N′-[(E)-4-Bromo­benzyl­idene]pyrazine-2-carbohydrazide

Shahid Hameed; Mushtaq Ahmad; M Nawaz Tahir; Muhammad Abdullah Shah; Hazoor Ahmad Shad

doi:10.1107/S1600536813016917

. 2013 Jun 22;69(Pt 7):o1141. doi: 10.1107/S1600536813016917

N′-[(E)-4-Bromobenzylidene]pyrazine-2-carbohydrazide

Shahid Hameed ^a, Mushtaq Ahmad ^a,^b, M Nawaz Tahir ^c,^*, Muhammad Abdullah Shah ^d, Hazoor Ahmad Shad ^e

PMCID: PMC3770406 PMID: 24046691

Abstract

In the title compound, C₁₂H₉BrN₄O, the N′-methylidenepyrazine-2-carbohydrazide and 4-bromobenzene groups are oriented at a dihedral angle of 10.57 (7)°. The hydrazide N—H group is involved in intramolecular N—H⋯N interaction, which generates an S(5) motif. A short C—H⋯O interaction is formed between the methylidene H atom and the carbonyl O atom. It connects molecules into chains extending along [100]. In addition, molecules are arranged into stacks extending along [010] via π–π interactions between pyrazine and benzene rings, with centroid–centroid distances of 3.837 (2) and 3.860 (2) Å.

Related literature

For a related crystal structure and related studies, see: Hearn & Cynamon (2004 ▶); Jin et al. (2006 ▶); Yuan et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶). graphic file with name e-69-o1141-scheme1.jpg

Experimental

Crystal data

C₁₂H₉BrN₄O
M _r = 305.14
Triclinic,
a = 5.8947 (9) Å
b = 7.6941 (12) Å
c = 14.029 (2) Å
α = 83.273 (7)°
β = 80.086 (7)°
γ = 72.440 (6)°
V = 596.11 (16) Å³
Z = 2
Mo Kα radiation
μ = 3.44 mm⁻¹
T = 296 K
0.26 × 0.22 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.425, T _max = 0.503
7382 measured reflections
2529 independent reflections
1403 reflections with I > 2σ(I)
R _int = 0.074

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.084
S = 0.94
2529 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.30 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.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813016917/gk2580sup1.cif

e-69-o1141-sup1.cif^{(20KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813016917/gk2580Isup2.hkl

e-69-o1141-Isup2.hkl^{(139KB, hkl)}

Click here for additional data file.^{(4.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813016917/gk2580Isup3.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
C6—H6⋯O1ⁱ	0.93	2.24	3.132 (4)	161
N3—H3A⋯N1	0.86	2.27	2.671 (3)	108

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Symmetry code: (i) Inline graphic .

Acknowledgments

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

supplementary crystallographic information

Comment

The title compound (Fig. 1) was prepared to study biological activities of hydrazone compounds (Hearn & Cynamon, 2004; Jin et al., 2006).

Crystals of the earlier reported 4-chlorobenzaldehyde(pyrazine-2-carbonyl) hydrazone (Yuan et al., 2006) are practically isostructural with the title compound.

In the title compound the N'-methylidenepyrazine-2-carbohydrazide (A) (C1–C6/N1–N4/O1) and 4-bromophenyl (B) (C7–C12/Br1) moieties are almost planar with r. m. s. deviations of 0.061 Å and 0.009 Å, respectively. The dihedral angle between A/B is 10.57 (7)°. There exists intramolecular N—H···.N hydrogen bond (Table 1, Fig. 2) forming S(5) motif (Bernstein et al., 1995). The intermolecular hydrogen bonds of C—H···.O type (Table 1, Fig. 2) generate C(6) chains (Bernstein et al., 1995) along the crystallographic a-axis. There exist π–π interactions with a distance of 3.838 (2) Å [Cg1—Cg2ⁱ & Cg2— Cg1ⁱ: i = -x, 2 - y, -z] and 3.860 (2) Å [Cg1—Cg2ⁱⁱ & Cg2—Cg1ⁱⁱ: ii = -x, 1 - y, -z], between the centroids of pyrazine (Cg1) and benzene (Cg2) rings.

Experimental

The title compound was prepared by the condensation of equimolar ratio of pyrazine-2-carbohydrazide (0.50 g, 3.6 mmol) and 4-bromobenzaldehyde (0.67 g, 3.6 mmol) in methanol by the reflux of 5 h. The resulting reaction mixture was allowed to cool over night. The precipitated solid was filtered, washed with petroleum ether and recrystalized from chloroform in petroleum ether and dried under reduced pressure over CaCl₂ to give white prisms. Rf: 0.40 (30% acetone in petroleum ether): Yield: 83%, soluble in chloroform; m.p. 546–547 K.