N′-[(E)-1-(2-Hy­droxy­phen­yl)ethyl­idene]pyrazine-2-carbohydrazide

Shahid Hameed; Mushtaq Ahmad; M Nawaz Tahir; Muhammad Israr; Muhammad Anwar

doi:10.1107/S1600536813022137

. 2013 Aug 14;69(Pt 9):o1419. doi: 10.1107/S1600536813022137

N′-[(E)-1-(2-Hydroxyphenyl)ethylidene]pyrazine-2-carbohydrazide

Shahid Hameed ^a, Mushtaq Ahmad ^a,^b, M Nawaz Tahir ^c,^*, Muhammad Israr ^d, Muhammad Anwar ^d

PMCID: PMC3884444 PMID: 24427054

Abstract

The title compound, C₁₃H₁₂N₄O₂, crystallized with two independent molecules (A and B) in the asymmetric unit. Molecule B is planar to within 0.044 (3) Å for all non-H atoms, while molecule A is slightly twisted, with a dihedral angle of 6.29 (4)° between the mean planes of the pyrazine-2-carbohydrazide and 1-(2-hydroxyphenyl)ethanone moieties (r.m.s. deviations = 0.0348 and 0.0428 Å, respectively). S(5) and S(6) ring motifs are formed in both molecules due to the presence of intramolecular O—H⋯N and N—H⋯N hydrogen bonds. In the crystal, molecules A and B are linked by a C—H⋯O hydrogen bond. They stack along the a-axis direction, forming columns with π–π interactions involving inversion-related pyrazine and benzene rings [centroid–centroid distances = 3.5489 (13)–3.8513 (16) Å].

Related literature

For a related crystal structure and other studies, see: Hameed et al. (2013 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). graphic file with name e-69-o1419-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₂N₄O₂
M _r = 256.27
Triclinic,
a = 7.1767 (7) Å
b = 10.1743 (10) Å
c = 17.1150 (17) Å
α = 86.172 (3)°
β = 85.275 (2)°
γ = 80.963 (4)°
V = 1228.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.28 × 0.23 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.973, T _max = 0.981
19042 measured reflections
4821 independent reflections
2608 reflections with I > 2σ(I)
R _int = 0.048

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.138
S = 1.00
4821 reflections
361 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813022137/su2634sup1.cif

e-69-o1419-sup1.cif^{(33.1KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813022137/su2634Isup2.hkl

e-69-o1419-Isup2.hkl^{(264.3KB, hkl)}

Click here for additional data file.^{(5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813022137/su2634Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.82	2.537 (2)	145
N2—H2A⋯N3	0.80 (2)	2.26 (2)	2.654 (3)	111.5 (17)
O3—H3A⋯N5	0.82	1.82	2.534 (3)	145
N6—H6⋯N7	0.80 (3)	2.21 (3)	2.628 (3)	113 (3)
C3—H3⋯O3ⁱ	0.93	2.59	3.403 (3)	146

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors acknowledge the provision of funds for the purchase of the diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan, and also thank the Higher Education Commission (HEC) of Pakistan for financial support. MA is grateful to the Pakistan Council of Scientific and Industrial Research (PCSIR) Laboratories of Pakistan for financial support through out his study leave.

supplementary crystallographic information

1. Comment

The title compound was prepared in continuation of our interest in the synthesis of compounds containing the moiety pyrazine-2-carbohydrazide (Hameed et al., 2013).

The title compound crystallized with two independent molecules (A and B) in the asymmetric unit, Fig. 1. In molecule A, the 1-(2-hydroxyphenyl)ethanone (C1—C8/O1) moiety and the pyrazine-2-carbohydrazide moiety (C9–C13/N1–N4/O2) are almost planar with r.m.s. deviations of 0.0348 Å and 0.0428 Å, respectively. They are inclined to one another by 6.289 (44)°. In molecule B, similar groups (C14—C21/O3) and (C22—C26/N5—N8/O4) are planar with r.m.s. deviations of 0.0111 and 0.019 Å, respectively, and are inclined to one another by only 0.305 (21)° i.e. almost coplanar.

There exist strong intramolecular N—H···N and O—H···N hydrogen bonds in each molecule (Table 1 and Fig. 1) forming S(5) and S(6) ring motifs (Bernstein et al., 1995).

In the crystal, molecules A and B are linked by a C—H···O hydrogen bond (Table 1 and Fig. 2). They stack along the a axis direction forming columns with π–π interactions involving inversion related pyrazine and benzene rings. The centroid-to-centroid distances are 3.5489 (13) Å [Cg1—Cg2ⁱ], 3.6289 (13) Å [Cg1—Cg2ⁱⁱ], 3.7738 (16) Å [Cg3—Cg4ⁱⁱⁱ], and 3.8513 (16) Å [Cg3—Cg4^iv], where Cg1, Cg2, Cg3 and Cg4 are the centroids of rings (C10/N3/C11/C12/N4/C13), (C1—C6), (C23/N7/C24/C25/N8/C26) and (C14—C19), respectively [symmetry codes: (i) = -x, - y, -z; (ii) = - x+1, - y, -z; (iii) = -x, - y+1, - z+1; (iv) = - x+1, - y+1, - z+1].

2. Experimental

The title compound was prepared by the condensation of an equimolar ratio of pyrazine-2-carbohydrazide (0.50 g, 3.6 mmol) and 1-(2-hydroxyphenyl)ethanone (0.45 ml, 3.6 mmol) in methanol by stirring well and then refluxing of 5 h. The resulting reaction mixture was allowed to cool over night. The precipitated solid was filtered, washed with petroleum ether and recrystallized from chloroform in petroleum ether and then dried under reduced pressure over CaCl₂ to give colourless prisms.