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Acta Crystallogr Sect E Struct Rep Online. 2008 September 1; 64(Pt 9): o1862.
Published online 2008 August 30. doi:  10.1107/S1600536808027128
PMCID: PMC2960616

(2E,3E)-3-(Pyrazin-2-yloxyimino)butan-2-one oxime

Abstract

In the title compound, C8H10N4O2, all non-H atoms are nearly coplanar [maximum deviation 0.1256 (16) Å for the methyl C furthest from the ring]. Inter­molecular O—H(...)N hydrogen bonds link adjacent mol­ecules into a one-dimensional zigzag chain along the c axis. There is also a weak π–π stacking inter­action between neighbouring pyrazine rings, with a centroid–centroid distance of 4.0432 (15) Å.

Related literature

For related papers, see: Wang et al. (2008 [triangle]); Khan et al. (1993 [triangle]).

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Object name is e-64-o1862-scheme1.jpg

Experimental

Crystal data

  • C8H10N4O2
  • M r = 194.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1862-efi1.jpg
  • a = 18.174 (4) Å
  • b = 10.962 (3) Å
  • c = 13.271 (3) Å
  • β = 132.217 (3)°
  • V = 1958.1 (8) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 298 (2) K
  • 0.48 × 0.40 × 0.28 mm

Data collection

  • Bruker SMART APEX CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.954, T max = 0.973
  • 5536 measured reflections
  • 2134 independent reflections
  • 1431 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.052
  • wR(F 2) = 0.172
  • S = 1.06
  • 2134 reflections
  • 129 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.16 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808027128/at2614sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808027128/at2614Isup2.hkl

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

supplementary crystallographic information

Comment

Pyrazine, (2E,3E)-butane-2,3-dione dioxime and their derivatives belong to useful compounds and a large number of complexes have been synthesized with them as ligands (Wang et al., (2008) and Khan et al. (1993)). We are interested in complexes with the title compound as ligand, therefore we synthesized the title compound and obtained its crystal structure (I).

Fig. 1 shows the molecular structure of the title compound and the all of non-hydrogen atoms define a plane with a maximum deviation of 0.1256 (16) Å for atom C4. There is a weak π-π stacking interaction involving symmetry-related pyrazine rings, which resulted in the formation of a dimer of two neighbor molecules, and the relevant distances being Cg1···Cg1i = 4.0432 (15) Å and Cg1···Cg1iperp = 3.248 Å and α = 5.71°; [symmetry code: (i) -x, y, 1/2-z; Cg1 is the centroid of the N1N2/C2C6C7C8 ring, Cg1···Cg2iperp is the perpendicular distance from ring Cg1 to ring Cg1i; α is the dihedral angle between ring plane Cg1 and ring plane Cg1i]. In addition to the π-π interaction there exists O1—H1···N2ii [symmetry code: (ii) x, 1-y,-1/2+z] hydrogen bond and it give rise a one-dimensional zigzag chain along c axis as shown in Fig. 2 (Table 1).

Experimental

Powder (2E,3E)-butane-2,3-dione O3-(2-pyrazyl) dioxime (0.3720 g, 1.92 mmole) was dissolved in 20 ml solution containing 10 ml chloroform and 10 ml me thanol, and the colorless single crystals were obtained after the solution had been allowed to stand at room temperature for a month.

Refinement

Oxygen-bound H atom was located in a difference Fourier map, and refined as riding in its as found position with O—H = 0.81 Å, Uiso(H) = 1.5Ueq(O). Other H atoms were placed in calculated positions (C—H = 0.96 Å for methyl group and C—H = 0.93 Å for pyrazinyl H atoms) and refined as riding with Uiso = 1.5Ueq(C) for methyl H and Uiso = 1.2Ueq(C) for pyrazinyl H atoms.

Figures

Fig. 1.
Structure of title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
Hydrogen bonds (dashed lines) between neighbouring molecules.

Crystal data

C8H10N4O2F000 = 816
Mr = 194.20Dx = 1.318 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 1722 reflections
a = 18.174 (4) Åθ = 2.4–25.5º
b = 10.962 (3) ŵ = 0.10 mm1
c = 13.271 (3) ÅT = 298 (2) K
β = 132.217 (3)ºBlock, colourless
V = 1958.1 (8) Å30.48 × 0.40 × 0.28 mm
Z = 8

Data collection

Bruker SMART APEX CCD diffractometer2134 independent reflections
Radiation source: fine-focus sealed tube1431 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.025
T = 293(2) Kθmax = 27.0º
[var phi] and ω scansθmin = 2.4º
Absorption correction: multi-scan(SADABS; Sheldrick, 1996)h = −22→23
Tmin = 0.954, Tmax = 0.973k = −13→13
5536 measured reflectionsl = −16→9

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.052H-atom parameters constrained
wR(F2) = 0.172  w = 1/[σ2(Fo2) + (0.1P)2 + 0.0347P] where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.045
2134 reflectionsΔρmax = 0.19 e Å3
129 parametersΔρmin = −0.16 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
C10.12820 (11)0.43770 (16)0.26471 (15)0.0584 (4)
C20.12053 (12)0.20436 (15)0.48282 (18)0.0630 (5)
H20.12340.28710.50060.076*
C30.12962 (12)0.56843 (16)0.29319 (16)0.0583 (4)
C40.13696 (16)0.60601 (15)0.4082 (2)0.0753 (6)
H4A0.19450.65660.47020.113*
H4B0.14260.53470.45500.113*
H4C0.07850.65080.37300.113*
C50.12486 (18)0.39842 (18)0.1538 (2)0.0813 (6)
H5A0.17070.33250.18570.122*
H5B0.14280.46580.12780.122*
H5C0.05890.37180.07660.122*
C60.12287 (11)0.16599 (15)0.38501 (16)0.0584 (4)
C70.11298 (15)−0.02865 (17)0.4241 (2)0.0813 (6)
H70.1096−0.11130.40560.098*
C80.11035 (14)0.00630 (17)0.5209 (2)0.0764 (6)
H80.1058−0.05300.56660.092*
N10.12018 (11)0.05109 (14)0.35580 (16)0.0742 (5)
N20.11418 (11)0.12313 (13)0.55072 (16)0.0716 (5)
N30.12995 (10)0.36663 (12)0.34221 (14)0.0600 (4)
N40.12369 (11)0.64309 (14)0.21366 (14)0.0661 (4)
O10.12332 (10)0.76336 (11)0.24571 (14)0.0821 (4)
H10.11300.80350.18630.123*
O20.12790 (9)0.24281 (11)0.30873 (12)0.0687 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0597 (9)0.0721 (11)0.0488 (9)0.0017 (7)0.0386 (8)−0.0016 (8)
C20.0751 (11)0.0516 (9)0.0704 (10)0.0022 (7)0.0522 (9)−0.0027 (8)
C30.0666 (10)0.0658 (11)0.0556 (9)0.0004 (7)0.0464 (8)−0.0025 (8)
C40.1091 (14)0.0730 (13)0.0787 (12)−0.0015 (10)0.0774 (12)−0.0034 (9)
C50.1160 (16)0.0838 (14)0.0661 (11)0.0031 (10)0.0701 (12)−0.0048 (9)
C60.0540 (9)0.0571 (10)0.0575 (9)−0.0021 (7)0.0348 (8)−0.0077 (8)
C70.0914 (13)0.0554 (11)0.0976 (14)−0.0045 (9)0.0637 (12)−0.0121 (11)
C80.0828 (12)0.0547 (12)0.0963 (15)−0.0014 (8)0.0620 (12)0.0023 (10)
N10.0824 (10)0.0619 (9)0.0805 (10)−0.0055 (7)0.0556 (9)−0.0162 (8)
N20.0881 (10)0.0589 (10)0.0842 (11)0.0021 (7)0.0647 (10)0.0014 (7)
N30.0698 (9)0.0601 (9)0.0577 (8)−0.0018 (6)0.0459 (8)−0.0046 (7)
N40.0831 (10)0.0687 (10)0.0660 (9)−0.0001 (7)0.0581 (8)−0.0013 (7)
O10.1258 (11)0.0661 (9)0.0898 (9)−0.0013 (7)0.0869 (9)−0.0011 (7)
O20.0858 (8)0.0665 (8)0.0648 (8)−0.0039 (6)0.0550 (7)−0.0097 (6)

Geometric parameters (Å, °)

C1—N31.273 (2)C5—H5B0.9600
C1—C31.478 (3)C5—H5C0.9600
C1—C51.495 (2)C6—N11.309 (2)
C2—N21.326 (2)C6—O21.366 (2)
C2—C61.392 (2)C7—N11.327 (2)
C2—H20.9300C7—C81.372 (3)
C3—N41.282 (2)C7—H70.9300
C3—C41.497 (2)C8—N21.328 (2)
C4—H4A0.9600C8—H80.9300
C4—H4B0.9600N3—O21.4209 (18)
C4—H4C0.9600N4—O11.3868 (18)
C5—H5A0.9600O1—H10.8074
N3—C1—C3113.57 (14)C1—C5—H5C109.5
N3—C1—C5125.55 (17)H5A—C5—H5C109.5
C3—C1—C5120.88 (15)H5B—C5—H5C109.5
N2—C2—C6120.13 (17)N1—C6—O2112.42 (14)
N2—C2—H2119.9N1—C6—C2123.25 (17)
C6—C2—H2119.9O2—C6—C2124.33 (16)
N4—C3—C1115.55 (14)N1—C7—C8122.47 (18)
N4—C3—C4124.34 (16)N1—C7—H7118.8
C1—C3—C4120.11 (14)C8—C7—H7118.8
C3—C4—H4A109.5N2—C8—C7121.37 (18)
C3—C4—H4B109.5N2—C8—H8119.3
H4A—C4—H4B109.5C7—C8—H8119.3
C3—C4—H4C109.5C6—N1—C7115.64 (16)
H4A—C4—H4C109.5C2—N2—C8117.12 (17)
H4B—C4—H4C109.5C1—N3—O2110.52 (14)
C1—C5—H5A109.5C3—N4—O1111.69 (13)
C1—C5—H5B109.5N4—O1—H1105.3
H5A—C5—H5B109.5C6—O2—N3110.96 (12)
N3—C1—C3—N4−177.17 (13)C6—C2—N2—C80.0 (2)
C5—C1—C3—N42.7 (2)C7—C8—N2—C20.1 (3)
N3—C1—C3—C42.5 (2)C3—C1—N3—O2179.69 (12)
C5—C1—C3—C4−177.62 (17)C5—C1—N3—O2−0.2 (2)
N2—C2—C6—N1−0.8 (2)C1—C3—N4—O1178.66 (13)
N2—C2—C6—O2179.03 (15)C4—C3—N4—O1−1.0 (2)
N1—C7—C8—N20.5 (3)N1—C6—O2—N3179.56 (12)
O2—C6—N1—C7−178.54 (14)C2—C6—O2—N3−0.3 (2)
C2—C6—N1—C71.3 (2)C1—N3—O2—C6−175.83 (12)
C8—C7—N1—C6−1.2 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···N2i0.811.982.774 (2)166

Symmetry codes: (i) x, −y+1, z−1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2614).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Khan, O., Stumpf, H., Pei, Y. & Sletten, J. (1993). Mol. Cryst. Liq. Cryst.233, 231–246.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Wang, W.-Z., Ismayilov, R. H., Lee, G.-H., Wang, H.-T., Wang, R.-R. & Peng, S.-M. (2008). Eur. J. Inorg. Chem. pp. 312–321.

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