H26 H 0.2751 0.3030 0.0102 0.036 Uiso 1 1 calc R . .
C27 C 0.4026(3) 0.2529(2) -0.0567(2) 0.0270(7) Uani 1 1 d . . .
C28 C 0.5261(3) 0.2332(2) -0.0589(2) 0.0265(7) Uani 1 1 d . . .
H28 H 0.5569 0.2081 -0.1027 0.032 Uiso 1 1 calc R . .
C29 C 0.6054(3) 0.2493(2) 0.00156(19) 0.0253(7) Uani 1 1 d . . .
H29 H 0.6894 0.2353 -0.0008 0.030 Uiso 1 1 calc R . .
C30 C 0.3173(4) 0.2362(3) -0.1231(2) 0.0338(8) Uani 1 1 d . . .
H30A H 0.2603 0.1914 -0.1106 0.051 Uiso 1 1 calc R . .
H30B H 0.3649 0.2191 -0.1660 0.051 Uiso 1 1 calc R . .
H30C H 0.2715 0.2872 -0.1357 0.051 Uiso 1 1 calc R . .
C31 C 0.6557(3) 0.2142(2) 0.2457(2) 0.0250(7) Uani 1 1 d . . .
C32 C 0.7437(4) 0.1886(2) 0.2988(2) 0.0287(8) Uani 1 1 d . . .
H32 H 0.8235 0.2117 0.2998 0.034 Uiso 1 1 calc R . .
C33 C 0.7111(4) 0.1282(2) 0.3500(2) 0.0310(8) Uani 1 1 d . . .
H33 H 0.7703 0.1093 0.3860 0.037 Uiso 1 1 calc R . .
C34 C 0.5937(4) 0.0945(2) 0.3504(2) 0.0291(7) Uani 1 1 d . . .
C35 C 0.5096(4) 0.1202(2) 0.2958(2) 0.0298(7) Uani 1 1 d . . .
H35 H 0.4302 0.0963 0.2943 0.036 Uiso 1 1 calc R . .
C36 C 0.5390(4) 0.1804(2) 0.2431(2) 0.0279(7) Uani 1 1 d . . .
H36 H 0.4805 0.1980 0.2061 0.033 Uiso 1 1 calc R . .
C37 C 0.5583(4) 0.0342(3) 0.4108(2) 0.0380(9) Uani 1 1 d . . .
H37A H 0.5349 0.0656 0.4552 0.057 Uiso 1 1 calc R . .
H37B H 0.6277 -0.0022 0.4238 0.057 Uiso 1 1 calc R . .
H37C H 0.4892 0.0000 0.3927 0.057 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 C31 2.186(4) . ?
Bi1 C17 2.195(3) . ?
Bi1 C24 2.205(3) . ?
Bi1 O1 2.249(2) . ?
Bi1 O4 2.257(2) . ?
Bi1 O5 2.905(3) . ?
Bi1 O2 2.983(3) . ?
O1 C1 1.296(4) . ?
O2 C1 1.236(4) . ?
O3 C3 1.324(4) . ?
O3 C8 1.438(5) . ?
O4 C9 1.288(4) . ?
O5 C9 1.237(4) . ?
O6 C11 1.371(5) . ?
O6 C16 1.434(4) . ?
C1 C2 1.504(5) . ?
C2 C7 1.399(5) . ?
C2 C3 1.419(5) . ?
C3 C4 1.409(5) . ?
C4 C5 1.386(5) . ?
C5 C6 1.388(6) . ?
C6 C7 1.383(5) . ?
C9 C10 1.499(5) . ?
C10 C15 1.399(5) . ?
C10 C11 1.406(5) . ?
C11 C12 1.391(5) . ?
C12 C13 1.364(6) . ?
C13 C14 1.386(6) . ?
C14 C15 1.379(5) . ?
C17 C22 1.379(5) . ?
C17 C18 1.386(5) . ?
C18 C19 1.398(5) . ?
C19 C20 1.387(6) . ?
C20 C21 1.393(6) . ?
C20 C23 1.511(5) . ?
C21 C22 1.394(6) . ?
C24 C29 1.395(5) . ?
C24 C25 1.399(5) . ?
C25 C26 1.392(5) . ?
C26 C27 1.391(5) . ?
C27 C28 1.391(5) . ?
C27 C30 1.512(5) . ?
C28 C29 1.391(5) . ?
C31 C36 1.387(5) . ?
C31 C32 1.394(5) . ?
C32 C33 1.385(5) . ?
C33 C34 1.394(5) . ?
C34 C35 1.384(5) . ?
C34 C37 1.508(5) . ?
C35 C36 1.392(5) . ?

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
C31 Bi1 C17 143.65(13) . . ?
C31 Bi1 C24 107.69(13) . . ?
C17 Bi1 C24 108.66(13) . . ?
C31 Bi1 O1 95.51(12) . . ?
C17 Bi1 O1 88.35(11) . . ?
C24 Bi1 O1 85.33(11) . . ?
C31 Bi1 O4 89.46(12) . . ?
C17 Bi1 O4 92.76(11) . . ?
C24 Bi1 O4 84.92(11) . . ?
O1 Bi1 O4 170.02(9) . . ?
C31 Bi1 O5 74.31(11) . . ?
C17 Bi1 O5 80.12(11) . . ?
C24 Bi1 O5 133.58(10) . . ?
O1 Bi1 O5 141.08(8) . . ?
O4 Bi1 O5 48.73(8) . . ?
C31 Bi1 O2 80.03(11) . . ?
C17 Bi1 O2 76.03(10) . . ?
C24 Bi1 O2 133.14(10) . . ?
O1 Bi1 O2 47.83(8) . . ?
O4 Bi1 O2 141.94(8) . . ?
O5 Bi1 O2 93.26(7) . . ?
C1 O1 Bi1 111.4(2) . . ?
C1 O2 Bi1 77.8(2) . . ?
C3 O3 C8 118.4(3) . . ?
C9 O4 Bi1 109.4(2) . . ?
C9 O5 Bi1 79.7(2) . . ?
C11 O6 C16 117.8(3) . . ?
O2 C1 O1 122.9(3) . . ?
O2 C1 C2 120.8(3) . . ?
O1 C1 C2 116.3(3) . . ?
C7 C2 C3 119.5(3) . . ?
C7 C2 C1 116.3(3) . . ?
C3 C2 C1 124.2(3) . . ?
O3 C3 C4 122.7(3) . . ?
O3 C3 C2 119.5(3) . . ?
C4 C3 C2 117.8(3) . . ?
C5 C4 C3 121.2(4) . . ?
C4 C5 C6 120.9(4) . . ?
C7 C6 C5 118.8(4) . . ?
C6 C7 C2 121.9(4) . . ?
O5 C9 O4 122.1(3) . . ?
O5 C9 C10 120.8(3) . . ?
O4 C9 C10 117.1(3) . . ?
C15 C10 C11 118.5(3) . . ?
C15 C10 C9 116.2(3) . . ?
C11 C10 C9 125.3(3) . . ?
O6 C11 C12 123.2(3) . . ?
O6 C11 C10 117.8(3) . . ?
C12 C11 C10 119.0(4) . . ?
C13 C12 C11 121.0(4) . . ?
C12 C13 C14 121.2(4) . . ?
C15 C14 C13 118.4(4) . . ?
C14 C15 C10 121.9(4) . . ?
C22 C17 C18 121.1(3) . . ?
C22 C17 Bi1 113.8(3) . . ?
C18 C17 Bi1 125.1(3) . . ?
C17 C18 C19 118.2(4) . . ?
C20 C19 C18 122.3(4) . . ?
C19 C20 C21 117.8(4) . . ?
C19 C20 C23 121.5(4) . . ?
C21 C20 C23 120.7(4) . . ?
C22 C21 C20 121.0(4) . . ?
C17 C22 C21 119.6(4) . . ?
C29 C24 C25 120.1(3) . . ?
C29 C24 Bi1 120.4(2) . . ?
C25 C24 Bi1 119.5(3) . . ?
C26 C25 C24 119.1(4) . . ?
C27 C26 C25 121.5(4) . . ?
C26 C27 C28 118.4(3) . . ?
C26 C27 C30 120.5(3) . . ?
C28 C27 C30 121.1(3) . . ?
C29 C28 C27 121.4(3) . . ?
C28 C29 C24 119.4(3) . . ?
C36 C31 C32 121.7(4) . . ?
C36 C31 Bi1 113.9(3) . . ?
C32 C31 Bi1 124.4(3) . . ?
C33 C32 C31 117.9(4) . . ?
C32 C33 C34 121.9(4) . . ?
C35 C34 C33 118.5(4) . . ?
C35 C34 C37 120.9(4) . . ?
C33 C34 C37 120.5(4) . . ?
C34 C35 C36 121.3(4) . . ?
C31 C36 C35 118.6(4) . . ?

_diffrn_measured_fraction_theta_max 0.761
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.949
_refine_diff_density_max         2.113
_refine_diff_density_min         -1.422
_refine_diff_density_rms         0.243
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb110-yc
_database_code_depnum_ccdc_archive 'CCDC 1420794'
_audit_update_record             
;
2015-08-27 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H39 Bi O6'
_chemical_formula_sum            'C39 H39 Bi O6'
_chemical_formula_weight         812.68

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   P21/c

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

_cell_length_a                   10.949(2)
_cell_length_b                   15.980(3)
_cell_length_c                   18.978(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.65(3)
_cell_angle_gamma                90.00
_cell_volume                     3313.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    61780
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1616
_exptl_absorpt_coefficient_mu    5.368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8556
_exptl_absorpt_correction_T_max  0.9483
_exptl_absorpt_process_details   
'SADABS: Sheldrick Acta Cryst. A51, (1995) 33-38'

_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            61780
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.67
_diffrn_reflns_theta_max         31.51
_reflns_number_total             9449
_reflns_number_gt                8638
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XSeed
_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. 
;

_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)+(0.0587P)²+4.0838P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0129(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         9449
_refine_ls_number_parameters     421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0316
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.002
_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 0.327957(9) 0.306795(6) 0.162930(5) 0.01929(6) Uani 1 1 d . . .
O1 O 0.49509(19) 0.37698(14) 0.20974(10) 0.0239(4) Uani 1 1 d . . .
O2 O 0.3659(2) 0.38922(15) 0.29385(11) 0.0259(4) Uani 1 1 d . . .
O3 O 0.7212(2) 0.43033(14) 0.23782(11) 0.0267(4) Uani 1 1 d . . .
O4 O 0.17631(19) 0.23595(14) 0.10077(11) 0.0235(4) Uani 1 1 d . . .
O5 O 0.0824(2) 0.27173(16) 0.19647(11) 0.0280(4) Uani 1 1 d . . .
O6 O 0.04576(19) 0.15824(14) -0.00077(11) 0.0228(4) Uani 1 1 d . . .
C1 C 0.4678(3) 0.40253(18) 0.27132(15) 0.0222(5) Uani 1 1 d . . .
C2 C 0.5624(3) 0.45082(18) 0.31528(14) 0.0211(5) Uani 1 1 d . . .
C3 C 0.5233(3) 0.48469(19) 0.37803(15) 0.0244(5) Uani 1 1 d . . .
H3 H 0.4421 0.4740 0.3905 0.029 Uiso 1 1 calc R . .
C4 C 0.5994(3) 0.5333(2) 0.42256(15) 0.0291(6) Uani 1 1 d . . .
H4 H 0.5706 0.5561 0.4647 0.035 Uiso 1 1 calc R . .
C5 C 0.7183(3) 0.5480(2) 0.40442(15) 0.0279(6) Uani 1 1 d . . .
H5 H 0.7709 0.5821 0.4340 0.034 Uiso 1 1 calc R . .
C6 C 0.7615(3) 0.5132(2) 0.34330(16) 0.0272(6) Uani 1 1 d . . .
H6 H 0.8440 0.5221 0.3324 0.033 Uiso 1 1 calc R . .
C7 C 0.6839(3) 0.46513(18) 0.29805(14) 0.0224(5) Uani 1 1 d . . .
C8 C 0.8441(3) 0.4454(2) 0.21916(17) 0.0284(6) Uani 1 1 d . . .
H8A H 0.9034 0.4189 0.2539 0.034 Uiso 1 1 calc R . .
H8B H 0.8610 0.5062 0.2180 0.034 Uiso 1 1 calc R . .
C9 C 0.8545(3) 0.4076(2) 0.14710(18) 0.0301(6) Uani 1 1 d . . .
H9A H 0.8370 0.3475 0.1490 0.045 Uiso 1 1 calc R . .
H9B H 0.9376 0.4161 0.1321 0.045 Uiso 1 1 calc R . .
H9C H 0.7956 0.4346 0.1133 0.045 Uiso 1 1 calc R . .
C10 C 0.0832(3) 0.23445(19) 0.13917(15) 0.0224(5) Uani 1 1 d . . .
C11 C -0.0258(3) 0.18381(19) 0.11281(17) 0.0237(6) Uani 1 1 d . . .
C12 C -0.1170(3) 0.1718(2) 0.16043(17) 0.0286(6) Uani 1 1 d . . .
H12 H -0.1072 0.1965 0.2060 0.034 Uiso 1 1 calc R . .
C13 C -0.2212(3) 0.1248(2) 0.14296(19) 0.0346(7) Uani 1 1 d . . .
H13 H -0.2809 0.1162 0.1764 0.041 Uiso 1 1 calc R . .
C14 C -0.2365(3) 0.0908(2) 0.0760(2) 0.0352(7) Uani 1 1 d . . .
H14 H -0.3083 0.0597 0.0632 0.042 Uiso 1 1 calc R . .
C15 C -0.1489(3) 0.1015(2) 0.02763(18) 0.0284(6) Uani 1 1 d . . .
H15 H -0.1614 0.0776 -0.0181 0.034 Uiso 1 1 calc R . .
C16 C -0.0414(3) 0.14709(19) 0.04504(16) 0.0242(5) Uani 1 1 d . . .
C17 C 0.0282(3) 0.1197(2) -0.06935(16) 0.0292(6) Uani 1 1 d . . .
H17A H -0.0449 0.1433 -0.0956 0.035 Uiso 1 1 calc R . .
H17B H 0.0165 0.0586 -0.0645 0.035 Uiso 1 1 calc R . .
C18 C 0.1412(4) 0.1376(3) -0.10762(19) 0.0399(8) Uani 1 1 d . . .
H18A H 0.1559 0.1981 -0.1081 0.060 Uiso 1 1 calc R . .
H18B H 0.1300 0.1170 -0.1562 0.060 Uiso 1 1 calc R . .
H18C H 0.2115 0.1094 -0.0835 0.060 Uiso 1 1 calc R . .
C19 C 0.2280(3) 0.42357(19) 0.13939(15) 0.0230(5) Uani 1 1 d . . .
C20 C 0.1863(3) 0.4765(2) 0.19047(16) 0.0274(6) Uani 1 1 d . . .
H20 H 0.2005 0.4639 0.2392 0.033 Uiso 1 1 calc R . .
C21 C 0.1231(3) 0.5489(2) 0.16882(18) 0.0309(6) Uani 1 1 d . . .
H21 H 0.0941 0.5856 0.2035 0.037 Uiso 1 1 calc R . .
C22 C 0.1015(3) 0.5685(2) 0.09792(19) 0.0304(6) Uani 1 1 d . . .
C23 C 0.0302(4) 0.6461(2) 0.0755(2) 0.0429(9) Uani 1 1 d . . .
H23A H 0.0612 0.6683 0.0319 0.064 Uiso 1 1 calc R . .
H23B H 0.0399 0.6885 0.1128 0.064 Uiso 1 1 calc R . .
H23C H -0.0566 0.6320 0.0673 0.064 Uiso 1 1 calc R . .
C24 C 0.1449(4) 0.5146(2) 0.04808(18) 0.0363(8) Uani 1 1 d . . .
H24 H 0.1314 0.5275 -0.0007 0.044 Uiso 1 1 calc R . .
C25 C 0.2081(3) 0.4418(2) 0.06826(17) 0.0322(7) Uani 1 1 d . . .
H25 H 0.2372 0.4052 0.0336 0.039 Uiso 1 1 calc R . .
C26 C 0.4408(3) 0.28098(19) 0.07307(15) 0.0222(5) Uani 1 1 d . . .
C27 C 0.3885(3) 0.24517(19) 0.01118(15) 0.0234(5) Uani 1 1 d . . .
H27 H 0.3039 0.2314 0.0074 0.028 Uiso 1 1 calc R . .
C28 C 0.4615(3) 0.22966(19) -0.04525(14) 0.0231(5) Uani 1 1 d . . .
H28 H 0.4259 0.2053 -0.0873 0.028 Uiso 1 1 calc R . .
C29 C 0.5856(3) 0.24950(19) -0.04057(15) 0.0242(5) Uani 1 1 d . . .
C30 C 0.6636(3) 0.2334(2) -0.10203(17) 0.0312(7) Uani 1 1 d . . .
H30A H 0.7143 0.1837 -0.0923 0.047 Uiso 1 1 calc R . .
H30B H 0.7164 0.2819 -0.1087 0.047 Uiso 1 1 calc R . .
H30C H 0.6106 0.2243 -0.1449 0.047 Uiso 1 1 calc R . .
C31 C 0.6362(3) 0.2843(2) 0.02188(16) 0.0264(6) Uani 1 1 d . . .
H31 H 0.7210 0.2974 0.0257 0.032 Uiso 1 1 calc R . .
C32 C 0.5659(3) 0.30014(19) 0.07870(17) 0.0251(6) Uani 1 1 d . . .
H32 H 0.6022 0.3237 0.1210 0.030 Uiso 1 1 calc R . .
C33 C 0.3592(3) 0.20835(18) 0.24253(15) 0.0215(5) Uani 1 1 d . . .
C34 C 0.4733(3) 0.1708(2) 0.24320(17) 0.0273(6) Uani 1 1 d . . .
H34 H 0.5284 0.1840 0.2081 0.033 Uiso 1 1 calc R . .
C35 C 0.5058(3) 0.1132(2) 0.29623(17) 0.0296(6) Uani 1 1 d . . .
H35 H 0.5834 0.0865 0.2968 0.035 Uiso 1 1 calc R . .
C36 C 0.4267(3) 0.09400(19) 0.34840(15) 0.0262(6) Uani 1 1 d . . .
C37 C 0.4655(4) 0.0363(2) 0.40835(18) 0.0342(7) Uani 1 1 d . . .
H37A H 0.4327 -0.0199 0.3984 0.051 Uiso 1 1 calc R . .
H37B H 0.4340 0.0573 0.4522 0.051 Uiso 1 1 calc R . .
H37C H 0.5551 0.0337 0.4135 0.051 Uiso 1 1 calc R . .
C38 C 0.3117(3) 0.1310(2) 0.34461(15) 0.0276(6) Uani 1 1 d . . .
H38 H 0.2556 0.1168 0.3789 0.033 Uiso 1 1 calc R . .
C39 C 0.2761(3) 0.18864(18) 0.29191(17) 0.0254(6) Uani 1 1 d . . .
H39 H 0.1972 0.2136 0.2900 0.030 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 C33 2.193(3) . ?
Bi1 C19 2.195(3) . ?
Bi1 C26 2.208(3) . ?
Bi1 O4 2.276(2) . ?
Bi1 O1 2.278(2) . ?
Bi1 O2 2.820(2) . ?
Bi1 O5 2.857(2) . ?
O1 C1 1.291(3) . ?
O2 C1 1.238(4) . ?
O3 C7 1.357(3) . ?
O3 C8 1.434(4) . ?
O4 C10 1.291(3) . ?
O5 C10 1.240(4) . ?
O6 C16 1.343(4) . ?
O6 C17 1.442(4) . ?
C1 C2 1.502(4) . ?
C2 C3 1.400(4) . ?
C2 C7 1.408(4) . ?
C3 C4 1.386(4) . ?
C4 C5 1.388(5) . ?
C5 C6 1.396(4) . ?
C6 C7 1.399(4) . ?
C8 C9 1.506(5) . ?
C10 C11 1.501(4) . ?
C11 C12 1.402(4) . ?
C11 C16 1.414(4) . ?
C12 C13 1.388(5) . ?
C13 C14 1.381(5) . ?
C14 C15 1.380(5) . ?
C15 C16 1.405(4) . ?
C17 C18 1.502(5) . ?
C19 C25 1.385(4) . ?
C19 C20 1.386(4) . ?
C20 C21 1.396(5) . ?
C21 C22 1.387(5) . ?
C22 C24 1.385(5) . ?
C22 C23 1.513(5) . ?
C24 C25 1.395(5) . ?
C26 C27 1.396(4) . ?
C26 C32 1.401(4) . ?
C27 C28 1.399(4) . ?
C28 C29 1.392(4) . ?
C29 C31 1.392(4) . ?
C29 C30 1.511(4) . ?
C31 C32 1.388(4) . ?
C33 C39 1.384(4) . ?
C33 C34 1.385(4) . ?
C34 C35 1.393(4) . ?
C35 C36 1.391(5) . ?
C36 C38 1.389(5) . ?
C36 C37 1.505(4) . ?
C38 C39 1.396(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
C33 Bi1 C19 143.53(11) . . ?
C33 Bi1 C26 109.12(11) . . ?
C19 Bi1 C26 107.34(11) . . ?
C33 Bi1 O4 94.42(10) . . ?
C19 Bi1 O4 88.83(10) . . ?
C26 Bi1 O4 86.12(9) . . ?
C33 Bi1 O1 89.90(10) . . ?
C19 Bi1 O1 92.21(10) . . ?
C26 Bi1 O1 85.30(9) . . ?
O4 Bi1 O1 171.27(7) . . ?
C33 Bi1 O2 73.76(9) . . ?
C19 Bi1 O2 79.96(9) . . ?
C26 Bi1 O2 135.22(9) . . ?
O4 Bi1 O2 138.66(7) . . ?
O1 Bi1 O2 49.96(7) . . ?
C33 Bi1 O5 79.26(10) . . ?
C19 Bi1 O5 75.41(9) . . ?
C26 Bi1 O5 135.75(9) . . ?
O4 Bi1 O5 49.63(7) . . ?
O1 Bi1 O5 138.90(7) . . ?
O2 Bi1 O5 89.04(7) . . ?
C1 O1 Bi1 106.38(18) . . ?
C1 O2 Bi1 82.02(17) . . ?
C7 O3 C8 118.5(2) . . ?
C10 O4 Bi1 107.04(17) . . ?
C10 O5 Bi1 80.78(17) . . ?
C16 O6 C17 117.9(2) . . ?
O2 C1 O1 121.6(3) . . ?
O2 C1 C2 120.1(3) . . ?
O1 C1 C2 118.3(3) . . ?
C3 C2 C7 118.6(3) . . ?
C3 C2 C1 115.7(3) . . ?
C7 C2 C1 125.7(3) . . ?
C4 C3 C2 122.1(3) . . ?
C3 C4 C5 118.7(3) . . ?
C4 C5 C6 120.8(3) . . ?
C5 C6 C7 120.3(3) . . ?
O3 C7 C6 122.6(3) . . ?
O3 C7 C2 117.9(3) . . ?
C6 C7 C2 119.5(3) . . ?
O3 C8 C9 106.5(3) . . ?
O5 C10 O4 122.4(3) . . ?
O5 C10 C11 120.1(3) . . ?
O4 C10 C11 117.5(3) . . ?
C12 C11 C16 118.6(3) . . ?
C12 C11 C10 116.3(3) . . ?
C16 C11 C10 125.0(3) . . ?
C13 C12 C11 121.9(3) . . ?
C14 C13 C12 118.8(3) . . ?
C15 C14 C13 121.0(3) . . ?
C14 C15 C16 120.9(3) . . ?
O6 C16 C15 122.4(3) . . ?
O6 C16 C11 118.9(3) . . ?
C15 C16 C11 118.7(3) . . ?
O6 C17 C18 106.7(3) . . ?
C25 C19 C20 121.0(3) . . ?
C25 C19 Bi1 115.0(2) . . ?
C20 C19 Bi1 124.0(2) . . ?
C19 C20 C21 118.6(3) . . ?
C22 C21 C20 121.5(3) . . ?
C24 C22 C21 118.5(3) . . ?
C24 C22 C23 120.7(3) . . ?
C21 C22 C23 120.7(3) . . ?
C22 C24 C25 121.1(3) . . ?
C19 C25 C24 119.2(3) . . ?
C27 C26 C32 120.0(3) . . ?
C27 C26 Bi1 120.5(2) . . ?
C32 C26 Bi1 119.5(2) . . ?
C26 C27 C28 119.5(3) . . ?
C29 C28 C27 120.9(3) . . ?
C31 C29 C28 118.6(3) . . ?
C31 C29 C30 120.7(3) . . ?
C28 C29 C30 120.6(3) . . ?
C32 C31 C29 121.6(3) . . ?
C31 C32 C26 119.3(3) . . ?
C39 C33 C34 121.8(3) . . ?
C39 C33 Bi1 123.3(2) . . ?
C34 C33 Bi1 114.7(2) . . ?
C33 C34 C35 118.8(3) . . ?
C36 C35 C34 121.2(3) . . ?
C38 C36 C35 118.2(3) . . ?
C38 C36 C37 120.8(3) . . ?
C35 C36 C37 120.9(3) . . ?
C36 C38 C39 121.9(3) . . ?
C33 C39 C38 118.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.856
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         2.753
_refine_diff_density_min         -1.648
_refine_diff_density_rms         0.164
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_yo_14
_database_code_depnum_ccdc_archive 'CCDC 1420795'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29 Bi N2 O8, C4 H8 O'
_chemical_formula_sum            'C39 H37 Bi N2 O9'
_chemical_formula_weight         886.69

# start Validation Reply Form
_vrf_PLAT230_yo_14               
;
PROBLEM: Hirshfeld Test Diff for    O8     --  N2      ..        7.9 su    
RESPONSE: The thermal ellipsoids of N2 & O7-O8 are relatively large, possibly 
indicating that these might be disordered but was not successfully modelled. 
Please see .cif for more details.
;
# end Validation Reply Form

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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   10.5176(3)
_cell_length_b                   27.1933(8)
_cell_length_c                   14.2016(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.235(2)
_cell_angle_gamma                90.00
_cell_volume                     3969.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    6850
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      25.53

_exptl_crystal_description       cubic
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.484
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    4.495
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.4668
_exptl_absorpt_correction_T_max  0.4668
_exptl_absorpt_process_details   SADABS-2014/3
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      123(2)
_diffrn_radiation_wavelength     0.71065
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'Omega Scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27244
_diffrn_reflns_av_R_equivalents  0.0411
_diffrn_reflns_av_sigmaI/netI    0.0489
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         28.33
_reflns_number_total             9783
_reflns_number_gt                7683
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker Apex2 v2014.7-1 (Bruker AXS, 2014)'
_computing_cell_refinement       'Bruker Apex2 v2014.7-1 (Bruker AXS, 2014)'
_computing_data_reduction        'Bruker Apex2 v2014.7-1 (Bruker AXS, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'X-Seed (Barbour, 1999)'
_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. 

 THF were modelled as partially occupied and refined as isotropic atoms 
 only. In the THF O10, C40-C43, the C-O bond distance was restrained to 1.35 
 and C-C distance restrained to 1.45.Analytical data (NMR & elemental analysis) 
 for the bulk product indicated that THF was not present, suggesting that they 
 could be easily lost from the crystal.

 The thermal ellipsoids of N2 & O7-O8 are relatively large, possibly indicating
 that these might be disordered. The bond distances of C33-N2 are larger than 
 anticipated, with 1.54, as compared to the aromatic carbon-nitrogen bond 
 distance of 1.48. However, they could not be modelled.
;

_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)+(0.0433P)²+10.0268P] 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         9783
_refine_ls_number_parameters     458
_refine_ls_number_restraints     23
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1029
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.002
_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 0.646669(17) 0.096189(6) 0.814215(13) 0.02440(6) Uani 1 1 d . . .
O1 O 0.5337(3) 0.04527(13) 0.6920(3) 0.0306(8) Uani 1 1 d . . .
N1 N 0.2302(7) -0.1543(3) 0.5412(5) 0.0690(19) Uani 1 1 d . . .
C1 C 0.4780(5) 0.09836(18) 0.8819(4) 0.0274(10) Uani 1 1 d . . .
O2 O 0.5842(4) -0.00081(13) 0.8225(3) 0.0327(8) Uani 1 1 d . . .
N2 N 0.9997(9) 0.2556(4) 1.3239(8) 0.104(3) Uani 1 1 d U . .
C2 C 0.4687(5) 0.0707(2) 0.9613(4) 0.0316(11) Uani 1 1 d . . .
H2A H 0.5368 0.0491 0.9903 0.038 Uiso 1 1 calc R . .
O3 O 0.1621(6) -0.1465(2) 0.4623(4) 0.0840(19) Uani 1 1 d . . .
C3 C 0.3559(5) 0.0755(2) 0.9980(4) 0.0350(12) Uani 1 1 d . . .
H3 H 0.3474 0.0566 1.0526 0.042 Uiso 1 1 calc R . .
O4 O 0.2384(7) -0.1936(2) 0.5835(4) 0.090(2) Uani 1 1 d . . .
C4 C 0.2564(5) 0.1070(2) 0.9566(4) 0.0336(12) Uani 1 1 d . . .
O5 O 0.7527(3) 0.15209(13) 0.9197(3) 0.0301(8) Uani 1 1 d . . .
C5 C 0.2706(5) 0.1344(2) 0.8776(4) 0.0356(12) Uani 1 1 d . . .
H5 H 0.2035 0.1565 0.8489 0.043 Uiso 1 1 calc R . .
O6 O 0.7708(3) 0.08646(12) 1.0136(3) 0.0309(8) Uani 1 1 d . . .
C6 C 0.3813(5) 0.1303(2) 0.8393(4) 0.0335(12) Uani 1 1 d . . .
H6 H 0.3900 0.1492 0.7848 0.040 Uiso 1 1 calc R . .
O7 O 0.9945(8) 0.2975(3) 1.3063(6) 0.118(3) Uani 1 1 d U . .
C7 C 0.1338(6) 0.1112(2) 0.9949(5) 0.0465(15) Uani 1 1 d . . .
H7A H 0.0955 0.1439 0.9798 0.070 Uiso 1 1 calc R . .
H7B H 0.1546 0.1065 1.0650 0.070 Uiso 1 1 calc R . .
H7C H 0.0717 0.0860 0.9650 0.070 Uiso 1 1 calc R . .
O8 O 1.0463(11) 0.2340(4) 1.3959(8) 0.160(4) Uani 1 1 d U . .
C8 C 0.6099(5) 0.15636(19) 0.7071(4) 0.0294(11) Uani 1 1 d . . .
C39 C 0.241(2) 0.2274(8) 0.6570(16) 0.097(6) Uiso 0.50 1 d P . .
H39A H 0.1594 0.2086 0.6337 0.117 Uiso 0.50 1 calc PR . .
H39B H 0.3158 0.2071 0.6494 0.117 Uiso 0.50 1 calc PR . .
C9 C 0.6479(6) 0.2036(2) 0.7339(5) 0.0460(15) Uani 1 1 d . . .
H9 H 0.6947 0.2101 0.7975 0.055 Uiso 1 1 calc R . .
O10 O 1.1819(15) 0.0564(6) 1.3602(12) 0.107(5) Uiso 0.50 1 d PD . .
C10 C 0.6178(8) 0.2417(2) 0.6680(5) 0.060(2) Uani 1 1 d . . .
H10 H 0.6439 0.2742 0.6874 0.072 Uiso 1 1 calc R . .
C11 C 0.5510(7) 0.2334(3) 0.5752(5) 0.0571(19) Uani 1 1 d . . .
C12 C 0.5150(7) 0.1860(3) 0.5495(5) 0.060(2) Uani 1 1 d . . .
H12 H 0.4703 0.1795 0.4853 0.072 Uiso 1 1 calc R . .
C13 C 0.5413(6) 0.1473(2) 0.6139(4) 0.0466(15) Uani 1 1 d . . .
H13 H 0.5128 0.1150 0.5946 0.056 Uiso 1 1 calc R . .
C14 C 0.5223(9) 0.2748(3) 0.5035(7) 0.087(3) Uani 1 1 d . . .
H14A H 0.5775 0.2715 0.4562 0.130 Uiso 1 1 calc R . .
H14B H 0.5402 0.3063 0.5372 0.130 Uiso 1 1 calc R . .
H14C H 0.4307 0.2735 0.4703 0.130 Uiso 1 1 calc R . .
C15 C 0.8311(4) 0.06034(18) 0.8088(4) 0.0252(10) Uani 1 1 d . . .
C16 C 0.9001(5) 0.0829(2) 0.7472(4) 0.0360(12) Uani 1 1 d . . .
H16 H 0.8665 0.1109 0.7100 0.043 Uiso 1 1 calc R . .
C17 C 1.0208(5) 0.0628(2) 0.7421(4) 0.0367(13) Uani 1 1 d . . .
H17 H 1.0699 0.0774 0.7006 0.044 Uiso 1 1 calc R . .
C18 C 1.0703(5) 0.0223(2) 0.7958(4) 0.0348(12) Uani 1 1 d . . .
C19 C 0.9990(5) 0.0014(2) 0.8574(4) 0.0338(12) Uani 1 1 d . . .
H19 H 1.0329 -0.0263 0.8953 0.041 Uiso 1 1 calc R . .
C20 C 0.8782(5) 0.02052(19) 0.8643(4) 0.0297(11) Uani 1 1 d . . .
H20 H 0.8297 0.0062 0.9066 0.036 Uiso 1 1 calc R . .
C21 C 1.1993(5) 0.0009(2) 0.7871(5) 0.0444(15) Uani 1 1 d . . .
H21A H 1.1859 -0.0229 0.7341 0.067 Uiso 1 1 calc R . .
H21B H 1.2393 -0.0156 0.8474 0.067 Uiso 1 1 calc R . .
H21C H 1.2566 0.0273 0.7740 0.067 Uiso 1 1 calc R . .
C22 C 0.5303(5) 0.00473(19) 0.7366(4) 0.0300(11) Uani 1 1 d . . .
C23 C 0.4536(5) -0.03745(19) 0.6824(4) 0.0302(11) Uani 1 1 d . . .
C24 C 0.3920(6) -0.0323(2) 0.5876(4) 0.0429(14) Uani 1 1 d . . .
H24 H 0.4000 -0.0026 0.5543 0.051 Uiso 1 1 calc R . .
C25 C 0.3179(7) -0.0707(3) 0.5407(5) 0.0542(18) Uani 1 1 d . . .
H25 H 0.2737 -0.0676 0.4754 0.065 Uiso 1 1 calc R . .
C26 C 0.3097(7) -0.1133(2) 0.5907(5) 0.0477(16) Uani 1 1 d . . .
C27 C 0.3716(7) -0.1190(2) 0.6837(5) 0.0527(17) Uani 1 1 d . . .
H27 H 0.3652 -0.1491 0.7163 0.063 Uiso 1 1 calc R . .
C28 C 0.4440(6) -0.0806(2) 0.7308(5) 0.0454(15) Uani 1 1 d . . .
H28 H 0.4870 -0.0840 0.7964 0.054 Uiso 1 1 calc R . .
C29 C 0.7898(5) 0.13015(19) 1.0014(4) 0.0271(10) Uani 1 1 d . . .
C30 C 0.8545(5) 0.1622(2) 1.0848(4) 0.0352(12) Uani 1 1 d . . .
C31 C 0.8731(7) 0.2119(3) 1.0699(6) 0.0581(19) Uani 1 1 d . . .
H31 H 0.8521 0.2255 1.0069 0.070 Uiso 1 1 calc R . .
C32 C 0.9237(8) 0.2416(3) 1.1499(7) 0.074(2) Uani 1 1 d . . .
H32 H 0.9367 0.2758 1.1422 0.089 Uiso 1 1 calc R . .
C33 C 0.9538(8) 0.2205(3) 1.2386(6) 0.070(2) Uani 1 1 d . . .
C34 C 0.9388(8) 0.1722(4) 1.2529(6) 0.072(2) Uani 1 1 d . . .
H34 H 0.9630 0.1587 1.3159 0.087 Uiso 1 1 calc R . .
C35 C 0.8882(7) 0.1426(3) 1.1758(5) 0.0517(17) Uani 1 1 d . . .
H35 H 0.8765 0.1084 1.1854 0.062 Uiso 1 1 calc R . .
O9 O 0.2510(17) 0.2413(7) 0.7473(13) 0.124(5) Uiso 0.50 1 d P . .
C36 C 0.320(3) 0.2896(12) 0.781(2) 0.154(11) Uiso 0.50 1 d P . .
H36A H 0.2760 0.3078 0.8252 0.185 Uiso 0.50 1 calc PR . .
H36B H 0.4126 0.2844 0.8121 0.185 Uiso 0.50 1 calc PR . .
C37 C 0.306(2) 0.3143(9) 0.6877(16) 0.105(7) Uiso 0.50 1 d P . .
H37A H 0.3919 0.3245 0.6767 0.127 Uiso 0.50 1 calc PR . .
H37B H 0.2503 0.3438 0.6853 0.127 Uiso 0.50 1 calc PR . .
C38 C 0.238(2) 0.2742(8) 0.6063(16) 0.098(6) Uiso 0.50 1 d P . .
H38A H 0.1476 0.2839 0.5774 0.118 Uiso 0.50 1 calc PR . .
H38B H 0.2876 0.2717 0.5545 0.118 Uiso 0.50 1 calc PR . .
C40 C 1.244(3) 0.0928(10) 1.4211(19) 0.148(11) Uiso 0.50 1 d PD . .
H40A H 1.2431 0.1241 1.3851 0.178 Uiso 0.50 1 calc PR . .
H40B H 1.3360 0.0835 1.4466 0.178 Uiso 0.50 1 calc PR . .
C41 C 1.176(2) 0.0995(8) 1.5023(19) 0.120(8) Uiso 0.50 1 d PD . .
H41A H 1.2374 0.0971 1.5655 0.144 Uiso 0.50 1 calc PR . .
H41B H 1.1304 0.1315 1.4979 0.144 Uiso 0.50 1 calc PR . .
C42 C 1.086(2) 0.0595(9) 1.4880(16) 0.116(8) Uiso 0.50 1 d PD . .
H42A H 1.1249 0.0290 1.5199 0.140 Uiso 0.50 1 calc PR . .
H42B H 1.0050 0.0674 1.5094 0.140 Uiso 0.50 1 calc PR . .
C43 C 1.068(2) 0.0570(9) 1.3921(16) 0.111(7) Uiso 0.50 1 d PD . .
H43A H 1.0157 0.0856 1.3635 0.133 Uiso 0.50 1 calc PR . .
H43B H 1.0182 0.0269 1.3695 0.133 Uiso 0.50 1 calc PR . .


_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 2.186(5) . ?
Bi1 C1 2.190(5) . ?
Bi1 C8 2.212(5) . ?
Bi1 O5 2.256(3) . ?
Bi1 O1 2.338(3) . ?
Bi1 O2 2.727(4) . ?
Bi1 O6 2.869(4) . ?
O1 C22 1.276(6) . ?
N1 O3 1.214(8) . ?
N1 O4 1.218(8) . ?
N1 C26 1.481(8) . ?
C1 C6 1.376(7) . ?
C1 C2 1.377(7) . ?
O2 C22 1.240(6) . ?
N2 O7 1.165(11) . ?
N2 O8 1.191(13) . ?
N2 C33 1.538(12) . ?
C2 C3 1.399(7) . ?
C3 C4 1.383(8) . ?
C4 C5 1.382(8) . ?
C4 C7 1.506(8) . ?
O5 C29 1.289(6) . ?
C5 C6 1.390(7) . ?
O6 C29 1.223(6) . ?
C8 C9 1.374(8) . ?
C8 C13 1.388(8) . ?
C39 O9 1.32(2) . ?
C39 C38 1.46(3) . ?
C9 C10 1.387(8) . ?
O10 C43 1.366(16) . ?
O10 C40 1.385(17) . ?
C10 C11 1.375(10) . ?
C11 C12 1.370(10) . ?
C11 C14 1.506(9) . ?
C12 C13 1.383(9) . ?
C15 C20 1.368(7) . ?
C15 C16 1.393(7) . ?
C16 C17 1.398(7) . ?
C17 C18 1.376(8) . ?
C18 C19 1.389(8) . ?
C18 C21 1.505(7) . ?
C19 C20 1.395(7) . ?
C22 C23 1.515(7) . ?
C23 C24 1.372(8) . ?
C23 C28 1.375(8) . ?
C24 C25 1.385(8) . ?
C25 C26 1.369(10) . ?
C26 C27 1.352(9) . ?
C27 C28 1.378(9) . ?
C29 C30 1.511(7) . ?
C30 C35 1.373(8) . ?
C30 C31 1.389(9) . ?
C31 C32 1.403(10) . ?
C32 C33 1.360(12) . ?
C33 C34 1.342(12) . ?
C34 C35 1.373(9) . ?
O9 C36 1.53(3) . ?
C36 C37 1.46(3) . ?
C37 C38 1.64(3) . ?
C40 C41 1.493(18) . ?
C41 C42 1.427(17) . ?
C42 C43 1.336(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C15 Bi1 C1 146.55(19) . . ?
C15 Bi1 C8 109.44(19) . . ?
C1 Bi1 C8 104.02(19) . . ?
C15 Bi1 O5 90.35(15) . . ?
C1 Bi1 O5 91.33(16) . . ?
C8 Bi1 O5 87.02(17) . . ?
C15 Bi1 O1 91.43(15) . . ?
C1 Bi1 O1 90.58(16) . . ?
C8 Bi1 O1 86.57(17) . . ?
O5 Bi1 O1 173.58(12) . . ?
C15 Bi1 O2 78.09(15) . . ?
C1 Bi1 O2 77.43(15) . . ?
C8 Bi1 O2 137.44(16) . . ?
O5 Bi1 O2 135.48(12) . . ?
O1 Bi1 O2 50.94(12) . . ?
C15 Bi1 O6 76.81(15) . . ?
C1 Bi1 O6 79.10(15) . . ?
C8 Bi1 O6 136.39(16) . . ?
O5 Bi1 O6 49.40(11) . . ?
O1 Bi1 O6 137.02(11) . . ?
O2 Bi1 O6 86.08(10) . . ?
C22 O1 Bi1 101.9(3) . . ?
O3 N1 O4 125.1(7) . . ?
O3 N1 C26 117.9(7) . . ?
O4 N1 C26 117.0(7) . . ?
C6 C1 C2 122.0(5) . . ?
C6 C1 Bi1 114.6(4) . . ?
C2 C1 Bi1 123.3(4) . . ?
C22 O2 Bi1 84.5(3) . . ?
O7 N2 O8 131.3(12) . . ?
O7 N2 C33 116.4(11) . . ?
O8 N2 C33 111.9(11) . . ?
C1 C2 C3 117.8(5) . . ?
C4 C3 C2 121.6(5) . . ?
C5 C4 C3 118.5(5) . . ?
C5 C4 C7 120.0(5) . . ?
C3 C4 C7 121.5(5) . . ?
C29 O5 Bi1 107.3(3) . . ?
C4 C5 C6 121.2(5) . . ?
C29 O6 Bi1 79.8(3) . . ?
C1 C6 C5 118.8(5) . . ?
C9 C8 C13 119.4(5) . . ?
C9 C8 Bi1 120.1(4) . . ?
C13 C8 Bi1 120.3(4) . . ?
O9 C39 C38 102.7(19) . . ?
C8 C9 C10 120.0(6) . . ?
C43 O10 C40 96.7(19) . . ?
C11 C10 C9 121.3(6) . . ?
C12 C11 C10 117.8(6) . . ?
C12 C11 C14 121.2(7) . . ?
C10 C11 C14 120.9(7) . . ?
C11 C12 C13 122.3(6) . . ?
C12 C13 C8 119.1(6) . . ?
C20 C15 C16 122.5(5) . . ?
C20 C15 Bi1 123.3(4) . . ?
C16 C15 Bi1 114.2(4) . . ?
C15 C16 C17 117.4(5) . . ?
C18 C17 C16 121.7(5) . . ?
C17 C18 C19 119.0(5) . . ?
C17 C18 C21 120.4(5) . . ?
C19 C18 C21 120.6(5) . . ?
C18 C19 C20 120.8(5) . . ?
C15 C20 C19 118.6(5) . . ?
O2 C22 O1 122.6(5) . . ?
O2 C22 C23 119.4(5) . . ?
O1 C22 C23 118.0(5) . . ?
C24 C23 C28 120.5(5) . . ?
C24 C23 C22 120.8(5) . . ?
C28 C23 C22 118.7(5) . . ?
C23 C24 C25 119.7(6) . . ?
C26 C25 C24 118.6(6) . . ?
C27 C26 C25 122.2(6) . . ?
C27 C26 N1 118.9(6) . . ?
C25 C26 N1 118.9(6) . . ?
C26 C27 C28 119.3(6) . . ?
C23 C28 C27 119.7(6) . . ?
O6 C29 O5 123.4(5) . . ?
O6 C29 C30 120.5(5) . . ?
O5 C29 C30 116.1(5) . . ?
C35 C30 C31 120.3(6) . . ?
C35 C30 C29 119.9(5) . . ?
C31 C30 C29 119.7(6) . . ?
C30 C31 C32 118.6(7) . . ?
C33 C32 C31 118.8(7) . . ?
C34 C33 C32 122.7(7) . . ?
C34 C33 N2 121.0(9) . . ?
C32 C33 N2 116.1(9) . . ?
C33 C34 C35 119.4(8) . . ?
C30 C35 C34 120.2(7) . . ?
C39 O9 C36 119(2) . . ?
C37 C36 O9 99(2) . . ?
C36 C37 C38 106(2) . . ?
C39 C38 C37 105.8(18) . . ?
O10 C40 C41 109(2) . . ?
C42 C41 C40 102(2) . . ?
C43 C42 C41 98(2) . . ?
C42 C43 O10 113(2) . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.33
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         1.255
_refine_diff_density_min         -1.434
_refine_diff_density_rms         0.133
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb111-yc
_database_code_depnum_ccdc_archive 'CCDC 1420796'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H29 Bi Cl2 O6'
_chemical_formula_sum            'C35 H29 Bi Cl2 O6'
_chemical_formula_weight         825.46

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

_vrf_PLAT029_vb111-yc            
;
PROBLEM: _diffrn_measured_fraction_theta_full Low .......      0.915 Note  
RESPONSE: Data was collected at the synchrotron MX1 beamline with 365 Phi scan, due to
hardwear constraints and deterioration of the crystal in the beam 
completness is low please see CIF for further details
;

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

_cell_length_a                   9.1030(18)
_cell_length_b                   10.781(2)
_cell_length_c                   18.399(4)
_cell_angle_alpha                98.62(3)
_cell_angle_beta                 96.46(3)
_cell_angle_gamma                113.48(3)
_cell_volume                     1607.7(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    30394
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_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    1.705
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    5.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8043
_exptl_absorpt_correction_T_max  0.8946
_exptl_absorpt_process_details   
'SADABS: Sheldrick Acta Cryst. A51, (1995) 33-38'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71080
_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            30394
_diffrn_reflns_av_R_equivalents  0.0405
_diffrn_reflns_av_sigmaI/netI    0.0341
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.14
_diffrn_reflns_theta_max         31.52
_reflns_number_total             7821
_reflns_number_gt                7442
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XSeed
_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 was collected with 365 Phi scan, with the minimum detector distance allowed
by the MX2 synchrotron beamline for a triclinic complex. Due to these hardwear 
limitiations the  overall completeness of the data is low. The data:parameter 
ration is greater than 10 which is well within the IUCR limit. 

There appears to be no other indications that their is anything else wrong 
with the data appart form low completness. All other analytical data 
(NMR and microanalysis) support the composition of the complex. The complex 
is also essentially isostructral in composition to the other structures 
reported in the same paper.

;

_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)+(0.0485P)²+4.5915P] 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         7821
_refine_ls_number_parameters     400
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0350
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0905
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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 0.846510(16) 0.673301(13) 0.740166(7) 0.02295(6) Uani 1 1 d . . .
Cl1 Cl 0.29809(19) 0.07435(15) 0.88642(8) 0.0505(3) Uani 1 1 d . . .
Cl2 Cl 1.63391(18) 1.13122(17) 0.65626(10) 0.0548(4) Uani 1 1 d . . .
O1 O 0.6516(4) 0.4928(3) 0.77543(19) 0.0317(6) Uani 1 1 d . . .
O2 O 0.4870(4) 0.5479(3) 0.70149(18) 0.0307(6) Uani 1 1 d . . .
O3 O 0.1760(4) 0.4247(4) 0.6951(2) 0.0418(8) Uani 1 1 d . . .
H3' H 0.2634 0.4796 0.6853 0.050 Uiso 1 1 calc R . .
O4 O 1.0639(4) 0.8454(3) 0.71448(18) 0.0302(6) Uani 1 1 d . . .
O5 O 0.8732(4) 0.8852(3) 0.64739(18) 0.0309(6) Uani 1 1 d . . .
O6 O 0.9688(5) 1.0871(4) 0.5744(2) 0.0389(8) Uani 1 1 d . . .
H6' H 0.9024 1.0273 0.5932 0.047 Uiso 1 1 calc R . .
C1 C 0.5081(5) 0.4761(4) 0.7454(2) 0.0270(8) Uani 1 1 d . . .
C2 C 0.3690(5) 0.3678(4) 0.7667(2) 0.0270(8) Uani 1 1 d . . .
C3 C 0.3954(6) 0.2829(5) 0.8127(2) 0.0306(8) Uani 1 1 d . . .
H3 H 0.5030 0.2932 0.8295 0.037 Uiso 1 1 calc R . .
C4 C 0.2656(6) 0.1853(5) 0.8331(3) 0.0344(9) Uani 1 1 d . . .
C5 C 0.1061(6) 0.1711(5) 0.8110(3) 0.0386(10) Uani 1 1 d . . .
H5 H 0.0179 0.1060 0.8277 0.046 Uiso 1 1 calc R . .
C6 C 0.0787(6) 0.2507(5) 0.7656(3) 0.0394(11) Uani 1 1 d . . .
H6 H -0.0296 0.2398 0.7499 0.047 Uiso 1 1 calc R . .
C7 C 0.2089(5) 0.3498(5) 0.7412(3) 0.0340(10) Uani 1 1 d . . .
C8 C 1.0183(5) 0.9092(4) 0.6689(2) 0.0256(7) Uani 1 1 d . . .
C9 C 1.1528(5) 1.0140(4) 0.6415(2) 0.0269(8) Uani 1 1 d . . .
C10 C 1.3141(6) 1.0288(4) 0.6612(3) 0.0314(9) Uani 1 1 d . . .
H10 H 1.3377 0.9757 0.6937 0.038 Uiso 1 1 calc R . .
C11 C 1.4369(6) 1.1202(5) 0.6333(3) 0.0364(10) Uani 1 1 d . . .
C12 C 1.4053(7) 1.2014(5) 0.5875(3) 0.0372(10) Uani 1 1 d . . .
H12 H 1.4913 1.2654 0.5691 0.045 Uiso 1 1 calc R . .
C13 C 1.2473(7) 1.1883(5) 0.5688(3) 0.0377(10) Uani 1 1 d . . .
H13 H 1.2256 1.2442 0.5377 0.045 Uiso 1 1 calc R . .
C14 C 1.1204(6) 1.0948(4) 0.5947(3) 0.0314(9) Uani 1 1 d . . .
C15 C 0.7993(5) 0.5528(4) 0.6274(2) 0.0258(7) Uani 1 1 d . . .
C16 C 0.7139(6) 0.5717(4) 0.5655(2) 0.0300(8) Uani 1 1 d . . .
H16 H 0.6706 0.6388 0.5707 0.036 Uiso 1 1 calc R . .
C17 C 0.6938(6) 0.4897(5) 0.4961(3) 0.0327(9) Uani 1 1 d . . .
H17 H 0.6353 0.5008 0.4533 0.039 Uiso 1 1 calc R . .
C18 C 0.7575(6) 0.3914(4) 0.4877(3) 0.0321(9) Uani 1 1 d . . .
C19 C 0.8445(6) 0.3772(5) 0.5502(3) 0.0359(10) Uani 1 1 d . . .
H19 H 0.8894 0.3112 0.5450 0.043 Uiso 1 1 calc R . .
C20 C 0.8671(6) 0.4583(5) 0.6207(3) 0.0322(9) Uani 1 1 d . . .
H20 H 0.9279 0.4488 0.6633 0.039 Uiso 1 1 calc R . .
C21 C 0.7297(8) 0.3000(5) 0.4121(3) 0.0454(12) Uani 1 1 d . . .
H21A H 0.6771 0.3309 0.3736 0.068 Uiso 1 1 calc R . .
H21B H 0.6593 0.2040 0.4128 0.068 Uiso 1 1 calc R . .
H21C H 0.8346 0.3060 0.4007 0.068 Uiso 1 1 calc R . .
C22 C 0.7784(5) 0.8196(4) 0.8083(2) 0.0278(8) Uani 1 1 d . . .
C23 C 0.6931(5) 0.8875(5) 0.7786(2) 0.0297(8) Uani 1 1 d . . .
H23 H 0.6508 0.8663 0.7264 0.036 Uiso 1 1 calc R . .
C24 C 0.6713(6) 0.9880(5) 0.8274(3) 0.0344(9) Uani 1 1 d . . .
H24 H 0.6141 1.0363 0.8079 0.041 Uiso 1 1 calc R . .
C25 C 0.7314(6) 1.0192(5) 0.9040(3) 0.0375(10) Uani 1 1 d . . .
C26 C 0.8106(7) 0.9451(6) 0.9320(3) 0.0431(11) Uani 1 1 d . . .
H26 H 0.8484 0.9627 0.9845 0.052 Uiso 1 1 calc R . .
C27 C 0.8357(6) 0.8449(5) 0.8843(3) 0.0362(10) Uani 1 1 d . . .
H27 H 0.8910 0.7951 0.9037 0.043 Uiso 1 1 calc R . .
C28 C 0.7137(8) 1.1314(7) 0.9564(4) 0.0542(15) Uani 1 1 d . . .
H28A H 0.7166 1.2049 0.9303 0.081 Uiso 1 1 calc R . .
H28B H 0.8035 1.1697 0.9997 0.081 Uiso 1 1 calc R . .
H28C H 0.6095 1.0927 0.9733 0.081 Uiso 1 1 calc R . .
C29 C 1.0244(5) 0.6351(4) 0.8144(2) 0.0267(8) Uani 1 1 d . . .
C30 C 1.1903(6) 0.7059(5) 0.8152(3) 0.0339(9) Uani 1 1 d . . .
H30 H 1.2267 0.7706 0.7841 0.041 Uiso 1 1 calc R . .
C31 C 1.3029(6) 0.6813(5) 0.8619(3) 0.0352(10) Uani 1 1 d . . .
H31 H 1.4160 0.7291 0.8621 0.042 Uiso 1 1 calc R . .
C32 C 1.2517(6) 0.5878(5) 0.9082(3) 0.0333(9) Uani 1 1 d . . .
C33 C 1.0857(7) 0.5178(5) 0.9059(3) 0.0371(10) Uani 1 1 d . . .
H33 H 1.0492 0.4522 0.9365 0.044 Uiso 1 1 calc R . .
C34 C 0.9711(6) 0.5409(5) 0.8601(3) 0.0344(9) Uani 1 1 d . . .
H34 H 0.8580 0.4929 0.8600 0.041 Uiso 1 1 calc R . .
C35 C 1.3742(8) 0.5621(6) 0.9586(3) 0.0473(13) Uani 1 1 d . . .
H35A H 1.3264 0.5265 1.0005 0.071 Uiso 1 1 calc R . .
H35B H 1.4719 0.6490 0.9781 0.071 Uiso 1 1 calc R . .
H35C H 1.4040 0.4941 0.9302 0.071 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 2.174(4) . ?
Bi1 C22 2.192(4) . ?
Bi1 C29 2.204(4) . ?
Bi1 O4 2.265(3) . ?
Bi1 O1 2.289(3) . ?
Cl1 C4 1.746(5) . ?
Cl2 C11 1.748(5) . ?
O1 C1 1.290(5) . ?
O2 C1 1.249(5) . ?
O3 C7 1.341(6) . ?
O4 C8 1.292(5) . ?
O5 C8 1.244(5) . ?
O6 C14 1.354(6) . ?
C1 C2 1.480(6) . ?
C2 C3 1.405(6) . ?
C2 C7 1.406(6) . ?
C3 C4 1.368(7) . ?
C4 C5 1.403(7) . ?
C5 C6 1.355(8) . ?
C6 C7 1.415(8) . ?
C8 C9 1.496(6) . ?
C9 C14 1.399(6) . ?
C9 C10 1.410(7) . ?
C10 C11 1.375(7) . ?
C11 C12 1.387(7) . ?
C12 C13 1.385(8) . ?
C13 C14 1.386(7) . ?
C15 C20 1.384(6) . ?
C15 C16 1.392(5) . ?
C16 C17 1.388(6) . ?
C17 C18 1.394(6) . ?
C18 C19 1.385(7) . ?
C18 C21 1.510(7) . ?
C19 C20 1.395(7) . ?
C22 C27 1.383(6) . ?
C22 C23 1.384(6) . ?
C23 C24 1.392(6) . ?
C24 C25 1.393(7) . ?
C25 C26 1.387(8) . ?
C25 C28 1.502(7) . ?
C26 C27 1.395(7) . ?
C29 C34 1.389(6) . ?
C29 C30 1.391(7) . ?
C30 C31 1.394(6) . ?
C31 C32 1.389(7) . ?
C32 C33 1.387(7) . ?
C32 C35 1.508(6) . ?
C33 C34 1.390(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
C15 Bi1 C22 142.57(16) . . ?
C15 Bi1 C29 110.09(15) . . ?
C22 Bi1 C29 107.33(16) . . ?
C15 Bi1 O4 90.16(14) . . ?
C22 Bi1 O4 92.61(14) . . ?
C29 Bi1 O4 86.61(15) . . ?
C15 Bi1 O1 91.95(15) . . ?
C22 Bi1 O1 90.17(15) . . ?
C29 Bi1 O1 85.78(14) . . ?
O4 Bi1 O1 172.36(11) . . ?
C1 O1 Bi1 110.0(3) . . ?
C8 O4 Bi1 111.3(3) . . ?
O2 C1 O1 122.2(4) . . ?
O2 C1 C2 121.6(4) . . ?
O1 C1 C2 116.2(4) . . ?
C3 C2 C7 119.5(4) . . ?
C3 C2 C1 120.6(4) . . ?
C7 C2 C1 119.9(4) . . ?
C4 C3 C2 119.7(4) . . ?
C3 C4 C5 121.2(5) . . ?
C3 C4 Cl1 119.6(4) . . ?
C5 C4 Cl1 119.2(4) . . ?
C6 C5 C4 119.5(5) . . ?
C5 C6 C7 121.0(5) . . ?
O3 C7 C2 122.0(5) . . ?
O3 C7 C6 119.1(4) . . ?
C2 C7 C6 118.9(5) . . ?
O5 C8 O4 123.5(4) . . ?
O5 C8 C9 121.1(4) . . ?
O4 C8 C9 115.4(4) . . ?
C14 C9 C10 119.5(4) . . ?
C14 C9 C8 121.0(4) . . ?
C10 C9 C8 119.5(4) . . ?
C11 C10 C9 119.7(4) . . ?
C10 C11 C12 120.9(5) . . ?
C10 C11 Cl2 118.4(4) . . ?
C12 C11 Cl2 120.7(4) . . ?
C13 C12 C11 119.4(4) . . ?
C12 C13 C14 121.0(4) . . ?
O6 C14 C13 118.0(4) . . ?
O6 C14 C9 122.5(4) . . ?
C13 C14 C9 119.5(5) . . ?
C20 C15 C16 121.8(4) . . ?
C20 C15 Bi1 114.7(3) . . ?
C16 C15 Bi1 123.5(3) . . ?
C17 C16 C15 118.1(4) . . ?
C16 C17 C18 121.6(4) . . ?
C19 C18 C17 118.8(4) . . ?
C19 C18 C21 120.5(4) . . ?
C17 C18 C21 120.7(5) . . ?
C18 C19 C20 121.0(4) . . ?
C15 C20 C19 118.7(4) . . ?
C27 C22 C23 122.0(4) . . ?
C27 C22 Bi1 114.2(3) . . ?
C23 C22 Bi1 123.7(3) . . ?
C22 C23 C24 118.0(4) . . ?
C23 C24 C25 121.6(4) . . ?
C26 C25 C24 118.6(5) . . ?
C26 C25 C28 119.7(5) . . ?
C24 C25 C28 121.7(5) . . ?
C25 C26 C27 120.9(5) . . ?
C22 C27 C26 118.8(5) . . ?
C34 C29 C30 120.2(4) . . ?
C34 C29 Bi1 120.1(3) . . ?
C30 C29 Bi1 119.7(3) . . ?
C29 C30 C31 119.7(5) . . ?
C32 C31 C30 120.9(5) . . ?
C33 C32 C31 118.4(4) . . ?
C33 C32 C35 121.1(5) . . ?
C31 C32 C35 120.5(5) . . ?
C32 C33 C34 121.9(5) . . ?
C29 C34 C33 119.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.730
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.915
_refine_diff_density_max         1.500
_refine_diff_density_min         -2.618
_refine_diff_density_rms         0.152
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_vb113-yc
_database_code_depnum_ccdc_archive 'CCDC 1420797'
_audit_update_record             
;
2015-09-24 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C49 H43 Bi Cl2 N2 O4'
_chemical_formula_sum            'C49 H43 Bi Cl2 N2 O4'
_chemical_formula_weight         1003.73

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   20.797(4)
_cell_length_b                   15.314(3)
_cell_length_c                   26.182(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     8339(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    184688
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       plate
_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    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4000
_exptl_absorpt_coefficient_mu    4.405
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8792
_exptl_absorpt_correction_T_max  0.9171
_exptl_absorpt_process_details   'SADABS:Sheldrick Acta Cryst.A51,(1995)33-38'

_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71080
_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            184688
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         1.56
_diffrn_reflns_theta_max         33.15
_reflns_number_total             14783
_reflns_number_gt                12788
_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, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XSeed
_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. 
;

_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)+(0.0681P)²+9.9931P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         14783
_refine_ls_number_parameters     536
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1131
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.048
_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 0.471720(5) 0.529509(6) 0.337042(4) 0.02280(4) Uani 1 1 d . . .
Cl1 Cl 0.55337(5) 0.12997(5) 0.59504(3) 0.03848(16) Uani 1 1 d . . .
Cl2 Cl 0.76373(5) 0.55414(7) 0.59810(3) 0.0483(2) Uani 1 1 d . . .
O1 O 0.41349(11) 0.40477(13) 0.32589(9) 0.0306(4) Uani 1 1 d . . .
O2 O 0.48152(10) 0.36752(13) 0.38731(8) 0.0288(4) Uani 1 1 d . . .
O3 O 0.52232(10) 0.66134(15) 0.33116(8) 0.0272(4) Uani 1 1 d . . .
O4 O 0.57934(10) 0.60186(12) 0.39373(8) 0.0278(4) Uani 1 1 d . . .
N1 N 0.49434(14) 0.20125(15) 0.40965(9) 0.0295(5) Uani 1 1 d . . .
N2 N 0.66858(12) 0.69943(15) 0.43921(9) 0.0273(4) Uani 1 1 d . . .
C1 C 0.44153(13) 0.34578(17) 0.35371(11) 0.0261(5) Uani 1 1 d . . .
C2 C 0.42566(13) 0.25402(18) 0.34243(10) 0.0246(5) Uani 1 1 d . . .
C3 C 0.38286(15) 0.23604(19) 0.30229(11) 0.0311(5) Uani 1 1 d . . .
H3 H 0.3659 0.2831 0.2829 0.037 Uiso 1 1 calc R . .
C4 C 0.36495(17) 0.1519(2) 0.29042(13) 0.0388(7) Uani 1 1 d . . .
H4 H 0.3362 0.1411 0.2629 0.047 Uiso 1 1 calc R . .
C5 C 0.38903(17) 0.0837(2) 0.31866(13) 0.0372(6) Uani 1 1 d . . .
H5 H 0.3760 0.0258 0.3109 0.045 Uiso 1 1 calc R . .
C6 C 0.43210(15) 0.09821(17) 0.35840(11) 0.0308(5) Uani 1 1 d . . .
H6 H 0.4482 0.0502 0.3774 0.037 Uiso 1 1 calc R . .
C7 C 0.45197(14) 0.18356(16) 0.37061(10) 0.0250(5) Uani 1 1 d . . .
C8 C 0.52349(13) 0.14242(18) 0.44406(11) 0.0264(5) Uani 1 1 d . . .
C9 C 0.55572(16) 0.06806(18) 0.42695(10) 0.0303(5) Uani 1 1 d . . .
H9 H 0.5571 0.0548 0.3915 0.036 Uiso 1 1 calc R . .
C10 C 0.58592(17) 0.0132(2) 0.46205(12) 0.0337(6) Uani 1 1 d . . .
H10 H 0.6064 -0.0386 0.4505 0.040 Uiso 1 1 calc R . .
C11 C 0.58637(17) 0.03346(19) 0.51346(13) 0.0336(6) Uani 1 1 d . . .
H11 H 0.6084 -0.0026 0.5373 0.040 Uiso 1 1 calc R . .
C12 C 0.55380(15) 0.10803(17) 0.52959(10) 0.0271(5) Uani 1 1 d . . .
C13 C 0.52102(13) 0.16359(18) 0.49625(11) 0.0251(5) Uani 1 1 d . . .
C14 C 0.48311(14) 0.2411(2) 0.51453(12) 0.0302(5) Uani 1 1 d . . .
H14A H 0.4731 0.2340 0.5509 0.045 Uiso 1 1 calc R . .
H14B H 0.4430 0.2454 0.4950 0.045 Uiso 1 1 calc R . .
H14C H 0.5085 0.2943 0.5097 0.045 Uiso 1 1 calc R . .
C15 C 0.56830(13) 0.66431(16) 0.36413(9) 0.0241(4) Uani 1 1 d . . .
C16 C 0.60726(12) 0.74671(16) 0.36560(9) 0.0229(4) Uani 1 1 d . . .
C17 C 0.59556(15) 0.80948(19) 0.32781(10) 0.0282(5) Uani 1 1 d . . .
H17 H 0.5642 0.7980 0.3023 0.034 Uiso 1 1 calc R . .
C18 C 0.62853(16) 0.8875(2) 0.32672(12) 0.0327(6) Uani 1 1 d . . .
H18 H 0.6199 0.9296 0.3009 0.039 Uiso 1 1 calc R . .
C19 C 0.67455(14) 0.90368(19) 0.36394(12) 0.0312(5) Uani 1 1 d . . .
H19 H 0.6975 0.9573 0.3636 0.037 Uiso 1 1 calc R . .
C20 C 0.68731(13) 0.84278(18) 0.40143(11) 0.0281(5) Uani 1 1 d . . .
H20 H 0.7192 0.8551 0.4264 0.034 Uiso 1 1 calc R . .
C21 C 0.65407(12) 0.76274(17) 0.40354(10) 0.0240(4) Uani 1 1 d . . .
C22 C 0.69092(13) 0.71073(18) 0.48977(10) 0.0255(5) Uani 1 1 d . . .
C23 C 0.68211(13) 0.78824(19) 0.51695(11) 0.0292(5) Uani 1 1 d . . .
H23 H 0.6645 0.8379 0.5003 0.035 Uiso 1 1 calc R . .
C24 C 0.69903(15) 0.7929(2) 0.56811(11) 0.0341(6) Uani 1 1 d . . .
H24 H 0.6937 0.8462 0.5862 0.041 Uiso 1 1 calc R . .
C25 C 0.72354(16) 0.7209(2) 0.59277(11) 0.0368(6) Uani 1 1 d . . .
H25 H 0.7336 0.7234 0.6281 0.044 Uiso 1 1 calc R . .
C26 C 0.73339(15) 0.6449(2) 0.56528(11) 0.0320(6) Uani 1 1 d . . .
C27 C 0.71913(13) 0.63739(19) 0.51336(10) 0.0276(5) Uani 1 1 d . . .
C28 C 0.73305(16) 0.5554(2) 0.48359(12) 0.0334(6) Uani 1 1 d . . .
H28A H 0.7791 0.5525 0.4758 0.050 Uiso 1 1 calc R . .
H28B H 0.7084 0.5559 0.4517 0.050 Uiso 1 1 calc R . .
H28C H 0.7207 0.5043 0.5039 0.050 Uiso 1 1 calc R . .
C29 C 0.40913(13) 0.57938(16) 0.27631(10) 0.0252(5) Uani 1 1 d . . .
C30 C 0.43450(14) 0.63202(17) 0.23752(10) 0.0263(5) Uani 1 1 d . . .
H30 H 0.4784 0.6489 0.2381 0.032 Uiso 1 1 calc R . .
C31 C 0.39419(15) 0.65935(19) 0.19786(10) 0.0301(5) Uani 1 1 d . . .
H31 H 0.4109 0.6958 0.1717 0.036 Uiso 1 1 calc R . .
C32 C 0.33019(16) 0.63410(19) 0.19613(11) 0.0322(6) Uani 1 1 d . . .
C33 C 0.2878(2) 0.6644(3) 0.15291(14) 0.0459(8) Uani 1 1 d . . .
H33A H 0.2845 0.7282 0.1536 0.069 Uiso 1 1 calc R . .
H33B H 0.2448 0.6388 0.1567 0.069 Uiso 1 1 calc R . .
H33C H 0.3064 0.6458 0.1203 0.069 Uiso 1 1 calc R . .
C34 C 0.30573(14) 0.58147(19) 0.23515(12) 0.0311(5) Uani 1 1 d . . .
H34 H 0.2618 0.5644 0.2344 0.037 Uiso 1 1 calc R . .
C35 C 0.34497(14) 0.55372(18) 0.27512(11) 0.0278(5) Uani 1 1 d . . .
H35 H 0.3280 0.5176 0.3014 0.033 Uiso 1 1 calc R . .
C36 C 0.42877(13) 0.56631(17) 0.41044(10) 0.0261(5) Uani 1 1 d . . .
C37 C 0.39369(14) 0.64382(19) 0.40970(11) 0.0299(5) Uani 1 1 d . . .
H37 H 0.3872 0.6747 0.3786 0.036 Uiso 1 1 calc R . .
C38 C 0.36831(14) 0.6752(2) 0.45548(12) 0.0326(6) Uani 1 1 d . . .
H38 H 0.3435 0.7273 0.4554 0.039 Uiso 1 1 calc R . .
C39 C 0.37896(14) 0.6312(2) 0.50118(11) 0.0313(5) Uani 1 1 d . . .
C40 C 0.35575(16) 0.6682(3) 0.55121(13) 0.0400(7) Uani 1 1 d . . .
H40A H 0.3339 0.6223 0.5707 0.060 Uiso 1 1 calc R . .
H40B H 0.3257 0.7162 0.5446 0.060 Uiso 1 1 calc R . .
H40C H 0.3925 0.6900 0.5708 0.060 Uiso 1 1 calc R . .
C41 C 0.41271(16) 0.5527(2) 0.50016(11) 0.0338(6) Uani 1 1 d . . .
H41 H 0.4187 0.5212 0.5310 0.041 Uiso 1 1 calc R . .
C42 C 0.43796(16) 0.51934(19) 0.45489(11) 0.0305(5) Uani 1 1 d . . .
H42 H 0.4609 0.4657 0.4546 0.037 Uiso 1 1 calc R . .
C43 C 0.55192(16) 0.45942(16) 0.30082(11) 0.0275(5) Uani 1 1 d . . .
C44 C 0.53456(16) 0.4122(2) 0.25766(12) 0.0345(6) Uani 1 1 d . . .
H44 H 0.4915 0.4135 0.2455 0.041 Uiso 1 1 calc R . .
C45 C 0.5809(2) 0.3633(2) 0.23252(12) 0.0411(7) Uani 1 1 d . . .
H45 H 0.5690 0.3297 0.2035 0.049 Uiso 1 1 calc R . .
C46 C 0.64400(19) 0.36259(19) 0.24901(13) 0.0402(7) Uani 1 1 d . . .
C47 C 0.6948(2) 0.3120(2) 0.22071(18) 0.0603(13) Uani 1 1 d . . .
H47A H 0.6769 0.2563 0.2090 0.090 Uiso 1 1 calc R . .
H47B H 0.7313 0.3009 0.2435 0.090 Uiso 1 1 calc R . .
H47C H 0.7094 0.3459 0.1912 0.090 Uiso 1 1 calc R . .
C48 C 0.66005(17) 0.4101(2) 0.29245(15) 0.0403(7) Uani 1 1 d . . .
H48 H 0.7032 0.4093 0.3044 0.048 Uiso 1 1 calc R . .
C49 C 0.61424(16) 0.45863(19) 0.31867(13) 0.0333(6) Uani 1 1 d . . .
H49 H 0.6257 0.4907 0.3484 0.040 Uiso 1 1 calc R . .
H1N H 0.499(2) 0.253(3) 0.4206(16) 0.043(11) Uiso 1 1 d . . .
H2N H 0.6465(19) 0.646(3) 0.4336(15) 0.034(10) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Bi1 C29 2.192(3) . ?
Bi1 C36 2.193(3) . ?
Bi1 C43 2.198(3) . ?
Bi1 O1 2.281(2) . ?
Bi1 O3 2.282(2) . ?
Bi1 O2 2.816(2) . ?
Bi1 O4 2.905(2) . ?
Cl1 C12 1.746(3) . ?
Cl2 C26 1.752(3) . ?
O1 C1 1.299(3) . ?
O2 C1 1.255(3) . ?
O3 C15 1.289(3) . ?
O4 C15 1.252(3) . ?
N1 C7 1.376(4) . ?
N1 C8 1.411(4) . ?
N2 C21 1.380(3) . ?
N2 C22 1.414(3) . ?
C1 C2 1.473(4) . ?
C2 C3 1.405(4) . ?
C2 C7 1.417(4) . ?
C3 C4 1.377(4) . ?
C4 C5 1.374(5) . ?
C5 C6 1.391(5) . ?
C6 C7 1.408(4) . ?
C8 C9 1.395(4) . ?
C8 C13 1.405(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.381(5) . ?
C11 C12 1.393(4) . ?
C12 C13 1.397(4) . ?
C13 C14 1.503(4) . ?
C15 C16 1.500(4) . ?
C16 C17 1.401(4) . ?
C16 C21 1.412(4) . ?
C17 C18 1.378(4) . ?
C18 C19 1.388(4) . ?
C19 C20 1.380(4) . ?
C20 C21 1.408(4) . ?
C22 C23 1.396(4) . ?
C22 C27 1.410(4) . ?
C23 C24 1.387(4) . ?
C24 C25 1.376(5) . ?
C25 C26 1.384(5) . ?
C26 C27 1.396(4) . ?
C27 C28 1.506(4) . ?
C29 C35 1.391(4) . ?
C29 C30 1.400(4) . ?
C30 C31 1.399(4) . ?
C31 C32 1.387(5) . ?
C32 C34 1.397(5) . ?
C32 C33 1.508(4) . ?
C34 C35 1.394(4) . ?
C36 C42 1.381(4) . ?
C36 C37 1.393(4) . ?
C37 C38 1.395(4) . ?
C38 C39 1.391(4) . ?
C39 C41 1.392(5) . ?
C39 C40 1.506(4) . ?
C41 C42 1.393(4) . ?
C43 C49 1.378(4) . ?
C43 C44 1.389(4) . ?
C44 C45 1.387(5) . ?
C45 C46 1.382(6) . ?
C46 C48 1.391(5) . ?
C46 C47 1.506(5) . ?
C48 C49 1.390(5) . ?

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
C29 Bi1 C36 107.71(10) . . ?
C29 Bi1 C43 107.92(10) . . ?
C36 Bi1 C43 144.35(10) . . ?
C29 Bi1 O1 83.32(9) . . ?
C36 Bi1 O1 96.38(9) . . ?
C43 Bi1 O1 86.49(9) . . ?
C29 Bi1 O3 85.22(9) . . ?
C36 Bi1 O3 91.13(9) . . ?
C43 Bi1 O3 93.03(9) . . ?
O1 Bi1 O3 167.78(7) . . ?
C29 Bi1 O2 133.55(8) . . ?
C36 Bi1 O2 81.16(8) . . ?
C43 Bi1 O2 73.53(8) . . ?
O1 Bi1 O2 50.23(7) . . ?
O3 Bi1 O2 141.05(7) . . ?
C29 Bi1 O4 134.04(8) . . ?
C36 Bi1 O4 76.59(8) . . ?
C43 Bi1 O4 79.75(9) . . ?
O1 Bi1 O4 142.56(6) . . ?
O3 Bi1 O4 48.84(6) . . ?
O2 Bi1 O4 92.37(6) . . ?
C1 O1 Bi1 105.81(17) . . ?
C1 O2 Bi1 81.85(15) . . ?
C15 O3 Bi1 109.15(17) . . ?
C15 O4 Bi1 80.44(15) . . ?
C7 N1 C8 128.6(2) . . ?
C21 N2 C22 128.3(2) . . ?
O2 C1 O1 120.4(2) . . ?
O2 C1 C2 122.8(2) . . ?
O1 C1 C2 116.8(2) . . ?
C3 C2 C7 119.0(2) . . ?
C3 C2 C1 118.6(2) . . ?
C7 C2 C1 122.4(2) . . ?
C4 C3 C2 121.6(3) . . ?
C5 C4 C3 119.4(3) . . ?
C4 C5 C6 121.1(3) . . ?
C5 C6 C7 120.5(3) . . ?
N1 C7 C6 122.6(2) . . ?
N1 C7 C2 118.9(2) . . ?
C6 C7 C2 118.4(3) . . ?
C9 C8 C13 121.2(3) . . ?
C9 C8 N1 121.5(3) . . ?
C13 C8 N1 117.3(2) . . ?
C10 C9 C8 119.8(3) . . ?
C11 C10 C9 120.7(3) . . ?
C10 C11 C12 118.4(3) . . ?
C11 C12 C13 123.2(3) . . ?
C11 C12 Cl1 117.2(2) . . ?
C13 C12 Cl1 119.6(2) . . ?
C12 C13 C8 116.7(2) . . ?
C12 C13 C14 122.6(3) . . ?
C8 C13 C14 120.7(2) . . ?
O4 C15 O3 121.6(2) . . ?
O4 C15 C16 121.9(2) . . ?
O3 C15 C16 116.6(2) . . ?
C17 C16 C21 119.8(2) . . ?
C17 C16 C15 117.7(2) . . ?
C21 C16 C15 122.4(2) . . ?
C18 C17 C16 121.6(3) . . ?
C17 C18 C19 118.9(3) . . ?
C20 C19 C18 120.8(3) . . ?
C19 C20 C21 121.5(3) . . ?
N2 C21 C20 122.1(2) . . ?
N2 C21 C16 120.3(2) . . ?
C20 C21 C16 117.5(2) . . ?
C23 C22 C27 120.6(2) . . ?
C23 C22 N2 122.6(2) . . ?
C27 C22 N2 116.7(2) . . ?
C24 C23 C22 120.2(3) . . ?
C25 C24 C23 120.4(3) . . ?
C24 C25 C26 119.0(3) . . ?
C25 C26 C27 123.0(3) . . ?
C25 C26 Cl2 117.8(2) . . ?
C27 C26 Cl2 119.3(2) . . ?
C26 C27 C22 116.7(3) . . ?
C26 C27 C28 122.1(3) . . ?
C22 C27 C28 121.2(2) . . ?
C35 C29 C30 120.5(2) . . ?
C35 C29 Bi1 119.17(19) . . ?
C30 C29 Bi1 120.2(2) . . ?
C31 C30 C29 119.0(3) . . ?
C32 C31 C30 121.1(3) . . ?
C31 C32 C34 119.1(3) . . ?
C31 C32 C33 120.0(3) . . ?
C34 C32 C33 120.9(3) . . ?
C35 C34 C32 120.8(3) . . ?
C29 C35 C34 119.5(3) . . ?
C42 C36 C37 121.8(3) . . ?
C42 C36 Bi1 123.2(2) . . ?
C37 C36 Bi1 114.84(19) . . ?
C36 C37 C38 118.7(3) . . ?
C39 C38 C37 120.7(3) . . ?
C38 C39 C41 118.8(3) . . ?
C38 C39 C40 121.0(3) . . ?
C41 C39 C40 120.2(3) . . ?
C39 C41 C42 121.5(3) . . ?
C36 C42 C41 118.3(3) . . ?
C49 C43 C44 121.1(3) . . ?
C49 C43 Bi1 124.9(2) . . ?
C44 C43 Bi1 114.1(2) . . ?
C45 C44 C43 119.1(3) . . ?
C46 C45 C44 121.1(3) . . ?
C45 C46 C48 118.7(3) . . ?
C45 C46 C47 121.2(4) . . ?
C48 C46 C47 120.2(4) . . ?
C49 C48 C46 121.3(3) . . ?
C43 C49 C48 118.8(3) . . ?


_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         2.637
_refine_diff_density_min         -4.440
_refine_diff_density_rms         0.142
