#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/33/29/4332992.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided the Crystal Eye server at
# http://wwmm.ch.cam.ac.uk/crystaleye/, created by Nick Day at the
# Peter Murray-Rust laboratory.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_4332992
loop_
_publ_author_name
'Roggan, Stefan'
'Limberg, Christian'
'Ziemer, Burkhard'
'Siemons, Maike'
'Simon, Ulrich'
_publ_section_title
;
 Reactivity and Properties of
 [−O−BiIII...OMo−]nChains
;
_journal_issue                   22
_journal_name_full               'Inorganic Chemistry'
_journal_page_first              9020
_journal_page_last               9031
_journal_paper_doi               10.1021/ic061198c
_journal_volume                  45
_journal_year                    2006
_chemical_formula_moiety         'C14 H15 Bi1 O1'
_chemical_formula_sum            'C14 H15 Bi O'
_chemical_formula_weight         816.48
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.8069(7)
_cell_length_b                   8.4987(6)
_cell_length_c                   21.1668(10)
_cell_measurement_reflns_used    5000
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      28.0
_cell_measurement_theta_min      4.0
_cell_volume                     2483.7(2)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.978
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0250
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            3344
_diffrn_reflns_theta_full        29.37
_diffrn_reflns_theta_max         29.37
_diffrn_reflns_theta_min         3.41
_exptl_absorpt_coefficient_mu    14.173
_exptl_absorpt_correction_T_max  0.1094
_exptl_absorpt_correction_T_min  0.0702
_exptl_absorpt_correction_type   numerical
_exptl_crystal_density_diffrn    2.183
_exptl_crystal_density_method    none
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.28
_refine_diff_density_max         1.706
_refine_diff_density_min         -1.962
_refine_diff_density_rms         0.155
_refine_ls_extinction_coef       0.00037(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3344
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.997
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0278
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0264P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0494
_reflns_number_gt                2564
_reflns_number_total             3344
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            ic061198csup3.cif
_cod_data_source_block           d:\x-data\rogg45
_cod_original_formula_sum        'C14 H15 Bi1 O1'
_cod_database_code               4332992
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, 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
C1 C 0.0801(4) 0.1999(5) 0.33154(18) 0.0133(8) Uani 1 1 d .
C2 C 0.0582(3) 0.1714(5) 0.39563(19) 0.0142(8) Uani 1 1 d .
C3 C 0.1269(4) 0.2106(6) 0.4412(2) 0.0194(9) Uani 1 1 d .
H3 H 0.1130 0.1902 0.4844 0.023 Uiso 1 1 calc R
C4 C 0.2148(4) 0.2786(6) 0.4256(2) 0.0214(10) Uani 1 1 d .
H4 H 0.2607 0.3028 0.4576 0.026 Uiso 1 1 calc R
C5 C 0.2357(4) 0.3111(7) 0.3625(2) 0.0225(10) Uani 1 1 d .
H5 H 0.2950 0.3602 0.3512 0.027 Uiso 1 1 calc R
C6 C 0.1685(4) 0.2708(6) 0.3163(2) 0.0172(8) Uani 1 1 d .
H6 H 0.1831 0.2919 0.2733 0.021 Uiso 1 1 calc R
C7 C -0.0369(4) 0.1012(6) 0.41637(19) 0.0198(10) Uani 1 1 d .
H7A H -0.0323 -0.0139 0.4155 0.024 Uiso 1 1 calc R
H7B H -0.0884 0.1356 0.3877 0.024 Uiso 1 1 calc R
H7C H -0.0518 0.1361 0.4594 0.024 Uiso 1 1 calc R
C8 C 0.0813(3) 0.0527(5) 0.18241(18) 0.0125(8) Uani 1 1 d .
C9 C 0.0593(3) 0.0637(5) 0.11718(18) 0.0143(8) Uani 1 1 d .
C10 C 0.1275(4) 0.0079(6) 0.0741(2) 0.0213(10) Uani 1 1 d .
H10 H 0.1151 0.0187 0.0302 0.026 Uiso 1 1 calc R
C11 C 0.2127(4) -0.0628(7) 0.0934(2) 0.0253(11) Uani 1 1 d .
H11 H 0.2573 -0.1018 0.0630 0.030 Uiso 1 1 calc R
C12 C 0.2328(4) -0.0763(7) 0.1573(2) 0.0225(10) Uani 1 1 d .
H12 H 0.2910 -0.1252 0.1710 0.027 Uiso 1 1 calc R
C13 C 0.1671(4) -0.0178(5) 0.20135(19) 0.0162(8) Uani 1 1 d .
H13 H 0.1813 -0.0264 0.2451 0.019 Uiso 1 1 calc R
C14 C -0.0350(4) 0.1266(6) 0.09424(19) 0.0210(10) Uani 1 1 d .
H14A H -0.0482 0.2278 0.1147 0.025 Uiso 1 1 calc R
H14B H -0.0868 0.0521 0.1045 0.025 Uiso 1 1 calc R
H14C H -0.0321 0.1414 0.0484 0.025 Uiso 1 1 calc R
O O 0.0115(2) 0.3824(3) 0.20916(13) 0.0154(6) Uani 1 1 d D
H1 H 0.043(4) 0.365(6) 0.1763(17) 0.019 Uiso 1 1 d D
Bi Bi -0.026511(10) 0.138844(16) 0.254679(5) 0.01129(5) Uani 1 1 d .
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
C6 C1 C2 118.9(4) . .
C6 C1 Bi 120.2(3) . .
C2 C1 Bi 120.9(3) . .
C3 C2 C1 118.6(4) . .
C3 C2 C7 119.1(4) . .
C1 C2 C7 122.3(4) . .
C4 C3 C2 122.0(4) . .
C4 C3 H3 119.0 . .
C2 C3 H3 119.0 . .
C3 C4 C5 119.6(4) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
C6 C5 C4 119.2(5) . .
C6 C5 H5 120.4 . .
C4 C5 H5 120.4 . .
C5 C6 C1 121.7(4) . .
C5 C6 H6 119.1 . .
C1 C6 H6 119.1 . .
C2 C7 H7A 109.5 . .
C2 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C2 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
C13 C8 C9 119.6(4) . .
C13 C8 Bi 120.5(3) . .
C9 C8 Bi 119.9(3) . .
C10 C9 C8 118.0(4) . .
C10 C9 C14 120.0(4) . .
C8 C9 C14 121.9(4) . .
C11 C10 C9 122.1(4) . .
C11 C10 H10 119.0 . .
C9 C10 H10 119.0 . .
C10 C11 C12 119.6(5) . .
C10 C11 H11 120.2 . .
C12 C11 H11 120.2 . .
C11 C12 C13 119.6(5) . .
C11 C12 H12 120.2 . .
C13 C12 H12 120.2 . .
C8 C13 C12 121.2(4) . .
C8 C13 H13 119.4 . .
C12 C13 H13 119.4 . .
C9 C14 H14A 109.5 . .
C9 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C9 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
Bi O Bi 135.61(13) 4 .
Bi O H1 113(4) 4 .
Bi O H1 108(4) . .
C8 Bi C1 97.65(16) . .
C8 Bi O 81.94(12) . 4_545
C1 Bi O 85.39(13) . 4_545
C8 Bi O 81.96(12) . .
C1 Bi O 86.98(13) . .
O Bi O 161.09(3) 4_545 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C6 1.399(7) .
C1 C2 1.411(5) .
C1 Bi 2.255(4) .
C2 C3 1.394(6) .
C2 C7 1.507(7) .
C3 C4 1.385(7) .
C3 H3 0.9500 .
C4 C5 1.393(7) .
C4 H4 0.9500 .
C5 C6 1.390(7) .
C5 H5 0.9500 .
C6 H6 0.9500 .
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C7 H7C 0.9800 .
C8 C13 1.387(6) .
C8 C9 1.417(5) .
C8 Bi 2.256(4) .
C9 C10 1.394(6) .
C9 C14 1.489(7) .
C10 C11 1.382(8) .
C10 H10 0.9500 .
C11 C12 1.386(7) .
C11 H11 0.9500 .
C12 C13 1.392(6) .
C12 H12 0.9500 .
C13 H13 0.9500 .
C14 H14A 0.9800 .
C14 H14B 0.9800 .
C14 H14C 0.9800 .
O Bi 2.319(3) 4
O Bi 2.343(3) .
O H1 0.83(4) .
Bi O 2.319(3) 4_545
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
_geom_torsion_site_symmetry_4
C6 C1 C2 C3 -1.9(6) . .
Bi C1 C2 C3 179.7(3) . .
C6 C1 C2 C7 177.7(4) . .
Bi C1 C2 C7 -0.7(6) . .
C1 C2 C3 C4 1.0(7) . .
C7 C2 C3 C4 -178.6(5) . .
C2 C3 C4 C5 0.8(8) . .
C3 C4 C5 C6 -1.7(8) . .
C4 C5 C6 C1 0.7(8) . .
C2 C1 C6 C5 1.1(7) . .
Bi C1 C6 C5 179.5(4) . .
C13 C8 C9 C10 -2.5(7) . .
Bi C8 C9 C10 -179.4(3) . .
C13 C8 C9 C14 175.1(5) . .
Bi C8 C9 C14 -1.9(6) . .
C8 C9 C10 C11 2.8(7) . .
C14 C9 C10 C11 -174.8(5) . .
C9 C10 C11 C12 -1.4(9) . .
C10 C11 C12 C13 -0.4(9) . .
C9 C8 C13 C12 0.8(7) . .
Bi C8 C13 C12 177.8(4) . .
C11 C12 C13 C8 0.6(8) . .
C13 C8 Bi C1 30.7(4) . .
C9 C8 Bi C1 -152.4(3) . .
C13 C8 Bi O -53.5(3) . 4_545
C9 C8 Bi O 123.4(3) . 4_545
C13 C8 Bi O 116.5(4) . .
C9 C8 Bi O -66.6(3) . .
C6 C1 Bi C8 39.7(4) . .
C2 C1 Bi C8 -141.9(3) . .
C6 C1 Bi O 120.9(4) . 4_545
C2 C1 Bi O -60.7(3) . 4_545
C6 C1 Bi O -41.8(4) . .
C2 C1 Bi O 136.6(4) . .
Bi O Bi C8 -145.3(2) 4 .
Bi O Bi C1 -47.1(2) 4 .
Bi O Bi O -113.4(3) 4 4_545
