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Acta Crystallogr Sect E Struct Rep Online. 2009 June 1; 65(Pt 6): o1244.
Published online 2009 May 14. doi:  10.1107/S1600536809016870
PMCID: PMC2969803

3-(2-Pyridylaminocarbonyl)propanoic acid

Abstract

In the crystal structure of the title compound, C9H10N2O3, the mol­ecules are linked by inter­molecular O—H(...)N and N—H(...)O hydrogen bonds, resulting in chains propagating in [010]. Weak intra­molecular and inter­molecular C—H(...)O inter­actions are also observed.

Related literature

For background on the pharmaceutical applications of this family of compounds, see: Narendar et al. (2003 [triangle]); Ravlee et al. (2003 [triangle]).

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Object name is e-65-o1244-scheme1.jpg

Experimental

Crystal data

  • C9H10N2O3
  • M r = 194.19
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1244-efi1.jpg
  • a = 12.7384 (10) Å
  • b = 5.0485 (5) Å
  • c = 13.8463 (12) Å
  • β = 92.924 (8)°
  • V = 889.29 (14) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 113 K
  • 0.22 × 0.04 × 0.03 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.995, T max = 0.996
  • 8079 measured reflections
  • 1972 independent reflections
  • 1297 reflections with I > 2σ(I)
  • R int = 0.074

Refinement

  • R[F 2 > 2σ(F 2)] = 0.048
  • wR(F 2) = 0.104
  • S = 0.97
  • 1972 reflections
  • 135 parameters
  • 1 restraint
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: CrystalClear (Rigaku, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: CrystalStructure (Rigaku, 2005 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536809016870/hb2960sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809016870/hb2960Isup2.hkl

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

supplementary crystallographic information

Comment

Pyridine derivatives substituted by N-alkylation show useful pharmaceutical properties (Narendar et al., 2003; Ravlee et al., 2003). In this paper, the structure of 4-oxo-4-(pyridin-2-ylamino)butanoic acid (I), is reported which was synthesized by acylating reation of pyridin-2-amine with pyrrolidine-2,5-dione. The pyridin ring system is essentially planar with mean deviations of 0.0013 Å. In addition, there are C—H···O interactions, as shown in Fig. 2 and detailed in Table 1.

Experimental

A solution of pyrrolidine-2,5-dione (1.0 g,10 mmol) in dimethylformamide (15 ml) was stirred at room temperature for 10 min. Pyridin-2-amine (0.94 g, 10 mmol) was added and the mixture was stirred for a further 3 h at 353 K. The resulting mixture was then poured into water (100 ml), yielding a white precipitate. The solid product was filtered off, washed with cold water and recrystallized from methnol, giving crystals of the title compound [yield: 1.17 g (61.4%)]. These were dissolved in mixture of methnol (10 ml) and water (3 ml) and the solution was kept at room temperature for 18 d. Natural evaporation of the solution gave colourless prisms of (I) (m.p. 454–455 K).

Refinement

The O- and N-bound H atoms were located in a difference map and their positions and Uiso values were freely refined. The C-bound H atoms were geometrically placed (C—H = 0.95–0.99Å) and refined as riding with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for H atoms).
Fig. 2.
Part of the crystal structure of (I), with hydrogen bonds shown as dashed lines.

Crystal data

C9H10N2O3F(000) = 408
Mr = 194.19Dx = 1.450 Mg m3
Monoclinic, P21/nMelting point = 454–455 K
Hall symbol: -P 2ynMo Kα radiation, λ = 0.71070 Å
a = 12.7384 (10) ÅCell parameters from 2970 reflections
b = 5.0485 (5) Åθ = 2.1–27.2°
c = 13.8463 (12) ŵ = 0.11 mm1
β = 92.924 (8)°T = 113 K
V = 889.29 (14) Å3Prism, colourless
Z = 40.22 × 0.04 × 0.03 mm

Data collection

Rigaku Saturn diffractometer1972 independent reflections
Radiation source: rotating anode1297 reflections with I > 2σ(I)
confocalRint = 0.074
Detector resolution: 14.63 pixels mm-1θmax = 27.2°, θmin = 2.1°
ω and [var phi] scansh = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)k = −6→6
Tmin = 0.995, Tmax = 0.996l = −17→17
8079 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.104w = 1/[σ2(Fo2) + (0.0361P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max = 0.001
1972 reflectionsΔρmax = 0.23 e Å3
135 parametersΔρmin = −0.22 e Å3
1 restraintExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.041 (3)

Special details

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.
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)

xyzUiso*/Ueq
O10.44178 (10)0.2594 (3)0.58044 (9)0.0272 (4)
H10.4642 (15)0.145 (4)0.6323 (13)0.041*
O20.34511 (10)0.4177 (3)0.69759 (9)0.0290 (4)
O30.12611 (10)0.3483 (3)0.52083 (9)0.0284 (4)
N10.08391 (12)0.5393 (3)0.66376 (11)0.0216 (4)
N2−0.02347 (12)0.4254 (3)0.78432 (11)0.0231 (4)
C10.37059 (14)0.4218 (4)0.61433 (13)0.0221 (4)
C20.32399 (15)0.6117 (4)0.54040 (13)0.0239 (5)
H2A0.30900.51710.47860.029*
H2B0.37530.75410.52880.029*
C30.22283 (14)0.7334 (4)0.57436 (13)0.0227 (5)
H3A0.23670.81940.63800.027*
H3B0.19720.87030.52770.027*
C40.14010 (14)0.5211 (4)0.58271 (13)0.0223 (5)
C50.00578 (14)0.3716 (4)0.69450 (13)0.0214 (5)
C6−0.04012 (15)0.1661 (4)0.63919 (13)0.0244 (5)
H6−0.01900.13170.57560.029*
C7−0.11649 (15)0.0153 (4)0.67911 (14)0.0265 (5)
H7−0.1484−0.12610.64310.032*
C8−0.14707 (15)0.0686 (4)0.77148 (13)0.0276 (5)
H8−0.1999−0.03380.79990.033*
C9−0.09839 (15)0.2750 (4)0.82096 (13)0.0256 (5)
H9−0.11900.31260.88450.031*
H1A0.1087 (16)0.673 (4)0.7090 (14)0.043 (6)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0313 (8)0.0289 (8)0.0218 (8)0.0121 (7)0.0044 (6)0.0043 (6)
O20.0352 (8)0.0350 (9)0.0172 (7)0.0102 (7)0.0057 (6)0.0054 (6)
O30.0363 (9)0.0269 (8)0.0221 (8)0.0033 (6)0.0026 (6)−0.0067 (6)
N10.0237 (9)0.0228 (10)0.0185 (8)−0.0006 (7)0.0019 (7)−0.0045 (7)
N20.0259 (9)0.0232 (9)0.0202 (8)−0.0010 (8)0.0006 (7)−0.0007 (7)
C10.0223 (10)0.0217 (11)0.0222 (10)−0.0005 (9)0.0007 (8)−0.0010 (9)
C20.0282 (11)0.0246 (11)0.0191 (10)0.0051 (9)0.0028 (8)0.0020 (8)
C30.0274 (11)0.0213 (11)0.0191 (10)0.0043 (9)0.0000 (8)0.0009 (8)
C40.0257 (11)0.0208 (11)0.0200 (10)0.0074 (9)−0.0031 (8)0.0008 (8)
C50.0234 (11)0.0214 (11)0.0191 (10)0.0037 (9)−0.0021 (8)0.0005 (8)
C60.0283 (12)0.0237 (11)0.0207 (10)0.0042 (9)−0.0033 (8)−0.0034 (8)
C70.0299 (11)0.0235 (12)0.0252 (11)0.0008 (9)−0.0063 (9)−0.0041 (9)
C80.0320 (12)0.0238 (11)0.0267 (11)−0.0057 (9)−0.0023 (9)0.0030 (9)
C90.0311 (12)0.0253 (12)0.0203 (10)−0.0022 (9)0.0008 (8)−0.0008 (9)

Geometric parameters (Å, °)

O1—C11.326 (2)C2—H2B0.9900
O1—H10.954 (17)C3—C41.512 (3)
O2—C11.214 (2)C3—H3A0.9900
O3—C41.229 (2)C3—H3B0.9900
N1—C41.365 (2)C5—C61.400 (2)
N1—C51.390 (2)C6—C71.373 (3)
N1—H1A0.96 (2)C6—H60.9500
N2—C91.340 (2)C7—C81.382 (2)
N2—C51.344 (2)C7—H70.9500
C1—C21.503 (2)C8—C91.377 (2)
C2—C31.523 (2)C8—H80.9500
C2—H2A0.9900C9—H90.9500
C1—O1—H1107.1 (12)H3A—C3—H3B108.2
C4—N1—C5128.65 (17)O3—C4—N1123.90 (19)
C4—N1—H1A114.5 (12)O3—C4—C3121.78 (18)
C5—N1—H1A116.3 (12)N1—C4—C3114.33 (16)
C9—N2—C5118.17 (16)N2—C5—N1113.37 (16)
O2—C1—O1123.11 (17)N2—C5—C6121.90 (18)
O2—C1—C2122.87 (17)N1—C5—C6124.73 (17)
O1—C1—C2114.02 (16)C7—C6—C5118.38 (18)
C1—C2—C3110.98 (16)C7—C6—H6120.8
C1—C2—H2A109.4C5—C6—H6120.8
C3—C2—H2A109.4C6—C7—C8120.21 (18)
C1—C2—H2B109.4C6—C7—H7119.9
C3—C2—H2B109.4C8—C7—H7119.9
H2A—C2—H2B108.0C9—C8—C7117.82 (18)
C4—C3—C2109.99 (15)C9—C8—H8121.1
C4—C3—H3A109.7C7—C8—H8121.1
C2—C3—H3A109.7N2—C9—C8123.51 (18)
C4—C3—H3B109.7N2—C9—H9118.2
C2—C3—H3B109.7C8—C9—H9118.2
O2—C1—C2—C3−16.5 (3)C4—N1—C5—N2171.25 (17)
O1—C1—C2—C3163.40 (16)C4—N1—C5—C6−9.1 (3)
C1—C2—C3—C4−64.77 (19)N2—C5—C6—C7−0.6 (3)
C5—N1—C4—O32.5 (3)N1—C5—C6—C7179.81 (16)
C5—N1—C4—C3−177.43 (15)C5—C6—C7—C80.5 (3)
C2—C3—C4—O3−42.8 (2)C6—C7—C8—C9−0.2 (3)
C2—C3—C4—N1137.14 (15)C5—N2—C9—C8−0.1 (3)
C9—N2—C5—N1−179.95 (15)C7—C8—C9—N20.0 (3)
C9—N2—C5—C60.4 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.95 (2)1.74 (2)2.690 (2)170 (2)
N1—H1A···O2ii0.96 (2)1.86 (2)2.824 (2)176.6 (19)
C6—H6···O30.952.312.893 (2)119
C3—H3A···O2ii0.992.603.445 (2)143
C3—H3B···O3iii0.992.583.408 (2)141
C7—H7···O3iv0.952.563.319 (2)137

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2960).

References

  • Narendar, P., Parthiban, J. & Anbalagan, N. (2003). Biol. Pharm. Bull 26, 182–187. [PubMed]
  • Ravlee, I., Sivakumar, R. & Muruganantham, N. (2003). Chem. Pharm. Bull.51, 162–170. [PubMed]
  • Rigaku (2005). CrystalClear and CrystalStructure Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography