#------------------------------------------------------------------------------
#$Date: 2016-08-07 12:01:11 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185407 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/03/95/7039511.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7039511
loop_
_publ_author_name
'Keogan, D. M.'
'Twamley, B.'
'Fitzgerald-Hughes, D'
'Griffith, D. M.'
_publ_section_title
;
 Novel class of Bi(iii) hydroxamato complexes: synthesis, urease
 inhibitory activity and activity against H. pylori.
;
_journal_issue                   27
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              11008
_journal_page_last               11014
_journal_paper_doi               10.1039/c5dt05061h
_journal_volume                  45
_journal_year                    2016
_chemical_formula_moiety
'C86 H84 Bi6 N16 O52, 2(N O3), 4(C H4 O), 4(H2 O)'
_chemical_formula_sum            'C90 H108 Bi6 N18 O66'
_chemical_formula_weight         3751.82
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2015-07-29 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;
_cell_angle_alpha                112.5660(10)
_cell_angle_beta                 116.5850(10)
_cell_angle_gamma                94.4850(10)
_cell_formula_units_Z            1
_cell_length_a                   15.0432(6)
_cell_length_b                   15.2366(5)
_cell_length_c                   16.5434(6)
_cell_measurement_reflns_used    9871
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.13
_cell_measurement_theta_min      2.34
_cell_volume                     2984.5(2)
_computing_cell_refinement       'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_data_collection       'APEX2 Ver. 2014.11-0 (Bruker-AXS, 2014)'
_computing_data_reduction        'SAINT+ Ver. 8.34A (Bruker-AXS, 2013)'
_computing_molecular_graphics    'SHELXTL (Bruker-AXS, 2008-2014)'
_computing_publication_material  'SHELXTL (Bruker-AXS, 2008-2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.258
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0333
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            111802
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.135
_diffrn_reflns_theta_min         1.518
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    8.926
_exptl_absorpt_correction_T_max  0.7837
_exptl_absorpt_correction_T_min  0.4747
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'SADABS-2014/5 (Bruker, 2014)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.087
_exptl_crystal_description       block
_exptl_crystal_F_000             1800
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_refine_diff_density_max         1.894
_refine_diff_density_min         -1.451
_refine_diff_density_rms         0.154
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     827
_refine_ls_number_reflns         17529
_refine_ls_number_restraints     14
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0254
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0199P)²+7.4613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0489
_refine_ls_wR_factor_ref         0.0533
_reflns_Friedel_coverage         0.000
_reflns_number_gt                14300
_reflns_number_total             17529
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5dt05061h2.cif
_cod_data_source_block           tcd192
_cod_depositor_comments
'Adding full bibliography for 7039510--7039511.cif.'
_cod_original_cell_volume        2984.48(19)
_cod_database_code               7039511
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.348
_shelx_estimated_absorpt_t_max   0.664
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
Bi1 Bi 0.58667(2) 0.60944(2) 0.49386(2) 0.01125(3) Uani 1 1 d . .
N1 N 0.0361(3) 0.5072(3) 0.3012(3) 0.0308(8) Uani 1 1 d . .
O1 O 0.9949(2) 0.7930(2) 0.8438(2) 0.0241(6) Uani 1 1 d . .
H1 H 1.0540 0.8055 0.8939 0.036 Uiso 1 1 calc R U
Bi2 Bi 0.41244(2) 0.61683(2) 0.22910(2) 0.01358(3) Uani 1 1 d . .
C2 C 1.0030(3) 0.8453(3) 0.7955(3) 0.0169(7) Uani 1 1 d . .
N2 N 0.7374(3) 0.1704(3) 0.9539(2) 0.0255(7) Uani 1 1 d . .
O2 O 0.0534(2) 0.4833(2) 0.22774(19) 0.0245(6) Uani 1 1 d . .
Bi3 Bi 0.24861(2) 0.52417(2) 0.31583(2) 0.01266(3) Uani 1 1 d . .
C3 C 1.0956(3) 0.9160(3) 0.8354(3) 0.0229(8) Uani 1 1 d . .
H3 H 1.1552 0.9286 0.8980 0.027 Uiso 1 1 calc R U
N3 N 0.6165(2) 0.8674(2) 0.6231(2) 0.0226(7) Uani 1 1 d . .
O3 O 0.1022(3) 0.5107(3) 0.3823(3) 0.0473(9) Uani 1 1 d . .
C4 C 1.1015(3) 0.9684(3) 0.7845(3) 0.0244(8) Uani 1 1 d . .
H4 H 1.1655 1.0158 0.8117 0.029 Uiso 1 1 calc R U
O4 O -0.0454(3) 0.5284(3) 0.2892(3) 0.0547(11) Uani 1 1 d . .
C5 C 1.0141(3) 0.9518(3) 0.6936(3) 0.0227(8) Uani 1 1 d . .
H5 H 1.0174 0.9886 0.6594 0.027 Uiso 1 1 calc R U
O5 O 0.4014(3) 0.7980(2) 0.2774(2) 0.0363(8) Uani 1 1 d D .
H5A H 0.3679(4) 0.8287(3) 0.3056(3) 0.044 Uiso 1 1 d DR U
H5B H 0.3823(3) 0.8134(3) 0.2274(5) 0.044 Uiso 1 1 d DR U
C6 C 0.9224(3) 0.8808(3) 0.6539(3) 0.0171(7) Uani 1 1 d . .
H6 H 0.8629 0.8689 0.5916 0.020 Uiso 1 1 calc R U
O6 O 0.3090(2) 0.5481(2) 0.0383(2) 0.0285(6) Uani 1 1 d D .
H6A H 0.2832(4) 0.5956(6) 0.0595(3) 0.09(2) Uiso 1 1 d DR .
C7 C 0.9148(3) 0.8262(3) 0.7028(3) 0.0151(7) Uani 1 1 d . .
O7 O 0.6720(2) 0.2071(2) 0.9124(2) 0.0322(7) Uani 1 1 d . .
C8 C 0.8142(3) 0.7495(3) 0.6516(3) 0.0148(7) Uani 1 1 d . .
O9 O 0.7077(2) 0.0815(2) 0.9380(2) 0.0383(8) Uani 1 1 d . .
N9 N 0.7963(2) 0.7063(2) 0.7005(2) 0.0152(6) Uani 1 1 d D .
H9 H 0.8432 0.7247 0.7647 0.018 Uiso 1 1 calc DR U
O10 O 0.70356(18) 0.63201(18) 0.65088(17) 0.0160(5) Uani 1 1 d . .
O11 O 0.74291(18) 0.72550(18) 0.55983(17) 0.0169(5) Uani 1 1 d . .
O12 O 0.5975(2) 0.21287(19) 0.3137(2) 0.0237(6) Uani 1 1 d . .
H12 H 0.5688 0.1519 0.2715 0.036 Uiso 1 1 calc R U
O13 O 0.7098(2) 0.9175(2) 0.6832(2) 0.0351(7) Uani 1 1 d . .
C13 C 0.6530(3) 0.2560(3) 0.2850(3) 0.0192(7) Uani 1 1 d . .
O14 O 0.5793(2) 0.7883(2) 0.6202(2) 0.0233(6) Uani 1 1 d . .
C14 C 0.6865(3) 0.2004(3) 0.2213(3) 0.0238(8) Uani 1 1 d . .
H14 H 0.6720 0.1305 0.1978 0.029 Uiso 1 1 calc R U
C15 C 0.7405(3) 0.2463(3) 0.1922(3) 0.0271(9) Uani 1 1 d . .
H15A H 0.7626 0.2075 0.1484 0.033 Uiso 1 1 calc R U
O15 O 0.5587(2) 0.8960(2) 0.5620(2) 0.0329(7) Uani 1 1 d . .
O16 O 0.8704(2) 0.4126(2) 0.0299(2) 0.0270(6) Uani 1 1 d D .
H16A H 0.9154(4) 0.4711(5) 0.0804(5) 0.032 Uiso 1 1 d DR U
H16B H 0.8477(3) 0.3521(5) 0.0200(2) 0.032 Uiso 1 1 d DR U
C16 C 0.7631(3) 0.3486(3) 0.2260(3) 0.0239(8) Uani 1 1 d . .
H16 H 0.7995 0.3794 0.2047 0.029 Uiso 1 1 calc R U
C17 C 0.7321(3) 0.4051(3) 0.2908(3) 0.0211(8) Uani 1 1 d . .
H17 H 0.7485 0.4751 0.3149 0.032 Uiso 1 1 calc R U
O17 O 0.0125(2) 0.6750(2) 0.4873(2) 0.0340(7) Uani 1 1 d D .
H17A H 0.0140(2) 0.6257(6) 0.4387(6) 0.041 Uiso 1 1 d DR U
O18 O 0.8003(2) 0.9321(2) 0.8790(2) 0.0366(7) Uani 1 1 d D .
H18B H 0.8153(3) 0.9974(6) 0.9248(4) 0.044 Uiso 1 1 d DR U
H18A H 0.7725(3) 0.9294(2) 0.8176(5) 0.044 Uiso 1 1 d DR U
C18 C 0.6772(3) 0.3607(3) 0.3215(3) 0.0168(7) Uani 1 1 d . .
O19 O 0.4860(2) -0.0172(2) 0.8002(2) 0.0279(6) Uani 1 1 d . .
H19 H 0.5505 0.0116 0.8380 0.042 Uiso 1 1 calc R U
C19 C 0.6422(3) 0.4247(3) 0.3868(3) 0.0162(7) Uani 1 1 d . .
N20 N 0.5921(2) 0.3868(2) 0.4200(2) 0.0152(6) Uani 1 1 d D .
H20 H 0.5817 0.3239 0.4063 0.018 Uiso 1 1 calc DR U
O20 O 0.8305(2) 0.2189(2) 1.0128(2) 0.0341(7) Uani 1 1 d . .
O21 O 0.55674(19) 0.44870(18) 0.47679(18) 0.0169(5) Uani 1 1 d . .
O22 O 0.65932(19) 0.51737(18) 0.41101(18) 0.0167(5) Uani 1 1 d . .
O23 O 0.8407(2) 0.7144(3) 0.4037(2) 0.0342(7) Uani 1 1 d . .
H23 H 0.8920 0.6923 0.4190 0.051 Uiso 1 1 calc R U
C24 C 0.8188(3) 0.7281(3) 0.3214(3) 0.0204(7) Uani 1 1 d . .
C25 C 0.8959(3) 0.7520(3) 0.3012(3) 0.0266(9) Uani 1 1 d . .
H25 H 0.9657 0.7555 0.3439 0.032 Uiso 1 1 calc R U
C26 C 0.8703(3) 0.7704(3) 0.2189(3) 0.0269(9) Uani 1 1 d . .
H26 H 0.9232 0.7878 0.2064 0.032 Uiso 1 1 calc R U
C27 C 0.7689(3) 0.7639(3) 0.1550(3) 0.0310(9) Uani 1 1 d . .
H27 H 0.7521 0.7766 0.0987 0.037 Uiso 1 1 calc R U
C28 C 0.6921(3) 0.7387(3) 0.1736(3) 0.0227(8) Uani 1 1 d . .
H28 H 0.6222 0.7337 0.1293 0.027 Uiso 1 1 calc R U
C29 C 0.7158(3) 0.7206(3) 0.2564(3) 0.0176(7) Uani 1 1 d . .
C30 C 0.6293(3) 0.6958(3) 0.2714(3) 0.0164(7) Uani 1 1 d . .
N31 N 0.6496(2) 0.6960(2) 0.3574(2) 0.0154(6) Uani 1 1 d D .
H31 H 0.7141 0.7077 0.4049 0.018 Uiso 1 1 calc DR U
O32 O 0.56842(18) 0.67746(19) 0.37218(18) 0.0162(5) Uani 1 1 d . .
O33 O 0.53457(18) 0.67695(19) 0.20233(18) 0.0182(5) Uani 1 1 d . .
O34 O 0.3239(2) 0.2201(2) 0.1533(2) 0.0275(6) Uani 1 1 d . .
H34A H 0.3052(14) 0.178(3) 0.1579(4) 0.041 Uiso 1 1 d R U
C35 C 0.3764(3) 0.2121(3) 0.1034(3) 0.0216(8) Uani 1 1 d . .
C36 C 0.3794(3) 0.1203(3) 0.0426(3) 0.0237(8) Uani 1 1 d . .
H36 H 0.3431 0.0606 0.0342 0.028 Uiso 1 1 calc R U
C37 C 0.4355(3) 0.1159(3) -0.0056(3) 0.0268(9) Uani 1 1 d . .
H37 H 0.4367 0.0530 -0.0474 0.032 Uiso 1 1 calc R U
C38 C 0.4897(3) 0.2023(3) 0.0065(3) 0.0259(8) Uani 1 1 d . .
H38 H 0.5292 0.1988 -0.0256 0.031 Uiso 1 1 calc R U
C39 C 0.4860(3) 0.2942(3) 0.0661(3) 0.0211(8) Uani 1 1 d . .
H39 H 0.5223 0.3536 0.0739 0.025 Uiso 1 1 calc R U
C40 C 0.4292(3) 0.2993(3) 0.1143(3) 0.0174(7) Uani 1 1 d . .
C41 C 0.4284(3) 0.4005(3) 0.1761(2) 0.0154(7) Uani 1 1 d . .
N42 N 0.3990(2) 0.4112(2) 0.2425(2) 0.0153(6) Uani 1 1 d D .
H42 H 0.3794 0.3599 0.2494 0.018 Uiso 1 1 calc DR U
O43 O 0.39992(18) 0.50481(17) 0.30063(17) 0.0145(5) Uani 1 1 d . .
O44 O 0.4578(2) 0.47493(19) 0.16727(19) 0.0190(5) Uani 1 1 d . .
O45 O 0.3621(2) 0.93521(19) 0.4273(2) 0.0232(6) Uani 1 1 d . .
H45 H 0.3826 0.9917 0.4338 0.035 Uiso 1 1 calc R U
C46 C 0.2970(3) 0.9376(3) 0.4644(3) 0.0186(7) Uani 1 1 d . .
C47 C 0.2709(3) 1.0238(3) 0.5034(3) 0.0240(8) Uani 1 1 d . .
H47 H 0.3006 1.0834 0.5069 0.029 Uiso 1 1 calc R U
C48 C 0.2021(3) 1.0223(3) 0.5369(3) 0.0280(9) Uani 1 1 d . .
H48 H 0.1833 1.0806 0.5617 0.034 Uiso 1 1 calc R U
C49 C 0.1597(3) 0.9362(3) 0.5349(3) 0.0270(9) Uani 1 1 d . .
H49 H 0.1136 0.9364 0.5597 0.032 Uiso 1 1 calc R U
C50 C 0.1852(3) 0.8505(3) 0.4964(3) 0.0217(8) Uani 1 1 d . .
H50 H 0.1555 0.7913 0.4936 0.026 Uiso 1 1 calc R U
C51 C 0.2545(3) 0.8508(3) 0.4616(3) 0.0176(7) Uani 1 1 d . .
C52 C 0.2733(3) 0.7539(3) 0.4162(2) 0.0148(7) Uani 1 1 d . .
N53 N 0.3656(2) 0.7546(2) 0.4269(2) 0.0158(6) Uani 1 1 d D .
H53 H 0.4153 0.8114 0.4606 0.019 Uiso 1 1 calc DR U
O54 O 0.38368(18) 0.66561(17) 0.38491(18) 0.0153(5) Uani 1 1 d . .
O55 O 0.20169(19) 0.67252(18) 0.3685(2) 0.0211(5) Uani 1 1 d . .
O56 O -0.0170(2) 0.39128(19) -0.10251(19) 0.0241(6) Uani 1 1 d . .
H56 H -0.0706 0.3870 -0.1535 0.036 Uiso 1 1 calc R U
C57 C -0.0246(3) 0.3013(3) -0.1043(3) 0.0190(7) Uani 1 1 d . .
C58 C -0.1020(3) 0.2153(3) -0.1909(3) 0.0258(9) Uani 1 1 d . .
H58 H -0.1530 0.2203 -0.2480 0.031 Uiso 1 1 calc R U
C59 C -0.1054(3) 0.1231(3) -0.1943(3) 0.0272(9) Uani 1 1 d . .
H59 H -0.1586 0.0651 -0.2534 0.033 Uiso 1 1 calc R U
C60 C -0.0314(3) 0.1150(3) -0.1120(3) 0.0248(8) Uani 1 1 d . .
H60 H -0.0321 0.0514 -0.1151 0.030 Uiso 1 1 calc R U
C61 C 0.0442(3) 0.2003(3) -0.0243(3) 0.0186(7) Uani 1 1 d . .
H61 H 0.0939 0.1946 0.0329 0.022 Uiso 1 1 calc R U
C62 C 0.0481(3) 0.2943(3) -0.0191(2) 0.0152(7) Uani 1 1 d . .
C63 C 0.1251(2) 0.3820(3) 0.0809(2) 0.0133(6) Uani 1 1 d . .
N64 N 0.1418(2) 0.4716(2) 0.0886(2) 0.0159(6) Uani 1 1 d D .
H64 H 0.1117 0.4794 0.0334 0.019 Uiso 1 1 calc DR U
O65 O 0.20673(18) 0.55383(17) 0.18364(17) 0.0154(5) Uani 1 1 d . .
O66 O 0.17313(18) 0.37160(17) 0.16103(17) 0.0152(5) Uani 1 1 d . .
C67 C 0.3437(4) 0.5273(4) -0.0307(3) 0.0428(12) Uani 1 1 d . .
H67A H 0.3612 0.5876 -0.0357 0.064 Uiso 1 1 calc R U
H67B H 0.2884 0.4745 -0.0982 0.064 Uiso 1 1 calc R U
H67C H 0.4056 0.5053 -0.0065 0.064 Uiso 1 1 calc R U
C68 C 0.4390(4) 0.0302(3) 0.7394(3) 0.0384(11) Uani 1 1 d . .
H68A H 0.4543 0.1010 0.7842 0.058 Uiso 1 1 calc R U
H68B H 0.3633 -0.0016 0.6974 0.058 Uiso 1 1 calc R U
H68C H 0.4671 0.0238 0.6949 0.058 Uiso 1 1 calc R U
C69 C 0.0164(6) 0.6490(5) 0.5617(4) 0.066(2) Uani 1 1 d . .
H69A H 0.0667 0.6117 0.5757 0.098 Uiso 1 1 calc R U
H69B H -0.0528 0.6076 0.5363 0.098 Uiso 1 1 calc R U
H69C H 0.0380 0.7098 0.6249 0.098 Uiso 1 1 calc R U
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'
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_3
O10 Bi1 O22 96.40(9) .
O10 Bi1 O11 70.28(8) .
O22 Bi1 O11 77.70(9) .
O10 Bi1 O21 76.79(8) .
O22 Bi1 O21 68.86(8) .
O11 Bi1 O21 129.38(9) .
O10 Bi1 O32 139.98(8) .
O22 Bi1 O32 78.25(8) .
O11 Bi1 O32 69.83(8) .
O21 Bi1 O32 133.86(8) .
O10 Bi1 O21 87.17(8) 2_666
O22 Bi1 O21 129.35(8) 2_666
O11 Bi1 O21 147.56(8) 2_666
O21 Bi1 O21 62.90(10) 2_666
O32 Bi1 O21 126.99(8) 2_666
O3 N1 O4 122.6(4) .
O3 N1 O2 118.9(4) .
O4 N1 O2 118.5(4) .
C2 O1 H1 109.5 .
O32 Bi2 O33 71.02(8) .
O32 Bi2 O44 87.69(9) .
O33 Bi2 O44 79.54(9) .
O32 Bi2 O43 77.40(8) .
O33 Bi2 O43 134.00(8) .
O44 Bi2 O43 66.41(8) .
O32 Bi2 O6 148.16(9) .
O33 Bi2 O6 79.32(9) .
O44 Bi2 O6 75.57(9) .
O43 Bi2 O6 118.15(9) .
O32 Bi2 O5 88.98(10) .
O33 Bi2 O5 80.47(10) .
O44 Bi2 O5 159.74(9) .
O43 Bi2 O5 132.05(8) .
O6 Bi2 O5 97.44(10) .
O32 Bi2 O54 71.88(8) .
O33 Bi2 O54 135.91(8) .
O44 Bi2 O54 121.71(8) .
O43 Bi2 O54 56.16(8) .
O6 Bi2 O54 139.93(8) .
O5 Bi2 O54 75.89(8) .
O1 C2 C3 121.8(3) .
O1 C2 C7 118.3(3) .
C3 C2 C7 119.9(3) .
O20 N2 O7 121.3(3) .
O20 N2 O9 119.2(3) .
O7 N2 O9 119.4(3) .
N1 O2 Bi3 103.6(2) .
O65 Bi3 O54 77.18(8) .
O65 Bi3 O55 79.12(9) .
O54 Bi3 O55 68.28(8) .
O65 Bi3 O66 69.55(8) .
O54 Bi3 O66 130.97(8) .
O55 Bi3 O66 134.66(8) .
O65 Bi3 O43 81.05(8) .
O54 Bi3 O43 60.70(8) .
O55 Bi3 O43 128.09(8) .
O66 Bi3 O43 79.03(8) .
O65 Bi3 O2 76.84(9) .
O54 Bi3 O2 134.08(9) .
O55 Bi3 O2 70.07(9) .
O66 Bi3 O2 71.43(8) .
O43 Bi3 O2 147.76(8) .
O65 Bi3 O10 132.73(8) 2_666
O54 Bi3 O10 118.88(8) 2_666
O55 Bi3 O10 147.47(8) 2_666
O66 Bi3 O10 67.48(7) 2_666
O43 Bi3 O10 72.43(7) 2_666
O2 Bi3 O10 106.58(8) 2_666
C4 C3 C2 120.5(3) .
C4 C3 H3 119.8 .
C2 C3 H3 119.8 .
O13 N3 O15 118.2(3) .
O13 N3 O14 122.1(3) .
O15 N3 O14 119.6(3) .
C3 C4 C5 120.2(3) .
C3 C4 H4 119.9 .
C5 C4 H4 119.9 .
C6 C5 C4 119.1(3) .
C6 C5 H5 120.5 .
C4 C5 H5 120.5 .
Bi2 O5 H5A 129.0 .
Bi2 O5 H5B 114.4 .
H5A O5 H5B 99.9 .
C5 C6 C7 121.9(3) .
C5 C6 H6 119.1 .
C7 C6 H6 119.1 .
C67 O6 Bi2 129.4(3) .
C67 O6 H6A 130.3 .
Bi2 O6 H6A 77.1 .
C6 C7 C2 118.4(3) .
C6 C7 C8 117.4(3) .
C2 C7 C8 124.1(3) .
O11 C8 N9 119.3(3) .
O11 C8 C7 120.3(3) .
N9 C8 C7 120.3(3) .
C8 N9 O10 120.0(3) .
C8 N9 H9 120.0 .
O10 N9 H9 120.0 .
N9 O10 Bi1 114.14(17) .
N9 O10 Bi3 107.62(17) 2_666
Bi1 O10 Bi3 121.58(10) 2_666
C8 O11 Bi1 115.9(2) .
C13 O12 H12 109.5 .
O12 C13 C14 122.0(3) .
O12 C13 C18 118.9(3) .
C14 C13 C18 119.2(3) .
C15 C14 C13 120.3(4) .
C15 C14 H14 119.8 .
C13 C14 H14 119.8 .
C14 C15 C16 121.0(4) .
C14 C15 H15A 119.5 .
C16 C15 H15A 119.5 .
H16A O16 H16B 139.2 .
C17 C16 C15 119.3(4) .
C17 C16 H16 120.3 .
C15 C16 H16 120.3 .
C16 C17 C18 121.0(4) .
C16 C17 H17 119.5 .
C18 C17 H17 119.5 .
C69 O17 H17A 111.1 .
H18B O18 H18A 106.1 .
C17 C18 C13 119.1(3) .
C17 C18 C19 118.1(3) .
C13 C18 C19 122.7(3) .
C68 O19 H19 109.5 .
O22 C19 N20 119.4(3) .
O22 C19 C18 120.1(3) .
N20 C19 C18 120.5(3) .
C19 N20 O21 118.2(3) .
C19 N20 H20 120.9 .
O21 N20 H20 120.9 .
N20 O21 Bi1 113.71(18) .
N20 O21 Bi1 125.40(18) 2_666
Bi1 O21 Bi1 117.10(10) 2_666
C19 O22 Bi1 119.3(2) .
C24 O23 H23 109.5 .
O23 C24 C29 118.2(3) .
O23 C24 C25 122.2(3) .
C29 C24 C25 119.5(3) .
C26 C25 C24 120.0(4) .
C26 C25 H25 120.0 .
C24 C25 H25 120.0 .
C27 C26 C25 120.8(4) .
C27 C26 H26 119.6 .
C25 C26 H26 119.6 .
C26 C27 C28 119.4(4) .
C26 C27 H27 120.3 .
C28 C27 H27 120.3 .
C27 C28 C29 121.0(4) .
C27 C28 H28 119.5 .
C29 C28 H28 119.5 .
C28 C29 C24 119.3(3) .
C28 C29 C30 117.3(3) .
C24 C29 C30 123.4(3) .
O33 C30 N31 119.6(3) .
O33 C30 C29 120.6(3) .
N31 C30 C29 119.8(3) .
C30 N31 O32 119.1(3) .
C30 N31 H31 120.5 .
O32 N31 H31 120.5 .
N31 O32 Bi2 113.02(18) .
N31 O32 Bi1 120.11(18) .
Bi2 O32 Bi1 115.78(10) .
C30 O33 Bi2 114.8(2) .
C35 O34 H34A 120.4 .
O34 C35 C36 122.2(4) .
O34 C35 C40 118.4(3) .
C36 C35 C40 119.4(4) .
C37 C36 C35 120.1(4) .
C37 C36 H36 119.9 .
C35 C36 H36 119.9 .
C38 C37 C36 120.7(4) .
C38 C37 H37 119.7 .
C36 C37 H37 119.7 .
C37 C38 C39 119.6(4) .
C37 C38 H38 120.2 .
C39 C38 H38 120.2 .
C38 C39 C40 120.2(4) .
C38 C39 H39 119.9 .
C40 C39 H39 119.9 .
C39 C40 C35 120.0(3) .
C39 C40 C41 116.9(3) .
C35 C40 C41 123.1(3) .
O44 C41 N42 120.6(3) .
O44 C41 C40 121.2(3) .
N42 C41 C40 118.1(3) .
C41 N42 O43 118.2(3) .
C41 N42 H42 120.9 .
O43 N42 H42 120.9 .
N42 O43 Bi3 118.98(18) .
N42 O43 Bi2 111.10(17) .
Bi3 O43 Bi2 101.41(9) .
C41 O44 Bi2 118.9(2) .
C46 O45 H45 109.5 .
O45 C46 C47 121.8(3) .
O45 C46 C51 118.7(3) .
C47 C46 C51 119.5(4) .
C48 C47 C46 120.0(4) .
C48 C47 H47 120.0 .
C46 C47 H47 120.0 .
C47 C48 C49 120.9(4) .
C47 C48 H48 119.5 .
C49 C48 H48 119.5 .
C50 C49 C48 119.5(4) .
C50 C49 H49 120.3 .
C48 C49 H49 120.3 .
C49 C50 C51 120.2(4) .
C49 C50 H50 119.9 .
C51 C50 H50 119.9 .
C50 C51 C46 119.8(3) .
C50 C51 C52 116.8(3) .
C46 C51 C52 123.3(3) .
O55 C52 N53 120.6(3) .
O55 C52 C51 120.4(3) .
N53 C52 C51 119.0(3) .
C52 N53 O54 119.5(3) .
C52 N53 H53 120.3 .
O54 N53 H53 120.3 .
N53 O54 Bi3 114.49(18) .
N53 O54 Bi2 121.28(18) .
Bi3 O54 Bi2 98.96(8) .
C52 O55 Bi3 116.4(2) .
C57 O56 H56 109.5 .
O56 C57 C62 119.2(3) .
O56 C57 C58 121.1(3) .
C62 C57 C58 119.7(3) .
C59 C58 C57 120.7(4) .
C59 C58 H58 119.6 .
C57 C58 H58 119.6 .
C60 C59 C58 120.0(4) .
C60 C59 H59 120.0 .
C58 C59 H59 120.0 .
C59 C60 C61 119.8(4) .
C59 C60 H60 120.1 .
C61 C60 H60 120.1 .
C60 C61 C62 120.9(3) .
C60 C61 H61 119.5 .
C62 C61 H61 119.5 .
C57 C62 C61 118.8(3) .
C57 C62 C63 123.9(3) .
C61 C62 C63 117.1(3) .
O66 C63 N64 119.2(3) .
O66 C63 C62 120.3(3) .
N64 C63 C62 120.5(3) .
C63 N64 O65 120.0(3) .
C63 N64 H64 120.0 .
O65 N64 H64 120.0 .
N64 O65 Bi3 114.59(18) .
C63 O66 Bi3 113.3(2) .
O6 C67 H67A 109.5 .
O6 C67 H67B 109.5 .
H67A C67 H67B 109.5 .
O6 C67 H67C 109.5 .
H67A C67 H67C 109.5 .
H67B C67 H67C 109.5 .
O19 C68 H68A 109.5 .
O19 C68 H68B 109.5 .
H68A C68 H68B 109.5 .
O19 C68 H68C 109.5 .
H68A C68 H68C 109.5 .
H68B C68 H68C 109.5 .
O17 C69 H69A 109.5 .
O17 C69 H69B 109.5 .
H69A C69 H69B 109.5 .
O17 C69 H69C 109.5 .
H69A C69 H69C 109.5 .
H69B C69 H69C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 O10 2.256(2) .
Bi1 O22 2.268(2) .
Bi1 O11 2.327(2) .
Bi1 O21 2.337(2) .
Bi1 O32 2.521(2) .
Bi1 O21 2.577(2) 2_666
N1 O3 1.239(5) .
N1 O4 1.240(5) .
N1 O2 1.279(4) .
O1 C2 1.360(4) .
O1 H1 0.8400 .
Bi2 O32 2.230(2) .
Bi2 O33 2.277(2) .
Bi2 O44 2.312(3) .
Bi2 O43 2.459(2) .
Bi2 O6 2.509(3) .
Bi2 O5 2.604(3) .
Bi2 O54 2.639(2) .
C2 C3 1.390(5) .
C2 C7 1.405(5) .
N2 O20 1.233(4) .
N2 O7 1.236(4) .
N2 O9 1.277(4) .
O2 Bi3 2.515(3) .
Bi3 O65 2.226(2) .
Bi3 O54 2.329(2) .
Bi3 O55 2.378(3) .
Bi3 O66 2.380(2) .
Bi3 O43 2.427(2) .
Bi3 O10 2.721(2) 2_666
C3 C4 1.388(6) .
C3 H3 0.9500 .
N3 O13 1.242(4) .
N3 O15 1.256(4) .
N3 O14 1.263(4) .
C4 C5 1.392(5) .
C4 H4 0.9500 .
C5 C6 1.384(5) .
C5 H5 0.9500 .
O5 H5A 0.877(7) .
O5 H5B 0.877(7) .
C6 C7 1.394(5) .
C6 H6 0.9500 .
O6 C67 1.398(5) .
O6 H6A 0.876(10) .
C7 C8 1.480(5) .
C8 O11 1.283(4) .
C8 N9 1.317(4) .
N9 O10 1.384(3) .
N9 H9 0.8800 .
O10 Bi3 2.721(2) 2_666
O12 C13 1.363(4) .
O12 H12 0.8400 .
C13 C14 1.393(5) .
C13 C18 1.421(5) .
C14 C15 1.380(6) .
C14 H14 0.9500 .
C15 C16 1.391(6) .
C15 H15A 0.9500 .
O16 H16A 0.882(7) .
O16 H16B 0.882(7) .
C16 C17 1.382(5) .
C16 H16 0.9500 .
C17 C18 1.396(5) .
C17 H17 0.9500 .
O17 C69 1.411(6) .
O17 H17A 0.875(10) .
O18 H18B 0.921(7) .
O18 H18A 0.890(7) .
C18 C19 1.474(5) .
O19 C68 1.426(5) .
O19 H19 0.8400 .
C19 O22 1.280(4) .
C19 N20 1.322(4) .
N20 O21 1.379(4) .
N20 H20 0.8800 .
O21 Bi1 2.577(2) 2_666
O23 C24 1.355(4) .
O23 H23 0.8400 .
C24 C29 1.399(5) .
C24 C25 1.401(5) .
C25 C26 1.387(5) .
C25 H25 0.9500 .
C26 C27 1.381(6) .
C26 H26 0.9500 .
C27 C28 1.385(5) .
C27 H27 0.9500 .
C28 C29 1.397(5) .
C28 H28 0.9500 .
C29 C30 1.476(5) .
C30 O33 1.282(4) .
C30 N31 1.315(4) .
N31 O32 1.377(4) .
N31 H31 0.8800 .
O34 C35 1.355(5) .
O34 H34A 0.73(5) .
C35 C36 1.393(5) .
C35 C40 1.399(5) .
C36 C37 1.387(6) .
C36 H36 0.9500 .
C37 C38 1.386(6) .
C37 H37 0.9500 .
C38 C39 1.392(5) .
C38 H38 0.9500 .
C39 C40 1.394(5) .
C39 H39 0.9500 .
C40 C41 1.492(5) .
C41 O44 1.268(4) .
C41 N42 1.318(4) .
N42 O43 1.375(4) .
N42 H42 0.8800 .
O45 C46 1.365(4) .
O45 H45 0.8400 .
C46 C47 1.397(5) .
C46 C51 1.399(5) .
C47 C48 1.376(6) .
C47 H47 0.9500 .
C48 C49 1.394(6) .
C48 H48 0.9500 .
C49 C50 1.385(5) .
C49 H49 0.9500 .
C50 C51 1.399(5) .
C50 H50 0.9500 .
C51 C52 1.493(5) .
C52 O55 1.265(4) .
C52 N53 1.317(4) .
N53 O54 1.378(4) .
N53 H53 0.8800 .
O56 C57 1.355(4) .
O56 H56 0.8400 .
C57 C62 1.396(5) .
C57 C58 1.398(5) .
C58 C59 1.380(6) .
C58 H58 0.9500 .
C59 C60 1.379(5) .
C59 H59 0.9500 .
C60 C61 1.390(5) .
C60 H60 0.9500 .
C61 C62 1.396(5) .
C61 H61 0.9500 .
C62 C63 1.487(5) .
C63 O66 1.275(4) .
C63 N64 1.314(4) .
N64 O65 1.385(3) .
N64 H64 0.8800 .
C67 H67A 0.9800 .
C67 H67B 0.9800 .
C67 H67C 0.9800 .
C68 H68A 0.9800 .
C68 H68B 0.9800 .
C68 H68C 0.9800 .
C69 H69A 0.9800 .
C69 H69B 0.9800 .
C69 H69C 0.9800 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O20 0.84 1.92 2.717(4) 159 2_767
O5 H5A O45 0.88 2.09 2.897(4) 153 .
O5 H5B O7 0.88 1.96 2.790(4) 158 2_666
O6 H6A O16 0.88 2.07 2.638(4) 121 2_665
N9 H9 O1 0.88 1.98 2.633(4) 130 .
N9 H9 O66 0.88 2.31 2.845(4) 120 2_666
O12 H12 O19 0.84 1.81 2.646(4) 170 2_656
O16 H16A O2 0.88 2.31 2.866(4) 121 1_655
O16 H16A O56 0.88 2.30 3.013(4) 138 2_665
O16 H16B O20 0.88 1.98 2.844(4) 167 1_554
O17 H17A N1 0.88 2.48 3.349(5) 171 .
O17 H17A O3 0.88 2.43 3.224(5) 151 .
O17 H17A O4 0.88 2.03 2.831(5) 152 .
O18 H18B O9 0.92 2.18 2.843(5) 129 1_565
O18 H18A O13 0.89 1.91 2.802(4) 178 .
O19 H19 O9 0.84 2.05 2.891(4) 176 .
N20 H20 O12 0.88 1.91 2.591(4) 132 .
O23 H23 O17 0.84 1.76 2.576(4) 163 1_655
N31 H31 O11 0.88 2.30 2.815(4) 117 .
N31 H31 O23 0.88 1.91 2.583(4) 132 .
O34 H34A O18 0.73 1.90 2.575(4) 153 2_666
C36 H36 O9 0.95 2.51 3.430(5) 163 2_656
N42 H42 O10 0.88 2.45 3.016(4) 123 2_666
N42 H42 O34 0.88 1.92 2.575(4) 130 .
O45 H45 O15 0.84 1.82 2.655(4) 170 2_676
N53 H53 O15 0.88 1.95 2.756(4) 152 .
N53 H53 O45 0.88 2.27 2.755(4) 115 .
O56 H56 O65 0.84 2.23 2.907(4) 138 2_565
N64 H64 O16 0.88 2.32 3.061(4) 142 2_665
N64 H64 O56 0.88 2.00 2.648(4) 130 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_4
O3 N1 O2 Bi3 -22.7(4) .
O4 N1 O2 Bi3 155.5(3) .
O1 C2 C3 C4 -179.9(4) .
C7 C2 C3 C4 0.3(6) .
C2 C3 C4 C5 1.1(6) .
C3 C4 C5 C6 -1.5(6) .
C4 C5 C6 C7 0.6(6) .
C5 C6 C7 C2 0.7(5) .
C5 C6 C7 C8 -177.7(3) .
O1 C2 C7 C6 179.0(3) .
C3 C2 C7 C6 -1.1(5) .
O1 C2 C7 C8 -2.7(5) .
C3 C2 C7 C8 177.2(3) .
C6 C7 C8 O11 9.5(5) .
C2 C7 C8 O11 -168.9(3) .
C6 C7 C8 N9 -169.4(3) .
C2 C7 C8 N9 12.3(5) .
O11 C8 N9 O10 3.5(5) .
C7 C8 N9 O10 -177.6(3) .
C8 N9 O10 Bi1 -7.0(4) .
C8 N9 O10 Bi3 131.1(3) 2_666
N9 C8 O11 Bi1 1.8(4) .
C7 C8 O11 Bi1 -177.1(2) .
O12 C13 C14 C15 178.6(4) .
C18 C13 C14 C15 -1.4(6) .
C13 C14 C15 C16 0.3(6) .
C14 C15 C16 C17 0.9(6) .
C15 C16 C17 C18 -1.0(6) .
C16 C17 C18 C13 -0.1(5) .
C16 C17 C18 C19 -177.1(3) .
O12 C13 C18 C17 -178.7(3) .
C14 C13 C18 C17 1.3(5) .
O12 C13 C18 C19 -1.9(5) .
C14 C13 C18 C19 178.2(3) .
C17 C18 C19 O22 2.3(5) .
C13 C18 C19 O22 -174.6(3) .
C17 C18 C19 N20 -178.3(3) .
C13 C18 C19 N20 4.8(5) .
O22 C19 N20 O21 2.4(5) .
C18 C19 N20 O21 -177.0(3) .
C19 N20 O21 Bi1 3.3(3) .
C19 N20 O21 Bi1 160.6(2) 2_666
N20 C19 O22 Bi1 -7.3(4) .
C18 C19 O22 Bi1 172.1(2) .
O23 C24 C25 C26 -176.5(4) .
C29 C24 C25 C26 1.7(6) .
C24 C25 C26 C27 -1.2(7) .
C25 C26 C27 C28 0.1(7) .
C26 C27 C28 C29 0.5(7) .
C27 C28 C29 C24 0.0(6) .
C27 C28 C29 C30 179.0(4) .
O23 C24 C29 C28 177.1(4) .
C25 C24 C29 C28 -1.1(6) .
O23 C24 C29 C30 -1.8(6) .
C25 C24 C29 C30 -180.0(4) .
C28 C29 C30 O33 10.4(5) .
C24 C29 C30 O33 -170.7(4) .
C28 C29 C30 N31 -167.6(3) .
C24 C29 C30 N31 11.3(6) .
O33 C30 N31 O32 -1.2(5) .
C29 C30 N31 O32 176.9(3) .
C30 N31 O32 Bi2 13.0(4) .
C30 N31 O32 Bi1 155.5(2) .
N31 C30 O33 Bi2 -11.2(4) .
C29 C30 O33 Bi2 170.7(3) .
O34 C35 C36 C37 -179.0(3) .
C40 C35 C36 C37 0.8(6) .
C35 C36 C37 C38 0.5(6) .
C36 C37 C38 C39 -1.4(6) .
C37 C38 C39 C40 0.8(5) .
C38 C39 C40 C35 0.5(5) .
C38 C39 C40 C41 -179.5(3) .
O34 C35 C40 C39 178.5(3) .
C36 C35 C40 C39 -1.3(5) .
O34 C35 C40 C41 -1.5(5) .
C36 C35 C40 C41 178.7(3) .
C39 C40 C41 O44 15.0(5) .
C35 C40 C41 O44 -165.0(3) .
C39 C40 C41 N42 -163.0(3) .
C35 C40 C41 N42 17.0(5) .
O44 C41 N42 O43 0.9(5) .
C40 C41 N42 O43 178.9(3) .
C41 N42 O43 Bi3 132.5(2) .
C41 N42 O43 Bi2 15.3(3) .
N42 C41 O44 Bi2 -18.8(4) .
C40 C41 O44 Bi2 163.2(2) .
O45 C46 C47 C48 177.7(3) .
C51 C46 C47 C48 -1.3(5) .
C46 C47 C48 C49 1.6(6) .
C47 C48 C49 C50 -1.6(6) .
C48 C49 C50 C51 1.2(6) .
C49 C50 C51 C46 -0.9(5) .
C49 C50 C51 C52 -176.8(3) .
O45 C46 C51 C50 -178.1(3) .
C47 C46 C51 C50 1.0(5) .
O45 C46 C51 C52 -2.5(5) .
C47 C46 C51 C52 176.6(3) .
C50 C51 C52 O55 31.9(5) .
C46 C51 C52 O55 -143.8(4) .
C50 C51 C52 N53 -147.9(3) .
C46 C51 C52 N53 36.3(5) .
O55 C52 N53 O54 0.4(5) .
C51 C52 N53 O54 -179.7(3) .
C52 N53 O54 Bi3 -6.8(4) .
C52 N53 O54 Bi2 111.7(3) .
N53 C52 O55 Bi3 6.1(4) .
C51 C52 O55 Bi3 -173.8(2) .
O56 C57 C58 C59 176.2(4) .
C62 C57 C58 C59 -2.2(6) .
C57 C58 C59 C60 -0.4(6) .
C58 C59 C60 C61 2.2(6) .
C59 C60 C61 C62 -1.6(6) .
O56 C57 C62 C61 -175.6(3) .
C58 C57 C62 C61 2.8(5) .
O56 C57 C62 C63 9.5(5) .
C58 C57 C62 C63 -172.1(3) .
C60 C61 C62 C57 -0.9(5) .
C60 C61 C62 C63 174.3(3) .
C57 C62 C63 O66 164.6(3) .
C61 C62 C63 O66 -10.4(5) .
C57 C62 C63 N64 -12.9(5) .
C61 C62 C63 N64 172.1(3) .
O66 C63 N64 O65 -3.2(5) .
C62 C63 N64 O65 174.3(3) .
C63 N64 O65 Bi3 -12.2(4) .
N64 C63 O66 Bi3 15.8(4) .
C62 C63 O66 Bi3 -161.7(2) .
