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ISSN: 2056-9890

3-(Pyridin-3-yl)propionic acid

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[Wang, Y.-H., Suen, M.-C., Lee, H.-T. & Wang, J.-C. (2006). Polyhedron, 25, 2944-2952.]). For graph-set nomenclature of hydrogen bonds, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H9NO2

  • Mr = 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[Bruker (1999). XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.995

  • 10553 measured reflections

  • 1729 independent reflections

  • 1341 reflections with I > 2σ(I)

  • Rint = 0.051

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.115

  • S = 1.02

  • 1729 reflections

  • 101 parameters

  • H-atom parameters constrained

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.26 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA 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[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[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.]) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1999[Brandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


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.

Refinement top

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 Uiso(H) = 1.2Ueq(C). The O-bound H atom were geometrically placed and refined as riding with Uiso(H) = 1.5Ueq(O).

Structure description 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).

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
[Figure 1] Fig. 1. View of (I) (50% probability displacement ellipsoids)
[Figure 2] 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
C8H9NO2F(000) = 320
Mr = 151.16Dx = 1.399 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3866 reflections
a = 6.7157 (4) Åθ = 0.4–30.0°
b = 14.6544 (13) ŵ = 0.10 mm1
c = 7.2993 (6) ÅT = 173 K
β = 92.566 (5)°Plate, colourless
V = 717.64 (10) Å30.42 × 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 scansRint = 0.051
Absorption correction: integration
(XPREP; Bruker, 1999)
θmax = 28°, θmin = 3.0°
Tmin = 0.967, Tmax = 0.995h = 87
10553 measured reflectionsk = 1919
1729 independent reflectionsl = 99
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullH-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 = 1.02Δρmax = 0.26 e Å3
1729 reflectionsΔρmin = 0.26 e Å3
101 parameters
Crystal data top
C8H9NO2V = 717.64 (10) Å3
Mr = 151.16Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.7157 (4) ŵ = 0.10 mm1
b = 14.6544 (13) ÅT = 173 K
c = 7.2993 (6) Å0.42 × 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)
Tmin = 0.967, Tmax = 0.995Rint = 0.051
10553 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.115H-atom parameters constrained
S = 1.02Δρmax = 0.26 e Å3
1729 reflectionsΔρmin = 0.26 e Å3
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
xyzUiso*/Ueq
C10.61989 (17)0.67074 (7)0.12796 (15)0.0187 (3)
C20.71028 (18)0.75445 (8)0.16533 (16)0.0198 (3)
H20.84190.7550.21860.024*
C30.43377 (18)0.83489 (8)0.05545 (16)0.0229 (3)
H30.36930.89160.03120.028*
C40.33224 (19)0.75458 (8)0.01309 (18)0.0242 (3)
H40.20030.75610.03950.029*
C50.42692 (18)0.67253 (8)0.04903 (16)0.0221 (3)
H50.36020.61690.01980.026*
C60.71897 (18)0.57984 (8)0.16581 (17)0.0236 (3)
H6A0.71490.54430.05030.028*
H6B0.63910.54610.25430.028*
C70.93261 (17)0.58303 (8)0.24056 (16)0.0215 (3)
H7A0.93660.61210.36310.026*
H7B1.01160.62140.1590.026*
C81.02756 (18)0.48938 (7)0.25664 (16)0.0206 (3)
N10.61911 (15)0.83489 (6)0.12917 (14)0.0212 (3)
O11.21073 (13)0.49226 (6)0.32765 (13)0.0294 (3)
H11.25660.4390.33620.044*
O20.94438 (13)0.41935 (6)0.20706 (13)0.0315 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0190 (6)0.0172 (6)0.0201 (6)0.0000 (4)0.0022 (4)0.0003 (4)
C20.0191 (6)0.0182 (6)0.0220 (6)0.0004 (4)0.0009 (4)0.0008 (4)
C30.0229 (6)0.0203 (6)0.0255 (6)0.0032 (5)0.0000 (5)0.0035 (4)
C40.0187 (6)0.0262 (6)0.0273 (6)0.0001 (5)0.0029 (5)0.0026 (5)
C50.0214 (6)0.0195 (6)0.0254 (6)0.0038 (4)0.0007 (5)0.0011 (4)
C60.0223 (6)0.0152 (5)0.0334 (7)0.0005 (4)0.0004 (5)0.0006 (5)
C70.0224 (6)0.0145 (5)0.0276 (6)0.0003 (4)0.0002 (5)0.0002 (4)
C80.0218 (6)0.0173 (6)0.0228 (6)0.0006 (4)0.0017 (5)0.0001 (4)
N10.0231 (5)0.0166 (5)0.0238 (5)0.0002 (4)0.0004 (4)0.0011 (4)
O10.0255 (5)0.0153 (4)0.0462 (6)0.0024 (3)0.0115 (4)0.0022 (4)
O20.0256 (5)0.0172 (4)0.0510 (6)0.0014 (3)0.0074 (4)0.0048 (4)
Geometric parameters (Å, º) top
C1—C21.3903 (16)C5—H50.95
C1—C51.3947 (17)C6—C71.5127 (16)
C1—C61.5090 (16)C6—H6A0.99
C2—N11.3489 (15)C6—H6B0.99
C2—H20.95C7—C81.5156 (15)
C3—N11.3338 (16)C7—H7A0.99
C3—C41.3881 (17)C7—H7B0.99
C3—H30.95C8—O21.2157 (14)
C4—C51.3798 (17)C8—O11.3140 (15)
C4—H40.95O1—H10.84
C2—C1—C5117.00 (10)C1—C6—H6A108.2
C2—C1—C6123.91 (10)C7—C6—H6A108.2
C5—C1—C6119.09 (10)C1—C6—H6B108.2
N1—C2—C1122.84 (11)C7—C6—H6B108.2
N1—C2—H2118.6H6A—C6—H6B107.4
C1—C2—H2118.6C6—C7—C8112.89 (9)
N1—C3—C4122.01 (11)C6—C7—H7A109
N1—C3—H3119C8—C7—H7A109
C4—C3—H3119C6—C7—H7B109
C5—C4—C3118.62 (11)C8—C7—H7B109
C5—C4—H4120.7H7A—C7—H7B107.8
C3—C4—H4120.7O2—C8—O1123.65 (10)
C4—C5—C1120.44 (11)O2—C8—C7123.72 (11)
C4—C5—H5119.8O1—C8—C7112.62 (9)
C1—C5—H5119.8C3—N1—C2119.09 (10)
C1—C6—C7116.24 (10)C8—O1—H1109.5
C5—C1—C2—N10.27 (18)C5—C1—C6—C7176.33 (10)
C6—C1—C2—N1179.56 (11)C1—C6—C7—C8174.20 (10)
N1—C3—C4—C50.09 (19)C6—C7—C8—O23.16 (17)
C3—C4—C5—C10.63 (18)C6—C7—C8—O1177.75 (10)
C2—C1—C5—C40.79 (18)C4—C3—N1—C20.62 (18)
C6—C1—C5—C4179.88 (10)C1—C2—N1—C30.43 (18)
C2—C1—C6—C72.95 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1i0.841.752.5868 (13)172
C3—H3···O1ii0.952.473.3468 (15)154
C5—H5···O2iii0.952.633.3328 (15)131
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x1, y+3/2, z1/2; (iii) x+1, y+1, z.

Experimental details

Crystal data
Chemical formulaC8H9NO2
Mr151.16
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)6.7157 (4), 14.6544 (13), 7.2993 (6)
β (°) 92.566 (5)
V3)717.64 (10)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.42 × 0.27 × 0.04
Data collection
DiffractometerNonius KappaCCD area-detector
Absorption correctionIntegration
(XPREP; Bruker, 1999)
Tmin, Tmax0.967, 0.995
No. of measured, independent and
observed [I > 2σ(I)] reflections
10553, 1729, 1341
Rint0.051
(sin θ/λ)max1)0.661
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.115, 1.02
No. of reflections1729
No. of parameters101
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O1—H1···N1i0.841.752.5868 (13)172
C3—H3···O1ii0.952.473.3468 (15)154
C5—H5···O2iii0.952.633.3328 (15)131
Symmetry codes: (i) x+2, y1/2, z+1/2; (ii) x1, y+3/2, z1/2; (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

First citationBernstein, 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
First citationBrandenburg, K. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.  Google Scholar
First citationBruker (1999). XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationNonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationOtwinowski, 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
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, Y.-H., Suen, M.-C., Lee, H.-T. & Wang, J.-C. (2006). Polyhedron, 25, 2944–2952.  Web of Science CSD CrossRef CAS Google Scholar

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