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

Chen, J.N.; Yang, L.Y.

doi:10.1107/S1600536808027128

organic compounds

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Volume 64| Part 9| September 2008| Page o1862

doi:10.1107/S1600536808027128

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

Ju Na Chen ^a ^* and Lin Yan Yang ^b

^aNaval Aeronautical and Astronautical University, Yantai 264001, People's Republic of China, and ^bDepartment of Chemistry, Shandong Normal University, Jinan 250014, People's Republic of China
^*Correspondence e-mail: chenjuna1982@yahoo.com.cn

(Received 14 August 2008; accepted 22 August 2008; online 30 August 2008)

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 ); Khan et al. (1993 ).

Experimental

Crystal data

C₈H₁₀N₄O₂
M_r = 194.20
Monoclinic, C 2/c
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 ) 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[F² > 2σ(F²)] = 0.052
wR(F²) = 0.172
S = 1.06
2134 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.81	1.98	2.774 (2)	166
Symmetry code: (i) $[x, -y+1, z-{\script{1\over 2}}]$ .

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

Supporting information

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

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

checkCIF report

Comment top

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···Cg1ⁱ_perp = 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···Cg2ⁱ_perp 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).

Related literature top

For related papers, see: Wang et al. (2008) and Khan et al. (1993).

Experimental top

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.

Computing details top

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

Figures top

	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.

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

Crystal data top

C₈H₁₀N₄O₂	F(000) = 816
M_r = 194.20	D_x = 1.318 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1722 reflections
a = 18.174 (4) Å	θ = 2.4–25.5°
b = 10.962 (3) Å	µ = 0.10 mm⁻¹
c = 13.271 (3) Å	T = 298 K
β = 132.217 (3)°	Block, colourless
V = 1958.1 (8) Å³	0.48 × 0.40 × 0.28 mm
Z = 8

Data collection top

Bruker SMART APEX CCD diffractometer	2134 independent reflections
Radiation source: fine-focus sealed tube	1431 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→23
T_min = 0.954, T_max = 0.973	k = −13→13
5536 measured reflections	l = −16→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.1P)² + 0.0347P] where P = (F_o² + 2F_c²)/3
2134 reflections	(Δ/σ)_max = 0.045
129 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₈H₁₀N₄O₂	V = 1958.1 (8) Å³
M_r = 194.20	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 18.174 (4) Å	µ = 0.10 mm⁻¹
b = 10.962 (3) Å	T = 298 K
c = 13.271 (3) Å	0.48 × 0.40 × 0.28 mm
β = 132.217 (3)°

Data collection top

Bruker SMART APEX CCD diffractometer	2134 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1431 reflections with I > 2σ(I)
T_min = 0.954, T_max = 0.973	R_int = 0.025
5536 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.172	H-atom parameters constrained
S = 1.06	Δρ_max = 0.19 e Å⁻³
2134 reflections	Δρ_min = −0.16 e Å⁻³
129 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
C1	0.12820 (11)	0.43770 (16)	0.26471 (15)	0.0584 (4)
C2	0.12053 (12)	0.20436 (15)	0.48282 (18)	0.0630 (5)
H2	0.1234	0.2871	0.5006	0.076*
C3	0.12962 (12)	0.56843 (16)	0.29319 (16)	0.0583 (4)
C4	0.13696 (16)	0.60601 (15)	0.4082 (2)	0.0753 (6)
H4A	0.1945	0.6566	0.4702	0.113*
H4B	0.1426	0.5347	0.4550	0.113*
H4C	0.0785	0.6508	0.3730	0.113*
C5	0.12486 (18)	0.39842 (18)	0.1538 (2)	0.0813 (6)
H5A	0.1707	0.3325	0.1857	0.122*
H5B	0.1428	0.4658	0.1278	0.122*
H5C	0.0589	0.3718	0.0766	0.122*
C6	0.12287 (11)	0.16599 (15)	0.38501 (16)	0.0584 (4)
C7	0.11298 (15)	−0.02865 (17)	0.4241 (2)	0.0813 (6)
H7	0.1096	−0.1113	0.4056	0.098*
C8	0.11035 (14)	0.00630 (17)	0.5209 (2)	0.0764 (6)
H8	0.1058	−0.0530	0.5666	0.092*
N1	0.12018 (11)	0.05109 (14)	0.35580 (16)	0.0742 (5)
N2	0.11418 (11)	0.12313 (13)	0.55072 (16)	0.0716 (5)
N3	0.12995 (10)	0.36663 (12)	0.34221 (14)	0.0600 (4)
N4	0.12369 (11)	0.64309 (14)	0.21366 (14)	0.0661 (4)
O1	0.12332 (10)	0.76336 (11)	0.24571 (14)	0.0821 (4)
H1	0.1130	0.8035	0.1863	0.123*
O2	0.12790 (9)	0.24281 (11)	0.30873 (12)	0.0687 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0597 (9)	0.0721 (11)	0.0488 (9)	0.0017 (7)	0.0386 (8)	−0.0016 (8)
C2	0.0751 (11)	0.0516 (9)	0.0704 (10)	0.0022 (7)	0.0522 (9)	−0.0027 (8)
C3	0.0666 (10)	0.0658 (11)	0.0556 (9)	0.0004 (7)	0.0464 (8)	−0.0025 (8)
C4	0.1091 (14)	0.0730 (13)	0.0787 (12)	−0.0015 (10)	0.0774 (12)	−0.0034 (9)
C5	0.1160 (16)	0.0838 (14)	0.0661 (11)	0.0031 (10)	0.0701 (12)	−0.0048 (9)
C6	0.0540 (9)	0.0571 (10)	0.0575 (9)	−0.0021 (7)	0.0348 (8)	−0.0077 (8)
C7	0.0914 (13)	0.0554 (11)	0.0976 (14)	−0.0045 (9)	0.0637 (12)	−0.0121 (11)
C8	0.0828 (12)	0.0547 (12)	0.0963 (15)	−0.0014 (8)	0.0620 (12)	0.0023 (10)
N1	0.0824 (10)	0.0619 (9)	0.0805 (10)	−0.0055 (7)	0.0556 (9)	−0.0162 (8)
N2	0.0881 (10)	0.0589 (10)	0.0842 (11)	0.0021 (7)	0.0647 (10)	0.0014 (7)
N3	0.0698 (9)	0.0601 (9)	0.0577 (8)	−0.0018 (6)	0.0459 (8)	−0.0046 (7)
N4	0.0831 (10)	0.0687 (10)	0.0660 (9)	−0.0001 (7)	0.0581 (8)	−0.0013 (7)
O1	0.1258 (11)	0.0661 (9)	0.0898 (9)	−0.0013 (7)	0.0869 (9)	−0.0011 (7)
O2	0.0858 (8)	0.0665 (8)	0.0648 (8)	−0.0039 (6)	0.0550 (7)	−0.0097 (6)

Geometric parameters (Å, º) top

C1—N3	1.273 (2)	C5—H5B	0.9600
C1—C3	1.478 (3)	C5—H5C	0.9600
C1—C5	1.495 (2)	C6—N1	1.309 (2)
C2—N2	1.326 (2)	C6—O2	1.366 (2)
C2—C6	1.392 (2)	C7—N1	1.327 (2)
C2—H2	0.9300	C7—C8	1.372 (3)
C3—N4	1.282 (2)	C7—H7	0.9300
C3—C4	1.497 (2)	C8—N2	1.328 (2)
C4—H4A	0.9600	C8—H8	0.9300
C4—H4B	0.9600	N3—O2	1.4209 (18)
C4—H4C	0.9600	N4—O1	1.3868 (18)
C5—H5A	0.9600	O1—H1	0.8074

N3—C1—C3	113.57 (14)	C1—C5—H5C	109.5
N3—C1—C5	125.55 (17)	H5A—C5—H5C	109.5
C3—C1—C5	120.88 (15)	H5B—C5—H5C	109.5
N2—C2—C6	120.13 (17)	N1—C6—O2	112.42 (14)
N2—C2—H2	119.9	N1—C6—C2	123.25 (17)
C6—C2—H2	119.9	O2—C6—C2	124.33 (16)
N4—C3—C1	115.55 (14)	N1—C7—C8	122.47 (18)
N4—C3—C4	124.34 (16)	N1—C7—H7	118.8
C1—C3—C4	120.11 (14)	C8—C7—H7	118.8
C3—C4—H4A	109.5	N2—C8—C7	121.37 (18)
C3—C4—H4B	109.5	N2—C8—H8	119.3
H4A—C4—H4B	109.5	C7—C8—H8	119.3
C3—C4—H4C	109.5	C6—N1—C7	115.64 (16)
H4A—C4—H4C	109.5	C2—N2—C8	117.12 (17)
H4B—C4—H4C	109.5	C1—N3—O2	110.52 (14)
C1—C5—H5A	109.5	C3—N4—O1	111.69 (13)
C1—C5—H5B	109.5	N4—O1—H1	105.3
H5A—C5—H5B	109.5	C6—O2—N3	110.96 (12)

N3—C1—C3—N4	−177.17 (13)	C6—C2—N2—C8	0.0 (2)
C5—C1—C3—N4	2.7 (2)	C7—C8—N2—C2	0.1 (3)
N3—C1—C3—C4	2.5 (2)	C3—C1—N3—O2	179.69 (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—O1	178.66 (13)
N2—C2—C6—O2	179.03 (15)	C4—C3—N4—O1	−1.0 (2)
N1—C7—C8—N2	0.5 (3)	N1—C6—O2—N3	179.56 (12)
O2—C6—N1—C7	−178.54 (14)	C2—C6—O2—N3	−0.3 (2)
C2—C6—N1—C7	1.3 (2)	C1—N3—O2—C6	−175.83 (12)
C8—C7—N1—C6	−1.2 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.81	1.98	2.774 (2)	166

Symmetry code: (i) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₈H₁₀N₄O₂
M_r	194.20
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	298
a, b, c (Å)	18.174 (4), 10.962 (3), 13.271 (3)
β (°)	132.217 (3)
V (Å³)	1958.1 (8)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.48 × 0.40 × 0.28

Data collection
Diffractometer	Bruker SMART APEX CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.954, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	5536, 2134, 1431
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.172, 1.06
No. of reflections	2134
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXTL (Sheldrick, 2008) and local programs.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.81	1.98	2.774 (2)	165.8

Symmetry code: (i) x, −y+1, z−1/2.

References

Bruker (1997). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Khan, O., Stumpf, H., Pei, Y. & Sletten, J. (1993). Mol. Cryst. Liq. Cryst. 233, 231–246. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. Web of Science CSD CrossRef CAS Google Scholar

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Page o1862

doi:10.1107/S1600536808027128

Open

access