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The structure of the title compound, [Bi2(C7H5O3)6(C10H8N2)2], consists of centrosymmetric dimeric units in which salicylate ligands bridge two metal centres. The Bi atom is eight-coordinated, with Bi—O and Bi—N bond lengths in the ranges 2.377 (3)–3.044 (3) and 2.387 (3)–2.511 (3) Å, respectively. Each of the salicylate ligands shows an intra­molecular hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680701642X/bt2330sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680701642X/bt2330Isup2.hkl
Contains datablock I

CCDC reference: 650578

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](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

Comment top

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.

Related literature top

For related literature, see: Briand & Burford (1999); Guo & Sadler (1999); Sadler et al. (1999); Suerbaum & Michetti (2003); Thompson & Orvig (2003); Thurston et al. (2002).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of the title compound, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. Dimeric units of the title compound. [Symmetry code: (i) 1 - x, -y, -z.]
Bis(µ-2-hydroxybenzoato-κ2O:O')bis[(2,2'-bipyridine-κ2N,N')bis(2- hydroxybenzoato-κ2O,O')bismuth(III)] top
Crystal data top
[Bi2(C7H5O3)6(C10H8N2)2]F(000) = 3024
Mr = 1552.98Dx = 1.834 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
a = 21.4583 (3) ÅCell parameters from 14948 reflections
b = 13.6698 (2) Åθ = 1.8–25.6°
c = 21.6097 (1) ŵ = 6.33 mm1
β = 117.472 (1)°T = 293 K
V = 5624.00 (12) Å3Block, colourless
Z = 40.2 × 0.1 × 0.1 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
5322 independent reflections
Radiation source: fine-focus sealed tube4590 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
φ and ω scansθmax = 25.6°, θmin = 1.8°
Absorption correction: empirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
h = 2618
Tmin = 0.486, Tmax = 1.000k = 1416
14948 measured reflectionsl = 2426
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.063H-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 parametersΔρmax = 0.81 e Å3
0 restraintsΔρmin = 1.26 e Å3
Crystal data top
[Bi2(C7H5O3)6(C10H8N2)2]V = 5624.00 (12) Å3
Mr = 1552.98Z = 4
Monoclinic, C2/cMo Kα radiation
a = 21.4583 (3) ŵ = 6.33 mm1
b = 13.6698 (2) ÅT = 293 K
c = 21.6097 (1) Å0.2 × 0.1 × 0.1 mm
β = 117.472 (1)°
Data collection top
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 = 1.000Rint = 0.028
14948 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0250 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0258P)2 + 23.4426P]
where P = (Fo2 + 2Fc2)/3
5322 reflectionsΔρmax = 0.81 e Å3
388 parametersΔρmin = 1.26 e Å3
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Bi10.557548 (7)0.053031 (12)0.039024 (7)0.02992 (6)
C10.5214 (2)0.3657 (3)0.0917 (3)0.0446 (12)
N10.68538 (18)0.0770 (3)0.04387 (18)0.0349 (8)
O10.50042 (16)0.1969 (2)0.12275 (17)0.0445 (8)
C20.4803 (3)0.3989 (5)0.1598 (4)0.0662 (16)
O40.58818 (17)0.0884 (3)0.05826 (16)0.0428 (7)
N20.62695 (18)0.0854 (3)0.09692 (17)0.0318 (8)
O20.58232 (17)0.2334 (2)0.01744 (16)0.0444 (8)
C30.4740 (4)0.4984 (6)0.1734 (5)0.104 (3)
H3A0.44700.51990.21890.125*
C40.5059 (5)0.5651 (5)0.1225 (7)0.108 (3)
H4A0.50250.63140.13330.130*
O30.4454 (3)0.3395 (4)0.2132 (3)0.1076 (19)
H3B0.45300.28260.19980.161*
C50.5443 (4)0.5338 (5)0.0534 (6)0.095 (3)
H5A0.56380.57980.01780.113*
C60.5535 (3)0.4343 (4)0.0374 (4)0.0620 (17)
H6A0.58040.41360.00840.074*
O60.6500 (2)0.2041 (4)0.16486 (18)0.0753 (13)
H6B0.62690.15660.14310.113*
C70.5352 (2)0.2600 (3)0.0758 (2)0.0357 (10)
O70.48413 (17)0.0242 (2)0.14704 (16)0.0454 (8)
C80.6552 (2)0.2260 (3)0.0570 (2)0.0364 (10)
O80.45182 (16)0.1136 (2)0.08025 (16)0.0422 (7)
C90.6689 (2)0.2569 (4)0.1239 (3)0.0491 (12)
O50.61390 (16)0.1012 (2)0.02946 (15)0.0393 (7)
C100.7060 (3)0.3428 (5)0.1511 (3)0.0734 (19)
H10A0.71470.36400.19520.088*
O90.36991 (19)0.2678 (3)0.13324 (18)0.0556 (9)
H10B0.39210.22780.10270.083*
C110.7299 (4)0.3963 (5)0.1127 (4)0.083 (2)
H11A0.75400.45430.13100.099*
C120.7190 (4)0.3663 (5)0.0476 (4)0.0771 (19)
H12A0.73680.40240.02290.093*
C130.6815 (3)0.2823 (4)0.0198 (3)0.0546 (13)
H13A0.67330.26230.02440.065*
C140.6168 (2)0.1345 (3)0.0270 (2)0.0340 (9)
C150.4140 (2)0.1663 (3)0.1969 (2)0.0383 (10)
C160.3771 (2)0.2473 (4)0.1911 (2)0.0420 (11)
C170.3459 (3)0.3119 (4)0.2465 (3)0.0544 (13)
H17A0.32100.36530.24270.065*
C180.3513 (3)0.2983 (5)0.3067 (3)0.0651 (16)
H18A0.33030.34280.34310.078*
C190.3876 (3)0.2187 (5)0.3139 (3)0.0677 (17)
H19A0.39160.20970.35450.081*
C200.4177 (3)0.1531 (4)0.2592 (2)0.0527 (13)
H20A0.44110.09870.26410.063*
C210.4519 (2)0.0972 (3)0.1377 (2)0.0344 (9)
C220.7282 (2)0.1021 (3)0.0166 (2)0.0337 (9)
C230.7133 (2)0.0643 (4)0.1133 (2)0.0441 (11)
H23A0.68380.04750.13240.053*
C240.7843 (3)0.0755 (4)0.1572 (3)0.0527 (13)
H24A0.80230.06580.20500.063*
C250.8278 (3)0.1012 (5)0.1290 (3)0.0568 (14)
H25A0.87570.10930.15760.068*
C260.7999 (2)0.1150 (4)0.0581 (3)0.0487 (12)
H26A0.82860.13260.03830.058*
C270.6946 (2)0.1129 (3)0.0610 (2)0.0327 (9)
C280.5949 (3)0.0908 (4)0.1671 (2)0.0432 (11)
H28A0.54810.07190.19160.052*
C290.6293 (3)0.1232 (4)0.2037 (3)0.0484 (12)
H29A0.60640.12430.25220.058*
C300.6978 (3)0.1540 (4)0.1674 (3)0.0501 (12)
H30A0.72130.17810.19110.060*
C310.7314 (2)0.1489 (4)0.0953 (3)0.0429 (11)
H31A0.77790.16920.07000.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Bi10.02658 (9)0.03395 (10)0.02873 (9)0.00108 (7)0.01234 (7)0.00507 (7)
C10.032 (2)0.034 (3)0.070 (3)0.0048 (19)0.025 (2)0.009 (2)
N10.0298 (18)0.040 (2)0.0309 (18)0.0038 (15)0.0108 (15)0.0025 (15)
O10.0339 (16)0.044 (2)0.0443 (18)0.0015 (14)0.0083 (14)0.0036 (15)
C20.048 (3)0.058 (4)0.079 (4)0.006 (3)0.017 (3)0.027 (3)
O40.0433 (18)0.049 (2)0.0395 (17)0.0098 (15)0.0222 (15)0.0006 (15)
N20.0301 (18)0.036 (2)0.0293 (18)0.0007 (15)0.0134 (15)0.0029 (15)
O20.0482 (19)0.0413 (19)0.0378 (17)0.0042 (15)0.0148 (15)0.0065 (14)
C30.071 (5)0.069 (5)0.151 (8)0.024 (4)0.034 (5)0.070 (6)
C40.074 (5)0.042 (4)0.204 (11)0.014 (4)0.060 (6)0.039 (6)
O30.101 (4)0.097 (4)0.076 (3)0.003 (3)0.001 (3)0.038 (3)
C50.068 (4)0.047 (4)0.172 (9)0.003 (3)0.059 (5)0.019 (5)
C60.051 (3)0.041 (3)0.106 (5)0.001 (2)0.047 (4)0.008 (3)
O60.064 (2)0.128 (4)0.041 (2)0.041 (3)0.0304 (19)0.030 (2)
C70.028 (2)0.040 (3)0.043 (3)0.0014 (19)0.020 (2)0.007 (2)
O70.0451 (18)0.0417 (19)0.0389 (17)0.0097 (15)0.0105 (15)0.0041 (14)
C80.033 (2)0.036 (3)0.037 (2)0.0035 (18)0.0127 (19)0.0045 (19)
O80.0476 (18)0.0439 (19)0.0367 (17)0.0040 (15)0.0207 (15)0.0061 (14)
C90.034 (2)0.065 (4)0.046 (3)0.006 (2)0.017 (2)0.017 (2)
O50.0432 (17)0.0426 (19)0.0347 (16)0.0098 (14)0.0201 (14)0.0088 (14)
C100.065 (4)0.078 (5)0.072 (4)0.023 (3)0.027 (3)0.044 (4)
O90.065 (2)0.051 (2)0.055 (2)0.0181 (18)0.0319 (19)0.0082 (17)
C110.082 (5)0.043 (4)0.101 (6)0.021 (3)0.023 (4)0.017 (4)
C120.091 (5)0.048 (4)0.080 (4)0.026 (3)0.029 (4)0.008 (3)
C130.059 (3)0.044 (3)0.052 (3)0.011 (2)0.018 (3)0.004 (2)
C140.034 (2)0.036 (3)0.031 (2)0.0019 (18)0.0141 (18)0.0006 (18)
C150.031 (2)0.042 (3)0.035 (2)0.0033 (19)0.0092 (18)0.001 (2)
C160.035 (2)0.044 (3)0.043 (3)0.000 (2)0.014 (2)0.002 (2)
C170.051 (3)0.045 (3)0.054 (3)0.006 (2)0.014 (3)0.010 (2)
C180.068 (4)0.065 (4)0.045 (3)0.007 (3)0.011 (3)0.022 (3)
C190.074 (4)0.087 (5)0.037 (3)0.011 (3)0.021 (3)0.012 (3)
C200.052 (3)0.061 (4)0.040 (3)0.007 (3)0.017 (2)0.003 (2)
C210.027 (2)0.033 (2)0.036 (2)0.0046 (18)0.0083 (18)0.0016 (19)
C220.028 (2)0.032 (2)0.040 (2)0.0027 (17)0.0150 (18)0.0056 (19)
C230.039 (2)0.057 (3)0.034 (2)0.007 (2)0.014 (2)0.002 (2)
C240.042 (3)0.066 (4)0.036 (3)0.008 (2)0.007 (2)0.005 (2)
C250.030 (2)0.080 (4)0.046 (3)0.001 (3)0.006 (2)0.013 (3)
C260.031 (2)0.066 (4)0.048 (3)0.002 (2)0.017 (2)0.009 (3)
C270.033 (2)0.030 (2)0.036 (2)0.0010 (17)0.0165 (18)0.0031 (18)
C280.043 (3)0.056 (3)0.030 (2)0.001 (2)0.017 (2)0.007 (2)
C290.060 (3)0.054 (3)0.038 (3)0.002 (2)0.028 (2)0.008 (2)
C300.058 (3)0.051 (3)0.055 (3)0.000 (2)0.038 (3)0.009 (2)
C310.039 (2)0.043 (3)0.054 (3)0.002 (2)0.028 (2)0.001 (2)
Geometric parameters (Å, º) top
Bi1—O72.377 (3)C10—C111.370 (10)
Bi1—N22.387 (3)C10—H10A0.9300
Bi1—O52.392 (3)O9—C161.358 (6)
Bi1—N12.511 (3)O9—H10B0.8200
Bi1—O22.520 (3)C11—C121.377 (10)
Bi1—O12.568 (3)C11—H11A0.9300
Bi1—O42.705 (3)C12—C131.371 (8)
Bi1—O8i2.801 (3)C12—H12A0.9300
C1—C21.399 (8)C13—H13A0.9300
C1—C61.409 (8)C15—C201.397 (7)
C1—C71.482 (6)C15—C161.400 (7)
N1—C231.345 (6)C15—C211.493 (6)
N1—C221.346 (5)C16—C171.386 (7)
O1—C71.278 (5)C17—C181.370 (8)
C2—O31.325 (8)C17—H17A0.9300
C2—C31.385 (9)C18—C191.389 (9)
O4—C141.269 (5)C18—H18A0.9300
N2—C271.347 (5)C19—C201.383 (7)
N2—C281.347 (5)C19—H19A0.9300
O2—C71.253 (5)C20—H20A0.9300
C3—C41.346 (13)C22—C261.389 (6)
C3—H3A0.9300C22—C271.494 (6)
C4—C51.398 (13)C23—C241.383 (7)
C4—H4A0.9300C23—H23A0.9300
O3—H3B0.8200C24—C251.375 (8)
C5—C61.395 (9)C24—H24A0.9300
C5—H5A0.9300C25—C261.377 (7)
C6—H6A0.9300C25—H25A0.9300
O6—C91.342 (6)C26—H26A0.9300
O6—H6B0.8200C27—C311.399 (6)
O7—C211.283 (5)C28—C291.381 (6)
C8—C91.401 (6)C28—H28A0.9300
C8—C131.405 (7)C29—C301.375 (7)
C8—C141.473 (6)C29—H29A0.9300
O8—C211.262 (5)C30—C311.384 (7)
O8—Bi1i2.801 (3)C30—H30A0.9300
C9—C101.388 (8)C31—H31A0.9300
O5—C141.277 (5)
O7—Bi1—N281.88 (11)C14—O5—Bi1101.3 (3)
O7—Bi1—O576.88 (11)C11—C10—C9119.8 (6)
N2—Bi1—O578.22 (11)C11—C10—H10A120.1
O7—Bi1—N1140.29 (12)C9—C10—H10A120.1
N2—Bi1—N167.01 (11)C16—O9—H10B109.5
O5—Bi1—N173.19 (11)C10—C11—C12121.6 (6)
O7—Bi1—O2127.14 (11)C10—C11—H11A119.2
N2—Bi1—O277.66 (11)C12—C11—H11A119.2
O5—Bi1—O2142.33 (11)C13—C12—C11119.1 (6)
N1—Bi1—O270.90 (11)C13—C12—H12A120.5
O7—Bi1—O176.31 (10)C11—C12—H12A120.5
N2—Bi1—O172.50 (11)C12—C13—C8121.2 (5)
O5—Bi1—O1142.54 (10)C12—C13—H13A119.4
N1—Bi1—O1114.34 (11)C8—C13—H13A119.4
O2—Bi1—O151.16 (10)O4—C14—O5120.6 (4)
O7—Bi1—O4105.02 (10)O4—C14—C8119.8 (4)
N2—Bi1—O4123.59 (10)O5—C14—C8119.6 (4)
O5—Bi1—O451.00 (9)C20—C15—C16118.3 (4)
N1—Bi1—O475.21 (11)C20—C15—C21119.6 (4)
O2—Bi1—O4126.92 (10)C16—C15—C21122.0 (4)
O1—Bi1—O4163.90 (10)O9—C16—C17116.7 (5)
O7—Bi1—O8i137.59 (10)O9—C16—C15123.7 (4)
N2—Bi1—O8i138.97 (11)C17—C16—C15119.6 (5)
O5—Bi1—O8i115.41 (10)C18—C17—C16121.0 (5)
N1—Bi1—O8i79.84 (10)C18—C17—H17A119.5
O2—Bi1—O8i68.84 (10)C16—C17—H17A119.5
O1—Bi1—O8i102.03 (10)C17—C18—C19120.7 (5)
O4—Bi1—O8i65.86 (9)C17—C18—H18A119.7
C2—C1—C6119.3 (5)C19—C18—H18A119.7
C2—C1—C7121.4 (5)C20—C19—C18118.6 (5)
C6—C1—C7119.2 (5)C20—C19—H19A120.7
C23—N1—C22118.6 (4)C18—C19—H19A120.7
C23—N1—Bi1123.8 (3)C19—C20—C15121.8 (5)
C22—N1—Bi1117.5 (3)C19—C20—H20A119.1
C7—O1—Bi192.5 (3)C15—C20—H20A119.1
O3—C2—C3117.2 (7)O8—C21—O7122.6 (4)
O3—C2—C1123.1 (6)O8—C21—C15118.9 (4)
C3—C2—C1119.6 (7)O7—C21—C15118.5 (4)
C14—O4—Bi186.9 (2)N1—C22—C26121.7 (4)
C27—N2—C28119.3 (4)N1—C22—C27116.3 (4)
C27—N2—Bi1121.1 (3)C26—C22—C27122.0 (4)
C28—N2—Bi1118.8 (3)N1—C23—C24122.3 (5)
C7—O2—Bi195.5 (3)N1—C23—H23A118.9
C4—C3—C2121.9 (8)C24—C23—H23A118.9
C4—C3—H3A119.0C25—C24—C23118.8 (5)
C2—C3—H3A119.0C25—C24—H24A120.6
C3—C4—C5119.5 (7)C23—C24—H24A120.6
C3—C4—H4A120.3C24—C25—C26119.5 (5)
C5—C4—H4A120.3C24—C25—H25A120.2
C2—O3—H3B109.5C26—C25—H25A120.2
C6—C5—C4120.6 (8)C25—C26—C22119.0 (5)
C6—C5—H5A119.7C25—C26—H26A120.5
C4—C5—H5A119.7C22—C26—H26A120.5
C5—C6—C1118.9 (7)N2—C27—C31121.0 (4)
C5—C6—H6A120.6N2—C27—C22116.9 (4)
C1—C6—H6A120.6C31—C27—C22122.1 (4)
C9—O6—H6B109.5N2—C28—C29122.2 (5)
O2—C7—O1120.5 (4)N2—C28—H28A118.9
O2—C7—C1119.9 (4)C29—C28—H28A118.9
O1—C7—C1119.6 (4)C30—C29—C28118.9 (5)
C21—O7—Bi1110.6 (3)C30—C29—H29A120.5
C9—C8—C13118.4 (4)C28—C29—H29A120.5
C9—C8—C14121.2 (4)C29—C30—C31119.5 (4)
C13—C8—C14120.3 (4)C29—C30—H30A120.2
C21—O8—Bi1i152.4 (3)C31—C30—H30A120.2
O6—C9—C10117.8 (5)C30—C31—C27119.0 (4)
O6—C9—C8122.3 (5)C30—C31—H31A120.5
C10—C9—C8119.9 (5)C27—C31—H31A120.5
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Bi2(C7H5O3)6(C10H8N2)2]
Mr1552.98
Crystal system, space groupMonoclinic, C2/c
Temperature (K)293
a, b, c (Å)21.4583 (3), 13.6698 (2), 21.6097 (1)
β (°) 117.472 (1)
V3)5624.00 (12)
Z4
Radiation typeMo Kα
µ (mm1)6.33
Crystal size (mm)0.2 × 0.1 × 0.1
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionEmpirical (using intensity measurements)
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.486, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
14948, 5322, 4590
Rint0.028
(sin θ/λ)max1)0.609
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.025, 0.063, 1.07
No. of reflections5322
No. of parameters388
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.0258P)2 + 23.4426P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å3)0.81, 1.26

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
Bi1—O72.377 (3)C2—O31.325 (8)
Bi1—N22.387 (3)O4—C141.269 (5)
Bi1—O52.392 (3)O2—C71.253 (5)
Bi1—N12.511 (3)O6—C91.342 (6)
Bi1—O22.520 (3)O7—C211.283 (5)
Bi1—O12.568 (3)C8—C141.473 (6)
Bi1—O42.705 (3)O8—C211.262 (5)
Bi1—O8i2.801 (3)O5—C141.277 (5)
O1—C71.278 (5)
O7—Bi1—N281.88 (11)O7—Bi1—O176.31 (10)
O7—Bi1—O576.88 (11)N2—Bi1—O172.50 (11)
N2—Bi1—O578.22 (11)O2—Bi1—O151.16 (10)
N2—Bi1—N167.01 (11)O5—Bi1—O451.00 (9)
O5—Bi1—N173.19 (11)N1—Bi1—O475.21 (11)
N2—Bi1—O277.66 (11)N1—Bi1—O8i79.84 (10)
N1—Bi1—O270.90 (11)O4—Bi1—O8i65.86 (9)
Symmetry code: (i) x+1, y, z.
 

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