2-Phenyl-N′-(2-phenyl­acet­yl)acetohydrazide

Hatem A Abdel-Aziz; Ching Kheng Quah; Hoong-Kun Fun

doi:10.1107/S1600536812019861

. 2012 May 12;68(Pt 6):o1680. doi: 10.1107/S1600536812019861

2-Phenyl-N′-(2-phenylacetyl)acetohydrazide

Hatem A Abdel-Aziz ^a, Ching Kheng Quah ^b,^‡, Hoong-Kun Fun ^b,^*,^§

PMCID: PMC3379276 PMID: 22719474

Abstract

In the title compound, C₁₆H₁₆N₂O₂, the N′-acetylacetohydrazide group is approximately planar (r.m.s. deviation = 0.018 Å for the eight non-H atoms) and makes dihedral angles of 81.92 (6) and 65.19 (6)° with the terminal phenyl rings. The phenyl rings form a dihedral angle of 62.60 (7)°. In the crystal, molecules are linked into sheets lying parallel to (001) by N—H⋯O and C—H⋯O hydrogen bonds. One O atom accepts one N—H⋯O and one C—H⋯O hydrogen bond and the other O atom accepts one N—H⋯O and two C—H⋯O hydrogen bonds. The N—H⋯O hydrogen bonds lead to R ₂ ²(8) loops and the C—H⋯O hydrogen bonds generate R ₂ ¹(6) loops.

Related literature

For general background to and the pharmaceutical applications of hydrazine derivatives, see: Bredihhin & Mäeorg (2008 ▶); Ragnarsson (2001 ▶); Ling et al. (2001 ▶). For further synthesis details, see: Magedov & Smushkevich (1991 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used in the data collection, see Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). graphic file with name e-68-o1680-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₆N₂O₂
M _r = 268.31
Triclinic,
a = 5.4531 (6) Å
b = 7.9283 (9) Å
c = 15.1758 (17) Å
α = 94.271 (2)°
β = 92.613 (2)°
γ = 90.830 (2)°
V = 653.50 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 100 K
0.35 × 0.14 × 0.05 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.968, T _max = 0.996
12991 measured reflections
3458 independent reflections
2428 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.134
S = 1.04
3458 reflections
245 parameters
All H-atom parameters refined
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812019861/hb6773sup1.cif

e-68-o1680-sup1.cif^{(23.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812019861/hb6773Isup2.hkl

e-68-o1680-Isup2.hkl^{(169.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812019861/hb6773Isup3.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
N2—H1N2⋯O1ⁱ	0.867 (16)	1.970 (16)	2.8076 (15)	162.4 (16)
C10—H10A⋯O1ⁱ	0.971 (16)	2.465 (16)	3.3103 (18)	145.3 (13)
N1—H1N1⋯O2ⁱⁱ	0.907 (16)	1.948 (16)	2.8283 (15)	163.2 (15)
C7—H7A⋯O2ⁱⁱ	0.973 (16)	2.479 (16)	3.3209 (18)	144.8 (13)
C7—H7B⋯O2ⁱⁱⁱ	1.00 (2)	2.56 (2)	3.4929 (19)	155.2 (13)

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

Acknowledgments

The authors thank Universiti Sains Malaysia for the Research University Grant (No. 1001/PFIZIK/811160) and the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University.

supplementary crystallographic information

Comment

Hydrazine derivatives are widely used in the pharmaceutical applications and also as precursors in organic synthesis (Bredihhin & Mäeorg, 2008). Several hydrazine derivatives were shown to be effective for treatment of tuberculosis, Parkinson's disease and hypertension (Ragnarsson, 2001). Moreover, some hydrazines possess neuroprotective activity and are used as antidepressant drugs (Ling et al., 2001).

In the title compound, Fig. 1, the N'-acetylacetohydrazide moiety (O1/O2/N1/N2/C7-C10) is approximately planar (r.m.s. deviation = 0.018 Å for the 8 non-H atoms) and makes dihedral angles of 81.92 (6) and 65.19 (6)° with the two terminal benzene rings (C1-C6 and C11-C16), respectively. The two benzene rings form a dihedral angle of 62.60 (7)°. Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal (Fig.2), molecules are linked into planes parallel to the (001) via intermolecular N1–H1N1···O2, C7–H7A···O2 and C7–H7B···O2 trifurcated acceptor bonds (Table 1) and N2–H1N2···O1 and C10–H10A···O1 bifurcated acceptor bonds (Table 1), generating R₂¹(6) ring motifs (Bernstein et al., 1995).

Experimental

The title compound was prepared by the reaction of 2-phenylacetyl chloride with 2-phenylacetohydrazide in the presence of sodium carbonate in water at 5-10 °C (Magedov & Smushkevich, 1991).