3-(Pyridin-3-yl)propionic acid

Abstract

In the crystal of the title compound, C₈H₉NO₂, mol­ecules assemble to form C(8) chains along the b axis by N—H⋯O hydrogen bonds, supported by weaker C—H⋯O hydrogen bonded-inter­actions between adjacent chains.

Related literature

For use of the title compound in coordination polymers, see: Wang et al. (2006 ▶). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

• C₈H₉NO₂

• M _r = 151.16

• Monoclinic,

• a = 6.7157 (4) Å

• b = 14.6544 (13) Å

• c = 7.2993 (6) Å

• β = 92.566 (5)°

• V = 717.64 (10) ų

• Z = 4

• Mo Kα radiation

• μ = 0.10 mm⁻¹

• T = 173 K

• 0.42 × 0.27 × 0.04 mm

Data collection

• Nonius KappaCCD area-detector diffractometer

• Absorption correction: integration (XPREP; Bruker, 1999 ▶) T _min = 0.967, T _max = 0.995

• 10553 measured reflections

• 1729 independent reflections

• 1341 reflections with I > 2σ(I)

• R _int = 0.051

Refinement

• R[F ² > 2σ(F ²)] = 0.040

• wR(F ²) = 0.115

• S = 1.02

• 1729 reflections

• 101 parameters

• H-atom parameters constrained

• Δρ_max = 0.26 e Å⁻³

• Δρ_min = −0.26 e Å⁻³

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO (Otwinowski & Minor, 1997 ▶) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1i	0.84	1.75	2.5868 (13)	172
C3—H3⋯O1ii	0.95	2.47	3.3468 (15)	154
C5—H5⋯O2iii	0.95	2.63	3.3328 (15)	131

Symmetry codes: (i) ; (ii) ; (iii) .

supplementary crystallographic information

Comment

The molecule 3-pyridinepropionic acid (I) has been used as a ligand to make coordination polymers using Ag, Cu and Zn (Wang et al., 2006). The crystal structure of the molecule itself has not been reported. The solid state packing involves forming chains of molecules, generated by hydrogen bonding interactions from the carboxylic acid H to the lone pair of the pyridine N atom. The chain, described using graph set notation (Bernstein et al., 1995) as C(8), is generated by the twofold screw axis inherent in the spacegroup P2₁/c, and runs along the crystallographic b axis (See Fig 2). Adjacent chains are stabilized by two C—H···O hydrogen bonds (See Table 1).

Experimental

Crystals where grown by slow evaporation at ambient conditions of a methanol solution of 3-pyridinepropionic acid.

Refinement

The C-bound H atoms were geometrically placed (C—H bond lengths of 0.95 (aromatic CH) and 0.99 (CH₂) Å) and refined as riding with U_iso(H) = 1.2U_eq(C). The O-bound H atom were geometrically placed and refined as riding with U_iso(H) = 1.5U_eq(O).

Figures

Fig. 1.

View of (I) (50% probability displacement ellipsoids)

Fig. 2.

Hydrogen bonding C(8) chain of (I) using N—H···O hydrogen bonds (red dashed lines), generated by the twofold screw axis. Symmetry code: (i) -x + 2, y - 1/2, -z + 1/2.

Crystal data

C8H9NO2	F(000) = 320
Mr = 151.16	Dx = 1.399 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3866 reflections
a = 6.7157 (4) Å	θ = 0.4–30.0°
b = 14.6544 (13) Å	µ = 0.10 mm−1
c = 7.2993 (6) Å	T = 173 K
β = 92.566 (5)°	Plate, colourless
V = 717.64 (10) Å3	0.42 × 0.27 × 0.04 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	1341 reflections with I > 2σ(I)
2.0° π and ω scans	Rint = 0.051
Absorption correction: integration (XPREP; Bruker, 1999)	θmax = 28°, θmin = 3.0°
Tmin = 0.967, Tmax = 0.995	h = −8→7
10553 measured reflections	k = −19→19
1729 independent reflections	l = −9→9

Refinement

Refinement on F2	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.040	w = 1/[σ2(Fo2) + (0.0616P)2 + 0.1772P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.115	(Δ/σ)max < 0.001
S = 1.02	Δρmax = 0.26 e Å−3
1729 reflections	Δρmin = −0.26 e Å−3
101 parameters

Special details

Experimental. Numerical integration absorption corrections based on indexed crystal faces were applied using the XPREP routine (Bruker, 1999)

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.61989 (17)	0.67074 (7)	0.12796 (15)	0.0187 (3)
C2	0.71028 (18)	0.75445 (8)	0.16533 (16)	0.0198 (3)
H2	0.8419	0.755	0.2186	0.024*
C3	0.43377 (18)	0.83489 (8)	0.05545 (16)	0.0229 (3)
H3	0.3693	0.8916	0.0312	0.028*
C4	0.33224 (19)	0.75458 (8)	0.01309 (18)	0.0242 (3)
H4	0.2003	0.7561	−0.0395	0.029*
C5	0.42692 (18)	0.67253 (8)	0.04903 (16)	0.0221 (3)
H5	0.3602	0.6169	0.0198	0.026*
C6	0.71897 (18)	0.57984 (8)	0.16581 (17)	0.0236 (3)
H6A	0.7149	0.5443	0.0503	0.028*
H6B	0.6391	0.5461	0.2543	0.028*
C7	0.93261 (17)	0.58303 (8)	0.24056 (16)	0.0215 (3)
H7A	0.9366	0.6121	0.3631	0.026*
H7B	1.0116	0.6214	0.159	0.026*
C8	1.02756 (18)	0.48938 (7)	0.25664 (16)	0.0206 (3)
N1	0.61911 (15)	0.83489 (6)	0.12917 (14)	0.0212 (3)
O1	1.21073 (13)	0.49226 (6)	0.32765 (13)	0.0294 (3)
H1	1.2566	0.439	0.3362	0.044*
O2	0.94438 (13)	0.41935 (6)	0.20706 (13)	0.0315 (3)

Atomic displacement parameters (Ų)

	U11	U22	U33	U12	U13	U23
C1	0.0190 (6)	0.0172 (6)	0.0201 (6)	0.0000 (4)	0.0022 (4)	0.0003 (4)
C2	0.0191 (6)	0.0182 (6)	0.0220 (6)	−0.0004 (4)	−0.0009 (4)	0.0008 (4)
C3	0.0229 (6)	0.0203 (6)	0.0255 (6)	0.0032 (5)	0.0000 (5)	0.0035 (4)
C4	0.0187 (6)	0.0262 (6)	0.0273 (6)	−0.0001 (5)	−0.0029 (5)	0.0026 (5)
C5	0.0214 (6)	0.0195 (6)	0.0254 (6)	−0.0038 (4)	0.0007 (5)	−0.0011 (4)
C6	0.0223 (6)	0.0152 (5)	0.0334 (7)	−0.0005 (4)	0.0004 (5)	−0.0006 (5)
C7	0.0224 (6)	0.0145 (5)	0.0276 (6)	0.0003 (4)	0.0002 (5)	0.0002 (4)
C8	0.0218 (6)	0.0173 (6)	0.0228 (6)	−0.0006 (4)	0.0017 (5)	−0.0001 (4)
N1	0.0231 (5)	0.0166 (5)	0.0238 (5)	−0.0002 (4)	−0.0004 (4)	0.0011 (4)
O1	0.0255 (5)	0.0153 (4)	0.0462 (6)	0.0024 (3)	−0.0115 (4)	−0.0022 (4)
O2	0.0256 (5)	0.0172 (4)	0.0510 (6)	−0.0014 (3)	−0.0074 (4)	−0.0048 (4)

Geometric parameters (Å, °)

C1—C2	1.3903 (16)	C5—H5	0.95
C1—C5	1.3947 (17)	C6—C7	1.5127 (16)
C1—C6	1.5090 (16)	C6—H6A	0.99
C2—N1	1.3489 (15)	C6—H6B	0.99
C2—H2	0.95	C7—C8	1.5156 (15)
C3—N1	1.3338 (16)	C7—H7A	0.99
C3—C4	1.3881 (17)	C7—H7B	0.99
C3—H3	0.95	C8—O2	1.2157 (14)
C4—C5	1.3798 (17)	C8—O1	1.3140 (15)
C4—H4	0.95	O1—H1	0.84
C2—C1—C5	117.00 (10)	C1—C6—H6A	108.2
C2—C1—C6	123.91 (10)	C7—C6—H6A	108.2
C5—C1—C6	119.09 (10)	C1—C6—H6B	108.2
N1—C2—C1	122.84 (11)	C7—C6—H6B	108.2
N1—C2—H2	118.6	H6A—C6—H6B	107.4
C1—C2—H2	118.6	C6—C7—C8	112.89 (9)
N1—C3—C4	122.01 (11)	C6—C7—H7A	109
N1—C3—H3	119	C8—C7—H7A	109
C4—C3—H3	119	C6—C7—H7B	109
C5—C4—C3	118.62 (11)	C8—C7—H7B	109
C5—C4—H4	120.7	H7A—C7—H7B	107.8
C3—C4—H4	120.7	O2—C8—O1	123.65 (10)
C4—C5—C1	120.44 (11)	O2—C8—C7	123.72 (11)
C4—C5—H5	119.8	O1—C8—C7	112.62 (9)
C1—C5—H5	119.8	C3—N1—C2	119.09 (10)
C1—C6—C7	116.24 (10)	C8—O1—H1	109.5
C5—C1—C2—N1	0.27 (18)	C5—C1—C6—C7	176.33 (10)
C6—C1—C2—N1	179.56 (11)	C1—C6—C7—C8	−174.20 (10)
N1—C3—C4—C5	0.09 (19)	C6—C7—C8—O2	3.16 (17)
C3—C4—C5—C1	0.63 (18)	C6—C7—C8—O1	−177.75 (10)
C2—C1—C5—C4	−0.79 (18)	C4—C3—N1—C2	−0.62 (18)
C6—C1—C5—C4	179.88 (10)	C1—C2—N1—C3	0.43 (18)
C2—C1—C6—C7	−2.95 (17)

Hydrogen-bond geometry (Å, °)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1i	0.84	1.75	2.5868 (13)	172
C3—H3···O1ii	0.95	2.47	3.3468 (15)	154
C5—H5···O2iii	0.95	2.63	3.3328 (15)	131

Symmetry codes: (i) −x+2, y−1/2, −z+1/2; (ii) x−1, −y+3/2, z−1/2; (iii) −x+1, −y+1, −z.