 
data_99src156
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C46 H37 Bi O6' 
_chemical_formula_weight          894.74 
 
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    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                    10.102(2) 
_cell_length_b                    20.609(4) 
_cell_length_c                    18.706(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  103.59(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      3785.4(13) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     114607
_cell_measurement_theta_min       1.98 
_cell_measurement_theta_max       27.5
 
_exptl_crystal_description        block 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.20 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.10 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.570 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1776 
_exptl_absorpt_coefficient_mu     4.707 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   ? 
_exptl_absorpt_correction_T_max   ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       293(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            MoK\a 
_diffrn_radiation_source          'Bruker-Nonius FR591 rotating anode' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker-Nonius KappaCCD' 
_diffrn_measurement_method        'Φ & ω scans' 
_diffrn_detector_area_resol_mean  9.091 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             114607 
_diffrn_reflns_av_R_equivalents   0.0766 
_diffrn_reflns_av_sigmaI/netI     0.0254 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -26 
_diffrn_reflns_limit_k_max        26 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          1.98 
_diffrn_reflns_theta_max          27.50 
_reflns_number_total              8684 
_reflns_number_gt                 7696 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'COLLECT (Hooft, 1998)'
_computing_cell_refinement        
'DENZO (Otwinowski & Minor) & COLLECT (Hooft, 1998)'
_computing_data_reduction         
'DENZO (Otwinowski & Minor) & COLLECT (Hooft, 1998)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_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 w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          8684 
_refine_ls_number_parameters      480 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0319 
_refine_ls_R_factor_gt            0.0267 
_refine_ls_wR_factor_ref          0.0878 
_refine_ls_wR_factor_gt           0.0794 
_refine_ls_goodness_of_fit_ref    0.751 
_refine_ls_restrained_S_all       0.751 
_refine_ls_shift/su_max           0.037 
_refine_ls_shift/su_mean          0.002 
 
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_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Bi1 Bi 0.358412(8) 0.358125(4) 0.402453(4) 0.01671(6) Uani 1 d . . . 
O1 O 0.45730(19) 0.26484(9) 0.45699(9) 0.0228(4) Uani 1 d . . . 
O2 O 0.5726(2) 0.33505(9) 0.53858(11) 0.0257(4) Uani 1 d . . . 
O3 O 0.6814(2) 0.24221(10) 0.63313(9) 0.0270(4) Uani 1 d . . . 
H3 H 0.6983 0.2811 0.6333 0.041 Uiso 1 calc R . . 
O4 O 0.26565(19) 0.43878(9) 0.32597(10) 0.0243(4) Uani 1 d . . . 
O5 O 0.37152(19) 0.50402(10) 0.41565(10) 0.0248(4) Uani 1 d . . . 
O6 O 0.23493(18) 0.60763(8) 0.34433(10) 0.0230(4) Uani 1 d . . . 
H6 H 0.2949 0.6085 0.3824 0.034 Uiso 1 calc R . . 
C1 C 0.5462(2) 0.27936(12) 0.51662(13) 0.0204(5) Uani 1 d . . . 
C2 C 0.6212(3) 0.22167(13) 0.55964(13) 0.0197(5) Uani 1 d . . . 
C3 C 0.5174(3) 0.16892(13) 0.56387(14) 0.0238(5) Uani 1 d . . . 
C4 C 0.4996(3) 0.11469(14) 0.51942(16) 0.0318(6) Uani 1 d . . . 
H4 H 0.5573 0.1076 0.4881 0.038 Uiso 1 calc R . . 
C5 C 0.3960(3) 0.07042(15) 0.52104(19) 0.0402(7) Uani 1 d . . . 
H5 H 0.3852 0.0341 0.4907 0.048 Uiso 1 calc R . . 
C6 C 0.3101(3) 0.07989(17) 0.56680(19) 0.0421(8) Uani 1 d . . . 
H6 H 0.2415 0.0501 0.5680 0.050 Uiso 1 calc R . . 
C7 C 0.3266(4) 0.13437(19) 0.6113(2) 0.0472(10) Uani 1 d . . . 
H7 H 0.2684 0.1413 0.6424 0.057 Uiso 1 calc R . . 
C8 C 0.4292(3) 0.17857(16) 0.60979(17) 0.0363(7) Uani 1 d . . . 
H8 H 0.4392 0.2151 0.6398 0.044 Uiso 1 calc R . . 
C9 C 0.7364(3) 0.19937(12) 0.52397(14) 0.0221(5) Uani 1 d . . . 
C10 C 0.7624(3) 0.22800(14) 0.46184(15) 0.0299(6) Uani 1 d . . . 
H10 H 0.7033 0.2595 0.4370 0.036 Uiso 1 calc R . . 
C11 C 0.8755(3) 0.21036(15) 0.43599(17) 0.0357(7) Uani 1 d . . . 
H11 H 0.8912 0.2298 0.3939 0.043 Uiso 1 calc R . . 
C12 C 0.9645(3) 0.16410(16) 0.47285(18) 0.0368(7) Uani 1 d . . . 
H12 H 1.0415 0.1530 0.4564 0.044 Uiso 1 calc R . . 
C13 C 0.9389(3) 0.13450(14) 0.5341(2) 0.0340(7) Uani 1 d . . . 
H13 H 0.9981 0.1028 0.5586 0.041 Uiso 1 calc R . . 
C14 C 0.8253(3) 0.15162(14) 0.55960(17) 0.0278(6) Uani 1 d . . . 
H14 H 0.8084 0.1310 0.6008 0.033 Uiso 1 calc R . . 
C15 C 0.3028(3) 0.49542(12) 0.35360(15) 0.0210(5) Uani 1 d . . . 
C16 C 0.2560(3) 0.55345(12) 0.30082(13) 0.0195(5) Uani 1 d . . . 
C17 C 0.1210(3) 0.53855(11) 0.24793(13) 0.0203(5) Uani 1 d . . . 
C18 C 0.1017(3) 0.54109(13) 0.17194(14) 0.0248(5) Uani 1 d . . . 
H18 H 0.1730 0.5542 0.1516 0.030 Uiso 1 calc R . . 
C19 C -0.0232(3) 0.52429(14) 0.12576(15) 0.0299(6) Uani 1 d . . . 
H19 H -0.0347 0.5260 0.0750 0.036 Uiso 1 calc R . . 
C20 C -0.1293(3) 0.50517(13) 0.15528(16) 0.0306(6) Uani 1 d . . . 
H20 H -0.2123 0.4935 0.1246 0.037 Uiso 1 calc R . . 
C21 C -0.1123(3) 0.50337(14) 0.23111(16) 0.0317(6) Uani 1 d . . . 
H21 H -0.1845 0.4911 0.2512 0.038 Uiso 1 calc R . . 
C22 C 0.0112(3) 0.51967(14) 0.27673(15) 0.0270(6) Uani 1 d . . . 
H22 H 0.0217 0.5181 0.3274 0.032 Uiso 1 calc R . . 
C23 C 0.3691(3) 0.56714(12) 0.26071(13) 0.0210(5) Uani 1 d . . . 
C24 C 0.4306(3) 0.51613(13) 0.23137(14) 0.0245(5) Uani 1 d . . . 
H24 H 0.4066 0.4735 0.2387 0.029 Uiso 1 calc R . . 
C25 C 0.5269(3) 0.52888(14) 0.19145(15) 0.0306(6) Uani 1 d . . . 
H25 H 0.5675 0.4946 0.1723 0.037 Uiso 1 calc R . . 
C26 C 0.5634(3) 0.59152(16) 0.17974(16) 0.0339(6) Uani 1 d . . . 
H26 H 0.6284 0.5997 0.1530 0.041 Uiso 1 calc R . . 
C27 C 0.5026(4) 0.64221(13) 0.2081(2) 0.0428(9) Uani 1 d . . . 
H27 H 0.5268 0.6847 0.2004 0.051 Uiso 1 calc R . . 
C28 C 0.4052(3) 0.63018(15) 0.24812(19) 0.0331(7) Uani 1 d . . . 
H28 H 0.3640 0.6647 0.2665 0.040 Uiso 1 calc R . . 
C29 C 0.2152(3) 0.29307(13) 0.32795(14) 0.0205(5) Uani 1 d . . . 
C30 C 0.2097(3) 0.22819(13) 0.34666(15) 0.0269(6) Uani 1 d . . . 
H30 H 0.2730 0.2112 0.3866 0.032 Uiso 1 calc R . . 
C31 C 0.1091(3) 0.18882(13) 0.30542(15) 0.0286(6) Uani 1 d . . . 
H31 H 0.1049 0.1453 0.3177 0.034 Uiso 1 calc R . . 
C32 C 0.0149(3) 0.21405(14) 0.24589(16) 0.0314(6) Uani 1 d . . . 
H32 H -0.0523 0.1874 0.2181 0.038 Uiso 1 calc R . . 
C33 C 0.0208(3) 0.27833(16) 0.22799(17) 0.0376(7) Uani 1 d . . . 
H33 H -0.0430 0.2951 0.1881 0.045 Uiso 1 calc R . . 
C34 C 0.1211(3) 0.31895(15) 0.26866(16) 0.0302(6) Uani 1 d . . . 
H34 H 0.1248 0.3625 0.2563 0.036 Uiso 1 calc R . . 
C35 C 0.5537(3) 0.37524(13) 0.37357(15) 0.0227(5) Uani 1 d . . . 
C36 C 0.5707(3) 0.34320(17) 0.31119(17) 0.0296(6) Uani 1 d . . . 
H36 H 0.4988 0.3207 0.2813 0.036 Uiso 1 calc R . . 
C37 C 0.6971(4) 0.34536(16) 0.29415(19) 0.0372(7) Uani 1 d . . . 
H37 H 0.7109 0.3244 0.2525 0.045 Uiso 1 calc R . . 
C38 C 0.8024(3) 0.37900(17) 0.33978(19) 0.0382(7) Uani 1 d . . . 
H38 H 0.8881 0.3794 0.3295 0.046 Uiso 1 calc R . . 
C39 C 0.7817(3) 0.41207(15) 0.40060(19) 0.0371(7) Uani 1 d . . . 
H39 H 0.8529 0.4355 0.4299 0.044 Uiso 1 calc R . . 
C40 C 0.6564(3) 0.41075(14) 0.41833(16) 0.0287(6) Uani 1 d . . . 
H40 H 0.6418 0.4330 0.4590 0.034 Uiso 1 calc R . . 
C41 C 0.2643(3) 0.37577(14) 0.49511(14) 0.0228(5) Uani 1 d . . . 
C42 C 0.3257(3) 0.41452(13) 0.55356(15) 0.0280(6) Uani 1 d . . . 
H42 H 0.4028 0.4388 0.5526 0.034 Uiso 1 calc R . . 
C43 C 0.2681(3) 0.41599(15) 0.61395(16) 0.0376(7) Uani 1 d . . . 
H43 H 0.3076 0.4413 0.6545 0.045 Uiso 1 calc R . . 
C44 C 0.1529(4) 0.3803(2) 0.6145(2) 0.0497(9) Uani 1 d . . . 
H44 H 0.1154 0.3817 0.6554 0.060 Uiso 1 calc R . . 
C45 C 0.0929(5) 0.3426(2) 0.5548(2) 0.0560(11) Uani 1 d . . . 
H45 H 0.0145 0.3191 0.5554 0.067 Uiso 1 calc R . . 
C46 C 0.1489(4) 0.3394(2) 0.4939(2) 0.0396(8) Uani 1 d . . . 
H46 H 0.1101 0.3136 0.4536 0.047 Uiso 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 C35 2.193(3) . ? 
Bi1 C41 2.194(3) . ? 
Bi1 C29 2.210(2) . ? 
Bi1 O4 2.2490(18) . ? 
Bi1 O1 2.2925(18) . ? 
O1 C1 1.292(3) . ? 
O2 C1 1.227(3) . ? 
O3 C2 1.430(3) . ? 
O4 C15 1.296(3) . ? 
O5 C15 1.217(3) . ? 
O6 C16 1.427(3) . ? 
C1 C2 1.533(3) . ? 
C2 C3 1.526(4) . ? 
C2 C9 1.541(4) . ? 
C3 C4 1.379(4) . ? 
C3 C8 1.389(4) . ? 
C4 C5 1.394(4) . ? 
C5 C6 1.369(5) . ? 
C6 C7 1.384(5) . ? 
C7 C8 1.386(5) . ? 
C9 C10 1.382(4) . ? 
C9 C14 1.392(4) . ? 
C10 C11 1.390(4) . ? 
C11 C12 1.379(4) . ? 
C12 C13 1.375(5) . ? 
C13 C14 1.389(4) . ? 
C15 C16 1.552(3) . ? 
C16 C17 1.516(3) . ? 
C16 C23 1.534(4) . ? 
C17 C18 1.390(4) . ? 
C17 C22 1.397(4) . ? 
C18 C19 1.395(4) . ? 
C19 C20 1.373(4) . ? 
C20 C21 1.389(4) . ? 
C21 C22 1.378(4) . ? 
C23 C28 1.384(4) . ? 
C23 C24 1.397(4) . ? 
C24 C25 1.384(4) . ? 
C25 C26 1.374(4) . ? 
C26 C27 1.380(5) . ? 
C27 C28 1.391(5) . ? 
C29 C30 1.387(4) . ? 
C29 C34 1.387(4) . ? 
C30 C31 1.384(4) . ? 
C31 C32 1.385(4) . ? 
C32 C33 1.371(4) . ? 
C33 C34 1.394(4) . ? 
C35 C40 1.380(4) . ? 
C35 C36 1.386(4) . ? 
C36 C37 1.388(5) . ? 
C37 C38 1.384(5) . ? 
C38 C39 1.384(5) . ? 
C39 C40 1.382(4) . ? 
C41 C46 1.382(4) . ? 
C41 C42 1.378(4) . ? 
C42 C43 1.387(4) . ? 
C43 C44 1.378(5) . ? 
C44 C45 1.379(6) . ? 
C45 C46 1.388(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 
C35 Bi1 C41 138.58(10) . . ? 
C35 Bi1 C29 115.82(10) . . ? 
C41 Bi1 C29 104.94(10) . . ? 
C35 Bi1 O4 89.36(9) . . ? 
C41 Bi1 O4 100.77(9) . . ? 
C29 Bi1 O4 86.22(9) . . ? 
C35 Bi1 O1 85.49(8) . . ? 
C41 Bi1 O1 90.68(9) . . ? 
C29 Bi1 O1 85.64(8) . . ? 
O4 Bi1 O1 167.36(7) . . ? 
C1 O1 Bi1 109.37(15) . . ? 
C15 O4 Bi1 111.95(15) . . ? 
O2 C1 O1 123.9(2) . . ? 
O2 C1 C2 120.5(2) . . ? 
O1 C1 C2 115.5(2) . . ? 
O3 C2 C3 107.6(2) . . ? 
O3 C2 C1 108.7(2) . . ? 
C3 C2 C1 108.6(2) . . ? 
O3 C2 C9 108.1(2) . . ? 
C3 C2 C9 114.1(2) . . ? 
C1 C2 C9 109.6(2) . . ? 
C4 C3 C8 118.5(3) . . ? 
C4 C3 C2 122.6(2) . . ? 
C8 C3 C2 118.6(3) . . ? 
C3 C4 C5 120.6(3) . . ? 
C6 C5 C4 120.7(3) . . ? 
C5 C6 C7 119.2(3) . . ? 
C6 C7 C8 120.4(3) . . ? 
C7 C8 C3 120.7(3) . . ? 
C10 C9 C14 118.4(3) . . ? 
C10 C9 C2 123.3(2) . . ? 
C14 C9 C2 118.1(2) . . ? 
C9 C10 C11 121.0(3) . . ? 
C12 C11 C10 120.0(3) . . ? 
C11 C12 C13 119.7(3) . . ? 
C12 C13 C14 120.4(3) . . ? 
C13 C14 C9 120.5(3) . . ? 
O5 C15 O4 123.9(2) . . ? 
O5 C15 C16 121.0(2) . . ? 
O4 C15 C16 115.1(2) . . ? 
O6 C16 C17 107.39(19) . . ? 
O6 C16 C23 111.3(2) . . ? 
C17 C16 C23 112.2(2) . . ? 
O6 C16 C15 107.70(19) . . ? 
C17 C16 C15 110.6(2) . . ? 
C23 C16 C15 107.59(19) . . ? 
C18 C17 C22 118.2(2) . . ? 
C18 C17 C16 123.2(2) . . ? 
C22 C17 C16 118.6(2) . . ? 
C17 C18 C19 120.9(3) . . ? 
C20 C19 C18 120.0(3) . . ? 
C19 C20 C21 119.8(3) . . ? 
C22 C21 C20 120.2(3) . . ? 
C21 C22 C17 121.0(3) . . ? 
C28 C23 C24 118.7(3) . . ? 
C28 C23 C16 120.8(2) . . ? 
C24 C23 C16 120.3(2) . . ? 
C25 C24 C23 120.2(3) . . ? 
C26 C25 C24 120.9(3) . . ? 
C25 C26 C27 119.3(3) . . ? 
C26 C27 C28 120.5(3) . . ? 
C23 C28 C27 120.4(3) . . ? 
C30 C29 C34 120.8(2) . . ? 
C30 C29 Bi1 119.02(18) . . ? 
C34 C29 Bi1 119.7(2) . . ? 
C31 C30 C29 119.5(2) . . ? 
C32 C31 C30 120.2(3) . . ? 
C33 C32 C31 119.9(3) . . ? 
C32 C33 C34 121.0(3) . . ? 
C29 C34 C33 118.6(3) . . ? 
C40 C35 C36 122.6(3) . . ? 
C40 C35 Bi1 121.8(2) . . ? 
C36 C35 Bi1 115.3(2) . . ? 
C37 C36 C35 118.7(3) . . ? 
C36 C37 C38 119.4(3) . . ? 
C37 C38 C39 120.7(3) . . ? 
C40 C39 C38 120.8(3) . . ? 
C35 C40 C39 117.7(3) . . ? 
C46 C41 C42 123.3(3) . . ? 
C46 C41 Bi1 114.7(2) . . ? 
C42 C41 Bi1 121.7(2) . . ? 
C41 C42 C43 117.5(3) . . ? 
C44 C43 C42 120.7(3) . . ? 
C43 C44 C45 120.4(3) . . ? 
C44 C45 C46 120.3(4) . . ? 
C41 C46 C45 117.7(3) . . ? 
 
_diffrn_measured_fraction_theta_max    0.971 
_diffrn_reflns_theta_full              27.50 
_diffrn_measured_fraction_theta_full   0.971 
_refine_diff_density_max    3.001 
_refine_diff_density_min   -1.986 
_refine_diff_density_rms    0.111 
