#------------------------------------------------------------------------------
#$Date: 2016-03-21 18:12:35 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178805 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/59/4105920.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_4105920
loop_
_publ_author_name
'Ian J. Casely'
'Joseph W. Ziller'
'Ming Fang'
'Filipp Furche'
'William J. Evans'
_publ_section_title
;
 Facile Bismuth-Oxygen Bond Cleavage, C-H Activation, and Formation of a
 Monodentate Carbon-Bound Oxyaryl Dianion, (C6H2tBu2-3,5-O-4)2-
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5244
_journal_page_last               5247
_journal_paper_doi               10.1021/ja201128d
_journal_volume                  133
_journal_year                    2011
_chemical_formula_sum            'C36 H53 Bi N2 O2'
_chemical_formula_weight         754.78
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL
_cell_angle_alpha                90.00
_cell_angle_beta                 130.6780(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            20
_cell_length_a                   53.677(3)
_cell_length_b                   10.8825(6)
_cell_length_c                   39.936(3)
_cell_measurement_reflns_used    9573
_cell_measurement_temperature    143(2)
_cell_measurement_theta_max      28.43
_cell_measurement_theta_min      2.39
_cell_volume                     17691.8(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      143(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_max       72
_diffrn_reflns_limit_h_min       -71
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       53
_diffrn_reflns_limit_l_min       -53
_diffrn_reflns_number            101132
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         28.62
_diffrn_reflns_theta_min         1.34
_exptl_absorpt_coefficient_mu    5.014
_exptl_absorpt_correction_T_max  0.4106
_exptl_absorpt_correction_T_min  0.3931
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_meas      ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             7640
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.22
_refine_diff_density_max         1.663
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     977
_refine_ls_number_reflns         20918
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0302
_refine_ls_R_factor_gt           0.0226
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0251P)²+17.5707P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0487
_refine_ls_wR_factor_ref         0.0507
_reflns_number_gt                18171
_reflns_number_total             20918
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja201128d_si_002.cif
_cod_data_source_block           ijc30
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        17692(2)
_cod_database_code               4105920
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
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 0.901496(2) 0.404439(8) 0.949119(3) 0.01811(2) Uani 1 1 d . . .
O1 O 0.84605(4) 0.36789(15) 0.89679(5) 0.0243(4) Uani 1 1 d . . .
O2 O 0.95770(4) 0.42551(15) 0.99945(5) 0.0241(4) Uani 1 1 d . . .
N1 N 0.88939(5) 0.31166(18) 0.99598(7) 0.0226(4) Uani 1 1 d . . .
N2 N 0.91598(5) 0.3558(2) 0.90156(7) 0.0252(4) Uani 1 1 d . . .
C1 C 0.90648(6) 0.2039(2) 0.94964(7) 0.0214(5) Uani 1 1 d . . .
C2 C 0.92102(6) 0.1542(2) 0.93390(8) 0.0269(5) Uani 1 1 d . . .
C3 C 0.92256(7) 0.0278(3) 0.93171(9) 0.0362(7) Uani 1 1 d . . .
H3A H 0.9321 -0.0072 0.9206 0.043 Uiso 1 1 calc R . .
C4 C 0.91013(7) -0.0476(3) 0.94575(10) 0.0400(7) Uani 1 1 d . . .
H4A H 0.9115 -0.1343 0.9446 0.048 Uiso 1 1 calc R . .
C5 C 0.89561(7) 0.0025(2) 0.96151(9) 0.0345(6) Uani 1 1 d . . .
H5A H 0.8871 -0.0499 0.9710 0.041 Uiso 1 1 calc R . .
C6 C 0.89358(6) 0.1297(2) 0.96326(8) 0.0243(5) Uani 1 1 d . . .
C7 C 0.87556(6) 0.1890(2) 0.97628(8) 0.0259(5) Uani 1 1 d . . .
H7A H 0.8520 0.1974 0.9499 0.031 Uiso 1 1 calc R . .
H7B H 0.8773 0.1360 0.9979 0.031 Uiso 1 1 calc R . .
C8 C 0.86509(7) 0.3851(2) 0.99382(9) 0.0304(6) Uani 1 1 d . . .
H8A H 0.8587 0.3402 1.0085 0.046 Uiso 1 1 calc R . .
H8B H 0.8456 0.3995 0.9629 0.046 Uiso 1 1 calc R . .
H8C H 0.8749 0.4641 1.0087 0.046 Uiso 1 1 calc R . .
C9 C 0.92014(6) 0.2974(2) 1.04241(8) 0.0279(6) Uani 1 1 d . . .
H9A H 0.9151 0.2603 1.0598 0.042 Uiso 1 1 calc R . .
H9B H 0.9302 0.3782 1.0547 0.042 Uiso 1 1 calc R . .
H9C H 0.9354 0.2443 1.0435 0.042 Uiso 1 1 calc R . .
C10 C 0.93571(6) 0.2418(3) 0.92166(9) 0.0299(6) Uani 1 1 d . . .
H10A H 0.9584 0.2630 0.9484 0.036 Uiso 1 1 calc R . .
H10B H 0.9369 0.2012 0.9005 0.036 Uiso 1 1 calc R . .
C11 C 0.88592(6) 0.3306(3) 0.85523(8) 0.0318(6) Uani 1 1 d . . .
H11A H 0.8922 0.3020 0.8384 0.048 Uiso 1 1 calc R . .
H11B H 0.8729 0.4060 0.8419 0.048 Uiso 1 1 calc R . .
H11C H 0.8728 0.2671 0.8549 0.048 Uiso 1 1 calc R . .
C12 C 0.93576(7) 0.4529(3) 0.90281(9) 0.0376(7) Uani 1 1 d . . .
H12A H 0.9426 0.4255 0.8865 0.056 Uiso 1 1 calc R . .
H12B H 0.9552 0.4698 0.9335 0.056 Uiso 1 1 calc R . .
H12C H 0.9226 0.5279 0.8892 0.056 Uiso 1 1 calc R . .
C13 C 0.82214(5) 0.3808(2) 0.85332(7) 0.0201(5) Uani 1 1 d . . .
C14 C 0.80577(6) 0.2753(2) 0.82671(8) 0.0236(5) Uani 1 1 d . . .
C15 C 0.77939(6) 0.2894(3) 0.78193(8) 0.0300(6) Uani 1 1 d . . .
H15A H 0.7679 0.2187 0.7643 0.036 Uiso 1 1 calc R . .
C16 C 0.76951(7) 0.4046(3) 0.76237(8) 0.0324(6) Uani 1 1 d . . .
H16A H 0.7514 0.4129 0.7317 0.039 Uiso 1 1 calc R . .
C17 C 0.78639(6) 0.5068(3) 0.78806(8) 0.0292(6) Uani 1 1 d . . .
H17A H 0.7802 0.5853 0.7744 0.035 Uiso 1 1 calc R . .
C18 C 0.81226(6) 0.4986(2) 0.83339(8) 0.0231(5) Uani 1 1 d . . .
C19 C 0.81712(7) 0.1485(2) 0.84757(9) 0.0304(6) Uani 1 1 d . . .
H19A H 0.8393 0.1580 0.8774 0.036 Uiso 1 1 calc R . .
C20 C 0.79427(9) 0.0943(3) 0.85437(11) 0.0447(8) Uani 1 1 d . . .
H20A H 0.7944 0.1475 0.8743 0.067 Uiso 1 1 calc R . .
H20B H 0.8020 0.0121 0.8673 0.067 Uiso 1 1 calc R . .
H20C H 0.7719 0.0888 0.8259 0.067 Uiso 1 1 calc R . .
C21 C 0.82059(7) 0.0594(3) 0.82120(10) 0.0381(7) Uani 1 1 d . . .
H21A H 0.8351 0.0955 0.8169 0.057 Uiso 1 1 calc R . .
H21B H 0.7989 0.0439 0.7924 0.057 Uiso 1 1 calc R . .
H21C H 0.8300 -0.0181 0.8374 0.057 Uiso 1 1 calc R . .
C22 C 0.82934(7) 0.6126(2) 0.86149(9) 0.0303(6) Uani 1 1 d . . .
H22A H 0.8400 0.5902 0.8926 0.036 Uiso 1 1 calc R . .
C23 C 0.80558(9) 0.7181(3) 0.84764(12) 0.0532(9) Uani 1 1 d . . .
H23A H 0.7881 0.6896 0.8474 0.080 Uiso 1 1 calc R . .
H23B H 0.7959 0.7462 0.8180 0.080 Uiso 1 1 calc R . .
H23C H 0.8175 0.7861 0.8686 0.080 Uiso 1 1 calc R . .
C24 C 0.85615(8) 0.6552(3) 0.86142(11) 0.0490(8) Uani 1 1 d . . .
H24A H 0.8723 0.5893 0.8726 0.073 Uiso 1 1 calc R . .
H24B H 0.8670 0.7278 0.8804 0.073 Uiso 1 1 calc R . .
H24C H 0.8465 0.6762 0.8312 0.073 Uiso 1 1 calc R . .
C25 C 0.97730(6) 0.4357(2) 1.04326(8) 0.0213(5) Uani 1 1 d . . .
C26 C 0.97848(6) 0.5453(2) 1.06351(8) 0.0251(5) Uani 1 1 d . . .
C27 C 0.99861(7) 0.5477(3) 1.10952(9) 0.0335(6) Uani 1 1 d . . .
H27A H 0.9991 0.6197 1.1233 0.040 Uiso 1 1 calc R . .
C28 C 1.01774(7) 0.4493(3) 1.13534(9) 0.0377(7) Uani 1 1 d . . .
H28A H 1.0310 0.4533 1.1665 0.045 Uiso 1 1 calc R . .
C29 C 1.01755(7) 0.3444(3) 1.11561(9) 0.0329(6) Uani 1 1 d . . .
H29A H 1.0312 0.2771 1.1336 0.039 Uiso 1 1 calc R . .
C30 C 0.99781(6) 0.3355(2) 1.07027(8) 0.0239(5) Uani 1 1 d . . .
C31 C 0.95802(6) 0.6553(2) 1.03580(9) 0.0279(6) Uani 1 1 d . . .
H31A H 0.9507 0.6427 1.0057 0.033 Uiso 1 1 calc R . .
C32 C 0.92715(7) 0.6669(3) 1.03053(10) 0.0359(7) Uani 1 1 d . . .
H32A H 0.9138 0.5923 1.0166 0.054 Uiso 1 1 calc R . .
H32B H 0.9143 0.7382 1.0120 0.054 Uiso 1 1 calc R . .
H32C H 0.9336 0.6777 1.0596 0.054 Uiso 1 1 calc R . .
C33 C 0.97764(7) 0.7751(2) 1.05410(10) 0.0354(6) Uani 1 1 d . . .
H33A H 0.9973 0.7670 1.0574 0.053 Uiso 1 1 calc R . .
H33B H 0.9842 0.7925 1.0829 0.053 Uiso 1 1 calc R . .
H33C H 0.9640 0.8426 1.0337 0.053 Uiso 1 1 calc R . .
C34 C 0.99769(6) 0.2226(2) 1.04773(9) 0.0285(6) Uani 1 1 d . . .
H34A H 0.9749 0.2135 1.0187 0.034 Uiso 1 1 calc R . .
C35 C 1.02047(7) 0.2421(3) 1.03782(10) 0.0403(7) Uani 1 1 d . . .
H35A H 1.0145 0.3185 1.0211 0.060 Uiso 1 1 calc R . .
H35B H 1.0183 0.1728 1.0204 0.060 Uiso 1 1 calc R . .
H35C H 1.0432 0.2475 1.0656 0.060 Uiso 1 1 calc R . .
C36 C 1.00617(8) 0.1031(3) 1.07330(11) 0.0467(8) Uani 1 1 d . . .
H36A H 0.9921 0.0942 1.0807 0.070 Uiso 1 1 calc R . .
H36B H 1.0292 0.1050 1.1005 0.070 Uiso 1 1 calc R . .
H36C H 1.0026 0.0334 1.0551 0.070 Uiso 1 1 calc R . .
Bi2 Bi 0.691522(2) 0.704713(9) 0.860037(3) 0.02281(3) Uani 1 1 d . . .
O3 O 0.65070(5) 0.58925(17) 0.80150(6) 0.0364(5) Uani 1 1 d . . .
O4 O 0.73878(4) 0.77107(16) 0.92749(6) 0.0294(4) Uani 1 1 d . . .
N3 N 0.69939(5) 0.5397(2) 0.90928(7) 0.0280(5) Uani 1 1 d . . .
N4 N 0.70374(6) 0.7744(2) 0.81035(7) 0.0333(5) Uani 1 1 d . . .
C37 C 0.72329(6) 0.5662(2) 0.86518(9) 0.0274(5) Uani 1 1 d . . .
C38 C 0.72822(7) 0.5664(3) 0.83512(10) 0.0371(7) Uani 1 1 d . . .
C39 C 0.75033(10) 0.4814(3) 0.84113(14) 0.0597(10) Uani 1 1 d . . .
H39A H 0.7542 0.4790 0.8211 0.072 Uiso 1 1 calc R . .
C40 C 0.76655(11) 0.4010(3) 0.87629(17) 0.0750(14) Uani 1 1 d . . .
H40A H 0.7819 0.3449 0.8805 0.090 Uiso 1 1 calc R . .
C41 C 0.76099(9) 0.4001(3) 0.90558(14) 0.0578(10) Uani 1 1 d . . .
H41A H 0.7723 0.3436 0.9295 0.069 Uiso 1 1 calc R . .
C42 C 0.73871(7) 0.4830(3) 0.89954(10) 0.0352(6) Uani 1 1 d . . .
C43 C 0.73268(7) 0.4920(3) 0.93120(9) 0.0338(6) Uani 1 1 d . . .
H43A H 0.7352 0.4098 0.9437 0.041 Uiso 1 1 calc R . .
H43B H 0.7492 0.5473 0.9559 0.041 Uiso 1 1 calc R . .
C44 C 0.69790(8) 0.5896(3) 0.94254(10) 0.0414(7) Uani 1 1 d . . .
H44A H 0.7037 0.5249 0.9637 0.062 Uiso 1 1 calc R . .
H44B H 0.6756 0.6187 0.9277 0.062 Uiso 1 1 calc R . .
H44C H 0.7134 0.6581 0.9583 0.062 Uiso 1 1 calc R . .
C45 C 0.67462(7) 0.4415(3) 0.88333(9) 0.0338(6) Uani 1 1 d . . .
H45A H 0.6789 0.3754 0.9032 0.051 Uiso 1 1 calc R . .
H45B H 0.6759 0.4089 0.8616 0.051 Uiso 1 1 calc R . .
H45C H 0.6526 0.4753 0.8681 0.051 Uiso 1 1 calc R . .
C46 C 0.70904(8) 0.6559(3) 0.79729(10) 0.0434(8) Uani 1 1 d . . .
H46A H 0.7211 0.6714 0.7867 0.052 Uiso 1 1 calc R . .
H46B H 0.6875 0.6194 0.7726 0.052 Uiso 1 1 calc R . .
C47 C 0.67754(7) 0.8451(3) 0.77087(9) 0.0474(8) Uani 1 1 d . . .
H47A H 0.6841 0.8636 0.7535 0.071 Uiso 1 1 calc R . .
H47B H 0.6739 0.9220 0.7799 0.071 Uiso 1 1 calc R . .
H47C H 0.6572 0.7967 0.7529 0.071 Uiso 1 1 calc R . .
C48 C 0.73443(7) 0.8455(3) 0.83793(9) 0.0342(6) Uani 1 1 d . . .
H48A H 0.7410 0.8659 0.8207 0.051 Uiso 1 1 calc R . .
H48B H 0.7517 0.7967 0.8638 0.051 Uiso 1 1 calc R . .
H48C H 0.7310 0.9215 0.8477 0.051 Uiso 1 1 calc R . .
C49 C 0.62405(6) 0.5955(2) 0.75910(8) 0.0285(6) Uani 1 1 d . . .
C50 C 0.60239(6) 0.6971(3) 0.74137(8) 0.0289(6) Uani 1 1 d . . .
C51 C 0.57461(7) 0.6964(3) 0.69670(9) 0.0335(6) Uani 1 1 d . . .
H51A H 0.5600 0.7644 0.6844 0.040 Uiso 1 1 calc R . .
C52 C 0.56783(8) 0.5978(3) 0.66968(9) 0.0410(8) Uani 1 1 d . . .
H52A H 0.5485 0.5978 0.6394 0.049 Uiso 1 1 calc R . .
C53 C 0.58921(7) 0.5007(3) 0.68684(9) 0.0402(7) Uani 1 1 d . . .
H53A H 0.5845 0.4343 0.6681 0.048 Uiso 1 1 calc R . .
C54 C 0.61755(7) 0.4969(3) 0.73105(9) 0.0344(6) Uani 1 1 d . . .
C55 C 0.61015(6) 0.8022(2) 0.77196(8) 0.0301(6) Uani 1 1 d . . .
H55A H 0.6340 0.8214 0.7899 0.036 Uiso 1 1 calc R . .
C56 C 0.60569(7) 0.7635(3) 0.80462(9) 0.0351(6) Uani 1 1 d . . .
H56A H 0.6178 0.6872 0.8194 0.053 Uiso 1 1 calc R . .
H56B H 0.5823 0.7502 0.7887 0.053 Uiso 1 1 calc R . .
H56C H 0.6141 0.8283 0.8267 0.053 Uiso 1 1 calc R . .
C57 C 0.59154(7) 0.9204(3) 0.74846(10) 0.0415(7) Uani 1 1 d . . .
H57A H 0.5943 0.9425 0.7272 0.062 Uiso 1 1 calc R . .
H57B H 0.6002 0.9865 0.7702 0.062 Uiso 1 1 calc R . .
H57C H 0.5682 0.9084 0.7328 0.062 Uiso 1 1 calc R . .
C58 C 0.64120(8) 0.3892(3) 0.75038(11) 0.0428(8) Uani 1 1 d . . .
H58A H 0.6628 0.4196 0.7779 0.051 Uiso 1 1 calc R . .
C59 C 0.64720(13) 0.3414(4) 0.72045(16) 0.0867(15) Uani 1 1 d . . .
H59A H 0.6641 0.2773 0.7359 0.130 Uiso 1 1 calc R . .
H59B H 0.6546 0.4090 0.7126 0.130 Uiso 1 1 calc R . .
H59C H 0.6268 0.3069 0.6936 0.130 Uiso 1 1 calc R . .
C60 C 0.63066(9) 0.2851(3) 0.76393(13) 0.0619(10) Uani 1 1 d . . .
H60A H 0.6476 0.2212 0.7789 0.093 Uiso 1 1 calc R . .
H60B H 0.6099 0.2503 0.7376 0.093 Uiso 1 1 calc R . .
H60C H 0.6276 0.3165 0.7840 0.093 Uiso 1 1 calc R . .
C61 C 0.75617(6) 0.8737(2) 0.93922(8) 0.0250(5) Uani 1 1 d . . .
C62 C 0.78930(6) 0.8653(2) 0.95650(8) 0.0275(5) Uani 1 1 d . . .
C63 C 0.80743(7) 0.9712(3) 0.96859(9) 0.0355(6) Uani 1 1 d . . .
H63A H 0.8294 0.9655 0.9799 0.043 Uiso 1 1 calc R . .
C64 C 0.79459(7) 1.0854(3) 0.96474(11) 0.0428(7) Uani 1 1 d . . .
H64A H 0.8075 1.1574 0.9733 0.051 Uiso 1 1 calc R . .
C65 C 0.76251(7) 1.0936(3) 0.94821(10) 0.0395(7) Uani 1 1 d . . .
H65A H 0.7536 1.1721 0.9456 0.047 Uiso 1 1 calc R . .
C66 C 0.74302(6) 0.9900(2) 0.93535(9) 0.0296(6) Uani 1 1 d . . .
C67 C 0.80324(6) 0.7391(3) 0.96124(9) 0.0308(6) Uani 1 1 d . . .
H67A H 0.7852 0.6899 0.9349 0.037 Uiso 1 1 calc R . .
C68 C 0.83195(7) 0.7402(3) 0.96171(11) 0.0475(8) Uani 1 1 d . . .
H68A H 0.8260 0.7892 0.9368 0.071 Uiso 1 1 calc R . .
H68B H 0.8369 0.6559 0.9591 0.071 Uiso 1 1 calc R . .
H68C H 0.8513 0.7763 0.9895 0.071 Uiso 1 1 calc R . .
C69 C 0.81311(7) 0.6728(3) 1.00199(9) 0.0373(7) Uani 1 1 d . . .
H69A H 0.7948 0.6749 1.0018 0.056 Uiso 1 1 calc R . .
H69B H 0.8322 0.7137 1.0286 0.056 Uiso 1 1 calc R . .
H69C H 0.8186 0.5873 1.0017 0.056 Uiso 1 1 calc R . .
C70 C 0.70768(6) 1.0028(3) 0.91652(9) 0.0329(6) Uani 1 1 d . . .
H70A H 0.6996 0.9188 0.9153 0.039 Uiso 1 1 calc R . .
C71 C 0.70464(8) 1.0829(3) 0.94513(10) 0.0434(7) Uani 1 1 d . . .
H71A H 0.6816 1.0851 0.9322 0.065 Uiso 1 1 calc R . .
H71B H 0.7121 1.1665 0.9465 0.065 Uiso 1 1 calc R . .
H71C H 0.7182 1.0484 0.9750 0.065 Uiso 1 1 calc R . .
C72 C 0.68542(8) 1.0531(3) 0.86966(10) 0.0503(8) Uani 1 1 d . . .
H72A H 0.6861 0.9982 0.8508 0.076 Uiso 1 1 calc R . .
H72B H 0.6930 1.1351 0.8697 0.076 Uiso 1 1 calc R . .
H72C H 0.6629 1.0586 0.8583 0.076 Uiso 1 1 calc R . .
Bi3 Bi 1.0000 0.166513(11) 1.2500 0.01943(3) Uani 1 2 d S . .
O5 O 0.96458(4) 0.15509(16) 1.17433(5) 0.0285(4) Uani 1 1 d . . .
N5 N 0.96195(5) 0.0960(2) 1.26225(7) 0.0363(6) Uani 1 1 d . . .
C73 C 1.0000 -0.0350(3) 1.2500 0.0314(9) Uani 1 2 d S . .
C74 C 0.98772(7) -0.0968(3) 1.26675(10) 0.0453(8) Uani 1 1 d . . .
C75 C 0.98802(8) -0.2247(3) 1.26651(13) 0.0767(16) Uani 1 1 d . . .
H75A H 0.9798 -0.2694 1.2780 0.092 Uiso 1 1 calc R . .
C76 C 1.0000 -0.2860(5) 1.2500 0.103(3) Uani 1 2 d S . .
H76 H 1.0000 -0.3733 1.2500 0.124 Uiso 1 2 calc SR . .
C77 C 0.97589(7) -0.0226(3) 1.28573(10) 0.0512(9) Uani 1 1 d . . .
H77A H 0.9589 -0.0696 1.2832 0.061 Uiso 1 1 calc R . .
H77B H 0.9944 -0.0071 1.3175 0.061 Uiso 1 1 calc R . .
C78 C 0.96090(8) 0.1839(4) 1.28945(11) 0.0624(12) Uani 1 1 d . . .
H78A H 0.9479 0.1491 1.2964 0.094 Uiso 1 1 calc R . .
H78B H 0.9508 0.2609 1.2731 0.094 Uiso 1 1 calc R . .
H78C H 0.9833 0.2000 1.3169 0.094 Uiso 1 1 calc R . .
C79 C 0.92837(6) 0.0767(3) 1.21936(9) 0.0355(7) Uani 1 1 d . . .
H79A H 0.9141 0.0450 1.2246 0.053 Uiso 1 1 calc R . .
H79B H 0.9292 0.0174 1.2016 0.053 Uiso 1 1 calc R . .
H79C H 0.9196 0.1550 1.2035 0.053 Uiso 1 1 calc R . .
C80 C 0.93251(6) 0.1771(2) 1.14315(8) 0.0238(5) Uani 1 1 d . . .
C81 C 0.91914(6) 0.2955(2) 1.13673(8) 0.0270(5) Uani 1 1 d . B .
C82 C 0.88546(7) 0.3120(3) 1.10415(9) 0.0329(6) Uani 1 1 d . . .
H82A H 0.8764 0.3911 1.1002 0.039 Uiso 1 1 calc R . .
C83 C 0.86488(7) 0.2170(3) 1.07753(10) 0.0364(7) Uani 1 1 d . . .
H83A H 0.8419 0.2304 1.0555 0.044 Uiso 1 1 calc R . .
C84 C 0.87799(7) 0.1014(3) 1.08310(9) 0.0326(6) Uani 1 1 d . . .
H84A H 0.8638 0.0360 1.0644 0.039 Uiso 1 1 calc R . .
C85 C 0.91126(6) 0.0796(2) 1.11521(8) 0.0260(5) Uani 1 1 d . . .
C86 C 0.94134(7) 0.4020(3) 1.16541(9) 0.0356(6) Uani 1 1 d . . .
H86A H 0.9642 0.3703 1.1829 0.043 Uiso 0.50 1 calc PR A 1
H86B H 0.9569 0.3702 1.1949 0.043 Uiso 0.50 1 d PR A 2
C87 C 0.93853(18) 0.5133(5) 1.13788(19) 0.056(2) Uani 0.603(9) 1 d P B 1
H87A H 0.9549 0.5758 1.1580 0.084 Uiso 0.603(9) 1 calc PR B 1
H87B H 0.9165 0.5489 1.1200 0.084 Uiso 0.603(9) 1 calc PR B 1
H87C H 0.9425 0.4843 1.1185 0.084 Uiso 0.603(9) 1 calc PR B 1
C88 C 0.93892(16) 0.4436(6) 1.1985(2) 0.0477(19) Uani 0.577(8) 1 d P B 1
H88A H 0.9551 0.5085 1.2168 0.072 Uiso 0.577(8) 1 calc PR B 1
H88B H 0.9432 0.3742 1.2173 0.072 Uiso 0.577(8) 1 calc PR B 1
H88C H 0.9168 0.4756 1.1833 0.072 Uiso 0.577(8) 1 calc PR B 1
C87B C 0.9597(2) 0.4405(9) 1.1545(3) 0.048(3) Uani 0.397(9) 1 d P B 2
H87D H 0.9451 0.4733 1.1243 0.073 Uiso 0.397(9) 1 calc PR B 2
H87E H 0.9721 0.3708 1.1562 0.073 Uiso 0.397(9) 1 calc PR B 2
H87F H 0.9750 0.5048 1.1751 0.073 Uiso 0.397(9) 1 calc PR B 2
C88B C 0.92095(19) 0.5018(7) 1.1665(3) 0.045(2) Uani 0.423(8) 1 d P B 2
H88D H 0.9358 0.5646 1.1885 0.067 Uiso 0.423(8) 1 calc PR B 2
H88E H 0.9089 0.4633 1.1744 0.067 Uiso 0.423(8) 1 calc PR B 2
H88F H 0.9054 0.5402 1.1374 0.067 Uiso 0.423(8) 1 calc PR B 2
C89 C 0.92662(7) -0.0446(2) 1.12146(9) 0.0323(6) Uani 1 1 d . . .
H89A H 0.9452 -0.0557 1.1538 0.039 Uiso 1 1 calc R . .
C90 C 0.94106(8) -0.0451(3) 1.09884(10) 0.0442(8) Uani 1 1 d . . .
H90A H 0.9553 0.0268 1.1084 0.066 Uiso 1 1 calc R . .
H90B H 0.9232 -0.0424 1.0668 0.066 Uiso 1 1 calc R . .
H90C H 0.9540 -0.1202 1.1069 0.066 Uiso 1 1 calc R . .
C91 C 0.90315(9) -0.1530(3) 1.10573(12) 0.0547(9) Uani 1 1 d . . .
H91A H 0.8940 -0.1507 1.1204 0.082 Uiso 1 1 calc R . .
H91B H 0.9151 -0.2302 1.1130 0.082 Uiso 1 1 calc R . .
H91C H 0.8853 -0.1476 1.0737 0.082 Uiso 1 1 calc R . .
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_1
_geom_angle_site_symmetry_3
C1 Bi1 O1 85.08(7) . .
C1 Bi1 O2 90.49(7) . .
O1 Bi1 O2 174.98(6) . .
C1 Bi1 N2 72.81(8) . .
O1 Bi1 N2 97.50(6) . .
O2 Bi1 N2 78.89(6) . .
C1 Bi1 N1 71.83(8) . .
O1 Bi1 N1 78.50(6) . .
O2 Bi1 N1 102.37(6) . .
N2 Bi1 N1 144.62(7) . .
C13 O1 Bi1 138.02(15) . .
C25 O2 Bi1 128.19(14) . .
C7 N1 C9 109.53(19) . .
C7 N1 C8 109.7(2) . .
C9 N1 C8 110.42(19) . .
C7 N1 Bi1 104.24(14) . .
C9 N1 Bi1 110.50(14) . .
C8 N1 Bi1 112.23(15) . .
C12 N2 C10 109.7(2) . .
C12 N2 C11 110.3(2) . .
C10 N2 C11 109.4(2) . .
C12 N2 Bi1 112.99(16) . .
C10 N2 Bi1 103.24(14) . .
C11 N2 Bi1 110.93(14) . .
C6 C1 C2 121.5(2) . .
C6 C1 Bi1 119.59(17) . .
C2 C1 Bi1 118.84(18) . .
C3 C2 C1 119.3(3) . .
C3 C2 C10 122.9(2) . .
C1 C2 C10 117.8(2) . .
C2 C3 C4 119.9(3) . .
C3 C4 C5 120.7(3) . .
C4 C5 C6 119.7(3) . .
C1 C6 C5 118.9(2) . .
C1 C6 C7 118.8(2) . .
C5 C6 C7 122.1(2) . .
N1 C7 C6 110.9(2) . .
N2 C10 C2 111.4(2) . .
O1 C13 C14 119.5(2) . .
O1 C13 C18 121.2(2) . .
C14 C13 C18 119.4(2) . .
C15 C14 C13 119.4(2) . .
C15 C14 C19 121.0(2) . .
C13 C14 C19 119.6(2) . .
C16 C15 C14 121.4(3) . .
C17 C16 C15 119.1(2) . .
C16 C17 C18 122.1(2) . .
C17 C18 C13 118.7(2) . .
C17 C18 C22 121.3(2) . .
C13 C18 C22 120.0(2) . .
C14 C19 C21 112.6(2) . .
C14 C19 C20 111.4(2) . .
C21 C19 C20 110.4(2) . .
C24 C22 C18 111.5(2) . .
C24 C22 C23 109.9(3) . .
C18 C22 C23 112.8(2) . .
O2 C25 C26 121.4(2) . .
O2 C25 C30 119.4(2) . .
C26 C25 C30 119.2(2) . .
C27 C26 C25 118.3(2) . .
C27 C26 C31 121.2(2) . .
C25 C26 C31 120.5(2) . .
C28 C27 C26 122.1(3) . .
C27 C28 C29 119.5(2) . .
C30 C29 C28 121.2(3) . .
C29 C30 C25 119.7(2) . .
C29 C30 C34 122.4(2) . .
C25 C30 C34 117.9(2) . .
C26 C31 C33 112.4(2) . .
C26 C31 C32 111.7(2) . .
C33 C31 C32 110.0(2) . .
C30 C34 C35 110.3(2) . .
C30 C34 C36 114.1(2) . .
C35 C34 C36 110.6(2) . .
C37 Bi2 O3 83.42(8) . .
C37 Bi2 O4 84.79(8) . .
O3 Bi2 O4 164.71(7) . .
C37 Bi2 N3 72.98(8) . .
O3 Bi2 N3 88.11(7) . .
O4 Bi2 N3 79.15(7) . .
C37 Bi2 N4 72.55(9) . .
O3 Bi2 N4 85.94(7) . .
O4 Bi2 N4 99.75(7) . .
N3 Bi2 N4 145.47(7) . .
C49 O3 Bi2 143.01(18) . .
C61 O4 Bi2 131.34(15) . .
C45 N3 C43 110.5(2) . .
C45 N3 C44 110.1(2) . .
C43 N3 C44 110.3(2) . .
C45 N3 Bi2 110.83(16) . .
C43 N3 Bi2 103.76(15) . .
C44 N3 Bi2 111.25(17) . .
C48 N4 C47 110.4(2) . .
C48 N4 C46 110.0(2) . .
C47 N4 C46 110.2(2) . .
C48 N4 Bi2 107.54(15) . .
C47 N4 Bi2 115.71(17) . .
C46 N4 Bi2 102.61(16) . .
C42 C37 C38 122.2(3) . .
C42 C37 Bi2 118.14(19) . .
C38 C37 Bi2 119.7(2) . .
C37 C38 C39 118.0(3) . .
C37 C38 C46 118.6(3) . .
C39 C38 C46 123.3(3) . .
C40 C39 C38 119.8(3) . .
C39 C40 C41 121.6(3) . .
C40 C41 C42 119.0(3) . .
C37 C42 C41 119.3(3) . .
C37 C42 C43 118.4(2) . .
C41 C42 C43 122.1(3) . .
N3 C43 C42 111.4(2) . .
N4 C46 C38 111.8(2) . .
O3 C49 C50 122.0(2) . .
O3 C49 C54 118.3(3) . .
C50 C49 C54 119.7(2) . .
C51 C50 C49 118.7(3) . .
C51 C50 C55 122.5(3) . .
C49 C50 C55 118.7(2) . .
C52 C51 C50 121.2(3) . .
C53 C52 C51 119.7(3) . .
C52 C53 C54 121.6(3) . .
C53 C54 C49 118.8(3) . .
C53 C54 C58 121.9(3) . .
C49 C54 C58 119.2(3) . .
C50 C55 C57 114.5(2) . .
C50 C55 C56 111.4(2) . .
C57 C55 C56 110.7(2) . .
C60 C58 C54 112.1(3) . .
C60 C58 C59 110.2(3) . .
C54 C58 C59 113.6(3) . .
O4 C61 C66 122.0(2) . .
O4 C61 C62 118.9(2) . .
C66 C61 C62 119.2(2) . .
C63 C62 C61 119.2(2) . .
C63 C62 C67 122.4(2) . .
C61 C62 C67 118.4(2) . .
C62 C63 C64 121.8(3) . .
C63 C64 C65 119.0(3) . .
C64 C65 C66 121.7(3) . .
C65 C66 C61 119.1(2) . .
C65 C66 C70 120.2(2) . .
C61 C66 C70 120.7(2) . .
C62 C67 C69 111.2(2) . .
C62 C67 C68 113.9(2) . .
C69 C67 C68 110.2(2) . .
C72 C70 C66 111.5(2) . .
C72 C70 C71 109.5(2) . .
C66 C70 C71 112.9(2) . .
C73 Bi3 O5 86.90(5) . .
C73 Bi3 O5 86.90(5) . 2_757
O5 Bi3 O5 173.79(9) . 2_757
C73 Bi3 N5 72.19(6) . 2_757
O5 Bi3 N5 78.92(7) . 2_757
O5 Bi3 N5 99.16(7) 2_757 2_757
C73 Bi3 N5 72.19(6) . .
O5 Bi3 N5 99.15(7) . .
O5 Bi3 N5 78.92(7) 2_757 .
N5 Bi3 N5 144.38(12) 2_757 .
C80 O5 Bi3 132.60(15) . .
C78 N5 C77 110.2(3) . .
C78 N5 C79 109.9(2) . .
C77 N5 C79 109.9(2) . .
C78 N5 Bi3 111.79(19) . .
C77 N5 Bi3 104.52(17) . .
C79 N5 Bi3 110.40(15) . .
C74 C73 C74 121.7(4) 2_757 .
C74 C73 Bi3 119.2(2) 2_757 .
C74 C73 Bi3 119.2(2) . .
C73 C74 C75 118.2(4) . .
C73 C74 C77 118.3(3) . .
C75 C74 C77 123.5(4) . .
C76 C75 C74 120.4(5) . .
C75 C76 C75 121.2(5) . 2_757
N5 C77 C74 110.7(2) . .
O5 C80 C81 121.8(2) . .
O5 C80 C85 119.1(2) . .
C81 C80 C85 119.1(2) . .
C82 C81 C80 119.0(3) . .
C82 C81 C86 120.8(2) . .
C80 C81 C86 120.2(2) . .
C83 C82 C81 121.8(3) . .
C82 C83 C84 119.4(3) . .
C85 C84 C83 121.3(3) . .
C84 C85 C80 119.5(2) . .
C84 C85 C89 122.8(2) . .
C80 C85 C89 117.7(2) . .
C87B C86 C81 111.4(4) . .
C88 C86 C81 115.2(3) . .
C87B C86 C88B 117.2(6) . .
C81 C86 C88B 109.4(4) . .
C88 C86 C87 111.4(4) . .
C81 C86 C87 112.9(3) . .
C85 C89 C90 109.7(2) . .
C85 C89 C91 113.9(2) . .
C90 C89 C91 110.7(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 C1 2.197(2) .
Bi1 O1 2.2969(16) .
Bi1 O2 2.3000(16) .
Bi1 N2 2.533(2) .
Bi1 N1 2.555(2) .
O1 C13 1.333(3) .
O2 C25 1.334(3) .
N1 C7 1.480(3) .
N1 C9 1.482(3) .
N1 C8 1.483(3) .
N2 C12 1.476(3) .
N2 C10 1.482(3) .
N2 C11 1.487(3) .
C1 C6 1.385(3) .
C1 C2 1.392(3) .
C2 C3 1.384(4) .
C2 C10 1.507(4) .
C3 C4 1.386(4) .
C4 C5 1.393(4) .
C5 C6 1.394(3) .
C6 C7 1.509(4) .
C13 C14 1.415(3) .
C13 C18 1.417(3) .
C14 C15 1.388(3) .
C14 C19 1.519(4) .
C15 C16 1.386(4) .
C16 C17 1.378(4) .
C17 C18 1.392(3) .
C18 C22 1.516(4) .
C19 C21 1.529(4) .
C19 C20 1.536(4) .
C22 C24 1.514(4) .
C22 C23 1.527(4) .
C25 C26 1.419(3) .
C25 C30 1.420(3) .
C26 C27 1.399(3) .
C26 C31 1.510(4) .
C27 C28 1.372(4) .
C28 C29 1.384(4) .
C29 C30 1.382(4) .
C30 C34 1.520(4) .
C31 C33 1.529(4) .
C31 C32 1.534(3) .
C34 C35 1.526(4) .
C34 C36 1.529(4) .
Bi2 C37 2.183(3) .
Bi2 O3 2.2732(18) .
Bi2 O4 2.3031(17) .
Bi2 N3 2.488(2) .
Bi2 N4 2.577(2) .
O3 C49 1.327(3) .
O4 C61 1.330(3) .
N3 C45 1.479(3) .
N3 C43 1.479(3) .
N3 C44 1.485(3) .
N4 C48 1.470(3) .
N4 C47 1.471(4) .
N4 C46 1.486(4) .
C37 C42 1.381(4) .
C37 C38 1.387(4) .
C38 C39 1.397(4) .
C38 C46 1.504(4) .
C39 C40 1.379(5) .
C40 C41 1.383(5) .
C41 C42 1.388(4) .
C42 C43 1.499(4) .
C49 C50 1.415(4) .
C49 C54 1.421(4) .
C50 C51 1.392(4) .
C50 C55 1.520(4) .
C51 C52 1.391(4) .
C52 C53 1.370(4) .
C53 C54 1.390(4) .
C54 C58 1.518(4) .
C55 C57 1.520(4) .
C55 C56 1.531(4) .
C58 C60 1.515(5) .
C58 C59 1.519(4) .
C61 C66 1.408(4) .
C61 C62 1.431(3) .
C62 C63 1.377(4) .
C62 C67 1.515(4) .
C63 C64 1.380(4) .
C64 C65 1.388(4) .
C65 C66 1.389(4) .
C66 C70 1.524(4) .
C67 C69 1.525(4) .
C67 C68 1.528(4) .
C70 C72 1.521(4) .
C70 C71 1.528(4) .
Bi3 C73 2.193(4) .
Bi3 O5 2.2961(17) .
Bi3 O5 2.2962(17) 2_757
Bi3 N5 2.511(2) 2_757
Bi3 N5 2.511(2) .
O5 C80 1.333(3) .
N5 C78 1.476(4) .
N5 C77 1.480(4) .
N5 C79 1.484(3) .
C73 C74 1.382(4) 2_757
C73 C74 1.382(4) .
C74 C75 1.392(5) .
C74 C77 1.503(5) .
C75 C76 1.359(5) .
C76 C75 1.359(5) 2_757
C80 C81 1.415(3) .
C80 C85 1.419(4) .
C81 C82 1.388(4) .
C81 C86 1.515(4) .
C82 C83 1.374(4) .
C83 C84 1.387(4) .
C84 C85 1.380(4) .
C85 C89 1.516(4) .
C86 C87B 1.377(8) .
C86 C88 1.479(6) .
C86 C88B 1.563(7) .
C86 C87 1.575(6) .
C89 C90 1.526(4) .
C89 C91 1.531(4) .
