3-(2-Pyridylaminocarbonyl)propanoic acid

Wang, C.-F.

doi:10.1107/S1600536809016870

organic compounds

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Volume 65| Part 6| June 2009| Page o1244

doi:10.1107/S1600536809016870

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3-(2-Pyridylaminocarbonyl)propanoic acid

Cheng-Feng Wang ^a ^*

^aCollege of Chemistry & Bioengineering, Changsha University of Science & Technology, Changsha 410076, People's Republic of China
^*Correspondence e-mail: wang2009chengfeng@126.com

(Received 27 April 2009; accepted 5 May 2009; online 14 May 2009)

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 ); Ravlee et al. (2003 ).

Experimental

Crystal data

C₉H₁₀N₂O₃
M_r = 194.19
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.048
wR(F²) = 0.104
S = 0.97
1972 reflections
135 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.954 (19)	1.744 (19)	2.690 (2)	170.4 (17)
N1—H1A⋯O2ⁱⁱ	0.96 (2)	1.86 (2)	2.824 (2)	176.6 (19)
C6—H6⋯O3	0.95	2.31	2.893 (2)	119
C3—H3A⋯O2ⁱⁱ	0.99	2.60	3.445 (2)	143
C3—H3B⋯O3ⁱⁱⁱ	0.99	2.58	3.408 (2)	141
C7—H7⋯O3^iv	0.95	2.56	3.319 (2)	137
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x, y+1, z; (iv) -x, -y, -z+1.

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

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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).

Computing details top

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

Figures top

	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.

3-(2-Pyridylaminocarbonyl)propanoic acid top

Crystal data top

C₉H₁₀N₂O₃	F(000) = 408
M_r = 194.19	D_x = 1.450 Mg m⁻³
Monoclinic, P2₁/n	Melting point = 454–455 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71070 Å
a = 12.7384 (10) Å	Cell parameters from 2970 reflections
b = 5.0485 (5) Å	θ = 2.1–27.2°
c = 13.8463 (12) Å	µ = 0.11 mm⁻¹
β = 92.924 (8)°	T = 113 K
V = 889.29 (14) Å³	Prism, colourless
Z = 4	0.22 × 0.04 × 0.03 mm

Data collection top

Rigaku Saturn diffractometer	1972 independent reflections
Radiation source: rotating anode	1297 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.074
Detector resolution: 14.63 pixels mm^-1	θ_max = 27.2°, θ_min = 2.1°
ω and ϕ scans	h = −16→16
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −6→6
T_min = 0.995, T_max = 0.996	l = −17→17
8079 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.048	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.0361P)²] where P = (F_o² + 2F_c²)/3
S = 0.97	(Δ/σ)_max = 0.001
1972 reflections	Δρ_max = 0.23 e Å⁻³
135 parameters	Δρ_min = −0.22 e Å⁻³
1 restraint	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.041 (3)

Crystal data top

C₉H₁₀N₂O₃	V = 889.29 (14) Å³
M_r = 194.19	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.7384 (10) Å	µ = 0.11 mm⁻¹
b = 5.0485 (5) Å	T = 113 K
c = 13.8463 (12) Å	0.22 × 0.04 × 0.03 mm
β = 92.924 (8)°

Data collection top

Rigaku Saturn diffractometer	1972 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1297 reflections with I > 2σ(I)
T_min = 0.995, T_max = 0.996	R_int = 0.074
8079 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	1 restraint
wR(F²) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 0.97	Δρ_max = 0.23 e Å⁻³
1972 reflections	Δρ_min = −0.22 e Å⁻³
135 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O1	0.44178 (10)	0.2594 (3)	0.58044 (9)	0.0272 (4)
H1	0.4642 (15)	0.145 (4)	0.6323 (13)	0.041*
O2	0.34511 (10)	0.4177 (3)	0.69759 (9)	0.0290 (4)
O3	0.12611 (10)	0.3483 (3)	0.52083 (9)	0.0284 (4)
N1	0.08391 (12)	0.5393 (3)	0.66376 (11)	0.0216 (4)
N2	−0.02347 (12)	0.4254 (3)	0.78432 (11)	0.0231 (4)
C1	0.37059 (14)	0.4218 (4)	0.61433 (13)	0.0221 (4)
C2	0.32399 (15)	0.6117 (4)	0.54040 (13)	0.0239 (5)
H2A	0.3090	0.5171	0.4786	0.029*
H2B	0.3753	0.7541	0.5288	0.029*
C3	0.22283 (14)	0.7334 (4)	0.57436 (13)	0.0227 (5)
H3A	0.2367	0.8194	0.6380	0.027*
H3B	0.1972	0.8703	0.5277	0.027*
C4	0.14010 (14)	0.5211 (4)	0.58271 (13)	0.0223 (5)
C5	0.00578 (14)	0.3716 (4)	0.69450 (13)	0.0214 (5)
C6	−0.04012 (15)	0.1661 (4)	0.63919 (13)	0.0244 (5)
H6	−0.0190	0.1317	0.5756	0.029*
C7	−0.11649 (15)	0.0153 (4)	0.67911 (14)	0.0265 (5)
H7	−0.1484	−0.1261	0.6431	0.032*
C8	−0.14707 (15)	0.0686 (4)	0.77148 (13)	0.0276 (5)
H8	−0.1999	−0.0338	0.7999	0.033*
C9	−0.09839 (15)	0.2750 (4)	0.82096 (13)	0.0256 (5)
H9	−0.1190	0.3126	0.8845	0.031*
H1A	0.1087 (16)	0.673 (4)	0.7090 (14)	0.043 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0313 (8)	0.0289 (8)	0.0218 (8)	0.0121 (7)	0.0044 (6)	0.0043 (6)
O2	0.0352 (8)	0.0350 (9)	0.0172 (7)	0.0102 (7)	0.0057 (6)	0.0054 (6)
O3	0.0363 (9)	0.0269 (8)	0.0221 (8)	0.0033 (6)	0.0026 (6)	−0.0067 (6)
N1	0.0237 (9)	0.0228 (10)	0.0185 (8)	−0.0006 (7)	0.0019 (7)	−0.0045 (7)
N2	0.0259 (9)	0.0232 (9)	0.0202 (8)	−0.0010 (8)	0.0006 (7)	−0.0007 (7)
C1	0.0223 (10)	0.0217 (11)	0.0222 (10)	−0.0005 (9)	0.0007 (8)	−0.0010 (9)
C2	0.0282 (11)	0.0246 (11)	0.0191 (10)	0.0051 (9)	0.0028 (8)	0.0020 (8)
C3	0.0274 (11)	0.0213 (11)	0.0191 (10)	0.0043 (9)	0.0000 (8)	0.0009 (8)
C4	0.0257 (11)	0.0208 (11)	0.0200 (10)	0.0074 (9)	−0.0031 (8)	0.0008 (8)
C5	0.0234 (11)	0.0214 (11)	0.0191 (10)	0.0037 (9)	−0.0021 (8)	0.0005 (8)
C6	0.0283 (12)	0.0237 (11)	0.0207 (10)	0.0042 (9)	−0.0033 (8)	−0.0034 (8)
C7	0.0299 (11)	0.0235 (12)	0.0252 (11)	0.0008 (9)	−0.0063 (9)	−0.0041 (9)
C8	0.0320 (12)	0.0238 (11)	0.0267 (11)	−0.0057 (9)	−0.0023 (9)	0.0030 (9)
C9	0.0311 (12)	0.0253 (12)	0.0203 (10)	−0.0022 (9)	0.0008 (8)	−0.0008 (9)

Geometric parameters (Å, º) top

O1—C1	1.326 (2)	C2—H2B	0.9900
O1—H1	0.954 (17)	C3—C4	1.512 (3)
O2—C1	1.214 (2)	C3—H3A	0.9900
O3—C4	1.229 (2)	C3—H3B	0.9900
N1—C4	1.365 (2)	C5—C6	1.400 (2)
N1—C5	1.390 (2)	C6—C7	1.373 (3)
N1—H1A	0.96 (2)	C6—H6	0.9500
N2—C9	1.340 (2)	C7—C8	1.382 (2)
N2—C5	1.344 (2)	C7—H7	0.9500
C1—C2	1.503 (2)	C8—C9	1.377 (2)
C2—C3	1.523 (2)	C8—H8	0.9500
C2—H2A	0.9900	C9—H9	0.9500

C1—O1—H1	107.1 (12)	H3A—C3—H3B	108.2
C4—N1—C5	128.65 (17)	O3—C4—N1	123.90 (19)
C4—N1—H1A	114.5 (12)	O3—C4—C3	121.78 (18)
C5—N1—H1A	116.3 (12)	N1—C4—C3	114.33 (16)
C9—N2—C5	118.17 (16)	N2—C5—N1	113.37 (16)
O2—C1—O1	123.11 (17)	N2—C5—C6	121.90 (18)
O2—C1—C2	122.87 (17)	N1—C5—C6	124.73 (17)
O1—C1—C2	114.02 (16)	C7—C6—C5	118.38 (18)
C1—C2—C3	110.98 (16)	C7—C6—H6	120.8
C1—C2—H2A	109.4	C5—C6—H6	120.8
C3—C2—H2A	109.4	C6—C7—C8	120.21 (18)
C1—C2—H2B	109.4	C6—C7—H7	119.9
C3—C2—H2B	109.4	C8—C7—H7	119.9
H2A—C2—H2B	108.0	C9—C8—C7	117.82 (18)
C4—C3—C2	109.99 (15)	C9—C8—H8	121.1
C4—C3—H3A	109.7	C7—C8—H8	121.1
C2—C3—H3A	109.7	N2—C9—C8	123.51 (18)
C4—C3—H3B	109.7	N2—C9—H9	118.2
C2—C3—H3B	109.7	C8—C9—H9	118.2

O2—C1—C2—C3	−16.5 (3)	C4—N1—C5—N2	171.25 (17)
O1—C1—C2—C3	163.40 (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—O3	2.5 (3)	N1—C5—C6—C7	179.81 (16)
C5—N1—C4—C3	−177.43 (15)	C5—C6—C7—C8	0.5 (3)
C2—C3—C4—O3	−42.8 (2)	C6—C7—C8—C9	−0.2 (3)
C2—C3—C4—N1	137.14 (15)	C5—N2—C9—C8	−0.1 (3)
C9—N2—C5—N1	−179.95 (15)	C7—C8—C9—N2	0.0 (3)
C9—N2—C5—C6	0.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.95 (2)	1.74 (2)	2.690 (2)	170 (2)
N1—H1A···O2ⁱⁱ	0.96 (2)	1.86 (2)	2.824 (2)	176.6 (19)
C6—H6···O3	0.95	2.31	2.893 (2)	119
C3—H3A···O2ⁱⁱ	0.99	2.60	3.445 (2)	143
C3—H3B···O3ⁱⁱⁱ	0.99	2.58	3.408 (2)	141
C7—H7···O3^iv	0.95	2.56	3.319 (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.

Experimental details

Crystal data
Chemical formula	C₉H₁₀N₂O₃
M_r	194.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	113
a, b, c (Å)	12.7384 (10), 5.0485 (5), 13.8463 (12)
β (°)	92.924 (8)
V (Å³)	889.29 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.22 × 0.04 × 0.03

Data collection
Diffractometer	Rigaku Saturn diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.995, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	8079, 1972, 1297
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.643

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.104, 0.97
No. of reflections	1972
No. of parameters	135
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.22

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), CrystalStructure (Rigaku, 2005).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.954 (19)	1.744 (19)	2.690 (2)	170.4 (17)
N1—H1A···O2ⁱⁱ	0.96 (2)	1.86 (2)	2.824 (2)	176.6 (19)
C6—H6···O3	0.95	2.31	2.893 (2)	119
C3—H3A···O2ⁱⁱ	0.99	2.60	3.445 (2)	143
C3—H3B···O3ⁱⁱⁱ	0.99	2.58	3.408 (2)	141
C7—H7···O3^iv	0.95	2.56	3.319 (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.

References

Narendar, P., Parthiban, J. & Anbalagan, N. (2003). Biol. Pharm. Bull. 26, 182–187. Web of Science CrossRef PubMed CAS Google Scholar
Ravlee, I., Sivakumar, R. & Muruganantham, N. (2003). Chem. Pharm. Bull. 51, 162–170. Web of Science CrossRef PubMed CAS Google Scholar
Rigaku (2005). CrystalClear and CrystalStructure. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1244

doi:10.1107/S1600536809016870

Open

access