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Acta Cryst. (2009). E65, o2081    [ doi:10.1107/S1600536809030207 ]

2,2'-Bipyridine-5,5'-dicarboxylic acid

C. Wang

Abstract top

The title molecule, C12H8N2O4, lies on an inversion center. In the crystal structure, intermolecular O-H...O hydrogen bonds connect molecules into one-dimensional chains along [1\overline{1}1].

Comment top

2,2'-bipyridine-5,5'-dicarboxylate acid is a potential multi-dentate ligand with a versatile coordination mode, which has been used in self-assembled porous coordination synthesis (Schokecht & Kempe, 2004). The crystals of the title compound were obtained unintentionally as the harvested product of the hydrothermal reaction of 2,2'-bipyridine-5,5'-dicarboxylate acid, Eu2O3 and 1,10-phenanthroline.

The molecular structure of the title compound is shown in Fig. 1. In the crystal structure, intermolecular O—H···O hydrogen bonds connect molecules into one-dimensional chains along [1 -1 1] (Fig. 2).

Related literature top

For synthetic applications of the title compound, see: Schokecht & Kempe (2004).

Experimental top

Yellow needle-like crystals of the title compound were obtained by hydrothermal reaction of 2,2'-bipyridine-5,5'-dicarboxylate acid (0.04884 g), 1,10-phenanthroline (0.0360 g), Eu2O3 (0.0702 g) and deionized water (15 ml) in a 23 ml teflon-lined reaction vesset at 433 K for 120 h, followed by slow cooling to room temperature.

Refinement top

All H atoms were placed in calculated positions and included in a riding-model approximation, with C—H = 0.93 Å, O-H = 0.82Å and Uiso(H)= 1.2Ueq(C) or 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound shown with 30% probabilty ellipsoids [symmetry code: (a) -x, -y+1, -z+1].
[Figure 2] Fig. 2. Part of the crystal structure of the title compound with hydrogen bonds shown as dashed lines. The one-dimensional hydrogen-bonded chains propagate along [1-11].
2,2'-Bipyridine-5,5'-dicarboxylic acid top
Crystal data top
C12H8N2O4Z = 1
Mr = 244.20F(000) = 126
Triclinic, P1Dx = 1.594 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 3.7384 (5) ÅCell parameters from 528 reflections
b = 6.3934 (8) Åθ = 3.2–27.6°
c = 10.7786 (13) ŵ = 0.12 mm−1
α = 98.774 (2)°T = 298 K
β = 92.567 (1)°Needle, yellow
γ = 90.000 (1)°0.15 × 0.11 × 0.08 mm
V = 254.34 (6) Å3
Data collection top
Bruker SMART CCD
diffractometer		893 independent reflections
Radiation source: fine-focus sealed tube657 reflections with I > 2σ(I)
graphiteRint = 0.023
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −4→4
Tmin = 0.982, Tmax = 0.990k = −7→7
1343 measured reflectionsl = −11→12
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)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.214H-atom parameters constrained
S = 1.14 w = 1/[σ2(Fo2) + (0.1116P)2 + 0.1159P]
where P = (Fo2 + 2Fc2)/3
893 reflections(Δ/σ)max < 0.001
82 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C12H8N2O4γ = 90.000 (1)°
Mr = 244.20V = 254.34 (6) Å3
Triclinic, P1Z = 1
a = 3.7384 (5) ÅMo Kα radiation
b = 6.3934 (8) ŵ = 0.12 mm−1
c = 10.7786 (13) ÅT = 298 K
α = 98.774 (2)°0.15 × 0.11 × 0.08 mm
β = 92.567 (1)°
Data collection top
Bruker SMART CCD
diffractometer		893 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		657 reflections with I > 2σ(I)
Tmin = 0.982, Tmax = 0.990Rint = 0.023
1343 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.071H-atom parameters constrained
wR(F2) = 0.214Δρmax = 0.33 e Å−3
S = 1.14Δρmin = −0.36 e Å−3
893 reflectionsAbsolute structure: ?
82 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
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
N10.1979 (7)0.2556 (4)0.5341 (2)0.0351 (8)
O10.5129 (7)−0.0316 (4)0.8383 (2)0.0492 (8)
H10.5614−0.07880.90360.074*
O20.2843 (7)0.2274 (4)0.9736 (2)0.0536 (9)
C10.3541 (8)0.1439 (5)0.8636 (3)0.0334 (8)
C20.2905 (8)0.1631 (5)0.6337 (3)0.0347 (9)
H20.39220.02930.61970.042*
C30.2438 (7)0.2552 (5)0.7571 (3)0.0307 (9)
C40.0964 (8)0.4566 (5)0.7784 (3)0.0353 (9)
H40.06400.52380.85980.042*
C5−0.0008 (8)0.5548 (5)0.6768 (3)0.0332 (8)
H5−0.10090.68920.68900.040*
C60.0520 (8)0.4512 (5)0.5562 (3)0.0295 (8)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0443 (16)0.0333 (15)0.0284 (15)0.0064 (12)−0.0011 (12)0.0079 (12)
O10.0724 (18)0.0463 (16)0.0308 (14)0.0208 (13)−0.0006 (12)0.0129 (11)
O20.083 (2)0.0525 (17)0.0267 (14)0.0231 (14)0.0056 (12)0.0108 (11)
C10.0347 (17)0.0366 (18)0.0297 (17)0.0043 (14)−0.0014 (13)0.0088 (14)
C20.0390 (18)0.0339 (18)0.0329 (18)0.0076 (14)−0.0009 (13)0.0108 (14)
C30.0309 (16)0.0350 (19)0.0271 (18)0.0003 (14)−0.0020 (13)0.0083 (14)
C40.0446 (19)0.0375 (19)0.0240 (16)0.0068 (15)0.0024 (13)0.0047 (13)
C50.0393 (18)0.0321 (17)0.0296 (17)0.0078 (14)0.0009 (13)0.0092 (14)
C60.0288 (15)0.0318 (18)0.0289 (17)−0.0009 (13)−0.0021 (12)0.0088 (14)
Geometric parameters (Å, °) top
N1—C21.335 (4)C2—H20.9300
N1—C61.357 (4)C3—C41.391 (4)
O1—C11.267 (4)C4—C51.378 (4)
O1—H10.8200C4—H40.9300
O2—C11.263 (4)C5—C61.388 (4)
C1—C31.484 (4)C5—H50.9300
C2—C31.388 (4)C6—C6i1.482 (6)
C2—N1—C6117.4 (3)C4—C3—C1120.8 (3)
C1—O1—H1109.5C5—C4—C3118.9 (3)
O2—C1—O1123.7 (3)C5—C4—H4120.5
O2—C1—C3118.7 (3)C3—C4—H4120.5
O1—C1—C3117.6 (3)C4—C5—C6119.3 (3)
N1—C2—C3123.8 (3)C4—C5—H5120.3
N1—C2—H2118.1C6—C5—H5120.3
C3—C2—H2118.1N1—C6—C5122.4 (3)
C2—C3—C4118.2 (3)N1—C6—C6i116.1 (3)
C2—C3—C1121.0 (3)C5—C6—C6i121.5 (4)
C6—N1—C2—C30.4 (5)C2—C3—C4—C50.8 (5)
N1—C2—C3—C4−0.9 (5)C1—C3—C4—C5179.7 (3)
N1—C2—C3—C1−179.8 (3)C3—C4—C5—C6−0.3 (5)
O2—C1—C3—C2−175.3 (3)C2—N1—C6—C50.2 (5)
O1—C1—C3—C24.4 (5)C2—N1—C6—C6i−179.3 (3)
O2—C1—C3—C45.9 (5)C4—C5—C6—N1−0.2 (5)
O1—C1—C3—C4−174.4 (3)C4—C5—C6—C6i179.2 (3)
Symmetry codes: (i) −x, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2ii0.821.822.625 (3)168
Symmetry codes: (ii) −x+1, −y, −z+2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.821.822.625 (3)168
Symmetry codes: (i) −x+1, −y, −z+2.
Acknowledgements top

The authors gratefully acknowledge the financial support of the Research Fund of Beijing University of Civil Engineering and Architecture (grant No. 100700502) and the Funding Project for Academic Human Resources Development in Institutions of Higher Learning Under the Jurisdiction of Beijing Municipality (grant No. BJE10016200611).

references
References top

Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.

Schokecht, B. & Kempe, R. (2004). Z. Anorg. Allg. Chem. 630, 1377-1379.

Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Spek, A. L. (2009). Acta Cryst. D65, 148–155.