#------------------------------------------------------------------------------
#$Date: 2016-03-21 07:39:14 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178575 $
#$URL: svn://www.crystallography.net/cod/cif/4/06/85/4068551.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_4068551
loop_
_publ_author_name
'Breunig, Hans J.'
'Haddad, Nawja'
'Lork, Enno'
'Mehring, Michael'
'Mügge, Clemens'
'Nolde, Christof'
'Raţ, Ciprian I.'
'Schürmann, Markus'
_publ_section_title
;
 Novel Sterically Congested Monoorganobismuth(III) Compounds: Synthesis,
 Structure, and Bismuth−Arene π Interaction in ArBiXY (X, Y = Br,
 I, OH, 2,6-Mes2-4-t-Bu-C6H2PHO2)
;
_journal_issue                   4
_journal_name_full               Organometallics
_journal_page_first              1202
_journal_paper_doi               10.1021/om800934c
_journal_volume                  28
_journal_year                    2009
_chemical_formula_moiety         'C56 H66 Bi2 Br4'
_chemical_formula_sum            'C56 H66 Bi2 Br4'
_chemical_formula_weight         1476.69
_chemical_melting_point          484.0(10)
_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           SHELXL-97
_cell_angle_alpha                92.1152(12)
_cell_angle_beta                 95.2567(13)
_cell_angle_gamma                106.5419(14)
_cell_formula_units_Z            1
_cell_length_a                   8.9597(3)
_cell_length_b                   11.1881(3)
_cell_length_c                   14.1175(6)
_cell_measurement_reflns_used    9742
_cell_measurement_temperature    173(1)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      3.37
_cell_volume                     1347.95(8)
_computing_cell_refinement
;
DENZO & SCALEPACK (Otwinowski & Minor, 1997)
;
_computing_data_collection       'COLLECT (Nonius, 1998)'
_computing_data_reduction
;
DENZO & SCALEPACK
;
_computing_molecular_graphics    'SHELXTL-Plus (Sheldrick, 1991)'
_computing_publication_material  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      173(1)
_diffrn_detector_area_resol_mean '19 vertical, 18 horizontal'
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method
;
 3 sets at different κ-angles and 250 frames via ω-rotation 
(Δ/ω=1°) at two times 60s per frame
;
_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  0.041
_diffrn_reflns_av_sigmaI/netI    0.1144
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9742
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.37
_diffrn_standards_decay_%        0
_diffrn_standards_number         none
_exptl_absorpt_coefficient_mu    9.517
_exptl_absorpt_correction_T_max  0.648
_exptl_absorpt_correction_T_min  0.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SCALEPACK (Otwinowski & Minor, 1997)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.967
_refine_diff_density_min         -0.842
_refine_diff_density_rms         0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     289
_refine_ls_number_reflns         4545
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.011
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0103P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0770
_refine_ls_wR_factor_ref         0.0833
_reflns_number_gt                3318
_reflns_number_total             4545
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om800934c_si_002.cif
_cod_data_source_block           compound3
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '483-485k' was changed to '484.0(10)'
- the average value was taken and precision was
estimated.

'_geom_bond_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (4
times).

'_geom_angle_publ_flag' value 'Y' changed to 'y' according
to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary
named 'cif_core.dic' version 2.4.2 from 2011-04-26 (6 times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not determined' 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        1347.94(8)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4068551
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
Bi1 Bi -0.59373(4) -0.14123(3) -0.12803(3) 0.02248(13) Uani 1 1 d .
Br1 Br -0.47772(12) -0.29344(8) -0.22844(8) 0.0391(3) Uani 1 1 d .
Br2 Br -0.31698(10) -0.04632(7) -0.02580(7) 0.0275(2) Uani 1 1 d .
C1 C -0.5975(9) 0.0065(7) -0.2333(6) 0.020(2) Uani 1 1 d .
C2 C -0.7390(9) -0.0327(7) -0.2929(6) 0.017(2) Uani 1 1 d .
C3 C -0.7810(9) 0.0463(7) -0.3536(7) 0.024(2) Uani 1 1 d .
H3 H -0.8757 0.0175 -0.3920 0.029 Uiso 1 1 calc R
C4 C -0.6894(10) 0.1685(7) -0.3611(6) 0.023(2) Uani 1 1 d .
C5 C -0.5489(10) 0.2045(7) -0.3009(6) 0.022(2) Uani 1 1 d .
H5 H -0.4840 0.2854 -0.3033 0.027 Uiso 1 1 calc R
C6 C -0.5004(9) 0.1283(7) -0.2384(6) 0.019(2) Uani 1 1 d .
C7 C -0.7404(10) 0.2559(7) -0.4297(7) 0.024(2) Uani 1 1 d .
C8 C -0.7639(12) 0.1961(8) -0.5312(7) 0.047(3) Uani 1 1 d .
H8A H -0.8393 0.1152 -0.5343 0.071 Uiso 1 1 calc R
H8B H -0.6661 0.1875 -0.5485 0.071 Uiso 1 1 calc R
H8C H -0.8011 0.2480 -0.5745 0.071 Uiso 1 1 calc R
C9 C -0.8983(11) 0.2687(9) -0.4063(8) 0.049(3) Uani 1 1 d .
H9A H -0.9753 0.1884 -0.4152 0.073 Uiso 1 1 calc R
H9B H -0.9295 0.3254 -0.4478 0.073 Uiso 1 1 calc R
H9C H -0.8894 0.3004 -0.3413 0.073 Uiso 1 1 calc R
C10 C -0.6258(11) 0.3838(8) -0.4259(8) 0.057(3) Uani 1 1 d .
H10A H -0.5283 0.3773 -0.4453 0.085 Uiso 1 1 calc R
H10B H -0.6089 0.4209 -0.3619 0.085 Uiso 1 1 calc R
H10C H -0.6669 0.4350 -0.4680 0.085 Uiso 1 1 calc R
C11 C -0.8432(9) -0.1656(7) -0.2937(6) 0.021(2) Uani 1 1 d .
C12 C -0.9590(9) -0.2024(7) -0.2318(6) 0.019(2) Uani 1 1 d .
C13 C -1.0535(10) -0.3240(7) -0.2375(6) 0.026(2) Uani 1 1 d .
H13 H -1.1278 -0.3477 -0.1946 0.031 Uiso 1 1 calc R
C14 C -1.0403(10) -0.4126(7) -0.3062(7) 0.024(2) Uani 1 1 d .
C15 C -0.9258(10) -0.3754(7) -0.3662(7) 0.028(2) Uani 1 1 d .
H15 H -0.9146 -0.4344 -0.4110 0.034 Uiso 1 1 calc R
C16 C -0.8265(9) -0.2556(7) -0.3638(6) 0.022(2) Uani 1 1 d .
C17 C -0.9847(10) -0.1119(7) -0.1563(7) 0.029(2) Uani 1 1 d .
H17A H -0.9222 -0.0287 -0.1655 0.043 Uiso 1 1 calc R
H17B H -0.9549 -0.1350 -0.0942 0.043 Uiso 1 1 calc R
H17C H -1.0933 -0.1148 -0.1617 0.043 Uiso 1 1 calc R
C18 C -1.1503(11) -0.5427(8) -0.3144(8) 0.043(3) Uani 1 1 d .
H18A H -1.2562 -0.5388 -0.3165 0.065 Uiso 1 1 calc R
H18B H -1.1275 -0.5865 -0.2603 0.065 Uiso 1 1 calc R
H18C H -1.1376 -0.5860 -0.3717 0.065 Uiso 1 1 calc R
C19 C -0.7067(10) -0.2180(8) -0.4337(7) 0.033(2) Uani 1 1 d .
H19A H -0.6151 -0.1570 -0.4029 0.050 Uiso 1 1 calc R
H19B H -0.7497 -0.1828 -0.4869 0.050 Uiso 1 1 calc R
H19C H -0.6788 -0.2901 -0.4558 0.050 Uiso 1 1 calc R
C21 C -0.3410(10) 0.1794(7) -0.1839(7) 0.024(2) Uani 1 1 d .
C22 C -0.2147(10) 0.1407(7) -0.2146(6) 0.023(2) Uani 1 1 d .
C23 C -0.0652(10) 0.1935(7) -0.1679(7) 0.026(2) Uani 1 1 d .
H23 H 0.0178 0.1691 -0.1889 0.032 Uiso 1 1 calc R
C24 C -0.0353(9) 0.2811(7) -0.0914(6) 0.020(2) Uani 1 1 d .
C25 C -0.1595(10) 0.3203(7) -0.0635(7) 0.026(2) Uani 1 1 d .
H25 H -0.1415 0.3788 -0.0121 0.031 Uiso 1 1 calc R
C26 C -0.3119(9) 0.2739(7) -0.1110(7) 0.024(2) Uani 1 1 d .
C27 C -0.2404(10) 0.0442(7) -0.2957(7) 0.031(2) Uani 1 1 d .
H27A H -0.2971 0.0674 -0.3495 0.046 Uiso 1 1 calc R
H27B H -0.2994 -0.0355 -0.2768 0.046 Uiso 1 1 calc R
H27C H -0.1410 0.0391 -0.3128 0.046 Uiso 1 1 calc R
C28 C 0.1292(10) 0.3374(7) -0.0425(7) 0.036(3) Uani 1 1 d .
H28A H 0.1252 0.3846 0.0149 0.053 Uiso 1 1 calc R
H28B H 0.1916 0.3915 -0.0843 0.053 Uiso 1 1 calc R
H28C H 0.1750 0.2718 -0.0271 0.053 Uiso 1 1 calc R
C29 C -0.4386(10) 0.3290(7) -0.0840(7) 0.028(2) Uani 1 1 d .
H29A H -0.5356 0.2638 -0.0859 0.042 Uiso 1 1 calc R
H29B H -0.4503 0.3897 -0.1282 0.042 Uiso 1 1 calc R
H29C H -0.4105 0.3684 -0.0208 0.042 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'
Br Br -0.2901 2.4595 '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
_geom_angle_publ_flag
C1 Bi1 Br1 100.67(19) . y
C1 Bi1 Br2 102.6(2) . y
Br1 Bi1 Br2 90.47(3) . y
C1 Bi1 Br2 85.78(19) 2_455 y
Br1 Bi1 Br2 169.29(3) 2_455 y
Br2 Bi1 Br2 79.72(3) 2_455 y
C6 C1 C2 118.6(7) . ?
C6 C1 Bi1 132.1(6) . ?
C2 C1 Bi1 108.5(5) . ?
C3 C2 C1 120.5(7) . ?
C3 C2 C11 119.1(7) . ?
C1 C2 C11 120.3(7) . ?
C2 C3 C4 123.3(8) . ?
C3 C4 C5 114.7(8) . ?
C3 C4 C7 122.1(8) . ?
C5 C4 C7 123.1(7) . ?
C6 C5 C4 124.4(7) . ?
C5 C6 C1 118.5(8) . ?
C5 C6 C21 117.3(7) . ?
C1 C6 C21 124.1(8) . ?
C10 C7 C9 108.8(7) . ?
C10 C7 C8 109.2(8) . ?
C9 C7 C8 107.3(8) . ?
C10 C7 C4 113.6(8) . ?
C9 C7 C4 109.0(7) . ?
C8 C7 C4 108.7(7) . ?
C12 C11 C16 119.0(7) . ?
C12 C11 C2 122.8(7) . ?
C16 C11 C2 118.2(7) . ?
C13 C12 C11 120.3(7) . ?
C13 C12 C17 117.8(7) . ?
C11 C12 C17 122.0(7) . ?
C12 C13 C14 121.5(8) . ?
C15 C14 C13 117.6(7) . ?
C15 C14 C18 121.8(8) . ?
C13 C14 C18 120.5(8) . ?
C14 C15 C16 123.8(8) . ?
C15 C16 C11 117.8(8) . ?
C15 C16 C19 121.8(8) . ?
C11 C16 C19 120.4(7) . ?
C26 C21 C22 119.6(8) . ?
C26 C21 C6 121.3(7) . ?
C22 C21 C6 118.7(7) . ?
C23 C22 C21 118.9(8) . ?
C23 C22 C27 120.0(7) . ?
C21 C22 C27 121.1(8) . ?
C24 C23 C22 122.5(8) . ?
C23 C24 C25 118.0(8) . ?
C23 C24 C28 121.2(7) . ?
C25 C24 C28 120.8(8) . ?
C24 C25 C26 121.8(8) . ?
C21 C26 C25 118.9(8) . ?
C21 C26 C29 121.5(8) . ?
C25 C26 C29 119.5(7) . ?
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 C1 2.269(8) . y
Bi1 Br1 2.6626(9) . y
Bi1 Br2 2.6629(10) . y
Bi1 Br2 3.2707(9) 2_455 y
C1 C6 1.401(10) . ?
C1 C2 1.403(11) . ?
C2 C3 1.358(11) . ?
C2 C11 1.513(10) . ?
C3 C4 1.394(10) . ?
C4 C5 1.400(12) . ?
C4 C7 1.531(12) . ?
C5 C6 1.374(11) . ?
C6 C21 1.503(12) . ?
C7 C10 1.501(11) . ?
C7 C9 1.526(11) . ?
C7 C8 1.529(12) . ?
C11 C12 1.399(11) . ?
C11 C16 1.434(11) . ?
C12 C13 1.377(10) . ?
C12 C17 1.521(10) . ?
C13 C14 1.399(11) . ?
C14 C15 1.372(11) . ?
C14 C18 1.500(10) . ?
C15 C16 1.379(10) . ?
C16 C19 1.507(11) . ?
C21 C26 1.399(11) . ?
C21 C22 1.418(11) . ?
C22 C23 1.392(12) . ?
C22 C27 1.500(11) . ?
C23 C24 1.384(11) . ?
C24 C25 1.390(11) . ?
C24 C28 1.516(11) . ?
C25 C26 1.410(11) . ?
C26 C29 1.507(11) . ?
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_1
Br1 Bi1 C1 C6 -103.7(7) .
Br2 Bi1 C1 C6 -10.8(7) .
Br2 Bi1 C1 C6 67.7(7) 2_455
Br1 Bi1 C1 C2 86.7(5) .
Br2 Bi1 C1 C2 179.6(5) .
Br2 Bi1 C1 C2 -101.9(5) 2_455
C6 C1 C2 C3 -0.6(12) .
Bi1 C1 C2 C3 170.6(6) .
C6 C1 C2 C11 176.6(7) .
Bi1 C1 C2 C11 -12.2(9) .
C1 C2 C3 C4 0.2(13) .
C11 C2 C3 C4 -177.1(7) .
C2 C3 C4 C5 0.0(12) .
C2 C3 C4 C7 -179.6(8) .
C3 C4 C5 C6 0.2(12) .
C7 C4 C5 C6 179.8(8) .
C4 C5 C6 C1 -0.6(12) .
C4 C5 C6 C21 176.0(8) .
C2 C1 C6 C5 0.8(11) .
Bi1 C1 C6 C5 -167.9(6) .
C2 C1 C6 C21 -175.6(8) .
Bi1 C1 C6 C21 15.7(12) .
C3 C4 C7 C10 179.3(8) .
C5 C4 C7 C10 -0.3(12) .
C3 C4 C7 C9 57.8(10) .
C5 C4 C7 C9 -121.7(9) .
C3 C4 C7 C8 -58.8(10) .
C5 C4 C7 C8 121.6(9) .
C3 C2 C11 C12 -94.0(10) .
C1 C2 C11 C12 88.7(10) .
C3 C2 C11 C16 83.1(10) .
C1 C2 C11 C16 -94.1(10) .
C16 C11 C12 C13 1.0(12) .
C2 C11 C12 C13 178.2(8) .
C16 C11 C12 C17 -179.4(7) .
C2 C11 C12 C17 -2.2(13) .
C11 C12 C13 C14 -1.9(13) .
C17 C12 C13 C14 178.4(8) .
C12 C13 C14 C15 2.2(13) .
C12 C13 C14 C18 -176.7(8) .
C13 C14 C15 C16 -1.7(14) .
C18 C14 C15 C16 177.2(8) .
C14 C15 C16 C11 0.8(13) .
C14 C15 C16 C19 -177.6(9) .
C12 C11 C16 C15 -0.5(12) .
C2 C11 C16 C15 -177.7(7) .
C12 C11 C16 C19 178.0(8) .
C2 C11 C16 C19 0.7(12) .
C5 C6 C21 C26 71.2(11) .
C1 C6 C21 C26 -112.4(9) .
C5 C6 C21 C22 -101.6(9) .
C1 C6 C21 C22 74.8(11) .
C26 C21 C22 C23 3.2(12) .
C6 C21 C22 C23 176.1(8) .
C26 C21 C22 C27 -177.0(8) .
C6 C21 C22 C27 -4.0(12) .
C21 C22 C23 C24 1.2(12) .
C27 C22 C23 C24 -178.7(8) .
C22 C23 C24 C25 -2.6(12) .
C22 C23 C24 C28 -179.6(8) .
C23 C24 C25 C26 -0.3(12) .
C28 C24 C25 C26 176.8(8) .
C22 C21 C26 C25 -5.9(12) .
C6 C21 C26 C25 -178.6(8) .
C22 C21 C26 C29 172.5(8) .
C6 C21 C26 C29 -0.2(12) .
C24 C25 C26 C21 4.5(13) .
C24 C25 C26 C29 -173.9(8) .
