3-(4-Pyrid-yl)benzoic acid.

The mol-ecule of the title compound, C(12)H(9)NO(2), is not planar, the benzene and pyridine rings making a dihedral angle of 32.14 (7)°. The carb-oxy group is slightly twisted with respect to the benzene ring by 11.95 (10)°. In the crystal structure, inter-molecular O-H⋯N hydrogen bonds link neighboring mol-ecules 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 = 199.20

Orthorhombic,

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[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 ▶); 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 ▶).

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

C12H9NO2	F(000) = 832
Mr = 199.20	Dx = 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

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

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 = 1.02	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2238P] where P = (Fo2 + 2Fc2)/3
2365 reflections	(Δ/σ)max = 0.001
137 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .