Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701642X/bt2330sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680701642X/bt2330Isup2.hkl |
CCDC reference: 650578
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.009 Å
- R factor = 0.025
- wR factor = 0.063
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Bi1 - O4 .. 10.29 su
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.53 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT143_ALERT_4_C su on c - Axis Small or Missing (x 100000) ..... 10 Ang. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.29 Ratio PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.75 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Bi1 - O1 .. 6.61 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C3 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C2 PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.531 Tmax scaled 0.531 Tmin scaled 0.258 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 13 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
A methanolic solution of [Bi(Hsal)3]n (Hsal = O2CC6H4-2-OH) was carefully layered with a methanolic solution of 2,2'-bipyridine. The colourless solution was allowed to stand undisturbed at room temperature for one week, during which time large colourless crystals of the title compound deposited on the wall of the tube.
All H atoms were included in calculated positions, with C—H = 0.93 Å and O—H = 0.82 Å, and with Uiso(H) = 1.2Ueq(C,O).
Bismuth compounds have long been associated with medicine and healthcare for the treatment of various diseases (Thompson & Orvig, 2003; Suerbaum & Michetti, 2003; Briand & Burford, 1999). Bismuth subsalicylate is used to treat some digestive tract disorders such as gastric ulcers and is effective against Helicobacter pylori infection (Guo & Sadler, 1999; Sadler et al., 1999). In the present study, we have synthesized and characterized an isomer of the previously reported compound bis[[(µ2-salicylato-O,O')(2,2'- bipyridine)bis(salicylate)bismuth(III)]toluene] (Thurston et al., 2002).
The asymmetric unit of the title compound is composed of one Bi atom, one 2,2'-bipyridine ligand and three salicylate ligands (Fig. 1). The Bi atoms have
two terminal salicylate ligands that chelate the metal through their carboxylate functionality. A third salicylate ion bridges two Bi atoms to form a dimer (Fig.2). The Bi—O(carboxylate) bond lengths range from 2.377 (3) to 2.801 (3) Å. The two N atoms of the 2,2'-bipyridine ligand coordinate to the Bi atom with bond lengths of 2.387 (3) and 2.511 (3) Å.
Each of the salicylate ligands shows an intramolecular H bond.
For related literature, see: Briand & Burford (1999); Guo & Sadler (1999); Sadler et al. (1999); Suerbaum & Michetti (2003); Thompson & Orvig (2003); Thurston et al. (2002).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
[Bi2(C7H5O3)6(C10H8N2)2] | F(000) = 3024 |
Mr = 1552.98 | Dx = 1.834 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 21.4583 (3) Å | Cell parameters from 14948 reflections |
b = 13.6698 (2) Å | θ = 1.8–25.6° |
c = 21.6097 (1) Å | µ = 6.33 mm−1 |
β = 117.472 (1)° | T = 293 K |
V = 5624.00 (12) Å3 | Block, colourless |
Z = 4 | 0.2 × 0.1 × 0.1 mm |
Bruker SMART CCD area-detector diffractometer | 5322 independent reflections |
Radiation source: fine-focus sealed tube | 4590 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 25.6°, θmin = 1.8° |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | h = −26→18 |
Tmin = 0.486, Tmax = 1.000 | k = −14→16 |
14948 measured reflections | l = −24→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.025 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0258P)2 + 23.4426P] where P = (Fo2 + 2Fc2)/3 |
5322 reflections | (Δ/σ)max = 0.003 |
388 parameters | Δρmax = 0.81 e Å−3 |
0 restraints | Δρmin = −1.26 e Å−3 |
[Bi2(C7H5O3)6(C10H8N2)2] | V = 5624.00 (12) Å3 |
Mr = 1552.98 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 21.4583 (3) Å | µ = 6.33 mm−1 |
b = 13.6698 (2) Å | T = 293 K |
c = 21.6097 (1) Å | 0.2 × 0.1 × 0.1 mm |
β = 117.472 (1)° |
Bruker SMART CCD area-detector diffractometer | 5322 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Sheldrick, 1996) | 4590 reflections with I > 2σ(I) |
Tmin = 0.486, Tmax = 1.000 | Rint = 0.028 |
14948 measured reflections |
R[F2 > 2σ(F2)] = 0.025 | 0 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0258P)2 + 23.4426P] where P = (Fo2 + 2Fc2)/3 |
5322 reflections | Δρmax = 0.81 e Å−3 |
388 parameters | Δρmin = −1.26 e Å−3 |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Bi1 | 0.557548 (7) | −0.053031 (12) | −0.039024 (7) | 0.02992 (6) | |
C1 | 0.5214 (2) | −0.3657 (3) | −0.0917 (3) | 0.0446 (12) | |
N1 | 0.68538 (18) | −0.0770 (3) | 0.04387 (18) | 0.0349 (8) | |
O1 | 0.50042 (16) | −0.1969 (2) | −0.12275 (17) | 0.0445 (8) | |
C2 | 0.4803 (3) | −0.3989 (5) | −0.1598 (4) | 0.0662 (16) | |
O4 | 0.58818 (17) | 0.0884 (3) | 0.05826 (16) | 0.0428 (7) | |
N2 | 0.62695 (18) | −0.0854 (3) | −0.09692 (17) | 0.0318 (8) | |
O2 | 0.58232 (17) | −0.2334 (2) | −0.01744 (16) | 0.0444 (8) | |
C3 | 0.4740 (4) | −0.4984 (6) | −0.1734 (5) | 0.104 (3) | |
H3A | 0.4470 | −0.5199 | −0.2189 | 0.125* | |
C4 | 0.5059 (5) | −0.5651 (5) | −0.1225 (7) | 0.108 (3) | |
H4A | 0.5025 | −0.6314 | −0.1333 | 0.130* | |
O3 | 0.4454 (3) | −0.3395 (4) | −0.2132 (3) | 0.1076 (19) | |
H3B | 0.4530 | −0.2826 | −0.1998 | 0.161* | |
C5 | 0.5443 (4) | −0.5338 (5) | −0.0534 (6) | 0.095 (3) | |
H5A | 0.5638 | −0.5798 | −0.0178 | 0.113* | |
C6 | 0.5535 (3) | −0.4343 (4) | −0.0374 (4) | 0.0620 (17) | |
H6A | 0.5804 | −0.4136 | 0.0084 | 0.074* | |
O6 | 0.6500 (2) | 0.2041 (4) | 0.16486 (18) | 0.0753 (13) | |
H6B | 0.6269 | 0.1566 | 0.1431 | 0.113* | |
C7 | 0.5352 (2) | −0.2600 (3) | −0.0758 (2) | 0.0357 (10) | |
O7 | 0.48413 (17) | 0.0242 (2) | −0.14704 (16) | 0.0454 (8) | |
C8 | 0.6552 (2) | 0.2260 (3) | 0.0570 (2) | 0.0364 (10) | |
O8 | 0.45182 (16) | 0.1136 (2) | −0.08025 (16) | 0.0422 (7) | |
C9 | 0.6689 (2) | 0.2569 (4) | 0.1239 (3) | 0.0491 (12) | |
O5 | 0.61390 (16) | 0.1012 (2) | −0.02946 (15) | 0.0393 (7) | |
C10 | 0.7060 (3) | 0.3428 (5) | 0.1511 (3) | 0.0734 (19) | |
H10A | 0.7147 | 0.3640 | 0.1952 | 0.088* | |
O9 | 0.36991 (19) | 0.2678 (3) | −0.13324 (18) | 0.0556 (9) | |
H10B | 0.3921 | 0.2278 | −0.1027 | 0.083* | |
C11 | 0.7299 (4) | 0.3963 (5) | 0.1127 (4) | 0.083 (2) | |
H11A | 0.7540 | 0.4543 | 0.1310 | 0.099* | |
C12 | 0.7190 (4) | 0.3663 (5) | 0.0476 (4) | 0.0771 (19) | |
H12A | 0.7368 | 0.4024 | 0.0229 | 0.093* | |
C13 | 0.6815 (3) | 0.2823 (4) | 0.0198 (3) | 0.0546 (13) | |
H13A | 0.6733 | 0.2623 | −0.0244 | 0.065* | |
C14 | 0.6168 (2) | 0.1345 (3) | 0.0270 (2) | 0.0340 (9) | |
C15 | 0.4140 (2) | 0.1663 (3) | −0.1969 (2) | 0.0383 (10) | |
C16 | 0.3771 (2) | 0.2473 (4) | −0.1911 (2) | 0.0420 (11) | |
C17 | 0.3459 (3) | 0.3119 (4) | −0.2465 (3) | 0.0544 (13) | |
H17A | 0.3210 | 0.3653 | −0.2427 | 0.065* | |
C18 | 0.3513 (3) | 0.2983 (5) | −0.3067 (3) | 0.0651 (16) | |
H18A | 0.3303 | 0.3428 | −0.3431 | 0.078* | |
C19 | 0.3876 (3) | 0.2187 (5) | −0.3139 (3) | 0.0677 (17) | |
H19A | 0.3916 | 0.2097 | −0.3545 | 0.081* | |
C20 | 0.4177 (3) | 0.1531 (4) | −0.2592 (2) | 0.0527 (13) | |
H20A | 0.4411 | 0.0987 | −0.2641 | 0.063* | |
C21 | 0.4519 (2) | 0.0972 (3) | −0.1377 (2) | 0.0344 (9) | |
C22 | 0.7282 (2) | −0.1021 (3) | 0.0166 (2) | 0.0337 (9) | |
C23 | 0.7133 (2) | −0.0643 (4) | 0.1133 (2) | 0.0441 (11) | |
H23A | 0.6838 | −0.0475 | 0.1324 | 0.053* | |
C24 | 0.7843 (3) | −0.0755 (4) | 0.1572 (3) | 0.0527 (13) | |
H24A | 0.8023 | −0.0658 | 0.2050 | 0.063* | |
C25 | 0.8278 (3) | −0.1012 (5) | 0.1290 (3) | 0.0568 (14) | |
H25A | 0.8757 | −0.1093 | 0.1576 | 0.068* | |
C26 | 0.7999 (2) | −0.1150 (4) | 0.0581 (3) | 0.0487 (12) | |
H26A | 0.8286 | −0.1326 | 0.0383 | 0.058* | |
C27 | 0.6946 (2) | −0.1129 (3) | −0.0610 (2) | 0.0327 (9) | |
C28 | 0.5949 (3) | −0.0908 (4) | −0.1671 (2) | 0.0432 (11) | |
H28A | 0.5481 | −0.0719 | −0.1916 | 0.052* | |
C29 | 0.6293 (3) | −0.1232 (4) | −0.2037 (3) | 0.0484 (12) | |
H29A | 0.6064 | −0.1243 | −0.2522 | 0.058* | |
C30 | 0.6978 (3) | −0.1540 (4) | −0.1674 (3) | 0.0501 (12) | |
H30A | 0.7213 | −0.1781 | −0.1911 | 0.060* | |
C31 | 0.7314 (2) | −0.1489 (4) | −0.0953 (3) | 0.0429 (11) | |
H31A | 0.7779 | −0.1692 | −0.0700 | 0.051* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Bi1 | 0.02658 (9) | 0.03395 (10) | 0.02873 (9) | −0.00108 (7) | 0.01234 (7) | −0.00507 (7) |
C1 | 0.032 (2) | 0.034 (3) | 0.070 (3) | −0.0048 (19) | 0.025 (2) | −0.009 (2) |
N1 | 0.0298 (18) | 0.040 (2) | 0.0309 (18) | −0.0038 (15) | 0.0108 (15) | −0.0025 (15) |
O1 | 0.0339 (16) | 0.044 (2) | 0.0443 (18) | 0.0015 (14) | 0.0083 (14) | −0.0036 (15) |
C2 | 0.048 (3) | 0.058 (4) | 0.079 (4) | −0.006 (3) | 0.017 (3) | −0.027 (3) |
O4 | 0.0433 (18) | 0.049 (2) | 0.0395 (17) | −0.0098 (15) | 0.0222 (15) | −0.0006 (15) |
N2 | 0.0301 (18) | 0.036 (2) | 0.0293 (18) | −0.0007 (15) | 0.0134 (15) | −0.0029 (15) |
O2 | 0.0482 (19) | 0.0413 (19) | 0.0378 (17) | −0.0042 (15) | 0.0148 (15) | −0.0065 (14) |
C3 | 0.071 (5) | 0.069 (5) | 0.151 (8) | −0.024 (4) | 0.034 (5) | −0.070 (6) |
C4 | 0.074 (5) | 0.042 (4) | 0.204 (11) | −0.014 (4) | 0.060 (6) | −0.039 (6) |
O3 | 0.101 (4) | 0.097 (4) | 0.076 (3) | −0.003 (3) | −0.001 (3) | −0.038 (3) |
C5 | 0.068 (4) | 0.047 (4) | 0.172 (9) | 0.003 (3) | 0.059 (5) | 0.019 (5) |
C6 | 0.051 (3) | 0.041 (3) | 0.106 (5) | −0.001 (2) | 0.047 (4) | 0.008 (3) |
O6 | 0.064 (2) | 0.128 (4) | 0.041 (2) | −0.041 (3) | 0.0304 (19) | −0.030 (2) |
C7 | 0.028 (2) | 0.040 (3) | 0.043 (3) | −0.0014 (19) | 0.020 (2) | −0.007 (2) |
O7 | 0.0451 (18) | 0.0417 (19) | 0.0389 (17) | 0.0097 (15) | 0.0105 (15) | −0.0041 (14) |
C8 | 0.033 (2) | 0.036 (3) | 0.037 (2) | −0.0035 (18) | 0.0127 (19) | −0.0045 (19) |
O8 | 0.0476 (18) | 0.0439 (19) | 0.0367 (17) | 0.0040 (15) | 0.0207 (15) | 0.0061 (14) |
C9 | 0.034 (2) | 0.065 (4) | 0.046 (3) | −0.006 (2) | 0.017 (2) | −0.017 (2) |
O5 | 0.0432 (17) | 0.0426 (19) | 0.0347 (16) | −0.0098 (14) | 0.0201 (14) | −0.0088 (14) |
C10 | 0.065 (4) | 0.078 (5) | 0.072 (4) | −0.023 (3) | 0.027 (3) | −0.044 (4) |
O9 | 0.065 (2) | 0.051 (2) | 0.055 (2) | 0.0181 (18) | 0.0319 (19) | 0.0082 (17) |
C11 | 0.082 (5) | 0.043 (4) | 0.101 (6) | −0.021 (3) | 0.023 (4) | −0.017 (4) |
C12 | 0.091 (5) | 0.048 (4) | 0.080 (4) | −0.026 (3) | 0.029 (4) | 0.008 (3) |
C13 | 0.059 (3) | 0.044 (3) | 0.052 (3) | −0.011 (2) | 0.018 (3) | 0.004 (2) |
C14 | 0.034 (2) | 0.036 (3) | 0.031 (2) | −0.0019 (18) | 0.0141 (18) | −0.0006 (18) |
C15 | 0.031 (2) | 0.042 (3) | 0.035 (2) | −0.0033 (19) | 0.0092 (18) | 0.001 (2) |
C16 | 0.035 (2) | 0.044 (3) | 0.043 (3) | 0.000 (2) | 0.014 (2) | 0.002 (2) |
C17 | 0.051 (3) | 0.045 (3) | 0.054 (3) | 0.006 (2) | 0.014 (3) | 0.010 (2) |
C18 | 0.068 (4) | 0.065 (4) | 0.045 (3) | 0.007 (3) | 0.011 (3) | 0.022 (3) |
C19 | 0.074 (4) | 0.087 (5) | 0.037 (3) | 0.011 (3) | 0.021 (3) | 0.012 (3) |
C20 | 0.052 (3) | 0.061 (4) | 0.040 (3) | 0.007 (3) | 0.017 (2) | 0.003 (2) |
C21 | 0.027 (2) | 0.033 (2) | 0.036 (2) | −0.0046 (18) | 0.0083 (18) | −0.0016 (19) |
C22 | 0.028 (2) | 0.032 (2) | 0.040 (2) | −0.0027 (17) | 0.0150 (18) | 0.0056 (19) |
C23 | 0.039 (2) | 0.057 (3) | 0.034 (2) | −0.007 (2) | 0.014 (2) | −0.002 (2) |
C24 | 0.042 (3) | 0.066 (4) | 0.036 (3) | −0.008 (2) | 0.007 (2) | 0.005 (2) |
C25 | 0.030 (2) | 0.080 (4) | 0.046 (3) | 0.001 (3) | 0.006 (2) | 0.013 (3) |
C26 | 0.031 (2) | 0.066 (4) | 0.048 (3) | 0.002 (2) | 0.017 (2) | 0.009 (3) |
C27 | 0.033 (2) | 0.030 (2) | 0.036 (2) | −0.0010 (17) | 0.0165 (18) | 0.0031 (18) |
C28 | 0.043 (3) | 0.056 (3) | 0.030 (2) | −0.001 (2) | 0.017 (2) | −0.007 (2) |
C29 | 0.060 (3) | 0.054 (3) | 0.038 (3) | −0.002 (2) | 0.028 (2) | −0.008 (2) |
C30 | 0.058 (3) | 0.051 (3) | 0.055 (3) | 0.000 (2) | 0.038 (3) | −0.009 (2) |
C31 | 0.039 (2) | 0.043 (3) | 0.054 (3) | 0.002 (2) | 0.028 (2) | −0.001 (2) |
Bi1—O7 | 2.377 (3) | C10—C11 | 1.370 (10) |
Bi1—N2 | 2.387 (3) | C10—H10A | 0.9300 |
Bi1—O5 | 2.392 (3) | O9—C16 | 1.358 (6) |
Bi1—N1 | 2.511 (3) | O9—H10B | 0.8200 |
Bi1—O2 | 2.520 (3) | C11—C12 | 1.377 (10) |
Bi1—O1 | 2.568 (3) | C11—H11A | 0.9300 |
Bi1—O4 | 2.705 (3) | C12—C13 | 1.371 (8) |
Bi1—O8i | 2.801 (3) | C12—H12A | 0.9300 |
C1—C2 | 1.399 (8) | C13—H13A | 0.9300 |
C1—C6 | 1.409 (8) | C15—C20 | 1.397 (7) |
C1—C7 | 1.482 (6) | C15—C16 | 1.400 (7) |
N1—C23 | 1.345 (6) | C15—C21 | 1.493 (6) |
N1—C22 | 1.346 (5) | C16—C17 | 1.386 (7) |
O1—C7 | 1.278 (5) | C17—C18 | 1.370 (8) |
C2—O3 | 1.325 (8) | C17—H17A | 0.9300 |
C2—C3 | 1.385 (9) | C18—C19 | 1.389 (9) |
O4—C14 | 1.269 (5) | C18—H18A | 0.9300 |
N2—C27 | 1.347 (5) | C19—C20 | 1.383 (7) |
N2—C28 | 1.347 (5) | C19—H19A | 0.9300 |
O2—C7 | 1.253 (5) | C20—H20A | 0.9300 |
C3—C4 | 1.346 (13) | C22—C26 | 1.389 (6) |
C3—H3A | 0.9300 | C22—C27 | 1.494 (6) |
C4—C5 | 1.398 (13) | C23—C24 | 1.383 (7) |
C4—H4A | 0.9300 | C23—H23A | 0.9300 |
O3—H3B | 0.8200 | C24—C25 | 1.375 (8) |
C5—C6 | 1.395 (9) | C24—H24A | 0.9300 |
C5—H5A | 0.9300 | C25—C26 | 1.377 (7) |
C6—H6A | 0.9300 | C25—H25A | 0.9300 |
O6—C9 | 1.342 (6) | C26—H26A | 0.9300 |
O6—H6B | 0.8200 | C27—C31 | 1.399 (6) |
O7—C21 | 1.283 (5) | C28—C29 | 1.381 (6) |
C8—C9 | 1.401 (6) | C28—H28A | 0.9300 |
C8—C13 | 1.405 (7) | C29—C30 | 1.375 (7) |
C8—C14 | 1.473 (6) | C29—H29A | 0.9300 |
O8—C21 | 1.262 (5) | C30—C31 | 1.384 (7) |
O8—Bi1i | 2.801 (3) | C30—H30A | 0.9300 |
C9—C10 | 1.388 (8) | C31—H31A | 0.9300 |
O5—C14 | 1.277 (5) | ||
O7—Bi1—N2 | 81.88 (11) | C14—O5—Bi1 | 101.3 (3) |
O7—Bi1—O5 | 76.88 (11) | C11—C10—C9 | 119.8 (6) |
N2—Bi1—O5 | 78.22 (11) | C11—C10—H10A | 120.1 |
O7—Bi1—N1 | 140.29 (12) | C9—C10—H10A | 120.1 |
N2—Bi1—N1 | 67.01 (11) | C16—O9—H10B | 109.5 |
O5—Bi1—N1 | 73.19 (11) | C10—C11—C12 | 121.6 (6) |
O7—Bi1—O2 | 127.14 (11) | C10—C11—H11A | 119.2 |
N2—Bi1—O2 | 77.66 (11) | C12—C11—H11A | 119.2 |
O5—Bi1—O2 | 142.33 (11) | C13—C12—C11 | 119.1 (6) |
N1—Bi1—O2 | 70.90 (11) | C13—C12—H12A | 120.5 |
O7—Bi1—O1 | 76.31 (10) | C11—C12—H12A | 120.5 |
N2—Bi1—O1 | 72.50 (11) | C12—C13—C8 | 121.2 (5) |
O5—Bi1—O1 | 142.54 (10) | C12—C13—H13A | 119.4 |
N1—Bi1—O1 | 114.34 (11) | C8—C13—H13A | 119.4 |
O2—Bi1—O1 | 51.16 (10) | O4—C14—O5 | 120.6 (4) |
O7—Bi1—O4 | 105.02 (10) | O4—C14—C8 | 119.8 (4) |
N2—Bi1—O4 | 123.59 (10) | O5—C14—C8 | 119.6 (4) |
O5—Bi1—O4 | 51.00 (9) | C20—C15—C16 | 118.3 (4) |
N1—Bi1—O4 | 75.21 (11) | C20—C15—C21 | 119.6 (4) |
O2—Bi1—O4 | 126.92 (10) | C16—C15—C21 | 122.0 (4) |
O1—Bi1—O4 | 163.90 (10) | O9—C16—C17 | 116.7 (5) |
O7—Bi1—O8i | 137.59 (10) | O9—C16—C15 | 123.7 (4) |
N2—Bi1—O8i | 138.97 (11) | C17—C16—C15 | 119.6 (5) |
O5—Bi1—O8i | 115.41 (10) | C18—C17—C16 | 121.0 (5) |
N1—Bi1—O8i | 79.84 (10) | C18—C17—H17A | 119.5 |
O2—Bi1—O8i | 68.84 (10) | C16—C17—H17A | 119.5 |
O1—Bi1—O8i | 102.03 (10) | C17—C18—C19 | 120.7 (5) |
O4—Bi1—O8i | 65.86 (9) | C17—C18—H18A | 119.7 |
C2—C1—C6 | 119.3 (5) | C19—C18—H18A | 119.7 |
C2—C1—C7 | 121.4 (5) | C20—C19—C18 | 118.6 (5) |
C6—C1—C7 | 119.2 (5) | C20—C19—H19A | 120.7 |
C23—N1—C22 | 118.6 (4) | C18—C19—H19A | 120.7 |
C23—N1—Bi1 | 123.8 (3) | C19—C20—C15 | 121.8 (5) |
C22—N1—Bi1 | 117.5 (3) | C19—C20—H20A | 119.1 |
C7—O1—Bi1 | 92.5 (3) | C15—C20—H20A | 119.1 |
O3—C2—C3 | 117.2 (7) | O8—C21—O7 | 122.6 (4) |
O3—C2—C1 | 123.1 (6) | O8—C21—C15 | 118.9 (4) |
C3—C2—C1 | 119.6 (7) | O7—C21—C15 | 118.5 (4) |
C14—O4—Bi1 | 86.9 (2) | N1—C22—C26 | 121.7 (4) |
C27—N2—C28 | 119.3 (4) | N1—C22—C27 | 116.3 (4) |
C27—N2—Bi1 | 121.1 (3) | C26—C22—C27 | 122.0 (4) |
C28—N2—Bi1 | 118.8 (3) | N1—C23—C24 | 122.3 (5) |
C7—O2—Bi1 | 95.5 (3) | N1—C23—H23A | 118.9 |
C4—C3—C2 | 121.9 (8) | C24—C23—H23A | 118.9 |
C4—C3—H3A | 119.0 | C25—C24—C23 | 118.8 (5) |
C2—C3—H3A | 119.0 | C25—C24—H24A | 120.6 |
C3—C4—C5 | 119.5 (7) | C23—C24—H24A | 120.6 |
C3—C4—H4A | 120.3 | C24—C25—C26 | 119.5 (5) |
C5—C4—H4A | 120.3 | C24—C25—H25A | 120.2 |
C2—O3—H3B | 109.5 | C26—C25—H25A | 120.2 |
C6—C5—C4 | 120.6 (8) | C25—C26—C22 | 119.0 (5) |
C6—C5—H5A | 119.7 | C25—C26—H26A | 120.5 |
C4—C5—H5A | 119.7 | C22—C26—H26A | 120.5 |
C5—C6—C1 | 118.9 (7) | N2—C27—C31 | 121.0 (4) |
C5—C6—H6A | 120.6 | N2—C27—C22 | 116.9 (4) |
C1—C6—H6A | 120.6 | C31—C27—C22 | 122.1 (4) |
C9—O6—H6B | 109.5 | N2—C28—C29 | 122.2 (5) |
O2—C7—O1 | 120.5 (4) | N2—C28—H28A | 118.9 |
O2—C7—C1 | 119.9 (4) | C29—C28—H28A | 118.9 |
O1—C7—C1 | 119.6 (4) | C30—C29—C28 | 118.9 (5) |
C21—O7—Bi1 | 110.6 (3) | C30—C29—H29A | 120.5 |
C9—C8—C13 | 118.4 (4) | C28—C29—H29A | 120.5 |
C9—C8—C14 | 121.2 (4) | C29—C30—C31 | 119.5 (4) |
C13—C8—C14 | 120.3 (4) | C29—C30—H30A | 120.2 |
C21—O8—Bi1i | 152.4 (3) | C31—C30—H30A | 120.2 |
O6—C9—C10 | 117.8 (5) | C30—C31—C27 | 119.0 (4) |
O6—C9—C8 | 122.3 (5) | C30—C31—H31A | 120.5 |
C10—C9—C8 | 119.9 (5) | C27—C31—H31A | 120.5 |
Symmetry code: (i) −x+1, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | [Bi2(C7H5O3)6(C10H8N2)2] |
Mr | 1552.98 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 21.4583 (3), 13.6698 (2), 21.6097 (1) |
β (°) | 117.472 (1) |
V (Å3) | 5624.00 (12) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 6.33 |
Crystal size (mm) | 0.2 × 0.1 × 0.1 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector |
Absorption correction | Empirical (using intensity measurements) (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.486, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14948, 5322, 4590 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.609 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.025, 0.063, 1.07 |
No. of reflections | 5322 |
No. of parameters | 388 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0258P)2 + 23.4426P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.81, −1.26 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.
Bi1—O7 | 2.377 (3) | C2—O3 | 1.325 (8) |
Bi1—N2 | 2.387 (3) | O4—C14 | 1.269 (5) |
Bi1—O5 | 2.392 (3) | O2—C7 | 1.253 (5) |
Bi1—N1 | 2.511 (3) | O6—C9 | 1.342 (6) |
Bi1—O2 | 2.520 (3) | O7—C21 | 1.283 (5) |
Bi1—O1 | 2.568 (3) | C8—C14 | 1.473 (6) |
Bi1—O4 | 2.705 (3) | O8—C21 | 1.262 (5) |
Bi1—O8i | 2.801 (3) | O5—C14 | 1.277 (5) |
O1—C7 | 1.278 (5) | ||
O7—Bi1—N2 | 81.88 (11) | O7—Bi1—O1 | 76.31 (10) |
O7—Bi1—O5 | 76.88 (11) | N2—Bi1—O1 | 72.50 (11) |
N2—Bi1—O5 | 78.22 (11) | O2—Bi1—O1 | 51.16 (10) |
N2—Bi1—N1 | 67.01 (11) | O5—Bi1—O4 | 51.00 (9) |
O5—Bi1—N1 | 73.19 (11) | N1—Bi1—O4 | 75.21 (11) |
N2—Bi1—O2 | 77.66 (11) | N1—Bi1—O8i | 79.84 (10) |
N1—Bi1—O2 | 70.90 (11) | O4—Bi1—O8i | 65.86 (9) |
Symmetry code: (i) −x+1, −y, −z. |
Bismuth compounds have long been associated with medicine and healthcare for the treatment of various diseases (Thompson & Orvig, 2003; Suerbaum & Michetti, 2003; Briand & Burford, 1999). Bismuth subsalicylate is used to treat some digestive tract disorders such as gastric ulcers and is effective against Helicobacter pylori infection (Guo & Sadler, 1999; Sadler et al., 1999). In the present study, we have synthesized and characterized an isomer of the previously reported compound bis[[(µ2-salicylato-O,O')(2,2'- bipyridine)bis(salicylate)bismuth(III)]toluene] (Thurston et al., 2002).
The asymmetric unit of the title compound is composed of one Bi atom, one 2,2'-bipyridine ligand and three salicylate ligands (Fig. 1). The Bi atoms have
two terminal salicylate ligands that chelate the metal through their carboxylate functionality. A third salicylate ion bridges two Bi atoms to form a dimer (Fig.2). The Bi—O(carboxylate) bond lengths range from 2.377 (3) to 2.801 (3) Å. The two N atoms of the 2,2'-bipyridine ligand coordinate to the Bi atom with bond lengths of 2.387 (3) and 2.511 (3) Å.
Each of the salicylate ligands shows an intramolecular H bond.