#------------------------------------------------------------------------------
#$Date: 2016-03-26 03:44:55 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180194 $
#$URL: svn://www.crystallography.net/cod/cif/7/10/90/7109045.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_7109045
loop_
_publ_author_name
'Philip C. Andrews'
'Victoria L. Blair'
'Richard L. Ferrero'
'Peter C. Junk'
'Ish Kumar'
_publ_section_title
;
 Making Bispirin: synthesis, structure and activity against Helicobacter
 pylori of bismuth(III) acetylsalicylate
;
_journal_name_full               Chem.Commun.
_journal_page_first              2870
_journal_paper_doi               10.1039/c3cc40645h
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C54 H42 Bi2 O24'
_chemical_formula_sum            'C54 H42 Bi2 O24'
_chemical_formula_weight         1492.84
_chemical_name_systematic
;
?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 109.82(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   12.631(3)
_cell_length_b                   18.890(4)
_cell_length_c                   11.552(2)
_cell_measurement_reflns_used    38098
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      29.61
_cell_measurement_theta_min      2.02
_cell_volume                     2593.0(11)
_computing_cell_refinement       'XDS (Kabasch, 1993)'
_computing_data_collection       'Blue Ice (McPhillips, 2002)'
_computing_data_reduction        'XDS (Kabasch, 1993)'
_computing_molecular_graphics    X-Seed
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device_type  'ADSC Quantum 315r CCD'
_diffrn_measurement_method       'φ scan'
_diffrn_radiation_monochromator  silicon
_diffrn_radiation_source         'MX2 beamline, Australian Synchrotron'
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            48984
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         29.61
_diffrn_reflns_theta_min         2.02
_diffrn_standards_number         0-
_exptl_absorpt_coefficient_mu    6.867
_exptl_absorpt_correction_T_max  0.8205
_exptl_absorpt_correction_T_min  0.6450
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1448
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_refine_diff_density_max         1.209
_refine_diff_density_min         -1.921
_refine_diff_density_rms         0.114
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         6938
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.084
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0283
_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)+(0.0304P)²+5.4134P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0700
_refine_ls_wR_factor_ref         0.0712
_reflns_number_gt                6435
_reflns_number_total             6938
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc40645h.txt
_cod_data_source_block           vb59
_cod_original_cell_volume        2592.9(9)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7109045
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -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
Bi1 Bi 0.076677(8) 0.497979(5) 0.849895(9) 0.01876(5) Uani 1 1 d .
O1 O 0.12688(17) 0.62530(11) 0.85432(18) 0.0227(4) Uani 1 1 d .
O2 O 0.20180(17) 0.55496(10) 1.01250(19) 0.0221(4) Uani 1 1 d .
O3 O 0.30463(18) 0.62217(12) 1.23633(19) 0.0261(4) Uani 1 1 d .
O4 O 0.1167(2) 0.62339(14) 1.1981(2) 0.0350(5) Uani 1 1 d .
O5 O 0.17973(17) 0.40443(11) 0.94851(19) 0.0222(4) Uani 1 1 d .
O6 O 0.06420(17) 0.43124(10) 1.04818(19) 0.0227(4) Uani 1 1 d .
O7 O 0.36102(17) 0.32047(10) 1.07737(19) 0.0232(4) Uani 1 1 d .
O8 O 0.4066(2) 0.42093(13) 1.1880(2) 0.0354(5) Uani 1 1 d .
O9 O 0.2202(2) 0.50124(10) 0.7798(2) 0.0239(4) Uani 1 1 d .
O10 O 0.09116(16) 0.42696(11) 0.66842(19) 0.0222(4) Uani 1 1 d .
O11 O 0.14059(16) 0.34829(10) 0.49670(18) 0.0206(4) Uani 1 1 d .
O12 O 0.03962(18) 0.43555(11) 0.3776(2) 0.0265(4) Uani 1 1 d .
C1 C 0.1894(2) 0.61707(14) 0.9640(3) 0.0203(5) Uani 1 1 d .
C2 C 0.2496(2) 0.67930(14) 1.0350(3) 0.0206(5) Uani 1 1 d .
C3 C 0.2541(3) 0.74042(16) 0.9685(3) 0.0263(6) Uani 1 1 d .
H3 H 0.2165 0.7412 0.8820 0.032 Uiso 1 1 calc R
C4 C 0.3125(3) 0.79982(17) 1.0266(3) 0.0321(7) Uani 1 1 d .
H4 H 0.3160 0.8407 0.9801 0.039 Uiso 1 1 calc R
C5 C 0.3659(3) 0.79937(17) 1.1531(3) 0.0328(7) Uani 1 1 d .
H5 H 0.4062 0.8400 1.1932 0.039 Uiso 1 1 calc R
C6 C 0.3606(3) 0.73991(17) 1.2211(3) 0.0276(6) Uani 1 1 d .
H6 H 0.3970 0.7399 1.3078 0.033 Uiso 1 1 calc R
C7 C 0.3022(2) 0.68039(15) 1.1625(3) 0.0233(5) Uani 1 1 d .
C8 C 0.2065(3) 0.59576(18) 1.2428(3) 0.0293(6) Uani 1 1 d .
C9 C 0.2305(3) 0.5284(2) 1.3141(4) 0.0432(9) Uani 1 1 d .
H9A H 0.1674 0.5171 1.3420 0.065 Uiso 1 1 calc R
H9B H 0.2994 0.5338 1.3855 0.065 Uiso 1 1 calc R
H9C H 0.2407 0.4901 1.2616 0.065 Uiso 1 1 calc R
C10 C 0.1397(2) 0.39224(13) 1.0349(2) 0.0195(5) Uani 1 1 d .
C11 C 0.1833(2) 0.33063(14) 1.1187(3) 0.0203(5) Uani 1 1 d .
C12 C 0.1134(2) 0.30146(15) 1.1779(3) 0.0230(5) Uani 1 1 d .
H12 H 0.0417 0.3220 1.1656 0.028 Uiso 1 1 calc R
C13 C 0.1471(3) 0.24288(15) 1.2545(3) 0.0248(5) Uani 1 1 d .
H13 H 0.0977 0.2228 1.2918 0.030 Uiso 1 1 calc R
C14 C 0.2524(3) 0.21400(14) 1.2762(3) 0.0237(5) Uani 1 1 d .
H14 H 0.2760 0.1746 1.3300 0.028 Uiso 1 1 calc R
C15 C 0.3238(2) 0.24228(14) 1.2197(3) 0.0225(5) Uani 1 1 d .
H15 H 0.3967 0.2228 1.2357 0.027 Uiso 1 1 calc R
C16 C 0.2885(2) 0.29913(14) 1.1398(3) 0.0217(5) Uani 1 1 d .
C17 C 0.4119(3) 0.38461(16) 1.1055(3) 0.0269(6) Uani 1 1 d .
C18 C 0.4742(3) 0.4015(2) 1.0189(3) 0.0374(7) Uani 1 1 d .
H18A H 0.4248 0.4280 0.9484 0.056 Uiso 1 1 calc R
H18B H 0.4976 0.3573 0.9900 0.056 Uiso 1 1 calc R
H18C H 0.5408 0.4300 1.0618 0.056 Uiso 1 1 calc R
C19 C 0.1846(2) 0.45557(13) 0.6910(2) 0.0182(5) Uani 1 1 d .
C20 C 0.2629(2) 0.43901(14) 0.6230(2) 0.0186(5) Uani 1 1 d .
C21 C 0.3683(2) 0.47200(15) 0.6594(3) 0.0230(5) Uani 1 1 d .
H21 H 0.3859 0.5070 0.7221 0.028 Uiso 1 1 calc R
C22 C 0.4475(3) 0.45453(17) 0.6057(3) 0.0286(6) Uani 1 1 d .
H22 H 0.5191 0.4768 0.6324 0.034 Uiso 1 1 calc R
C23 C 0.4218(3) 0.40434(18) 0.5129(3) 0.0299(6) Uani 1 1 d .
H23 H 0.4761 0.3924 0.4759 0.036 Uiso 1 1 calc R
C24 C 0.3173(2) 0.37135(15) 0.4734(3) 0.0244(5) Uani 1 1 d .
H24 H 0.2996 0.3373 0.4090 0.029 Uiso 1 1 calc R
C25 C 0.2391(2) 0.38867(14) 0.5288(2) 0.0192(5) Uani 1 1 d .
C26 C 0.0428(2) 0.37937(15) 0.4279(3) 0.0227(5) Uani 1 1 d .
C27 C -0.0550(3) 0.33435(19) 0.4256(3) 0.0330(7) Uani 1 1 d .
H27A H -0.0604 0.3326 0.5082 0.049 Uiso 1 1 calc R
H27B H -0.0444 0.2864 0.3992 0.049 Uiso 1 1 calc R
H27C H -0.1243 0.3546 0.3680 0.049 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 -4.028 10.608 '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
O9 Bi1 O5 78.70(8) . .
O9 Bi1 O2 82.17(8) . .
O5 Bi1 O2 80.43(8) . .
O9 Bi1 O1 75.32(7) . .
O5 Bi1 O1 130.34(7) . .
O2 Bi1 O1 54.79(7) . .
O9 Bi1 O10 54.52(7) . .
O5 Bi1 O10 79.23(7) . .
O2 Bi1 O10 134.86(7) . .
O1 Bi1 O10 115.97(6) . .
O9 Bi1 O6 128.28(8) . .
O5 Bi1 O6 52.33(6) . .
O2 Bi1 O6 75.00(7) . .
O1 Bi1 O6 121.97(6) . .
O10 Bi1 O6 119.99(7) . .
O9 Bi1 C1 78.36(8) . .
O5 Bi1 C1 106.38(9) . .
O2 Bi1 C1 27.67(8) . .
O1 Bi1 C1 27.16(8) . .
O10 Bi1 C1 130.97(7) . .
O6 Bi1 C1 98.45(8) . .
O9 Bi1 O6 149.02(6) . 3_567
O5 Bi1 O6 120.23(6) . 3_567
O2 Bi1 O6 77.78(7) . 3_567
O1 Bi1 O6 73.84(6) . 3_567
O10 Bi1 O6 146.62(7) . 3_567
O6 Bi1 O6 68.37(7) . 3_567
C1 Bi1 O6 72.89(7) . 3_567
O9 Bi1 O12 83.10(8) . 3_566
O5 Bi1 O12 147.45(7) . 3_566
O2 Bi1 O12 123.58(7) . 3_566
O1 Bi1 O12 68.79(7) . 3_566
O10 Bi1 O12 68.23(7) . 3_566
O6 Bi1 O12 147.54(6) . 3_566
C1 Bi1 O12 95.95(8) . 3_566
O6 Bi1 O12 88.56(6) 3_567 3_566
O9 Bi1 O12 137.35(7) . 3_567
O5 Bi1 O12 82.96(5) . 3_567
O2 Bi1 O12 56.85(5) . 3_567
O1 Bi1 O12 88.44(5) . 3_567
O10 Bi1 O12 155.47(5) . 3_567
O6 Bi1 O12 36.03(4) . 3_567
C1 Bi1 O12 70.43(6) . 3_567
O6 Bi1 O12 39.08(5) 3_567 3_567
O12 Bi1 O12 127.56(5) 3_566 3_567
C1 O1 Bi1 88.27(16) . .
C1 O2 Bi1 97.15(17) . .
C8 O3 C7 119.6(2) . .
C10 O5 Bi1 102.77(16) . .
C10 O6 Bi1 84.49(15) . .
C17 O7 C16 118.2(2) . .
C19 O9 Bi1 99.37(16) . .
C19 O10 Bi1 85.78(15) . .
C26 O11 C25 118.1(2) . .
O1 C1 O2 119.6(3) . .
O1 C1 C2 119.2(2) . .
O2 C1 C2 121.2(3) . .
O1 C1 Bi1 64.58(15) . .
O2 C1 Bi1 55.18(14) . .
C2 C1 Bi1 175.45(19) . .
C7 C2 C3 118.3(3) . .
C7 C2 C1 124.4(2) . .
C3 C2 C1 117.3(3) . .
C4 C3 C2 121.1(3) . .
C3 C4 C5 119.7(3) . .
C6 C5 C4 120.2(3) . .
C5 C6 C7 120.0(3) . .
O3 C7 C6 116.4(3) . .
O3 C7 C2 122.8(3) . .
C6 C7 C2 120.7(3) . .
O4 C8 O3 124.4(3) . .
O4 C8 C9 126.7(3) . .
O3 C8 C9 109.0(3) . .
O6 C10 O5 120.4(2) . .
O6 C10 C11 120.4(2) . .
O5 C10 C11 119.2(2) . .
C16 C11 C12 117.8(2) . .
C16 C11 C10 124.3(2) . .
C12 C11 C10 117.9(2) . .
C13 C12 C11 121.0(3) . .
C14 C13 C12 120.0(3) . .
C13 C14 C15 120.2(3) . .
C14 C15 C16 119.9(3) . .
C15 C16 C11 121.1(3) . .
C15 C16 O7 116.5(2) . .
C11 C16 O7 122.3(2) . .
O8 C17 O7 123.5(3) . .
O8 C17 C18 126.4(3) . .
O7 C17 C18 110.0(3) . .
O10 C19 O9 120.3(2) . .
O10 C19 C20 123.5(2) . .
O9 C19 C20 116.2(2) . .
C25 C20 C21 117.9(2) . .
C25 C20 C19 123.2(2) . .
C21 C20 C19 118.9(2) . .
C22 C21 C20 121.2(3) . .
C21 C22 C23 119.7(3) . .
C22 C23 C24 120.6(3) . .
C25 C24 C23 119.2(3) . .
C24 C25 C20 121.4(3) . .
C24 C25 O11 117.2(2) . .
C20 C25 O11 120.9(2) . .
O12 C26 O11 122.7(3) . .
O12 C26 C27 127.0(3) . .
O11 C26 C27 110.3(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Bi1 O9 2.223(2) .
Bi1 O5 2.260(2) .
Bi1 O2 2.274(2) .
Bi1 O1 2.483(2) .
Bi1 O10 2.547(2) .
Bi1 O6 2.666(2) .
Bi1 C1 2.748(3) .
Bi1 O6 2.7860(19) 3_567
Bi1 O12 2.833(2) 3_566
Bi1 O12 9.605(3) 3_567
O1 C1 1.255(4) .
O2 C1 1.286(3) .
O3 C8 1.361(4) .
O3 C7 1.386(3) .
O4 C8 1.195(4) .
O5 C10 1.283(3) .
O6 C10 1.255(3) .
O7 C17 1.358(4) .
O7 C16 1.403(3) .
O8 C17 1.195(4) .
O9 C19 1.298(3) .
O10 C19 1.243(3) .
O11 C26 1.355(3) .
O11 C25 1.399(3) .
O12 C26 1.204(3) .
C1 C2 1.486(4) .
C2 C7 1.396(4) .
C2 C3 1.399(4) .
C3 C4 1.385(4) .
C4 C5 1.386(5) .
C5 C6 1.385(5) .
C6 C7 1.389(4) .
C8 C9 1.489(5) .
C10 C11 1.494(4) .
C11 C16 1.400(4) .
C11 C12 1.401(4) .
C12 C13 1.390(4) .
C13 C14 1.379(4) .
C14 C15 1.387(4) .
C15 C16 1.387(4) .
C17 C18 1.501(5) .
C19 C20 1.490(3) .
C20 C25 1.399(4) .
C20 C21 1.400(4) .
C21 C22 1.383(4) .
C22 C23 1.385(4) .
C23 C24 1.389(4) .
C24 C25 1.386(3) .
C26 C27 1.492(4) .
