#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/36/4303657.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_4303657
loop_
_publ_author_name
'Xiaodi Kou'
'Xiaoyu Wang'
'Daniel Mendoza-Espinosa'
'Lev N. Zakharov'
'Arnold L. Rheingold'
'William H. Watson'
'Kimberly A. Brien'
'L. Kasun Jayarathna'
'Tracy A. Hanna'
_publ_section_title
;
Bismuth Aryloxides
;
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              11002
_journal_page_last               11016
_journal_paper_doi               10.1021/ic901134t
_journal_volume                  48
_journal_year                    2009
_chemical_formula_sum            'C36 H51 Bi O3'
_chemical_formula_weight         740.75
_chemical_name_systematic
; 

 ? 

;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 108.751(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.545(3)
_cell_length_b                   28.528(6)
_cell_length_c                   10.836(2)
_cell_measurement_temperature    203(2)
_cell_volume                     3379.5(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_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  0.0261
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            37349
_diffrn_reflns_theta_full        27.00
_diffrn_reflns_theta_max         27.00
_diffrn_reflns_theta_min         1.99
_exptl_absorpt_coefficient_mu    5.249
_exptl_absorpt_correction_T_max  0.6789
_exptl_absorpt_correction_T_min  0.3020
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Rod
_exptl_crystal_F_000             1496
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.064
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     373
_refine_ls_number_reflns         7318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0198
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0267P)²+1.0750P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0476
_refine_ls_wR_factor_ref         0.0495
_reflns_number_gt                6470
_reflns_number_total             7318
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901134t_si_001_01.cif
_cod_data_source_block           tcu03
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               4303657
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'
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 0.371401(7) 0.167568(3) 0.413889(8) 0.03041(4) Uani 1 1 d . . .
O1 O 0.44456(15) 0.10390(6) 0.38508(16) 0.0356(4) Uani 1 1 d . . .
O2 O 0.19215(14) 0.14392(6) 0.34648(17) 0.0374(4) Uani 1 1 d . . .
O3 O 0.37260(16) 0.19791(6) 0.23650(16) 0.0371(4) Uani 1 1 d . . .
C1 C 0.5372(2) 0.09612(8) 0.3326(2) 0.0348(5) Uani 1 1 d . . .
C2 C 0.6588(2) 0.10440(9) 0.4079(3) 0.0401(6) Uani 1 1 d . . .
C3 C 0.7494(3) 0.09343(10) 0.3536(3) 0.0527(7) Uani 1 1 d . . .
H3 H 0.8319 0.0986 0.4023 0.063 Uiso 1 1 calc R . .
C4 C 0.7205(3) 0.07513(12) 0.2301(4) 0.0638(9) Uani 1 1 d . . .
H4 H 0.7830 0.0677 0.1951 0.077 Uiso 1 1 calc R . .
C5 C 0.6010(3) 0.06768(11) 0.1583(3) 0.0586(8) Uani 1 1 d . . .
H5 H 0.5826 0.0554 0.0737 0.070 Uiso 1 1 calc R . .
C6 C 0.5057(3) 0.07766(9) 0.2065(3) 0.0444(6) Uani 1 1 d . . .
C7 C 0.3743(3) 0.06717(11) 0.1311(3) 0.0538(7) Uani 1 1 d . . .
H7 H 0.3227 0.0890 0.1619 0.065 Uiso 1 1 calc R . .
C8 C 0.3425(4) 0.01824(14) 0.1593(5) 0.0850(12) Uani 1 1 d . . .
H8A H 0.3899 -0.0040 0.1274 0.128 Uiso 1 1 calc R . .
H8B H 0.2560 0.0127 0.1160 0.128 Uiso 1 1 calc R . .
H8C H 0.3611 0.0143 0.2525 0.128 Uiso 1 1 calc R . .
C9 C 0.3457(5) 0.0750(2) -0.0143(4) 0.145(3) Uani 1 1 d . . .
H9A H 0.3498 0.1082 -0.0313 0.217 Uiso 1 1 calc R . .
H9B H 0.2642 0.0634 -0.0602 0.217 Uiso 1 1 calc R . .
H9C H 0.4049 0.0583 -0.0442 0.217 Uiso 1 1 calc R . .
C10 C 0.6886(2) 0.12345(9) 0.5452(3) 0.0440(6) Uani 1 1 d . . .
H10 H 0.6266 0.1476 0.5432 0.053 Uiso 1 1 calc R . .
C11 C 0.6778(3) 0.08543(11) 0.6402(3) 0.0546(7) Uani 1 1 d . . .
H11A H 0.5961 0.0722 0.6104 0.082 Uiso 1 1 calc R . .
H11B H 0.6931 0.0990 0.7261 0.082 Uiso 1 1 calc R . .
H11C H 0.7372 0.0610 0.6445 0.082 Uiso 1 1 calc R . .
C12 C 0.8137(3) 0.14703(13) 0.5962(4) 0.0710(10) Uani 1 1 d . . .
H12A H 0.8773 0.1238 0.6051 0.107 Uiso 1 1 calc R . .
H12B H 0.8235 0.1611 0.6804 0.107 Uiso 1 1 calc R . .
H12C H 0.8198 0.1711 0.5354 0.107 Uiso 1 1 calc R . .
C13 C 0.1440(2) 0.10020(8) 0.3060(2) 0.0331(5) Uani 1 1 d . . .
C14 C 0.1617(2) 0.06301(8) 0.3935(2) 0.0356(5) Uani 1 1 d . . .
C15 C 0.1042(2) 0.02061(9) 0.3479(3) 0.0439(6) Uani 1 1 d . . .
H15 H 0.1146 -0.0047 0.4059 0.053 Uiso 1 1 calc R . .
C16 C 0.0327(3) 0.01490(10) 0.2203(3) 0.0498(7) Uani 1 1 d . . .
H16 H -0.0042 -0.0142 0.1914 0.060 Uiso 1 1 calc R . .
C17 C 0.0151(2) 0.05205(11) 0.1350(3) 0.0493(7) Uani 1 1 d . . .
H17 H -0.0348 0.0481 0.0480 0.059 Uiso 1 1 calc R . .
C18 C 0.0697(2) 0.09533(10) 0.1751(3) 0.0421(6) Uani 1 1 d . . .
C19 C 0.2349(3) 0.06771(9) 0.5362(3) 0.0432(6) Uani 1 1 d . . .
H19 H 0.2701 0.0997 0.5497 0.052 Uiso 1 1 calc R . .
C20 C 0.1508(3) 0.06298(13) 0.6204(3) 0.0651(9) Uani 1 1 d . . .
H20A H 0.1177 0.0314 0.6124 0.098 Uiso 1 1 calc R . .
H20B H 0.0842 0.0853 0.5912 0.098 Uiso 1 1 calc R . .
H20C H 0.1973 0.0692 0.7109 0.098 Uiso 1 1 calc R . .
C21 C 0.3404(3) 0.03315(12) 0.5797(3) 0.0615(8) Uani 1 1 d . . .
H21A H 0.3085 0.0017 0.5787 0.092 Uiso 1 1 calc R . .
H21B H 0.3919 0.0409 0.6673 0.092 Uiso 1 1 calc R . .
H21C H 0.3883 0.0348 0.5208 0.092 Uiso 1 1 calc R . .
C22 C 0.0437(3) 0.13747(12) 0.0856(3) 0.0612(9) Uani 1 1 d . . .
H22 H 0.1216 0.1548 0.1023 0.073 Uiso 1 1 calc R . .
C23 C -0.0459(4) 0.17019(13) 0.1201(5) 0.0974(17) Uani 1 1 d . . .
H23A H -0.1242 0.1546 0.1025 0.146 Uiso 1 1 calc R . .
H23B H -0.0563 0.1985 0.0679 0.146 Uiso 1 1 calc R . .
H23C H -0.0140 0.1783 0.2118 0.146 Uiso 1 1 calc R . .
C24 C -0.0008(4) 0.12436(18) -0.0581(4) 0.1132(19) Uani 1 1 d . . .
H24A H 0.0586 0.1039 -0.0769 0.170 Uiso 1 1 calc R . .
H24B H -0.0107 0.1526 -0.1106 0.170 Uiso 1 1 calc R . .
H24C H -0.0787 0.1082 -0.0786 0.170 Uiso 1 1 calc R . .
C25 C 0.4041(2) 0.24440(8) 0.2404(2) 0.0337(5) Uani 1 1 d . . .
C26 C 0.3183(2) 0.27939(9) 0.2410(2) 0.0383(5) Uani 1 1 d . . .
C27 C 0.3546(3) 0.32586(9) 0.2463(3) 0.0420(6) Uani 1 1 d . . .
H27 H 0.2978 0.3495 0.2460 0.050 Uiso 1 1 calc R . .
C28 C 0.4715(3) 0.33830(9) 0.2522(3) 0.0461(7) Uani 1 1 d . . .
H28 H 0.4945 0.3700 0.2576 0.055 Uiso 1 1 calc R . .
C29 C 0.5546(3) 0.30378(9) 0.2500(2) 0.0411(6) Uani 1 1 d . . .
H29 H 0.6341 0.3124 0.2534 0.049 Uiso 1 1 calc R . .
C30 C 0.5233(2) 0.25649(9) 0.2428(2) 0.0357(5) Uani 1 1 d . . .
C31 C 0.1910(3) 0.26668(10) 0.2407(3) 0.0515(7) Uani 1 1 d . . .
H31 H 0.1771 0.2331 0.2177 0.062 Uiso 1 1 calc R . .
C32 C 0.1790(4) 0.27379(14) 0.3757(4) 0.0792(11) Uani 1 1 d . . .
H32A H 0.2408 0.2554 0.4390 0.119 Uiso 1 1 calc R . .
H32B H 0.0984 0.2638 0.3748 0.119 Uiso 1 1 calc R . .
H32C H 0.1903 0.3067 0.3991 0.119 Uiso 1 1 calc R . .
C33 C 0.0922(3) 0.29520(14) 0.1406(4) 0.0740(10) Uani 1 1 d . . .
H33A H 0.0982 0.3278 0.1673 0.111 Uiso 1 1 calc R . .
H33B H 0.0122 0.2831 0.1350 0.111 Uiso 1 1 calc R . .
H33C H 0.1038 0.2927 0.0560 0.111 Uiso 1 1 calc R . .
C34 C 0.6122(2) 0.21839(9) 0.2357(3) 0.0411(6) Uani 1 1 d . . .
H34 H 0.5979 0.1915 0.2864 0.049 Uiso 1 1 calc R . .
C35 C 0.7471(3) 0.23203(12) 0.2955(4) 0.0683(9) Uani 1 1 d . . .
H35A H 0.7667 0.2567 0.2438 0.102 Uiso 1 1 calc R . .
H35B H 0.7981 0.2049 0.2969 0.102 Uiso 1 1 calc R . .
H35C H 0.7618 0.2432 0.3838 0.102 Uiso 1 1 calc R . .
C36 C 0.5851(3) 0.20168(14) 0.0965(3) 0.0733(10) Uani 1 1 d . . .
H36A H 0.5006 0.1914 0.0626 0.110 Uiso 1 1 calc R . .
H36B H 0.6388 0.1758 0.0945 0.110 Uiso 1 1 calc R . .
H36C H 0.5984 0.2272 0.0434 0.110 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'
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
_geom_angle_publ_flag
O1 Bi1 O2 94.06(7) . . ?
O1 Bi1 O3 95.74(6) . . ?
O2 Bi1 O3 96.35(7) . . ?
C1 O1 Bi1 127.66(14) . . ?
C13 O2 Bi1 131.39(14) . . ?
C25 O3 Bi1 116.56(13) . . ?
O1 C1 C2 119.8(2) . . ?
O1 C1 C6 118.1(2) . . ?
C2 C1 C6 122.0(2) . . ?
C3 C2 C1 117.8(3) . . ?
C3 C2 C10 122.1(2) . . ?
C1 C2 C10 120.1(2) . . ?
C4 C3 C2 121.2(3) . . ?
C5 C4 C3 119.9(3) . . ?
C4 C5 C6 122.1(3) . . ?
C5 C6 C1 117.1(3) . . ?
C5 C6 C7 122.5(3) . . ?
C1 C6 C7 120.4(3) . . ?
C8 C7 C6 110.2(3) . . ?
C8 C7 C9 111.2(4) . . ?
C6 C7 C9 112.3(3) . . ?
C2 C10 C12 113.8(3) . . ?
C2 C10 C11 111.4(2) . . ?
C12 C10 C11 110.0(3) . . ?
O2 C13 C14 121.1(2) . . ?
O2 C13 C18 117.5(2) . . ?
C14 C13 C18 121.2(2) . . ?
C15 C14 C13 118.1(2) . . ?
C15 C14 C19 119.1(2) . . ?
C13 C14 C19 122.7(2) . . ?
C16 C15 C14 121.6(3) . . ?
C15 C16 C17 119.7(3) . . ?
C16 C17 C18 121.2(3) . . ?
C17 C18 C13 118.1(2) . . ?
C17 C18 C22 121.9(3) . . ?
C13 C18 C22 119.9(2) . . ?
C14 C19 C21 112.9(2) . . ?
C14 C19 C20 110.3(2) . . ?
C21 C19 C20 110.8(3) . . ?
C18 C22 C24 113.2(3) . . ?
C18 C22 C23 109.8(3) . . ?
C24 C22 C23 111.7(3) . . ?
O3 C25 C26 120.3(2) . . ?
O3 C25 C30 119.0(2) . . ?
C26 C25 C30 120.7(2) . . ?
C27 C26 C25 118.3(2) . . ?
C27 C26 C31 120.6(2) . . ?
C25 C26 C31 121.0(2) . . ?
C28 C27 C26 121.8(2) . . ?
C27 C28 C29 119.4(2) . . ?
C28 C29 C30 121.6(3) . . ?
C29 C30 C25 118.2(2) . . ?
C29 C30 C34 122.0(2) . . ?
C25 C30 C34 119.8(2) . . ?
C26 C31 C32 110.7(3) . . ?
C26 C31 C33 112.1(3) . . ?
C32 C31 C33 109.4(3) . . ?
C30 C34 C36 110.5(2) . . ?
C30 C34 C35 114.2(2) . . ?
C36 C34 C35 111.0(3) . . ?
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 O1 2.0685(16) . ?
Bi1 O2 2.0735(16) . ?
Bi1 O3 2.1122(16) . ?
O1 C1 1.381(3) . ?
O2 C13 1.378(3) . ?
O3 C25 1.372(3) . ?
C1 C2 1.399(3) . ?
C1 C6 1.399(4) . ?
C2 C3 1.391(4) . ?
C2 C10 1.516(4) . ?
C3 C4 1.374(5) . ?
C4 C5 1.366(5) . ?
C5 C6 1.390(4) . ?
C6 C7 1.504(4) . ?
C7 C8 1.499(5) . ?
C7 C9 1.519(5) . ?
C10 C12 1.527(4) . ?
C10 C11 1.528(4) . ?
C13 C14 1.393(3) . ?
C13 C18 1.409(3) . ?
C14 C15 1.392(3) . ?
C14 C19 1.511(3) . ?
C15 C16 1.373(4) . ?
C16 C17 1.378(4) . ?
C17 C18 1.391(4) . ?
C18 C22 1.513(4) . ?
C19 C21 1.520(4) . ?
C19 C20 1.538(4) . ?
C22 C24 1.522(5) . ?
C22 C23 1.526(6) . ?
C25 C26 1.408(3) . ?
C25 C30 1.410(3) . ?
C26 C27 1.386(3) . ?
C26 C31 1.512(4) . ?
C27 C28 1.377(4) . ?
C28 C29 1.380(4) . ?
C29 C30 1.392(3) . ?
C30 C34 1.514(3) . ?
C31 C32 1.527(4) . ?
C31 C33 1.531(4) . ?
C34 C36 1.515(4) . ?
C34 C35 1.532(4) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660753
