#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/30/36/4303658.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_4303658
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 H58 Bi Cl O2'
_chemical_formula_weight         767.25
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                78.5150(10)
_cell_angle_beta                 85.6060(10)
_cell_angle_gamma                72.4230(10)
_cell_formula_units_Z            2
_cell_length_a                   9.6368(5)
_cell_length_b                   13.9869(8)
_cell_length_c                   14.2872(8)
_cell_measurement_temperature    213(2)
_cell_volume                     1798.81(17)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector Bruker Apex'
_diffrn_measurement_method       'phi and omega 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  0.0810
_diffrn_reflns_av_sigmaI/netI    0.0678
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10587
_diffrn_reflns_theta_full        22.50
_diffrn_reflns_theta_max         22.50
_diffrn_reflns_theta_min         1.55
_exptl_absorpt_coefficient_mu    5.003
_exptl_absorpt_correction_T_max  0.8967
_exptl_absorpt_correction_T_min  0.3254
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            Red
_exptl_crystal_density_diffrn    1.417
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             780
_exptl_crystal_size_max          .52
_exptl_crystal_size_mid          .20
_exptl_crystal_size_min          .09
_refine_diff_density_max         1.117
_refine_diff_density_min         -1.477
_refine_diff_density_rms         0.120
_refine_ls_extinction_coef       0.0007(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4714
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0309
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.007
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0438P)²+0.5430P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0816
_reflns_number_gt                4448
_reflns_number_total             4714
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ic901134t_si_001_02.cif
_cod_data_source_block           w859m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
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               4303658
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Bi1 Bi 0.595244(17) 0.316730(12) 0.068232(12) 0.02650(12) Uani 1 1 d . . .
Cl1 Cl 0.67405(15) 0.47338(9) 0.05205(10) 0.0378(3) Uani 1 1 d . . .
O1 O 0.6631(4) 0.2302(2) 0.2030(2) 0.0304(8) Uani 1 1 d . . .
O2 O 0.7885(3) 0.2352(2) 0.0079(2) 0.0259(8) Uani 1 1 d . . .
C1 C 0.5622(5) 0.1910(4) 0.2619(3) 0.0262(11) Uani 1 1 d . . .
C2 C 0.5434(5) 0.0967(4) 0.2533(3) 0.0260(11) Uani 1 1 d . . .
C3 C 0.4293(5) 0.0680(4) 0.3061(3) 0.0274(11) Uani 1 1 d . . .
H3 H 0.4122 0.0081 0.2983 0.033 Uiso 1 1 calc R . .
C4 C 0.3400(5) 0.1240(4) 0.3698(3) 0.0279(11) Uani 1 1 d . . .
C5 C 0.3767(6) 0.2087(4) 0.3836(4) 0.0315(12) Uani 1 1 d . . .
H5 H 0.3239 0.2443 0.4296 0.038 Uiso 1 1 calc R . .
C6 C 0.4849(6) 0.2439(4) 0.3347(3) 0.0282(11) Uani 1 1 d . . .
C7 C 0.6436(6) 0.0230(4) 0.1914(4) 0.0293(12) Uani 1 1 d . . .
C8 C 0.6318(7) -0.0865(4) 0.2247(5) 0.0456(15) Uani 1 1 d . . .
H8A H 0.5392 -0.0892 0.2068 0.068 Uiso 1 1 calc R . .
H8B H 0.6404 -0.1051 0.2929 0.068 Uiso 1 1 calc R . .
H8C H 0.7084 -0.1333 0.1952 0.068 Uiso 1 1 calc R . .
C9 C 0.5967(7) 0.0563(5) 0.0882(4) 0.0513(16) Uani 1 1 d . . .
H9A H 0.6180 0.1191 0.0616 0.077 Uiso 1 1 calc R . .
H9B H 0.4940 0.0664 0.0852 0.077 Uiso 1 1 calc R . .
H9C H 0.6485 0.0047 0.0525 0.077 Uiso 1 1 calc R . .
C10 C 0.8032(7) 0.0145(5) 0.1992(5) 0.0518(16) Uani 1 1 d . . .
H10A H 0.8614 -0.0361 0.1643 0.078 Uiso 1 1 calc R . .
H10B H 0.8302 -0.0050 0.2651 0.078 Uiso 1 1 calc R . .
H10C H 0.8190 0.0792 0.1730 0.078 Uiso 1 1 calc R . .
C11 C 0.2201(6) 0.0855(4) 0.4265(4) 0.0288(12) Uani 1 1 d . . .
C12 C 0.1250(9) 0.0618(8) 0.3604(5) 0.087(3) Uani 1 1 d . . .
H12A H 0.0361 0.0567 0.3932 0.130 Uiso 1 1 calc R . .
H12B H 0.1753 -0.0017 0.3407 0.130 Uiso 1 1 calc R . .
H12C H 0.1032 0.1154 0.3052 0.130 Uiso 1 1 calc R . .
C13 C 0.1249(11) 0.1601(7) 0.4839(8) 0.116(5) Uani 1 1 d . . .
H13A H 0.0577 0.1296 0.5223 0.173 Uiso 1 1 calc R . .
H13B H 0.0718 0.2203 0.4415 0.173 Uiso 1 1 calc R . .
H13C H 0.1842 0.1780 0.5245 0.173 Uiso 1 1 calc R . .
C14 C 0.2907(9) -0.0148(7) 0.4928(6) 0.086(3) Uani 1 1 d . . .
H14A H 0.3544 -0.0040 0.5355 0.129 Uiso 1 1 calc R . .
H14B H 0.3456 -0.0642 0.4557 0.129 Uiso 1 1 calc R . .
H14C H 0.2165 -0.0395 0.5292 0.129 Uiso 1 1 calc R . .
C15 C 0.5282(7) 0.3335(4) 0.3615(4) 0.0375(14) Uani 1 1 d . . .
C16 C 0.4853(8) 0.4294(4) 0.2830(4) 0.0509(17) Uani 1 1 d . . .
H16A H 0.5010 0.4859 0.3049 0.076 Uiso 1 1 calc R . .
H16B H 0.3844 0.4450 0.2685 0.076 Uiso 1 1 calc R . .
H16C H 0.5437 0.4173 0.2266 0.076 Uiso 1 1 calc R . .
C17 C 0.6917(7) 0.3008(5) 0.3813(5) 0.0548(17) Uani 1 1 d . . .
H17A H 0.7458 0.2884 0.3235 0.082 Uiso 1 1 calc R . .
H17B H 0.7160 0.2395 0.4288 0.082 Uiso 1 1 calc R . .
H17C H 0.7155 0.3539 0.4040 0.082 Uiso 1 1 calc R . .
C18 C 0.4491(8) 0.3616(5) 0.4550(5) 0.0542(17) Uani 1 1 d . . .
H18A H 0.4844 0.4118 0.4745 0.081 Uiso 1 1 calc R . .
H18B H 0.4675 0.3017 0.5041 0.081 Uiso 1 1 calc R . .
H18C H 0.3463 0.3889 0.4444 0.081 Uiso 1 1 calc R . .
C19 C 0.8628(5) 0.2781(3) -0.0675(3) 0.0260(11) Uani 1 1 d . . .
C20 C 0.8174(5) 0.2895(4) -0.1621(3) 0.0270(11) Uani 1 1 d . . .
C21 C 0.8867(6) 0.3408(4) -0.2338(3) 0.0296(12) Uani 1 1 d . . .
H21 H 0.8540 0.3527 -0.2958 0.035 Uiso 1 1 calc R . .
C22 C 1.0018(5) 0.3754(4) -0.2192(3) 0.0267(11) Uani 1 1 d . . .
C23 C 1.0536(5) 0.3520(4) -0.1264(3) 0.0272(11) Uani 1 1 d . . .
H23 H 1.1343 0.3713 -0.1153 0.033 Uiso 1 1 calc R . .
C24 C 0.9898(5) 0.3010(3) -0.0495(3) 0.0245(11) Uani 1 1 d . . .
C25 C 1.0704(6) 0.2594(4) 0.0463(3) 0.0293(12) Uani 1 1 d . . .
C26 C 0.9852(7) 0.2977(5) 0.1329(4) 0.0458(15) Uani 1 1 d . . .
H26A H 0.9048 0.2697 0.1471 0.069 Uiso 1 1 calc R . .
H26B H 0.9492 0.3708 0.1191 0.069 Uiso 1 1 calc R . .
H26C H 1.0480 0.2766 0.1869 0.069 Uiso 1 1 calc R . .
C27 C 1.1097(8) 0.1424(5) 0.0650(5) 0.0494(17) Uani 1 1 d . . .
H27A H 1.1598 0.1151 0.1244 0.074 Uiso 1 1 calc R . .
H27B H 1.1715 0.1168 0.0141 0.074 Uiso 1 1 calc R . .
H27C H 1.0223 0.1224 0.0683 0.074 Uiso 1 1 calc R . .
C28 C 1.2142(7) 0.2861(6) 0.0429(5) 0.0568(18) Uani 1 1 d . . .
H28A H 1.1946 0.3589 0.0306 0.085 Uiso 1 1 calc R . .
H28B H 1.2761 0.2583 -0.0071 0.085 Uiso 1 1 calc R . .
H28C H 1.2620 0.2578 0.1030 0.085 Uiso 1 1 calc R . .
C29 C 0.7095(6) 0.2373(4) -0.1884(4) 0.0314(13) Uani 1 1 d . . .
C30 C 0.5568(6) 0.2735(4) -0.1459(4) 0.0353(13) Uani 1 1 d . . .
H30A H 0.5552 0.2393 -0.0806 0.053 Uiso 1 1 calc R . .
H30B H 0.4889 0.2580 -0.1818 0.053 Uiso 1 1 calc R . .
H30C H 0.5303 0.3458 -0.1483 0.053 Uiso 1 1 calc R . .
C31 C 0.6899(7) 0.2546(5) -0.2958(4) 0.0475(16) Uani 1 1 d . . .
H31A H 0.6415 0.3254 -0.3190 0.071 Uiso 1 1 calc R . .
H31B H 0.6324 0.2138 -0.3093 0.071 Uiso 1 1 calc R . .
H31C H 0.7835 0.2356 -0.3269 0.071 Uiso 1 1 calc R . .
C32 C 0.7740(6) 0.1218(4) -0.1552(4) 0.0374(13) Uani 1 1 d . . .
H32A H 0.8631 0.0980 -0.1899 0.056 Uiso 1 1 calc R . .
H32B H 0.7060 0.0877 -0.1669 0.056 Uiso 1 1 calc R . .
H32C H 0.7932 0.1074 -0.0881 0.056 Uiso 1 1 calc R . .
C33 C 1.0692(6) 0.4347(4) -0.3031(3) 0.0292(12) Uani 1 1 d . . .
C34 C 0.9708(10) 0.5421(5) -0.3274(6) 0.076(3) Uani 1 1 d . . .
H34A H 0.9535 0.5727 -0.2715 0.114 Uiso 1 1 calc R . .
H34B H 0.8800 0.5413 -0.3499 0.114 Uiso 1 1 calc R . .
H34C H 1.0162 0.5810 -0.3764 0.114 Uiso 1 1 calc R . .
C35 C 1.0847(11) 0.3847(7) -0.3911(5) 0.085(3) Uani 1 1 d . . .
H35A H 1.1463 0.4119 -0.4380 0.127 Uiso 1 1 calc R . .
H35B H 0.9904 0.3986 -0.4175 0.127 Uiso 1 1 calc R . .
H35C H 1.1269 0.3123 -0.3729 0.127 Uiso 1 1 calc R . .
C36 C 1.2193(9) 0.4351(8) -0.2797(6) 0.106(4) Uani 1 1 d . . .
H36A H 1.2650 0.4626 -0.3364 0.159 Uiso 1 1 calc R . .
H36B H 1.2769 0.3666 -0.2557 0.159 Uiso 1 1 calc R . .
H36C H 1.2113 0.4764 -0.2322 0.159 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'
Cl Cl 0.1484 0.1585 '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
O2 Bi1 O1 89.54(12) . . ?
O2 Bi1 Cl1 93.53(9) . . ?
O1 Bi1 Cl1 106.11(10) . . ?
C1 O1 Bi1 118.0(3) . . ?
C19 O2 Bi1 123.8(3) . . ?
O1 C1 C2 120.3(4) . . ?
O1 C1 C6 119.5(4) . . ?
C2 C1 C6 120.1(5) . . ?
C3 C2 C1 117.2(4) . . ?
C3 C2 C7 118.7(4) . . ?
C1 C2 C7 124.0(4) . . ?
C4 C3 C2 123.7(5) . . ?
C5 C4 C3 115.7(5) . . ?
C5 C4 C11 123.9(4) . . ?
C3 C4 C11 120.1(5) . . ?
C6 C5 C4 125.0(5) . . ?
C5 C6 C1 117.2(5) . . ?
C5 C6 C15 121.4(4) . . ?
C1 C6 C15 121.3(5) . . ?
C9 C7 C10 110.7(5) . . ?
C9 C7 C8 106.9(5) . . ?
C10 C7 C8 105.7(4) . . ?
C9 C7 C2 110.0(4) . . ?
C10 C7 C2 112.4(4) . . ?
C8 C7 C2 110.8(4) . . ?
C13 C11 C12 108.4(7) . . ?
C13 C11 C14 109.5(7) . . ?
C12 C11 C14 106.3(6) . . ?
C13 C11 C4 113.1(5) . . ?
C12 C11 C4 110.6(5) . . ?
C14 C11 C4 108.7(5) . . ?
C17 C15 C16 111.2(5) . . ?
C17 C15 C18 106.3(5) . . ?
C16 C15 C18 107.7(5) . . ?
C17 C15 C6 110.1(4) . . ?
C16 C15 C6 111.2(5) . . ?
C18 C15 C6 110.2(5) . . ?
O2 C19 C24 119.4(4) . . ?
O2 C19 C20 119.3(4) . . ?
C24 C19 C20 121.1(4) . . ?
C21 C20 C19 116.9(5) . . ?
C21 C20 C29 119.5(4) . . ?
C19 C20 C29 123.2(4) . . ?
C20 C21 C22 124.1(4) . . ?
C21 C22 C23 116.9(4) . . ?
C21 C22 C33 120.4(4) . . ?
C23 C22 C33 122.7(4) . . ?
C24 C23 C22 122.9(5) . . ?
C23 C24 C19 117.1(4) . . ?
C23 C24 C25 119.5(4) . . ?
C19 C24 C25 122.8(4) . . ?
C26 C25 C28 106.0(5) . . ?
C26 C25 C27 108.5(5) . . ?
C28 C25 C27 106.8(5) . . ?
C26 C25 C24 115.1(4) . . ?
C28 C25 C24 112.0(4) . . ?
C27 C25 C24 108.2(4) . . ?
C31 C29 C30 105.7(5) . . ?
C31 C29 C32 106.4(5) . . ?
C30 C29 C32 110.0(5) . . ?
C31 C29 C20 112.4(5) . . ?
C30 C29 C20 114.2(4) . . ?
C32 C29 C20 107.8(4) . . ?
C34 C33 C36 110.3(7) . . ?
C34 C33 C35 108.4(6) . . ?
C36 C33 C35 107.5(6) . . ?
C34 C33 C22 109.2(5) . . ?
C36 C33 C22 111.4(4) . . ?
C35 C33 C22 110.1(5) . . ?
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 O2 2.091(3) . ?
Bi1 O1 2.094(3) . ?
Bi1 Cl1 2.4915(13) . ?
O1 C1 1.404(6) . ?
O2 C19 1.385(6) . ?
C1 C2 1.414(7) . ?
C1 C6 1.427(7) . ?
C2 C3 1.400(7) . ?
C2 C7 1.551(7) . ?
C3 C4 1.393(7) . ?
C4 C5 1.386(8) . ?
C4 C11 1.530(7) . ?
C5 C6 1.371(7) . ?
C6 C15 1.557(7) . ?
C7 C9 1.515(8) . ?
C7 C10 1.518(8) . ?
C7 C8 1.547(7) . ?
C11 C13 1.500(9) . ?
C11 C12 1.511(9) . ?
C11 C14 1.525(9) . ?
C15 C17 1.534(9) . ?
C15 C16 1.538(9) . ?
C15 C18 1.546(8) . ?
C19 C24 1.410(7) . ?
C19 C20 1.416(7) . ?
C20 C21 1.379(7) . ?
C20 C29 1.543(8) . ?
C21 C22 1.381(7) . ?
C22 C23 1.395(7) . ?
C22 C33 1.535(7) . ?
C23 C24 1.394(7) . ?
C24 C25 1.544(7) . ?
C25 C26 1.529(7) . ?
C25 C28 1.536(8) . ?
C25 C27 1.535(8) . ?
C29 C31 1.523(8) . ?
C29 C30 1.525(8) . ?
C29 C32 1.535(8) . ?
C33 C34 1.504(9) . ?
C33 C36 1.511(9) . ?
C33 C35 1.533(9) . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30660754
