organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(S)-5-Oxo-N-phenyl­pyrrolidine-2-carboxamide

aKey Laboratory of Green Chemical Technology, College of Heilongjiang Province, School of Chemistry and Environmental Engineering, Harbin University of Science and Technology, Harbin 150040, People's Republic of China
*Correspondence e-mail: liubo@hrbust.edu.cn

(Received 24 August 2011; accepted 16 September 2011; online 30 September 2011)

The title compound, C11H12N2O2, shows an S configuration, in which the pyrrolidinone ring is twisted with respect to the phenyl plane, making a dihedral angle of 70.73 (7)°. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, building up a layer parallel to (001).

Related literature

For the synthesis of the title compound, see Feng et al. (2010[Feng, Q., Liu, Z.-L., Xiong, L.-X., Wang, M.-Z., Li, Y.-Q. & Li, Z.-M. (2010). J. Agric. Food Chem. 58, 12327-12336.]). For its chemical properties, including assignment of absolute structure, see: Brunel et al. (1999[Brunel, J. M., Constantieux, T. & Bunono, G. (1999). J. Org. Chem. 64, 8940-8942.]).

[Scheme 1]

Experimental

Crystal data
  • C11H12N2O2

  • Mr = 204.23

  • Monoclinic, P 21

  • a = 4.919 (3) Å

  • b = 9.995 (7) Å

  • c = 10.382 (7) Å

  • β = 99.05 (3)°

  • V = 504.1 (6) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.23 × 0.18 × 0.16 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: multi-scan ABSCOR (Higashi, 1995[Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.979, Tmax = 0.985

  • 3688 measured reflections

  • 2184 independent reflections

  • 1997 reflections with I > 2σ(I)

  • Rint = 0.014

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.082

  • S = 1.05

  • 2184 reflections

  • 145 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.17 e Å−3

  • Δρmin = −0.11 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H11⋯O2i 0.89 (1) 1.98 (1) 2.869 (2) 172 (2)
N2—H12⋯O1ii 0.89 (1) 2.19 (1) 3.038 (2) 158 (2)
Symmetry codes: (i) [-x+2, y+{\script{1\over 2}}, -z+1]; (ii) x+1, y, z.

Data collection: RAPID-AUTO (Rigaku, 1998[Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: CrystalClear (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

The title compound is an intermediate in the synthesis of highly potent and selective insecticide (Feng et al., 2010). Herein, we report its synthesis and crystal structure.

The pyrrolidinone ring is twisted with respect to phenyl plane with a dihedral angle of 70.73 (7) ° (Fig. 1).

Themolecules are linked by N—H···O hydrogen bonds into planar structure parallel to the (0 0 1) plane (Fig. 2, Table 1).

Related literature top

For the synthesis of the title compound, see Feng et al. (2010). For its chemical properties, see: Brunel et al. (1999).

Experimental top

The title compound was synthesized as the reference method (Feng et al., 2010; Brunel et al., 1999): a mixture of L-glutamic acid (3 g) and aniline (18 mL) was stirred at 195-200 °C. After 30 min, the mixture became clear, and the water formed was removed by azeotropic distillation. Stirring was maintained for 4 h. Excess of aniline was then recovered at 60-70 °C under reduced pressure distillation. The hot oily residue was swirled with acetone (25 mL) to lead to the formation of a brown solid, which was collected by filtration and dissolved in hot methanol (40 mL). The solution was slowly cooled to room temperature to afford crystalline optically pure (S)-N-phenylpyrrolidine-2-carboxamide as white crystals in 85% with the specific rotation about [α]20D + 18.0 (c 1.0, MeOH, 24 °C).

Refinement top

H atoms bound to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (aromatic); C—H = 0.97 Å (methylene), and C—H = 0.98 Å (methine), and with Uiso(H) = 1.2Ueq(C), while N-bound H atoms were found from difference Fourier and were refined using restraints [ N—H = 0.90 (1)Å].

Structure description top

The title compound is an intermediate in the synthesis of highly potent and selective insecticide (Feng et al., 2010). Herein, we report its synthesis and crystal structure.

The pyrrolidinone ring is twisted with respect to phenyl plane with a dihedral angle of 70.73 (7) ° (Fig. 1).

Themolecules are linked by N—H···O hydrogen bonds into planar structure parallel to the (0 0 1) plane (Fig. 2, Table 1).

For the synthesis of the title compound, see Feng et al. (2010). For its chemical properties, see: Brunel et al. (1999).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); 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: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular view of the title compound. Ellipsoids are drawn at the 50% probability level for non-H atoms.
[Figure 2] Fig. 2. A partial packing view, showing hydrogen-bonding layer structure parallel to the (0 0 1) plane.
(S)-5-Oxo-N-phenylpyrrolidine-2-carboxamide top
Crystal data top
C11H12N2O2F(000) = 216
Mr = 204.23Dx = 1.345 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 1906 reflections
a = 4.919 (3) Åθ = 2.9–28.3°
b = 9.995 (7) ŵ = 0.09 mm1
c = 10.382 (7) ÅT = 296 K
β = 99.05 (3)°Block, yellow
V = 504.1 (6) Å30.23 × 0.18 × 0.16 mm
Z = 2
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2184 independent reflections
Radiation source: fine-focus sealed tube1997 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.014
ω scansθmax = 28.4°, θmin = 2.0°
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
h = 46
Tmin = 0.979, Tmax = 0.985k = 1213
3688 measured reflectionsl = 1311
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.032H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.082 w = 1/[σ2(Fo2) + (0.0429P)2 + 0.035P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2184 reflectionsΔρmax = 0.17 e Å3
145 parametersΔρmin = 0.11 e Å3
3 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.024 (6)
Crystal data top
C11H12N2O2V = 504.1 (6) Å3
Mr = 204.23Z = 2
Monoclinic, P21Mo Kα radiation
a = 4.919 (3) ŵ = 0.09 mm1
b = 9.995 (7) ÅT = 296 K
c = 10.382 (7) Å0.23 × 0.18 × 0.16 mm
β = 99.05 (3)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2184 independent reflections
Absorption correction: multi-scan
ABSCOR (Higashi, 1995)
1997 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.985Rint = 0.014
3688 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0323 restraints
wR(F2) = 0.082H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.17 e Å3
2184 reflectionsΔρmin = 0.11 e Å3
145 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
C10.5338 (3)0.92196 (15)0.78902 (13)0.0367 (3)
C20.4415 (4)1.02616 (18)0.85717 (15)0.0487 (4)
H20.49341.11340.84160.058*
C30.2721 (4)1.0014 (2)0.94858 (18)0.0615 (5)
H30.21181.07210.99510.074*
C40.1922 (4)0.8728 (2)0.97111 (16)0.0602 (5)
H40.07670.85611.03210.072*
C50.2838 (4)0.7705 (2)0.90327 (17)0.0586 (5)
H50.22970.68350.91850.070*
C60.4553 (4)0.79267 (18)0.81216 (16)0.0483 (4)
H60.51710.72140.76700.058*
C70.7855 (2)0.87730 (14)0.60470 (12)0.0337 (3)
C80.9689 (3)0.94686 (15)0.51984 (13)0.0360 (3)
H81.08711.01370.57000.043*
C90.7915 (3)1.01089 (16)0.40036 (14)0.0413 (3)
H9A0.61151.03550.41970.050*
H9B0.88011.08980.37190.050*
C100.7685 (3)0.90159 (17)0.29767 (14)0.0449 (4)
H10A0.60000.85080.29600.054*
H10B0.77220.93910.21180.054*
C111.0170 (3)0.81512 (14)0.33982 (14)0.0373 (3)
N10.7110 (2)0.95458 (13)0.69845 (11)0.0385 (3)
N21.1299 (2)0.85149 (13)0.46021 (11)0.0388 (3)
O10.7047 (2)0.76321 (11)0.58091 (10)0.0443 (3)
O21.1033 (3)0.72678 (12)0.27523 (12)0.0538 (3)
H110.784 (3)1.0363 (11)0.7055 (16)0.041 (4)*
H121.273 (3)0.8084 (17)0.5056 (15)0.050 (5)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0352 (6)0.0417 (8)0.0334 (6)0.0014 (6)0.0056 (5)0.0025 (5)
C20.0548 (9)0.0447 (9)0.0494 (8)0.0007 (7)0.0166 (7)0.0014 (7)
C30.0635 (10)0.0709 (13)0.0555 (10)0.0069 (10)0.0262 (8)0.0052 (9)
C40.0541 (9)0.0852 (15)0.0446 (8)0.0073 (10)0.0178 (7)0.0076 (10)
C50.0620 (10)0.0636 (12)0.0523 (9)0.0153 (9)0.0157 (8)0.0113 (8)
C60.0559 (9)0.0435 (9)0.0477 (8)0.0071 (7)0.0146 (7)0.0024 (7)
C70.0301 (5)0.0332 (7)0.0371 (6)0.0013 (5)0.0034 (5)0.0012 (5)
C80.0322 (6)0.0332 (7)0.0437 (7)0.0036 (5)0.0091 (5)0.0042 (6)
C90.0433 (7)0.0323 (7)0.0505 (8)0.0080 (6)0.0147 (6)0.0060 (6)
C100.0453 (7)0.0479 (9)0.0415 (7)0.0079 (7)0.0067 (6)0.0015 (6)
C110.0379 (7)0.0317 (7)0.0452 (7)0.0000 (5)0.0151 (6)0.0031 (6)
N10.0439 (6)0.0332 (7)0.0403 (6)0.0069 (5)0.0127 (5)0.0030 (5)
N20.0295 (5)0.0416 (7)0.0461 (6)0.0063 (5)0.0086 (4)0.0022 (5)
O10.0458 (5)0.0333 (5)0.0561 (6)0.0059 (4)0.0152 (5)0.0061 (4)
O20.0670 (7)0.0397 (7)0.0591 (7)0.0090 (5)0.0236 (6)0.0055 (5)
Geometric parameters (Å, º) top
C1—C21.376 (2)C7—C81.524 (2)
C1—C61.381 (2)C8—N21.4400 (19)
C1—N11.4170 (19)C8—C91.539 (2)
C2—C31.380 (3)C8—H80.9800
C2—H20.9300C9—C101.518 (2)
C3—C41.375 (3)C9—H9A0.9700
C3—H30.9300C9—H9B0.9700
C4—C51.358 (3)C10—C111.505 (2)
C4—H40.9300C10—H10A0.9700
C5—C61.381 (2)C10—H10B0.9700
C5—H50.9300C11—O21.2244 (18)
C6—H60.9300C11—N21.336 (2)
C7—O11.2201 (19)N1—H110.891 (9)
C7—N11.3380 (19)N2—H120.893 (9)
C2—C1—C6119.69 (14)N2—C8—H8111.0
C2—C1—N1117.01 (14)C7—C8—H8111.0
C6—C1—N1123.30 (13)C9—C8—H8111.0
C1—C2—C3120.12 (18)C10—C9—C8103.69 (13)
C1—C2—H2119.9C10—C9—H9A111.0
C3—C2—H2119.9C8—C9—H9A111.0
C4—C3—C2120.27 (18)C10—C9—H9B111.0
C4—C3—H3119.9C8—C9—H9B111.0
C2—C3—H3119.9H9A—C9—H9B109.0
C5—C4—C3119.24 (16)C11—C10—C9104.00 (13)
C5—C4—H4120.4C11—C10—H10A111.0
C3—C4—H4120.4C9—C10—H10A111.0
C4—C5—C6121.53 (19)C11—C10—H10B111.0
C4—C5—H5119.2C9—C10—H10B111.0
C6—C5—H5119.2H10A—C10—H10B109.0
C1—C6—C5119.15 (17)O2—C11—N2125.43 (14)
C1—C6—H6120.4O2—C11—C10126.21 (14)
C5—C6—H6120.4N2—C11—C10108.36 (13)
O1—C7—N1124.68 (13)C7—N1—C1128.11 (13)
O1—C7—C8120.86 (13)C7—N1—H11115.8 (12)
N1—C7—C8114.32 (12)C1—N1—H11116.1 (11)
N2—C8—C7111.24 (12)C11—N2—C8113.99 (11)
N2—C8—C9102.08 (12)C11—N2—H12122.6 (12)
C7—C8—C9110.08 (12)C8—N2—H12122.2 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O2i0.89 (1)1.98 (1)2.869 (2)172 (2)
N2—H12···O1ii0.89 (1)2.19 (1)3.038 (2)158 (2)
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC11H12N2O2
Mr204.23
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)4.919 (3), 9.995 (7), 10.382 (7)
β (°) 99.05 (3)
V3)504.1 (6)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.23 × 0.18 × 0.16
Data collection
DiffractometerRigaku R-AXIS RAPID
Absorption correctionMulti-scan
ABSCOR (Higashi, 1995)
Tmin, Tmax0.979, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
3688, 2184, 1997
Rint0.014
(sin θ/λ)max1)0.669
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.082, 1.05
No. of reflections2184
No. of parameters145
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.17, 0.11

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H11···O2i0.891 (9)1.984 (10)2.869 (2)172.2 (16)
N2—H12···O1ii0.893 (9)2.192 (11)3.038 (2)157.7 (16)
Symmetry codes: (i) x+2, y+1/2, z+1; (ii) x+1, y, z.
 

Acknowledgements

The authors thank the National Natural Science Foundation of China (No. 20272011) and Harbin University of Science and Technology for supporting this work.

References

First citationBrunel, J. M., Constantieux, T. & Bunono, G. (1999). J. Org. Chem. 64, 8940–8942.  Web of Science CSD CrossRef PubMed CAS Google Scholar
First citationFeng, Q., Liu, Z.-L., Xiong, L.-X., Wang, M.-Z., Li, Y.-Q. & Li, Z.-M. (2010). J. Agric. Food Chem. 58, 12327–12336.  Web of Science CSD CrossRef CAS PubMed Google Scholar
First citationHigashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationRigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
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