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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1239.
Published online 2009 May 14. doi:  10.1107/S1600536809015530
PMCID: PMC2969741

3-(4-Pyrid­yl)benzoic acid

Abstract

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.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-o1239-scheme1.jpg

Experimental

Crystal data

  • C12H9NO2
  • M r = 199.20
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1239-efi1.jpg
  • a = 13.839 (3) Å
  • b = 7.013 (7) Å
  • c = 19.469 (10) Å
  • V = 1890 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 K
  • 0.33 × 0.25 × 0.20 mm

Data collection

  • Bruker APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2005 [triangle]) T min = 0.958, T max = 0.979
  • 11481 measured reflections
  • 2365 independent reflections
  • 1480 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.135
  • S = 1.03
  • 2365 reflections
  • 137 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.19 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809015530/dn2447sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015530/dn2447Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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).

Experimental

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

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).

Figures

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.
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.

Crystal data

C12H9NO2F(000) = 832
Mr = 199.20Dx = 1.400 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2abCell parameters from 1695 reflections
a = 13.839 (3) Åθ = 2.6–24.3°
b = 7.013 (7) ŵ = 0.10 mm1
c = 19.469 (10) ÅT = 296 K
V = 1890 (2) Å3Block, colorless
Z = 80.33 × 0.25 × 0.20 mm

Data collection

Bruker APEX2 CCD area-detector diffractometer2365 independent reflections
Radiation source: fine-focus sealed tube1480 reflections with I > 2σ(I)
graphiteRint = 0.041
[var phi] and ω scansθmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)h = −12→18
Tmin = 0.958, Tmax = 0.979k = −9→8
11481 measured reflectionsl = −25→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2238P] where P = (Fo2 + 2Fc2)/3
2365 reflections(Δ/σ)max = 0.001
137 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special details

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)

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)

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, °)

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, °)

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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2447).

References

  • 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. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography