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Acta Crystallogr Sect E Struct Rep Online. 2008 December 1; 64(Pt 12): o2418.
Published online 2008 November 22. doi:  10.1107/S1600536808038488
PMCID: PMC2960094

N-(2-Formamido­eth­yl)formamide

Abstract

The complete molecule of the title compound, C4H8N2O2, is generated by a crystallographic inversion center. The occurence of N—H(...)O hydrogen bonds results in the formation of a two-dimensional infinite network parallel to the (010) plane. In this plane, the hydrogen bonds define graph-set motif R 4 4(22) in a centrosymmetric array by the association of four mol­ecules.

Related literature

For general background, see: Yang et al. (2007 [triangle]). For related structures, see: Goss et al. (1996 [triangle]). For graph-set notation, see: Bernstein et al. (1995 [triangle]); Etter et al. (1990 [triangle]).

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Object name is e-64-o2418-scheme1.jpg

Experimental

Crystal data

  • C4H8N2O2
  • M r = 116.12
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2418-efi3.jpg
  • a = 8.7138 (17) Å
  • b = 6.6714 (13) Å
  • c = 9.3162 (19) Å
  • V = 541.58 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.12 mm−1
  • T = 113 (2) K
  • 0.32 × 0.26 × 0.16 mm

Data collection

  • Rigaku Saturn diffractometer
  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 [triangle]) T min = 0.964, T max = 0.982
  • 2736 measured reflections
  • 467 independent reflections
  • 431 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.027
  • wR(F 2) = 0.073
  • S = 1.11
  • 467 reflections
  • 40 parameters
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.15 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: ORTEPIII (Burnett & Johnson, 1996 [triangle]), ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2003 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808038488/dn2396sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038488/dn2396Isup2.hkl

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

supplementary crystallographic information

Comment

N-(2-Formylaminoethyl)formamide is a plasticizer to prepare thermoplastic starch. The mechanical properties of N-(2-Formylaminoethyl)formamide plasticized starch were enhanced compared with the conventional glycerol plasticized one (Yang,et al., 2007).

The molecule of (I) has a center of symmetry at the mid-point of the central C2—C2i bond (Fig. 1).

Intermolecular N—H···O hydrogen bonds link the molecule to form a two dimensionnal network parallel to the (0 1 0) plane. In this plane, the hydrogen bonds define rings by associating 4 molécules displaying graph set motif R44(21) (Etter et al., 1990; Bernstein et al., 1995).

Therefore, the OH group of the starch can also form intermolecular O—H···O hydrogen bonds with the N-(2-Formylaminoethyl)formamide, the mechanical properties of the plasticized starch is then enhanced.

Experimental

Methyl formate (500 ml) was placed in a 1000 ml flask cooled by ice-bath and ethylenediamine (250 ml) was slowly added. Subsequently, ice-bath was removed and the mixture was refluxed for 10 h. After standing overnight, the product was isolated by filtration. The solids obtained by filtration were recrystallized from anhydrous ethyl alcohol in 95% yield. Colorless crystals of N-(2-Formylaminoethyl)formamide were obtained by slow evaporation of a solution of anhydrous methyl alcohol at 278 k(m.p. 381 k).

Refinement

The N-bound H atoms were located in a difference map and freely refined with Uiso(H) = 1.2 Ueq(N)], H atoms attached to carbon were positioned geometrically and treated as riding on their parent atoms [C—H distances are 0.93 Å for CH and 0.97 Å for CH2 groups, both with Uiso(H) = 1.2 Ueq(C)].

Figures

Fig. 1.
A view of the molecular structure of (I) with the atom-labeling scheme. Displacement ellopsoids are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii. [Symmetry code:(i) 1-x, 1-y, 1-z ]
Fig. 2.
Partial packing view showing the formation of the two dimensional network through N-H···O hydrogen bonds which are shown as dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity. [Symmetry code: (i) ...

Crystal data

C4H8N2O2F000 = 248
Mr = 116.12Dx = 1.424 Mg m3
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 1513 reflections
a = 8.7138 (17) Åθ = 3.1–27.8º
b = 6.6714 (13) ŵ = 0.12 mm1
c = 9.3162 (19) ÅT = 113 (2) K
V = 541.58 (19) Å3Block, colorless
Z = 40.32 × 0.26 × 0.16 mm

Data collection

Rigaku Saturn diffractometer467 independent reflections
Radiation source: rotating anode431 reflections with I > 2σ(I)
Monochromator: confocalRint = 0.035
T = 113(2) Kθmax = 25.0º
ω scansθmin = 4.4º
Absorption correction: multi-scan(CrystalClear; Rigaku, 2005)h = −10→7
Tmin = 0.964, Tmax = 0.982k = −7→7
2736 measured reflectionsl = −9→11

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.073  w = 1/[σ2(Fo2) + (0.0378P)2 + 0.1199P] where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
467 reflectionsΔρmax = 0.21 e Å3
40 parametersΔρmin = −0.15 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

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 > 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
C10.26367 (12)0.50564 (15)0.69236 (11)0.0165 (3)
H10.16160.47440.71100.020*
C20.45751 (11)0.59669 (16)0.51762 (12)0.0158 (3)
H2A0.51020.66590.59480.019*
H2B0.45750.68350.43410.019*
N10.30073 (10)0.55554 (13)0.56027 (10)0.0160 (3)
H1A0.2325 (15)0.5444 (19)0.4965 (17)0.019*
O10.35499 (8)0.49743 (11)0.79307 (8)0.0209 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0155 (5)0.0165 (6)0.0175 (6)0.0003 (4)0.0024 (5)−0.0025 (4)
C20.0170 (6)0.0170 (6)0.0133 (6)−0.0011 (4)0.0004 (4)0.0009 (4)
N10.0140 (5)0.0196 (5)0.0143 (5)0.0010 (4)−0.0027 (3)−0.0015 (4)
O10.0200 (4)0.0288 (5)0.0139 (5)−0.0006 (3)−0.0002 (3)0.0012 (3)

Geometric parameters (Å, °)

C1—O11.2314 (13)C2—C2i1.523 (2)
C1—N11.3151 (14)C2—H2A0.9700
C1—H10.9300C2—H2B0.9700
C2—N11.4490 (15)N1—H1A0.844 (15)
O1—C1—N1124.44 (10)N1—C2—H2B109.5
O1—C1—H1117.8C2i—C2—H2B109.5
N1—C1—H1117.8H2A—C2—H2B108.0
N1—C2—C2i110.91 (11)C1—N1—C2122.41 (9)
N1—C2—H2A109.5C1—N1—H1A117.6 (9)
C2i—C2—H2A109.5C2—N1—H1A119.2 (9)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1A···O1ii0.844 (15)2.062 (16)2.8570 (13)156.9 (12)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DN2396).

References

  • Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl.34, 1555–1573.
  • Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.
  • Etter, M. C., MacDonald, J. C. & Bernstein, J. (1990). Acta Cryst. B46, 256–262. [PubMed]
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Goss, J. D., Folting, C. R., Santarsiero, K. B. D. & Hollingsworth, M. D. (1996). J. Am. Chem. Soc. pp. 9432–9433.
  • Rigaku (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.
  • Yang, J. H., Yu, J. G., Feng, Y. & Ma, X. F. (2007). Carbohydr. Polym. pp. 197–203.

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