N′-(Di-2-pyridylmethyl­ene)benzo­hydrazide

Ismail Warad; Mohammed Al-Nuri; Saud Al-Resayes; Khalid Al-Farhan; Mohamed Ghazzali

doi:10.1107/S1600536809022090

. 2009 Jun 17;65(Pt 7):o1597. doi: 10.1107/S1600536809022090

N′-(Di-2-pyridylmethylene)benzohydrazide

Ismail Warad ^a,^*, Mohammed Al-Nuri ^b, Saud Al-Resayes ^a, Khalid Al-Farhan ^a, Mohamed Ghazzali ^a

PMCID: PMC2969230 PMID: 21582871

Abstract

In the title Schiff base, C₁₈H₁₄N₄O, the amido –NH– unit is connected to one of the two pyridyl N atoms at an N(—H)⋯N distance of 2.624 (2) Å. The molecular packing features an intermolecular C—H⋯N R ₂ ²(6) hydrogen-bonding ring motif.

Related literature

For medicinal applications of benzohydrazides, see: Raparti et al. (2009 ▶); Zhong et al. (2007 ▶). For a previous study on the synthesis of benzohyrazide derivatives, see: Abu-El-Halawa et al. (2007 ▶). For ring-motif analysis; see: Bernstein et al. (1995 ▶); Grell et al. (1999 ▶).

Experimental

Crystal data

C₁₈H₁₄N₄O
M _r = 302.33
Monoclinic,
a = 8.2741 (5) Å
b = 22.1436 (14) Å
c = 8.8006 (5) Å
β = 108.974 (2)°
V = 1524.82 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.50 × 0.30 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2007 ▶) T _min = 0.968, T _max = 0.989
33115 measured reflections
3491 independent reflections
2329 reflections with I > 2δ(I)
R _int = 0.050

Refinement

R[F ² > 2σ(F ²)] = 0.053
wR(F ²) = 0.169
S = 0.99
3491 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2007 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2006 ▶) and PLUTO (Motherwell et al., 1999 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022090/ng2595sup1.cif

e-65-o1597-sup1.cif^{(16.8KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809022090/ng2595Isup2.hkl

e-65-o1597-Isup2.hkl^{(171.2KB, hkl)}

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
N1—H7⋯N3	0.86	1.94	2.624 (2)	136
C9—H9⋯N4	0.93	2.45	2.973 (2)	115

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Acknowledgments

IW and SAR thank SABIC for financial support.

supplementary crystallographic information

Comment

Benzohydrazide derivatives were known as good antitumor and antimycobacterial agent (Raparti et al. 2009; Zhong et al. 2007). The molecular packing of the title compound is supported by C— H···N intermolecular hydrogen bondings at D···A distance of 2.956 (1) and D— H···A angle of 128.92 (1)° that is recognized by R₂²(6) second order ring motif, as earlier defined (Bernstein et al. 1995; Grell et al. 1999) and calculated with Pluto (Motherwell et al., 1999), see Figure 2.

Experimental

Equimolar amounts of di-2-pyridyl ketone and benzohydrazide were mixed in ethanol.(Abu-El-Halawa et al. 2007) Five drops of conc. HCl were added and the mixture was refluxed for 8–10 h. After cooling, distilled water was added up to 1:3 volume ratio followed by addition of several drops of sodium hydroxide solution. The product was re-crystallized twice by water. IR, cm^-1 (CHCl₃): 3280, 3210, 3100, 3020, 1660, 1620, 1600, 1580, 1480, 1450, 1350, 1160, 1040, 770, 660. ¹H NMR (p.p.m.): 10.70 (bs, 1H exchangeable with D₂O), 8.83 (cp, 2H of two pyridine rings), 8.02 (cp, 2H of two pyridine rings), 7.99 (cp, 2H of two pyridine rings), 7.95 (cp, 2H of benzene ring), 7.62 (cp, 2H of two pyridine rings), 7.44 (cp, 2H of benzene ring) p.p.m.; ¹³C NMR (p.p.m.): 163.0, 155.6, 152.6, 149.2, 136.1, 134.2, 132.2, 128.9, 127.5, 126.2, 123.9.