3-(4-Pyrid­yl)benzoic acid

Xing, J.

doi:10.1107/S1600536809015530

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1239

doi:10.1107/S1600536809015530

Open

access

3-(4-Pyridyl)benzoic acid

Jianxin Xing ^a ^*

^aDepartment of Biology, Dezhou University, Dezhou Shandong 253023, People's Republic of China
^*Correspondence e-mail: dzxingjianxin@yahoo.cn

(Received 11 April 2009; accepted 26 April 2009; online 14 May 2009)

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 ); Luo et al. (2007 ).

Experimental

Crystal data

C₁₂H₉NO₂
M_r = 199.20
Orthorhombic, P b c a
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 ) 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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.135
S = 1.03
2365 reflections
137 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯N1ⁱ	0.82	1.83	2.6526 (18)	178
Symmetry code: (i) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 ).

Supporting information

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

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

checkCIF report

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.

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

	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.

3-(4-Pyridyl)benzoic acid top

Crystal data top

C₁₂H₉NO₂	F(000) = 832
M_r = 199.20	D_x = 1.400 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1695 reflections
a = 13.839 (3) Å	θ = 2.6–24.3°
b = 7.013 (7) Å	µ = 0.10 mm⁻¹
c = 19.469 (10) Å	T = 296 K
V = 1890 (2) Å³	Block, colorless
Z = 8	0.33 × 0.25 × 0.20 mm

Data collection top

Bruker APEX2 CCD area-detector diffractometer	2365 independent reflections
Radiation source: fine-focus sealed tube	1480 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.041
ϕ and ω scans	θ_max = 28.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −12→18
T_min = 0.958, T_max = 0.979	k = −9→8
11481 measured reflections	l = −25→26

Refinement top

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0645P)² + 0.2238P] where P = (F_o² + 2F_c²)/3
2365 reflections	(Δ/σ)_max = 0.001
137 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₂H₉NO₂	V = 1890 (2) Å³
M_r = 199.20	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 13.839 (3) Å	µ = 0.10 mm⁻¹
b = 7.013 (7) Å	T = 296 K
c = 19.469 (10) Å	0.33 × 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)
T_min = 0.958, T_max = 0.979	R_int = 0.041
11481 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.03	Δρ_max = 0.24 e Å⁻³
2365 reflections	Δρ_min = −0.19 e Å⁻³
137 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.40429 (11)	0.07701 (18)	0.11778 (6)	0.0584 (4)
O2	0.36926 (10)	−0.18026 (17)	0.17987 (6)	0.0522 (4)
H2	0.3707	−0.2322	0.1422	0.078*
N1	0.37092 (10)	−0.1441 (2)	0.55920 (6)	0.0404 (4)
C1	0.32413 (12)	0.1110 (2)	0.48533 (8)	0.0394 (4)
H1	0.2910	0.2254	0.4801	0.047*
C2	0.32519 (12)	0.0204 (2)	0.54811 (8)	0.0409 (4)
H2A	0.2924	0.0767	0.5845	0.049*
C3	0.41717 (12)	−0.2214 (2)	0.50565 (8)	0.0412 (4)
H3	0.4495	−0.3362	0.5123	0.049*
C4	0.41965 (13)	−0.1406 (2)	0.44148 (8)	0.0384 (4)
H4	0.4527	−0.2007	0.4059	0.046*
C5	0.37253 (11)	0.0313 (2)	0.42988 (7)	0.0333 (4)
C6	0.37464 (11)	0.1281 (2)	0.36208 (7)	0.0351 (4)
C7	0.37848 (12)	0.0237 (2)	0.30137 (8)	0.0367 (4)
H7	0.3784	−0.1088	0.3034	0.044*
C8	0.38238 (11)	0.1135 (2)	0.23794 (8)	0.0370 (4)
C9	0.38217 (13)	0.3104 (2)	0.23504 (9)	0.0449 (4)
H9	0.3859	0.3718	0.1928	0.054*
C10	0.37647 (14)	0.4159 (2)	0.29454 (9)	0.0517 (5)
H10	0.3752	0.5484	0.2922	0.062*
C11	0.37260 (13)	0.3262 (2)	0.35748 (9)	0.0449 (4)
H11	0.3686	0.3989	0.3973	0.054*
C12	0.38692 (12)	0.0033 (2)	0.17260 (8)	0.0405 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0891 (11)	0.0554 (8)	0.0308 (7)	−0.0103 (7)	0.0039 (6)	0.0069 (6)
O2	0.0824 (10)	0.0435 (7)	0.0306 (6)	−0.0105 (7)	0.0057 (6)	−0.0034 (5)
N1	0.0462 (9)	0.0433 (8)	0.0316 (7)	−0.0036 (6)	−0.0016 (6)	0.0014 (6)
C1	0.0434 (10)	0.0387 (9)	0.0361 (9)	0.0052 (7)	0.0005 (7)	−0.0049 (7)
C2	0.0436 (10)	0.0468 (10)	0.0322 (9)	−0.0013 (8)	0.0036 (7)	−0.0073 (7)
C3	0.0483 (10)	0.0375 (8)	0.0377 (9)	0.0036 (8)	−0.0022 (7)	0.0007 (7)
C4	0.0460 (10)	0.0373 (9)	0.0319 (8)	0.0016 (7)	0.0039 (7)	−0.0037 (7)
C5	0.0374 (8)	0.0340 (8)	0.0285 (8)	−0.0034 (7)	−0.0011 (6)	−0.0023 (6)
C6	0.0381 (9)	0.0342 (8)	0.0330 (8)	−0.0005 (7)	0.0009 (7)	0.0000 (6)
C7	0.0452 (9)	0.0319 (8)	0.0330 (8)	−0.0011 (7)	0.0011 (7)	0.0008 (6)
C8	0.0406 (9)	0.0385 (9)	0.0320 (8)	−0.0026 (7)	−0.0008 (7)	0.0013 (6)
C9	0.0567 (11)	0.0409 (10)	0.0370 (9)	−0.0037 (8)	−0.0058 (8)	0.0095 (7)
C10	0.0732 (14)	0.0300 (9)	0.0519 (11)	0.0004 (9)	−0.0051 (9)	0.0038 (8)
C11	0.0590 (11)	0.0359 (9)	0.0399 (9)	0.0018 (8)	−0.0004 (8)	−0.0047 (7)
C12	0.0468 (10)	0.0423 (10)	0.0324 (9)	−0.0017 (7)	−0.0010 (7)	0.0035 (7)

Geometric parameters (Å, º) top

O1—C12	1.2102 (18)	C5—C6	1.485 (2)
O2—C12	1.318 (2)	C6—C7	1.391 (2)
O2—H2	0.8200	C6—C11	1.393 (2)
N1—C2	1.333 (2)	C7—C8	1.387 (2)
N1—C3	1.338 (2)	C7—H7	0.9300
C1—C2	1.378 (2)	C8—C9	1.382 (2)
C1—C5	1.388 (2)	C8—C12	1.490 (2)
C1—H1	0.9300	C9—C10	1.377 (2)
C2—H2A	0.9300	C9—H9	0.9300
C3—C4	1.372 (2)	C10—C11	1.379 (2)
C3—H3	0.9300	C10—H10	0.9300
C4—C5	1.389 (2)	C11—H11	0.9300
C4—H4	0.9300

C12—O2—H2	109.5	C11—C6—C5	120.85 (13)
C2—N1—C3	116.83 (14)	C8—C7—C6	121.25 (15)
C2—C1—C5	119.96 (15)	C8—C7—H7	119.4
C2—C1—H1	120.0	C6—C7—H7	119.4
C5—C1—H1	120.0	C9—C8—C7	119.33 (15)
N1—C2—C1	123.21 (15)	C9—C8—C12	118.92 (14)
N1—C2—H2A	118.4	C7—C8—C12	121.75 (15)
C1—C2—H2A	118.4	C10—C9—C8	120.19 (15)
N1—C3—C4	123.66 (16)	C10—C9—H9	119.9
N1—C3—H3	118.2	C8—C9—H9	119.9
C4—C3—H3	118.2	C9—C10—C11	120.32 (16)
C3—C4—C5	119.64 (15)	C9—C10—H10	119.8
C3—C4—H4	120.2	C11—C10—H10	119.8
C5—C4—H4	120.2	C10—C11—C6	120.77 (15)
C1—C5—C4	116.70 (14)	C10—C11—H11	119.6
C1—C5—C6	121.14 (14)	C6—C11—H11	119.6
C4—C5—C6	122.15 (14)	O1—C12—O2	123.30 (16)
C7—C6—C11	118.12 (14)	O1—C12—C8	122.67 (16)
C7—C6—C5	121.03 (14)	O2—C12—C8	114.03 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	1.83	2.6526 (18)	178

Symmetry code: (i) x, −y−1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₉NO₂
M_r	199.20
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	13.839 (3), 7.013 (7), 19.469 (10)
V (Å³)	1890 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.33 × 0.25 × 0.20

Data collection
Diffractometer	Bruker APEX2 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.958, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	11481, 2365, 1480
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.135, 1.03
No. of reflections	2365
No. of parameters	137
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.19

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 1999), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···N1ⁱ	0.82	1.83	2.6526 (18)	177.7

Symmetry code: (i) x, −y−1/2, z−1/2.

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Brandenburg, K. & Putz, H. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc.,Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Lu, T. B. & Luck, R. L. (2003). Inorg. Chim. Acta, 351, 345–355. Web of Science CSD CrossRef CAS Google Scholar
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. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1239

doi:10.1107/S1600536809015530

Open

access