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Acta Cryst. (2009). E65, o1239    [ doi:10.1107/S1600536809015530 ]

3-(4-Pyridyl)benzoic acid

J. Xing

Abstract top

The molecule of the title compound, C12H9NO2, is not planar, the benzene and pyridine rings making a dihedral angle of 32.14 (7)°. The carboxy group is slightly twisted with respect to the benzene ring by 11.95 (10)°. In the crystal structure, intermolecular O-H...N hydrogen bonds link neighboring molecules into infinite chains along the c axis.

Comment top

As part of an ongoing investigation into coordination polymer with pyridine carboxylate (Lu et al., 2003; Luo et al., 2007), the crystal structure of the title compound is presented here.

The molecule of the title compound, C12H9NO2, is not planar, the phenyl and the pyridine rings make a dihedral angle of 32.14 (7)° (Fig. 1). The acetic group is slightly twisted with respect to the phenyl ring by 11.95 (10)°. In the crystal structure, intermolecular O—H···N hydrogen bonds link neighboring molecules into infinite chains along the c axis (Table 1, Fig. 2).

Related literature top

For coordination polymers with pyridine carboxylate, see: Lu & Luck (2003); Luo et al. (2007).

Experimental top

Commercially available 3-Pyrid-4-ylbenzoic acid was further purified by repeated recrystallization anhydrous ethanol from. Single crystals suitable for X-ray analysis were grown by slow evaporation of an anhydrous ethanol solution at room temperature.

Refinement top

All H atoms attached to C atoms and O atom were fixed geometrically and treated as riding with C—H = 0.93 Å and O—H = 0.82 Å with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(O).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound with the atom labeling scheme. Displacement ellipsoids are drawn at the 50% probalility level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Partial packing view showing the formation of infinite chain through the O-H···N hydrogen bondings. H bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity.
3-(4-Pyridyl)benzoic acid top
Crystal data top
C12H9NO2F000 = 832
Mr = 199.20Dx = 1.400 Mg m−3
Orthorhombic, PbcaMo Kα radiation
λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 1695 reflections
a = 13.839 (3) Åθ = 2.6–24.3º
b = 7.013 (7) ŵ = 0.10 mm−1
c = 19.469 (10) ÅT = 296 K
V = 1890 (2) Å3Block, colorless
Z = 80.33 × 0.25 × 0.20 mm
Data collection top
Bruker APEX2 CCD area-detector
diffractometer		2365 independent reflections
Radiation source: fine-focus sealed tube1480 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 293 Kθmax = 28.5º
φ and ω scansθmin = 2.1º
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −12→18
Tmin = 0.958, Tmax = 0.979k = −9→8
11481 measured reflectionsl = −25→26
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.135  w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2238P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
2365 reflectionsΔρmax = 0.24 e Å−3
137 parametersΔρmin = −0.18 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
Crystal data top
C12H9NO2V = 1890 (2) Å3
Mr = 199.20Z = 8
Orthorhombic, PbcaMo Kα
a = 13.839 (3) ŵ = 0.10 mm−1
b = 7.013 (7) ÅT = 296 K
c = 19.469 (10) Å0.33 × 0.25 × 0.20 mm
Data collection top
Bruker APEX2 CCD area-detector
diffractometer		2365 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		1480 reflections with I > 2σ(I)
Tmin = 0.958, Tmax = 0.979Rint = 0.041
11481 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045137 parameters
wR(F2) = 0.135H-atom parameters constrained
S = 1.03Δρmax = 0.24 e Å−3
2365 reflectionsΔρmin = −0.18 e Å−3
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O10.40429 (11)0.07701 (18)0.11778 (6)0.0584 (4)
O20.36926 (10)−0.18026 (17)0.17987 (6)0.0522 (4)
H20.3707−0.23220.14220.078*
N10.37092 (10)−0.1441 (2)0.55920 (6)0.0404 (4)
C10.32413 (12)0.1110 (2)0.48533 (8)0.0394 (4)
H10.29100.22540.48010.047*
C20.32519 (12)0.0204 (2)0.54811 (8)0.0409 (4)
H2A0.29240.07670.58450.049*
C30.41717 (12)−0.2214 (2)0.50565 (8)0.0412 (4)
H30.4495−0.33620.51230.049*
C40.41965 (13)−0.1406 (2)0.44148 (8)0.0384 (4)
H40.4527−0.20070.40590.046*
C50.37253 (11)0.0313 (2)0.42988 (7)0.0333 (4)
C60.37464 (11)0.1281 (2)0.36208 (7)0.0351 (4)
C70.37848 (12)0.0237 (2)0.30137 (8)0.0367 (4)
H70.3784−0.10880.30340.044*
C80.38238 (11)0.1135 (2)0.23794 (8)0.0370 (4)
C90.38217 (13)0.3104 (2)0.23504 (9)0.0449 (4)
H90.38590.37180.19280.054*
C100.37647 (14)0.4159 (2)0.29454 (9)0.0517 (5)
H100.37520.54840.29220.062*
C110.37260 (13)0.3262 (2)0.35748 (9)0.0449 (4)
H110.36860.39890.39730.054*
C120.38692 (12)0.0033 (2)0.17260 (8)0.0405 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0891 (11)0.0554 (8)0.0308 (7)−0.0103 (7)0.0039 (6)0.0069 (6)
O20.0824 (10)0.0435 (7)0.0306 (6)−0.0105 (7)0.0057 (6)−0.0034 (5)
N10.0462 (9)0.0433 (8)0.0316 (7)−0.0036 (6)−0.0016 (6)0.0014 (6)
C10.0434 (10)0.0387 (9)0.0361 (9)0.0052 (7)0.0005 (7)−0.0049 (7)
C20.0436 (10)0.0468 (10)0.0322 (9)−0.0013 (8)0.0036 (7)−0.0073 (7)
C30.0483 (10)0.0375 (8)0.0377 (9)0.0036 (8)−0.0022 (7)0.0007 (7)
C40.0460 (10)0.0373 (9)0.0319 (8)0.0016 (7)0.0039 (7)−0.0037 (7)
C50.0374 (8)0.0340 (8)0.0285 (8)−0.0034 (7)−0.0011 (6)−0.0023 (6)
C60.0381 (9)0.0342 (8)0.0330 (8)−0.0005 (7)0.0009 (7)0.0000 (6)
C70.0452 (9)0.0319 (8)0.0330 (8)−0.0011 (7)0.0011 (7)0.0008 (6)
C80.0406 (9)0.0385 (9)0.0320 (8)−0.0026 (7)−0.0008 (7)0.0013 (6)
C90.0567 (11)0.0409 (10)0.0370 (9)−0.0037 (8)−0.0058 (8)0.0095 (7)
C100.0732 (14)0.0300 (9)0.0519 (11)0.0004 (9)−0.0051 (9)0.0038 (8)
C110.0590 (11)0.0359 (9)0.0399 (9)0.0018 (8)−0.0004 (8)−0.0047 (7)
C120.0468 (10)0.0423 (10)0.0324 (9)−0.0017 (7)−0.0010 (7)0.0035 (7)
Geometric parameters (Å, °) top
O1—C121.2102 (18)C5—C61.485 (2)
O2—C121.318 (2)C6—C71.391 (2)
O2—H20.8200C6—C111.393 (2)
N1—C21.333 (2)C7—C81.387 (2)
N1—C31.338 (2)C7—H70.9300
C1—C21.378 (2)C8—C91.382 (2)
C1—C51.388 (2)C8—C121.490 (2)
C1—H10.9300C9—C101.377 (2)
C2—H2A0.9300C9—H90.9300
C3—C41.372 (2)C10—C111.379 (2)
C3—H30.9300C10—H100.9300
C4—C51.389 (2)C11—H110.9300
C4—H40.9300
C12—O2—H2109.5C11—C6—C5120.85 (13)
C2—N1—C3116.83 (14)C8—C7—C6121.25 (15)
C2—C1—C5119.96 (15)C8—C7—H7119.4
C2—C1—H1120.0C6—C7—H7119.4
C5—C1—H1120.0C9—C8—C7119.33 (15)
N1—C2—C1123.21 (15)C9—C8—C12118.92 (14)
N1—C2—H2A118.4C7—C8—C12121.75 (15)
C1—C2—H2A118.4C10—C9—C8120.19 (15)
N1—C3—C4123.66 (16)C10—C9—H9119.9
N1—C3—H3118.2C8—C9—H9119.9
C4—C3—H3118.2C9—C10—C11120.32 (16)
C3—C4—C5119.64 (15)C9—C10—H10119.8
C3—C4—H4120.2C11—C10—H10119.8
C5—C4—H4120.2C10—C11—C6120.77 (15)
C1—C5—C4116.70 (14)C10—C11—H11119.6
C1—C5—C6121.14 (14)C6—C11—H11119.6
C4—C5—C6122.15 (14)O1—C12—O2123.30 (16)
C7—C6—C11118.12 (14)O1—C12—C8122.67 (16)
C7—C6—C5121.03 (14)O2—C12—C8114.03 (14)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1i0.821.832.6526 (18)178
Symmetry codes: (i) x, −y−1/2, z−1/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1i0.821.832.6526 (18)178
Symmetry codes: (i) x, −y−1/2, z−1/2.
references
References top

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.

Brandenburg, K. & Putz, H. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.

Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc.,Madison, Wisconsin, USA.

Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.

Lu, T. B. & Luck, R. L. (2003). Inorg. Chim. Acta, 351, 345–355.

Luo, J. H., Zhao, Y. S., Xu, H. W., Kinnibrugh, T. L., Yang, D. L., Timofeeva, T. V., Daemen, L. L., Zhang, J. Z., Bao, W., Thompson, J. D. & Currier, R. P. (2007). Inorg. Chem. 46, 9021–9023.

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