#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/36/2213684.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# 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_2213684
loop_
_publ_author_name
'Yong-Jing Wang'
'Jun Zhao'
'Zhen-Hua Dang'
'Li Xu'
_publ_section_title
Bis(μ-2-hydroxybenzoato-κ²O:O')bis[(2,2'-bipyridine-κ²N,N')bis(2-hydroxybenzoato-κ²O,O')bismuth(III)]
_journal_coeditor_code           BT2330
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              m1770
_journal_page_last               m1771
_journal_paper_doi               10.1107/S160053680701642X
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          '[Bi2 (C7 H5 O3)6 (C10 H8 N2)2]'
_chemical_formula_moiety         'C62 H46 Bi2 N4 O18'
_chemical_formula_sum            'C62 H46 Bi2 N4 O18'
_chemical_formula_weight         1552.98
_chemical_name_systematic
;
Bis(μ-2-hydroxybenzoato-κ²O:O')bis[(2,2'-bipyridine-κ²N,N')bis(2-
hydroxybenzoato-κ²O,O')bismuth(III)]
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 117.4720(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   21.4583(3)
_cell_length_b                   13.6698(2)
_cell_length_c                   21.60970(10)
_cell_measurement_reflns_used    14948
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.64
_cell_measurement_theta_min      1.83
_cell_volume                     5624.00(13)
_computing_cell_refinement       'SAINT (Bruker, 1997)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 1999)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0267
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14948
_diffrn_reflns_theta_full        25.64
_diffrn_reflns_theta_max         25.64
_diffrn_reflns_theta_min         1.83
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    6.330
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.486062
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.834
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             3024
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.813
_refine_diff_density_min         -1.257
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     388
_refine_ls_number_reflns         5322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0253
_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)+(0.0258P)²+23.4426P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0583
_refine_ls_wR_factor_ref         0.0632
_reflns_number_gt                4590
_reflns_number_total             5322
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt2330.cif
_cod_data_source_block           I
_cod_original_cell_volume        5624.00(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2213684
_cod_database_fobs_code          2213684
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
Bi Bi1 0.557548(7) -0.053031(12) -0.039024(7) 0.02992(6) Uani d . 1
C C1 0.5214(2) -0.3657(3) -0.0917(3) 0.0446(12) Uani d . 1
N N1 0.68538(18) -0.0770(3) 0.04387(18) 0.0349(8) Uani d . 1
O O1 0.50042(16) -0.1969(2) -0.12275(17) 0.0445(8) Uani d . 1
C C2 0.4803(3) -0.3989(5) -0.1598(4) 0.0662(16) Uani d . 1
O O4 0.58818(17) 0.0884(3) 0.05826(16) 0.0428(7) Uani d . 1
N N2 0.62695(18) -0.0854(3) -0.09692(17) 0.0318(8) Uani d . 1
O O2 0.58232(17) -0.2334(2) -0.01744(16) 0.0444(8) Uani d . 1
C C3 0.4740(4) -0.4984(6) -0.1734(5) 0.104(3) Uani d . 1
H H3A 0.4470 -0.5199 -0.2189 0.125 Uiso calc R 1
C C4 0.5059(5) -0.5651(5) -0.1225(7) 0.108(3) Uani d . 1
H H4A 0.5025 -0.6314 -0.1333 0.130 Uiso calc R 1
O O3 0.4454(3) -0.3395(4) -0.2132(3) 0.1076(19) Uani d . 1
H H3B 0.4530 -0.2826 -0.1998 0.161 Uiso calc R 1
C C5 0.5443(4) -0.5338(5) -0.0534(6) 0.095(3) Uani d . 1
H H5A 0.5638 -0.5798 -0.0178 0.113 Uiso calc R 1
C C6 0.5535(3) -0.4343(4) -0.0374(4) 0.0620(17) Uani d . 1
H H6A 0.5804 -0.4136 0.0084 0.074 Uiso calc R 1
O O6 0.6500(2) 0.2041(4) 0.16486(18) 0.0753(13) Uani d . 1
H H6B 0.6269 0.1566 0.1431 0.113 Uiso calc R 1
C C7 0.5352(2) -0.2600(3) -0.0758(2) 0.0357(10) Uani d . 1
O O7 0.48413(17) 0.0242(2) -0.14704(16) 0.0454(8) Uani d . 1
C C8 0.6552(2) 0.2260(3) 0.0570(2) 0.0364(10) Uani d . 1
O O8 0.45182(16) 0.1136(2) -0.08025(16) 0.0422(7) Uani d . 1
C C9 0.6689(2) 0.2569(4) 0.1239(3) 0.0491(12) Uani d . 1
O O5 0.61390(16) 0.1012(2) -0.02946(15) 0.0393(7) Uani d . 1
C C10 0.7060(3) 0.3428(5) 0.1511(3) 0.0734(19) Uani d . 1
H H10A 0.7147 0.3640 0.1952 0.088 Uiso calc R 1
O O9 0.36991(19) 0.2678(3) -0.13324(18) 0.0556(9) Uani d . 1
H H10B 0.3921 0.2278 -0.1027 0.083 Uiso calc R 1
C C11 0.7299(4) 0.3963(5) 0.1127(4) 0.083(2) Uani d . 1
H H11A 0.7540 0.4543 0.1310 0.099 Uiso calc R 1
C C12 0.7190(4) 0.3663(5) 0.0476(4) 0.0771(19) Uani d . 1
H H12A 0.7368 0.4024 0.0229 0.093 Uiso calc R 1
C C13 0.6815(3) 0.2823(4) 0.0198(3) 0.0546(13) Uani d . 1
H H13A 0.6733 0.2623 -0.0244 0.065 Uiso calc R 1
C C14 0.6168(2) 0.1345(3) 0.0270(2) 0.0340(9) Uani d . 1
C C15 0.4140(2) 0.1663(3) -0.1969(2) 0.0383(10) Uani d . 1
C C16 0.3771(2) 0.2473(4) -0.1911(2) 0.0420(11) Uani d . 1
C C17 0.3459(3) 0.3119(4) -0.2465(3) 0.0544(13) Uani d . 1
H H17A 0.3210 0.3653 -0.2427 0.065 Uiso calc R 1
C C18 0.3513(3) 0.2983(5) -0.3067(3) 0.0651(16) Uani d . 1
H H18A 0.3303 0.3428 -0.3431 0.078 Uiso calc R 1
C C19 0.3876(3) 0.2187(5) -0.3139(3) 0.0677(17) Uani d . 1
H H19A 0.3916 0.2097 -0.3545 0.081 Uiso calc R 1
C C20 0.4177(3) 0.1531(4) -0.2592(2) 0.0527(13) Uani d . 1
H H20A 0.4411 0.0987 -0.2641 0.063 Uiso calc R 1
C C21 0.4519(2) 0.0972(3) -0.1377(2) 0.0344(9) Uani d . 1
C C22 0.7282(2) -0.1021(3) 0.0166(2) 0.0337(9) Uani d . 1
C C23 0.7133(2) -0.0643(4) 0.1133(2) 0.0441(11) Uani d . 1
H H23A 0.6838 -0.0475 0.1324 0.053 Uiso calc R 1
C C24 0.7843(3) -0.0755(4) 0.1572(3) 0.0527(13) Uani d . 1
H H24A 0.8023 -0.0658 0.2050 0.063 Uiso calc R 1
C C25 0.8278(3) -0.1012(5) 0.1290(3) 0.0568(14) Uani d . 1
H H25A 0.8757 -0.1093 0.1576 0.068 Uiso calc R 1
C C26 0.7999(2) -0.1150(4) 0.0581(3) 0.0487(12) Uani d . 1
H H26A 0.8286 -0.1326 0.0383 0.058 Uiso calc R 1
C C27 0.6946(2) -0.1129(3) -0.0610(2) 0.0327(9) Uani d . 1
C C28 0.5949(3) -0.0908(4) -0.1671(2) 0.0432(11) Uani d . 1
H H28A 0.5481 -0.0719 -0.1916 0.052 Uiso calc R 1
C C29 0.6293(3) -0.1232(4) -0.2037(3) 0.0484(12) Uani d . 1
H H29A 0.6064 -0.1243 -0.2522 0.058 Uiso calc R 1
C C30 0.6978(3) -0.1540(4) -0.1674(3) 0.0501(12) Uani d . 1
H H30A 0.7213 -0.1781 -0.1911 0.060 Uiso calc R 1
C C31 0.7314(2) -0.1489(4) -0.0953(3) 0.0429(11) Uani d . 1
H H31A 0.7779 -0.1692 -0.0700 0.051 Uiso calc R 1
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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O7 Bi1 N2 . 81.88(11) y
O7 Bi1 O5 . 76.88(11) y
N2 Bi1 O5 . 78.22(11) y
O7 Bi1 N1 . 140.29(12) ?
N2 Bi1 N1 . 67.01(11) y
O5 Bi1 N1 . 73.19(11) y
O7 Bi1 O2 . 127.14(11) ?
N2 Bi1 O2 . 77.66(11) y
O5 Bi1 O2 . 142.33(11) ?
N1 Bi1 O2 . 70.90(11) y
O7 Bi1 O1 . 76.31(10) y
N2 Bi1 O1 . 72.50(11) y
O5 Bi1 O1 . 142.54(10) ?
N1 Bi1 O1 . 114.34(11) ?
O2 Bi1 O1 . 51.16(10) y
O7 Bi1 O4 . 105.02(10) ?
N2 Bi1 O4 . 123.59(10) ?
O5 Bi1 O4 . 51.00(9) y
N1 Bi1 O4 . 75.21(11) y
O2 Bi1 O4 . 126.92(10) ?
O1 Bi1 O4 . 163.90(10) ?
O7 Bi1 O8 5_655 137.59(10) ?
N2 Bi1 O8 5_655 138.97(11) ?
O5 Bi1 O8 5_655 115.41(10) ?
N1 Bi1 O8 5_655 79.84(10) y
O2 Bi1 O8 5_655 68.84(10) ?
O1 Bi1 O8 5_655 102.03(10) ?
O4 Bi1 O8 5_655 65.86(9) y
C2 C1 C6 . 119.3(5) ?
C2 C1 C7 . 121.4(5) ?
C6 C1 C7 . 119.2(5) ?
C23 N1 C22 . 118.6(4) ?
C23 N1 Bi1 . 123.8(3) ?
C22 N1 Bi1 . 117.5(3) ?
C7 O1 Bi1 . 92.5(3) ?
O3 C2 C3 . 117.2(7) ?
O3 C2 C1 . 123.1(6) ?
C3 C2 C1 . 119.6(7) ?
C14 O4 Bi1 . 86.9(2) ?
C27 N2 C28 . 119.3(4) ?
C27 N2 Bi1 . 121.1(3) ?
C28 N2 Bi1 . 118.8(3) ?
C7 O2 Bi1 . 95.5(3) ?
C4 C3 C2 . 121.9(8) ?
C4 C3 H3A . 119.0 ?
C2 C3 H3A . 119.0 ?
C3 C4 C5 . 119.5(7) ?
C3 C4 H4A . 120.3 ?
C5 C4 H4A . 120.3 ?
C2 O3 H3B . 109.5 ?
C6 C5 C4 . 120.6(8) ?
C6 C5 H5A . 119.7 ?
C4 C5 H5A . 119.7 ?
C5 C6 C1 . 118.9(7) ?
C5 C6 H6A . 120.6 ?
C1 C6 H6A . 120.6 ?
C9 O6 H6B . 109.5 ?
O2 C7 O1 . 120.5(4) ?
O2 C7 C1 . 119.9(4) ?
O1 C7 C1 . 119.6(4) ?
C21 O7 Bi1 . 110.6(3) ?
C9 C8 C13 . 118.4(4) ?
C9 C8 C14 . 121.2(4) ?
C13 C8 C14 . 120.3(4) ?
C21 O8 Bi1 5_655 152.4(3) ?
O6 C9 C10 . 117.8(5) ?
O6 C9 C8 . 122.3(5) ?
C10 C9 C8 . 119.9(5) ?
C14 O5 Bi1 . 101.3(3) ?
C11 C10 C9 . 119.8(6) ?
C11 C10 H10A . 120.1 ?
C9 C10 H10A . 120.1 ?
C16 O9 H10B . 109.5 ?
C10 C11 C12 . 121.6(6) ?
C10 C11 H11A . 119.2 ?
C12 C11 H11A . 119.2 ?
C13 C12 C11 . 119.1(6) ?
C13 C12 H12A . 120.5 ?
C11 C12 H12A . 120.5 ?
C12 C13 C8 . 121.2(5) ?
C12 C13 H13A . 119.4 ?
C8 C13 H13A . 119.4 ?
O4 C14 O5 . 120.6(4) ?
O4 C14 C8 . 119.8(4) ?
O5 C14 C8 . 119.6(4) ?
C20 C15 C16 . 118.3(4) ?
C20 C15 C21 . 119.6(4) ?
C16 C15 C21 . 122.0(4) ?
O9 C16 C17 . 116.7(5) ?
O9 C16 C15 . 123.7(4) ?
C17 C16 C15 . 119.6(5) ?
C18 C17 C16 . 121.0(5) ?
C18 C17 H17A . 119.5 ?
C16 C17 H17A . 119.5 ?
C17 C18 C19 . 120.7(5) ?
C17 C18 H18A . 119.7 ?
C19 C18 H18A . 119.7 ?
C20 C19 C18 . 118.6(5) ?
C20 C19 H19A . 120.7 ?
C18 C19 H19A . 120.7 ?
C19 C20 C15 . 121.8(5) ?
C19 C20 H20A . 119.1 ?
C15 C20 H20A . 119.1 ?
O8 C21 O7 . 122.6(4) ?
O8 C21 C15 . 118.9(4) ?
O7 C21 C15 . 118.5(4) ?
N1 C22 C26 . 121.7(4) ?
N1 C22 C27 . 116.3(4) ?
C26 C22 C27 . 122.0(4) ?
N1 C23 C24 . 122.3(5) ?
N1 C23 H23A . 118.9 ?
C24 C23 H23A . 118.9 ?
C25 C24 C23 . 118.8(5) ?
C25 C24 H24A . 120.6 ?
C23 C24 H24A . 120.6 ?
C24 C25 C26 . 119.5(5) ?
C24 C25 H25A . 120.2 ?
C26 C25 H25A . 120.2 ?
C25 C26 C22 . 119.0(5) ?
C25 C26 H26A . 120.5 ?
C22 C26 H26A . 120.5 ?
N2 C27 C31 . 121.0(4) ?
N2 C27 C22 . 116.9(4) ?
C31 C27 C22 . 122.1(4) ?
N2 C28 C29 . 122.2(5) ?
N2 C28 H28A . 118.9 ?
C29 C28 H28A . 118.9 ?
C30 C29 C28 . 118.9(5) ?
C30 C29 H29A . 120.5 ?
C28 C29 H29A . 120.5 ?
C29 C30 C31 . 119.5(4) ?
C29 C30 H30A . 120.2 ?
C31 C30 H30A . 120.2 ?
C30 C31 C27 . 119.0(4) ?
C30 C31 H31A . 120.5 ?
C27 C31 H31A . 120.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Bi1 O7 . 2.377(3) y
Bi1 N2 . 2.387(3) y
Bi1 O5 . 2.392(3) y
Bi1 N1 . 2.511(3) y
Bi1 O2 . 2.520(3) y
Bi1 O1 . 2.568(3) y
Bi1 O4 . 2.705(3) y
Bi1 O8 5_655 2.801(3) y
C1 C2 . 1.399(8) ?
C1 C6 . 1.409(8) ?
C1 C7 . 1.482(6) ?
N1 C23 . 1.345(6) ?
N1 C22 . 1.346(5) ?
O1 C7 . 1.278(5) y
C2 O3 . 1.325(8) y
C2 C3 . 1.385(9) ?
O4 C14 . 1.269(5) y
N2 C27 . 1.347(5) ?
N2 C28 . 1.347(5) ?
O2 C7 . 1.253(5) y
C3 C4 . 1.346(13) ?
C3 H3A . 0.9300 ?
C4 C5 . 1.398(13) ?
C4 H4A . 0.9300 ?
O3 H3B . 0.8200 ?
C5 C6 . 1.395(9) ?
C5 H5A . 0.9300 ?
C6 H6A . 0.9300 ?
O6 C9 . 1.342(6) y
O6 H6B . 0.8200 ?
O7 C21 . 1.283(5) y
C8 C9 . 1.401(6) ?
C8 C13 . 1.405(7) ?
C8 C14 . 1.473(6) y
O8 C21 . 1.262(5) y
O8 Bi1 5_655 2.801(3) ?
C9 C10 . 1.388(8) ?
O5 C14 . 1.277(5) y
C10 C11 . 1.370(10) ?
C10 H10A . 0.9300 ?
O9 C16 . 1.358(6) ?
O9 H10B . 0.8200 ?
C11 C12 . 1.377(10) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.371(8) ?
C12 H12A . 0.9300 ?
C13 H13A . 0.9300 ?
C15 C20 . 1.397(7) ?
C15 C16 . 1.400(7) ?
C15 C21 . 1.493(6) ?
C16 C17 . 1.386(7) ?
C17 C18 . 1.370(8) ?
C17 H17A . 0.9300 ?
C18 C19 . 1.389(9) ?
C18 H18A . 0.9300 ?
C19 C20 . 1.383(7) ?
C19 H19A . 0.9300 ?
C20 H20A . 0.9300 ?
C22 C26 . 1.389(6) ?
C22 C27 . 1.494(6) ?
C23 C24 . 1.383(7) ?
C23 H23A . 0.9300 ?
C24 C25 . 1.375(8) ?
C24 H24A . 0.9300 ?
C25 C26 . 1.377(7) ?
C25 H25A . 0.9300 ?
C26 H26A . 0.9300 ?
C27 C31 . 1.399(6) ?
C28 C29 . 1.381(6) ?
C28 H28A . 0.9300 ?
C29 C30 . 1.375(7) ?
C29 H29A . 0.9300 ?
C30 C31 . 1.384(7) ?
C30 H30A . 0.9300 ?
C31 H31A . 0.9300 ?
