2-Amino-N′-phenyl­benzohydrazide

Víctor Kesternich; Paulo Gahona; Marcia Pérez-Fehrmann; Iván Brito; Matías López-Rodríguez

doi:10.1107/S1600536812022362

. 2012 May 23;68(Pt 6):o1847. doi: 10.1107/S1600536812022362

2-Amino-N′-phenylbenzohydrazide

Víctor Kesternich ^a, Paulo Gahona ^a, Marcia Pérez-Fehrmann ^a, Iván Brito ^b,^*, Matías López-Rodríguez ^c

PMCID: PMC3379416 PMID: 22719614

Abstract

In the title compound, C₁₃H₁₃N₃O, the NNCO unit forms dihedral angles of 35.8 (1) and 84.0 (1)° with the benzene and phenyl rings, respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains parallel to the c axis. Neighbouring chains are linked by weak N—H⋯N hydrogen bonds, forming R ⁴ ₄(20) rings, and resulting in the formation of a two-dimensional network lying parallel to (010). The packing also features π–π stacking interactions between phenyl rings [centroid–centroid distance = 3.803 (2) Å].

Related literature

For the pharmacological activity of quinazolinones, see: Kamal et al. (2010 ▶) and of benzotriazepinones, see: Filippakopoulos et al. (2012 ▶); Spencer et al. (2008 ▶). For the synthesis of the starting material 1H-benzo[d][1,3]oxazine-2,4-dione, see: Iwakura et al. (1976 ▶); Leiby & Heindel (1976 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). graphic file with name e-68-o1847-scheme1.jpg

Experimental

Crystal data

C₁₃H₁₃N₃O
M _r = 227.26
Monoclinic,
a = 6.1190 (12) Å
b = 19.921 (4) Å
c = 9.6490 (19) Å
β = 94.08 (3)°
V = 1173.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.40 × 0.21 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
17096 measured reflections
2923 independent reflections
2330 reflections with I > 2σ(I)
R _int = 0.092

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.163
S = 1.09
2923 reflections
162 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.49 e Å⁻³

Data collection: COLLECT (Nonius, 2000 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: OLEX2 (Dolomanov et al., 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022362/ds2196sup1.cif

e-68-o1847-sup1.cif^{(16.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022362/ds2196Isup2.hkl

e-68-o1847-Isup2.hkl^{(140.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812022362/ds2196Isup3.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
N1—H1⋯O1ⁱ	0.86	2.07	2.903 (2)	162
N3—H3A⋯O1	0.86 (3)	2.21 (3)	2.845 (2)	131 (2)
N2—H2⋯N3ⁱⁱ	0.86	2.54	3.126 (3)	126

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

We are grateful to the Consejo Superior de Investigaciones Científicas (CSIC) of Spain for the award of a licence for the use of the Cambridge Structural Database (CSD).

supplementary crystallographic information

Comment

The 2-amino-N'-phenylbenzohydrazide 2 is a key intermediate to obtain quinazolinones and benzotriazepines derivatives. The quinazolinone nucleous and its derivatives have been extensively studied because of their wide range of pharmacological activities, including antiviral, antibacterial, antifungal, antimalarial, anticancer, antihypertensive, diuretic, anticonvulsant and anti-inflammatory (Kamal et al., 2010). On the other hand, the benzotriazepinones have been described as efficient enzymatic inhibitors (Filippakopoulos et al., 2012; Spencer et al., 2008). We report herein on the synthesis and crystal structure of the title compound, a member of this important family of compounds. In the title molecule, Fig. 1, the NNCO moiety form a dihedral angle of 35.8 (1)° and 84.0 (1)° with benzene and phenyl rings respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. In the crystal the molecules are packed viaπ–π stacking interaction [centroid–centroid distance 3.803 (2) Å] and linked by N1—H1···O1(x, -y + 3/2, z + 1/2) weak hydrogen bond to form a C(4) chain running parallel to the c axis, which are linked to neighboring chains by N2—H3···N3(x - 1, y, z) weak hydrogen bond to form R⁴₄(20) centrosymmetric rings (Bernstein et al., 1995). One intramolecular N—H···O hydrogen bond is observed too, Fig.2, Table1.

Experimental

The synthesis of the 2-amino-N'-phenylbenzohydrazide 2 was done starting of isatoic anhydride (1H-benzo[d][1,3]oxazine-2,4-dione) (Leiby & Heindel 1976; Iwakura et al., 1976), which was treated with phenyl hydrazine in DMF at reflux by 2 h to give an 82% yield. The product was crystallized in ethyl acetate with melting point 227–228 °C. UV λ(MeOH) 310, 280 and 225 nm, λ(MeONa) 340, 265 and 225 nm. IR cm^-1, (Nujol), 3300 (NH), 1670 (carbonyl).