3-(Pyridin-3-yl)propionic acid

Lemmerer, A.

doi:10.1107/S1600536810052384

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o215

https://doi.org/10.1107/S1600536810052384

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3-(Pyridin-3-yl)propionic acid

Andreas Lemmerer ^a ^*

^aMolecular Sciences Institute, School of Chemistry, University of the Witwatersrand, Private Bag, PO WITS, 2050 Johannesburg, South Africa
^*Correspondence e-mail: andreas.lemmerer@wits.ac.za

(Received 1 December 2010; accepted 14 December 2010; online 24 December 2010)

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, P 2₁ /c
a = 6.7157 (4) Å
b = 14.6544 (13) Å
c = 7.2993 (6) Å
β = 92.566 (5)°
V = 717.64 (10) Å³
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[F² > 2σ(F²)] = 0.040
wR(F²) = 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

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) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810052384/fj2372sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810052384/fj2372Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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 top

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

Structure description top

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).

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); data reduction: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998); 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).

Figures top

	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.

3-(Pyridin-3-yl)propionic acid top

Crystal data top

C₈H₉NO₂	F(000) = 320
M_r = 151.16	D_x = 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 top

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

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.040	w = 1/[σ²(F_o²) + (0.0616P)² + 0.1772P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.115	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.26 e Å⁻³
1729 reflections	Δρ_min = −0.26 e Å⁻³
101 parameters

Crystal data top

C₈H₉NO₂	V = 717.64 (10) Å³
M_r = 151.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.7157 (4) Å	µ = 0.10 mm⁻¹
b = 14.6544 (13) Å	T = 173 K
c = 7.2993 (6) Å	0.42 × 0.27 × 0.04 mm
β = 92.566 (5)°

Data collection top

Nonius KappaCCD area-detector diffractometer	1729 independent reflections
Absorption correction: integration (XPREP; Bruker, 1999)	1341 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.995	R_int = 0.051
10553 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	Δρ_max = 0.26 e Å⁻³
1729 reflections	Δρ_min = −0.26 e Å⁻³
101 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
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 (Å²) top

	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, º) top

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, º) top

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.

Experimental details

Crystal data
Chemical formula	C₈H₉NO₂
M_r	151.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	173
a, b, c (Å)	6.7157 (4), 14.6544 (13), 7.2993 (6)
β (°)	92.566 (5)
V (Å³)	717.64 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.42 × 0.27 × 0.04

Data collection
Diffractometer	Nonius KappaCCD area-detector
Absorption correction	Integration (XPREP; Bruker, 1999)
T_min, T_max	0.967, 0.995
No. of measured, independent and observed [I > 2σ(I)] reflections	10553, 1729, 1341
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.115, 1.02
No. of reflections	1729
No. of parameters	101
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.26

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Nonius, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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.

Acknowledgements

The University of the Witwatersrand and the Molecular Sciences Institute are thanked for providing the infrastructure and financial support to do this work.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (1999). XPREP. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Y.-H., Suen, M.-C., Lee, H.-T. & Wang, J.-C. (2006). Polyhedron, 25, 2944–2952. Web of Science CSD CrossRef CAS Google Scholar