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#$Date: 2025-08-22 01:24:23 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/11/44/7114414.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_7114414
loop_
_publ_author_name
'Thurston, John H.'
'Marlier, Elodie M.'
'Whitmire, Kenton H.'
_publ_section_title
;
 Towards a molecular model for bismuth(iii) subsalicylate. Synthesis and
 solid-state structure of [Bi(Hsal)3(bipy)(C7H8]2 and
 [Bi(Hsal)(sal)(1,10-phenanthroline)(C7H8]2
;
_journal_issue                   23
_journal_name_full               'Chemical Communications'
_journal_page_first              2834
_journal_paper_doi               10.1039/b209188g
_journal_year                    2002
_chemical_formula_moiety         Bi2(sal)2(salH)2(1,10-phenanthroline)2(tol)2
_chemical_formula_sum            'C66 H48 Bi2 N4 O12'
_chemical_formula_weight         1507.04
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_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                 107.167(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.022(2)
_cell_length_b                   24.530(5)
_cell_length_c                   12.195(3)
_cell_measurement_reflns_used    865
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      46.328
_cell_measurement_theta_min      4.822
_cell_volume                     2864.4(11)
_computing_cell_refinement       'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_data_collection       'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_data_reduction        'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_molecular_graphics    'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_publication_material  'SHELXTL 6.10 (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART 1K; CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0464
_diffrn_reflns_av_sigmaI/netI    0.0424
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12698
_diffrn_reflns_theta_full        23.28
_diffrn_reflns_theta_max         23.28
_diffrn_reflns_theta_min         1.66
_exptl_absorpt_coefficient_mu    6.204
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_correction_T_min  0.829181
_exptl_absorpt_correction_type   'empirical with SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.747
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'thin plate'
_exptl_crystal_F_000             1468
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.395
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.973
_refine_ls_hydrogen_treatment    'riding model'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4113
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.973
_refine_ls_R_factor_all          0.0422
_refine_ls_R_factor_gt           0.0281
_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)+(0.0328P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0616
_refine_ls_wR_factor_ref         0.0652
_reflns_number_gt                3167
_reflns_number_total             4113
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b209188g.txt
_cod_data_source_block           3
_cod_original_cell_volume        2864.3(10)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7114414
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Bi1 Bi -0.92349(2) 0.528156(8) -0.330547(18) 0.05090(10) Uani 1 1 d .
N1 N -0.6775(4) 0.48398(17) -0.2840(4) 0.0498(11) Uani 1 1 d .
C1 C -0.6535(6) 0.4402(3) -0.3377(5) 0.0641(16) Uani 1 1 d .
H1A H -0.7281 0.4245 -0.3931 0.077 Uiso 1 1 calc R
N2 N -0.7248(4) 0.57381(19) -0.1684(4) 0.0537(12) Uani 1 1 d .
C2 C -0.5217(7) 0.4160(3) -0.3157(6) 0.0791(19) Uani 1 1 d .
H2A H -0.5095 0.3853 -0.3565 0.095 Uiso 1 1 calc R
C3 C -0.4113(7) 0.4381(3) -0.2337(6) 0.0723(18) Uani 1 1 d .
H3A H -0.3230 0.4226 -0.2182 0.087 Uiso 1 1 calc R
C4 C -0.4323(6) 0.4841(2) -0.1735(5) 0.0570(16) Uani 1 1 d .
C5 C -0.3233(6) 0.5101(3) -0.0835(6) 0.0702(19) Uani 1 1 d .
H5A H -0.2331 0.4961 -0.0648 0.084 Uiso 1 1 calc R
C6 C -0.3476(6) 0.5526(3) -0.0279(5) 0.0705(18) Uani 1 1 d .
H6A H -0.2753 0.5676 0.0306 0.085 Uiso 1 1 calc R
C7 C -0.4832(5) 0.5762(3) -0.0553(5) 0.0578(15) Uani 1 1 d .
C8 C -0.5114(7) 0.6230(3) -0.0006(5) 0.0777(19) Uani 1 1 d .
H8A H -0.4402 0.6394 0.0568 0.093 Uiso 1 1 calc R
C9 C -0.6419(7) 0.6447(3) -0.0305(6) 0.083(2) Uani 1 1 d .
H9A H -0.6612 0.6761 0.0048 0.100 Uiso 1 1 calc R
C10 C -0.7454(6) 0.6186(3) -0.1155(5) 0.0686(17) Uani 1 1 d .
H10A H -0.8347 0.6335 -0.1364 0.082 Uiso 1 1 calc R
C11 C -0.5939(5) 0.5529(2) -0.1400(5) 0.0517(14) Uani 1 1 d .
C12 C -0.5688(5) 0.5059(2) -0.2009(5) 0.0497(14) Uani 1 1 d .
O21 O -1.2311(6) 0.6625(2) -0.1852(6) 0.127(2) Uani 1 1 d .
O22 O -1.0687(5) 0.59171(18) -0.2407(4) 0.0843(13) Uani 1 1 d .
O23 O -1.1712(4) 0.53162(19) -0.3700(4) 0.0742(12) Uani 1 1 d .
C21 C -1.3348(6) 0.6400(2) -0.2600(4) 0.107(3) Uani 1 1 d G
C22 C -1.4659(7) 0.6633(2) -0.2775(5) 0.115(3) Uani 1 1 d G
H22A H -1.4759 0.6942 -0.2364 0.138 Uiso 1 1 calc R
C23 C -1.5819(5) 0.6405(3) -0.3564(6) 0.128(4) Uani 1 1 d G
H23A H -1.6696 0.6561 -0.3681 0.154 Uiso 1 1 calc R
C24 C -1.5669(4) 0.5943(3) -0.4178(5) 0.123(3) Uani 1 1 d G
H24A H -1.6446 0.5791 -0.4706 0.147 Uiso 1 1 calc R
C25 C -1.4359(5) 0.5710(2) -0.4004(4) 0.089(3) Uani 1 1 d G
H25A H -1.4259 0.5401 -0.4415 0.106 Uiso 1 1 calc R
C26 C -1.3198(4) 0.5938(2) -0.3214(4) 0.080(2) Uani 1 1 d G
C27 C -1.1793(6) 0.5709(3) -0.3094(6) 0.0690(18) Uani 1 1 d .
O31 O -0.9352(4) 0.47371(16) -0.1990(3) 0.0632(10) Uani 1 1 d .
O32 O -0.9823(4) 0.45302(16) -0.4373(3) 0.0583(10) Uani 1 1 d .
O33 O -1.0911(5) 0.37915(19) -0.5048(4) 0.0925(15) Uani 1 1 d .
C31 C -1.0014(3) 0.42530(13) -0.2078(3) 0.0545(15) Uani 1 1 d G
C32 C -1.0106(4) 0.40584(18) -0.1033(3) 0.0638(16) Uani 1 1 d G
H32A H -0.9734 0.4260 -0.0367 0.077 Uiso 1 1 calc R
C33 C -1.0756(4) 0.35622(19) -0.0982(3) 0.082(2) Uani 1 1 d G
H33A H -1.0818 0.3432 -0.0283 0.098 Uiso 1 1 calc R
C34 C -1.1313(4) 0.32607(14) -0.1978(4) 0.088(2) Uani 1 1 d G
H34A H -1.1748 0.2929 -0.1944 0.106 Uiso 1 1 calc R
C35 C -1.1221(4) 0.34553(15) -0.3023(3) 0.0744(18) Uani 1 1 d G
H35A H -1.1594 0.3254 -0.3689 0.089 Uiso 1 1 calc R
C36 C -1.0571(4) 0.39515(16) -0.3074(3) 0.0532(14) Uani 1 1 d G
C37 C -1.0451(5) 0.4091(3) -0.4224(5) 0.0560(15) Uani 1 1 d .
C41 C -0.9561(9) 0.7495(3) -0.2438(14) 0.192(8) Uani 1 1 d GD
H41A H -1.0312 0.7327 -0.2967 0.231 Uiso 1 1 calc R
C42 C -0.9618(11) 0.7604(4) -0.1334(16) 0.209(9) Uani 1 1 d G
H42A H -1.0407 0.7509 -0.1124 0.251 Uiso 1 1 calc R
C43 C -0.8495(18) 0.7854(5) -0.0544(9) 0.183(5) Uani 1 1 d G
H43A H -0.8533 0.7927 0.0194 0.219 Uiso 1 1 calc R
C44 C -0.7316(12) 0.7996(3) -0.0858(11) 0.280(16) Uani 1 1 d G
H44A H -0.6564 0.8164 -0.0330 0.335 Uiso 1 1 calc R
C45 C -0.7259(8) 0.7888(4) -0.1962(14) 0.210(10) Uani 1 1 d GD
H45A H -0.6470 0.7983 -0.2173 0.253 Uiso 1 1 calc R
C46 C -0.8382(15) 0.7637(5) -0.2753(9) 0.39(3) Uani 1 1 d GD
C47 C -0.832(3) 0.7547(9) -0.356(3) 0.54(3) Uani 1 1 d D
H47A H -0.7433 0.7668 -0.3624 0.808 Uiso 1 1 calc R
H47B H -0.9058 0.7729 -0.4123 0.808 Uiso 1 1 calc R
H47C H -0.8402 0.7161 -0.3681 0.808 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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
O31 Bi1 O32 81.77(14) . .
O31 Bi1 O23 83.60(15) . .
O32 Bi1 O23 80.31(15) . .
O31 Bi1 O22 83.98(15) . .
O32 Bi1 O22 131.26(14) . .
O23 Bi1 O22 51.84(15) . .
O31 Bi1 N1 80.36(14) . .
O32 Bi1 N1 81.57(13) . .
O23 Bi1 N1 157.29(14) . .
O22 Bi1 N1 140.82(15) . .
O31 Bi1 N2 84.09(14) . .
O32 Bi1 N2 143.84(14) . .
O23 Bi1 N2 130.81(15) . .
O22 Bi1 N2 79.60(14) . .
N1 Bi1 N2 63.28(14) . .
O31 Bi1 O32 143.93(13) . 3_364
O32 Bi1 O32 65.59(15) . 3_364
O23 Bi1 O32 76.44(14) . 3_364
O22 Bi1 O32 105.68(13) . 3_364
N1 Bi1 O32 108.10(13) . 3_364
N2 Bi1 O32 131.48(13) . 3_364
O31 Bi1 C27 84.89(16) . .
O32 Bi1 C27 105.4(2) . .
O23 Bi1 C27 25.24(16) . .
O22 Bi1 C27 26.72(17) . .
N1 Bi1 C27 162.62(17) . .
N2 Bi1 C27 106.2(2) . .
O32 Bi1 C27 89.24(16) 3_364 .
C1 N1 C12 118.0(5) . .
C1 N1 Bi1 122.1(3) . .
C12 N1 Bi1 119.9(3) . .
N1 C1 C2 123.4(6) . .
C10 N2 C11 118.0(5) . .
C10 N2 Bi1 122.2(4) . .
C11 N2 Bi1 119.8(4) . .
C3 C2 C1 119.1(6) . .
C2 C3 C4 119.4(6) . .
C3 C4 C12 117.8(5) . .
C3 C4 C5 123.9(6) . .
C12 C4 C5 118.2(6) . .
C6 C5 C4 122.1(6) . .
C5 C6 C7 121.0(6) . .
C11 C7 C8 117.5(5) . .
C11 C7 C6 120.1(6) . .
C8 C7 C6 122.4(6) . .
C9 C8 C7 120.5(6) . .
C8 C9 C10 117.9(6) . .
N2 C10 C9 123.9(6) . .
N2 C11 C7 122.2(6) . .
N2 C11 C12 118.5(5) . .
C7 C11 C12 119.4(5) . .
N1 C12 C4 122.2(6) . .
N1 C12 C11 118.6(5) . .
C4 C12 C11 119.2(5) . .
C27 O22 Bi1 88.2(4) . .
C27 O23 Bi1 99.0(4) . .
O21 C21 C22 117.5(5) . .
O21 C21 C26 122.5(5) . .
C22 C21 C26 120.0 . .
C21 C22 C23 120.0 . .
C22 C23 C24 120.0 . .
C25 C24 C23 120.0 . .
C24 C25 C26 120.0 . .
C25 C26 C21 120.0 . .
C25 C26 C27 119.4(5) . .
C21 C26 C27 120.5(5) . .
O23 C27 O22 120.5(6) . .
O23 C27 C26 117.8(6) . .
O22 C27 C26 121.7(7) . .
O23 C27 Bi1 55.8(3) . .
O22 C27 Bi1 65.1(3) . .
C26 C27 Bi1 169.6(5) . .
C31 O31 Bi1 129.1(3) . .
C37 O32 Bi1 131.7(4) . .
C37 O32 Bi1 104.6(3) . 3_364
Bi1 O32 Bi1 114.41(15) . 3_364
O31 C31 C32 113.2(3) . .
O31 C31 C36 126.8(3) . .
C32 C31 C36 120.0 . .
C31 C32 C33 120.0 . .
C34 C33 C32 120.0 . .
C35 C34 C33 120.0 . .
C34 C35 C36 120.0 . .
C35 C36 C31 120.0 . .
C35 C36 C37 114.4(4) . .
C31 C36 C37 125.4(4) . .
O33 C37 O32 118.1(6) . .
O33 C37 C36 121.5(5) . .
O32 C37 C36 120.4(5) . .
C42 C41 C46 120.0 . .
C41 C42 C43 120.0 . .
C42 C43 C44 120.0 . .
C45 C44 C43 120.0 . .
C46 C45 C44 120.0 . .
C47 C46 C45 119.4(7) . .
C47 C46 C41 120.5(7) . .
C45 C46 C41 120.0 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 O31 2.117(4) .
Bi1 O32 2.233(4) .
Bi1 O23 2.387(4) .
Bi1 O22 2.587(4) .
Bi1 N1 2.598(4) .
Bi1 N2 2.609(4) .
Bi1 O32 2.747(4) 3_364
Bi1 C27 2.851(6) .
N1 C1 1.317(7) .
N1 C12 1.360(6) .
C1 C2 1.400(8) .
N2 C10 1.321(7) .
N2 C11 1.355(6) .
C2 C3 1.366(8) .
C3 C4 1.396(8) .
C4 C12 1.414(7) .
C4 C5 1.448(8) .
C5 C6 1.305(9) .
C6 C7 1.423(8) .
C7 C11 1.396(7) .
C7 C8 1.398(8) .
C8 C9 1.359(8) .
C9 C10 1.388(8) .
C11 C12 1.434(8) .
O21 C21 1.287(7) .
O22 C27 1.282(7) .
O23 C27 1.231(8) .
C21 C22 1.3900 .
C21 C26 1.3900 .
C22 C23 1.3900 .
C23 C24 1.3900 .
C24 C25 1.3900 .
C25 C26 1.3900 .
C26 C27 1.484(7) .
O31 C31 1.349(5) .
O32 C37 1.287(6) .
O32 Bi1 2.747(4) 3_364
O33 C37 1.219(6) .
C31 C32 1.3900 .
C31 C36 1.3900 .
C32 C33 1.3900 .
C33 C34 1.3900 .
C34 C35 1.3900 .
C35 C36 1.3900 .
C36 C37 1.484(7) .
C41 C42 1.3900 .
C41 C46 1.3900 .
C42 C43 1.3900 .
C43 C44 1.3900 .
C44 C45 1.3900 .
C45 C46 1.3900 .
C46 C47 1.03(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139184967
