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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2776.
Published online 2009 October 17. doi:  10.1107/S1600536809039646
PMCID: PMC2971405

2-(3-Oxocyclo­hex-1-enylamino)acetic acid

Abstract

The six-membered ring of the title compound, C8H11NO3, adopts an envelope shape with the C atom in the meta position of the carbonyl representing the flap. This atom is disordered over two positions in an 0.865 (6): 0.135 (6) ratio. In the crystal, a two-dimensional supra­molecular network parallel to the ac plane is built up from O—H(...)O and N—H(...)O hydrogen bonds.

Related literature

For a related structure, see: Lalancette et al. (2001 [triangle])

An external file that holds a picture, illustration, etc.
Object name is e-65-o2776-scheme1.jpg

Experimental

Crystal data

  • C8H11NO3
  • M r = 169.18
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2776-efi1.jpg
  • a = 5.138 (1) Å
  • b = 12.983 (3) Å
  • c = 12.345 (3) Å
  • β = 92.89 (3)°
  • V = 822.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 291 K
  • 0.35 × 0.31 × 0.23 mm

Data collection

  • Rigaku R-AXIS RAPID diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.964, T max = 0.977
  • 7743 measured reflections
  • 1854 independent reflections
  • 1461 reflections with I > 2σ(I)
  • R int = 0.032

Refinement

  • R[F 2 > 2σ(F 2)] = 0.041
  • wR(F 2) = 0.117
  • S = 1.13
  • 1854 reflections
  • 127 parameters
  • 8 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.19 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809039646/ng2648sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809039646/ng2648Isup2.hkl

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

Acknowledgments

This study was supported by the Open Topics Foundation for the Key Laboratory of Polyoxometalate Science of the Ministry of Education of Northeast Normal University.

supplementary crystallographic information

Comment

As shown in the scheme, the title compound is a resonance body of the (E)-2-(3-oxocyclohexylideneamino)acetic acid, which can be verified by the existence of the shorter single C—C bond distance and the emergence of the imino group (Figure 1). The C5 atom of the cyclohexane is disordered over two positions with site occupation 0.84 and 0.16 for C5, C5' and their appended H atoms, respectively.

In the crystal structure, a two-dimensional supramolecular network is built up by O—H···O and N—H···O hydrogen bonds between the ketone, the imino group and the carboxyl, along ac plane (Table 1, Figure 2).

Experimental

Title compound was prepared from 1,3-cyclohexanedione (11.2 g, 0.1 mol) and 2-aminoacetic acid (7.5 g, 0.1 mol) in 100 ml DMSO solution at 100 °C for 24 h. Needle crystals for X-ray diffraction analysis were produced from a ethanol and cyclohexane mixed solution.

Refinement

H atoms bonded to C atoms were placed in calculated positions and treated as riding on their parent atoms, with C—H = 0.93 Å (C2—H2A), C—H = 0.97 Å (methylene), and with Uiso(H) = 1.2Ueq(C). H atoms of the carboxyl group and imino group were located in a difference Fourier map and were freely refined with O—H = 0.85 Å, N—H = 0.85 Å. The C5 atom of the cyclohexane is disordered over two positions with site occupation 0.84 and 0.16 for C5, C5' and their appended H atoms, respectively.

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids at the 30% probability level for non-H atoms.
Fig. 2.
A partial packing view, showing the two-dimensional network. Dashed lines indicate the hydrogen-bonding interactions and no involving H atoms have been omitted.

Crystal data

C8H11NO3F(000) = 360
Mr = 169.18Dx = 1.366 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6177 reflections
a = 5.138 (1) Åθ = 3.1–27.5°
b = 12.983 (3) ŵ = 0.11 mm1
c = 12.345 (3) ÅT = 291 K
β = 92.89 (3)°Block, colorless
V = 822.4 (3) Å30.35 × 0.31 × 0.23 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID diffractometer1854 independent reflections
Radiation source: fine-focus sealed tube1461 reflections with I > 2σ(I)
graphiteRint = 0.032
ω scansθmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −6→5
Tmin = 0.964, Tmax = 0.977k = −16→16
7743 measured reflectionsl = −15→15

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.041Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.13w = 1/[σ2(Fo2) + (0.0593P)2 + 0.1182P] where P = (Fo2 + 2Fc2)/3
1854 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.18 e Å3
8 restraintsΔρmin = −0.19 e Å3

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*/UeqOcc. (<1)
C5'−0.308 (3)1.0310 (8)0.2164 (12)0.043 (4)0.135 (6)
H5'1−0.44531.04720.26480.052*0.135 (6)
H5'2−0.28801.09000.16930.052*0.135 (6)
C5−0.1653 (5)1.01745 (14)0.16773 (17)0.0444 (7)0.865 (6)
H5A−0.02830.99870.12020.053*0.865 (6)
H5B−0.22261.08670.14890.053*0.865 (6)
C10.0056 (2)0.90870 (10)0.31865 (10)0.0301 (3)
C2−0.1357 (3)0.82688 (10)0.27717 (11)0.0331 (3)
H2A−0.09410.76080.30150.040*
C3−0.3418 (3)0.83987 (10)0.19878 (10)0.0323 (3)
C4−0.3913 (3)0.94381 (12)0.15005 (13)0.0439 (4)
H4A−0.54400.97340.18110.053*
H4B−0.42920.93600.07270.053*
C6−0.0589 (3)1.01603 (11)0.28306 (13)0.0445 (4)
H6A0.09681.05830.28970.053*
H6B−0.18661.04500.32970.053*
C70.2932 (3)0.79797 (11)0.43069 (11)0.0348 (3)
H7A0.34070.75600.36980.042*
H7B0.15340.76330.46610.042*
C80.5245 (3)0.80897 (10)0.50935 (10)0.0324 (3)
H10.274 (3)0.9517 (10)0.4179 (13)0.053 (5)*
H20.762 (3)0.7271 (19)0.5786 (16)0.089 (8)*
N10.2035 (2)0.89704 (9)0.39184 (9)0.0350 (3)
O10.5998 (2)0.89070 (8)0.54410 (10)0.0549 (4)
O20.6287 (2)0.72005 (8)0.53416 (8)0.0425 (3)
O3−0.4844 (2)0.76566 (8)0.16931 (9)0.0468 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C5'0.044 (7)0.025 (5)0.059 (7)0.005 (4)−0.011 (5)0.004 (4)
C50.0481 (13)0.0335 (9)0.0494 (12)−0.0016 (8)−0.0183 (10)0.0112 (7)
C10.0275 (6)0.0328 (7)0.0291 (6)0.0012 (5)−0.0077 (5)−0.0014 (5)
C20.0330 (7)0.0294 (7)0.0353 (7)−0.0022 (5)−0.0134 (5)0.0034 (5)
C30.0288 (6)0.0369 (7)0.0302 (6)−0.0024 (5)−0.0083 (5)−0.0024 (5)
C40.0399 (8)0.0430 (8)0.0464 (8)0.0020 (6)−0.0205 (6)0.0053 (6)
C60.0435 (8)0.0295 (7)0.0579 (9)0.0025 (6)−0.0221 (7)−0.0043 (6)
C70.0318 (7)0.0362 (7)0.0350 (7)−0.0053 (5)−0.0132 (6)0.0044 (5)
C80.0305 (6)0.0356 (7)0.0300 (6)−0.0006 (5)−0.0093 (5)0.0010 (5)
N10.0328 (6)0.0323 (6)0.0379 (6)−0.0032 (5)−0.0172 (5)−0.0015 (4)
O10.0560 (7)0.0383 (6)0.0662 (7)0.0015 (5)−0.0378 (6)−0.0078 (5)
O20.0438 (6)0.0385 (6)0.0431 (6)0.0038 (4)−0.0195 (5)0.0021 (4)
O30.0441 (6)0.0423 (6)0.0510 (6)−0.0104 (4)−0.0254 (5)−0.0008 (5)

Geometric parameters (Å, °)

C5'—C41.448 (12)C3—C41.494 (2)
C5'—C61.500 (12)C4—H4A0.9700
C5'—H5'10.9700C4—H4B0.9700
C5'—H5'20.9700C6—H6A0.9700
C5—C61.499 (2)C6—H6B0.9700
C5—C41.511 (2)C7—N11.4403 (17)
C5—H5A0.9700C7—C81.5030 (18)
C5—H5B0.9700C7—H7A0.9700
C1—N11.3344 (17)C7—H7B0.9700
C1—C21.3710 (18)C8—O11.2013 (17)
C1—C61.4931 (19)C8—O21.3025 (17)
C2—C31.4082 (18)N1—H10.853 (9)
C2—H2A0.9300O2—H20.862 (10)
C3—O31.2533 (16)
C4—C5'—C6115.4 (8)C5'—C4—H4B132.6
C4—C5'—H5'1108.4C3—C4—H4B108.9
C6—C5'—H5'1108.4C5—C4—H4B108.9
C4—C5'—H5'2108.4H4A—C4—H4B107.7
C6—C5'—H5'2108.4C1—C6—C5110.84 (13)
H5'1—C5'—H5'2107.5C1—C6—C5'116.9 (4)
C6—C5—C4111.72 (16)C5—C6—C5'38.4 (6)
C6—C5—H5A109.3C1—C6—H6A109.5
C4—C5—H5A109.3C5—C6—H6A109.5
C6—C5—H5B109.3C5'—C6—H6A130.6
C4—C5—H5B109.3C1—C6—H6B109.5
H5A—C5—H5B107.9C5—C6—H6B109.5
N1—C1—C2122.41 (12)C5'—C6—H6B72.0
N1—C1—C6117.07 (12)H6A—C6—H6B108.1
C2—C1—C6120.52 (12)N1—C7—C8111.08 (11)
C1—C2—C3121.96 (12)N1—C7—H7A109.4
C1—C2—H2A119.0C8—C7—H7A109.4
C3—C2—H2A119.0N1—C7—H7B109.4
O3—C3—C2121.05 (13)C8—C7—H7B109.4
O3—C3—C4119.49 (12)H7A—C7—H7B108.0
C2—C3—C4119.46 (12)O1—C8—O2125.30 (13)
C5'—C4—C3116.0 (5)O1—C8—C7122.99 (12)
C5'—C4—C538.9 (6)O2—C8—C7111.71 (11)
C3—C4—C5113.54 (12)C1—N1—C7123.16 (11)
C5'—C4—H4A71.8C1—N1—H1117.2 (13)
C3—C4—H4A108.9C7—N1—H1119.6 (13)
C5—C4—H4A108.9C8—O2—H2111.1 (17)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.85 (1)2.19 (1)3.0266 (17)167 (2)
O2—H2···O3ii0.86 (1)1.68 (1)2.5369 (16)176 (2)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2648).

References

  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Lalancette, R. A. & Thompson, H. W. (2001). Acta Cryst. C57, 1434–1435. [PubMed]
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Rigaku/MSC (2002). CrystalClear Rigaku/MSC Inc., The Woodlands, Texas, USA.
  • 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