4-{[2-(2,4-Dinitro­phen­yl)hydrazinyl­idene](phen­yl)meth­yl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate

Omoruyi G Idemudia; Alexander P Sadimenko; Eric C Hosten

doi:10.1107/S1600536812044935

. 2012 Nov 17;68(Pt 12):o3380. doi: 10.1107/S1600536812044935

4-{[2-(2,4-Dinitrophenyl)hydrazinylidene](phenyl)methyl}-5-methyl-2-phenyl-1H-pyrazol-3(2H)-one ethanol monosolvate

Omoruyi G Idemudia ^a,^*, Alexander P Sadimenko ^a, Eric C Hosten ^b

PMCID: PMC3588976 PMID: 23476212

Abstract

In the title compound, C₂₃H₁₈N₆O₅·C₂H₆O, all three benzene rings lie in an approximate plane [maximum deviation = 0.2688 (16) Å] that makes an angle of 53.56 (3)° with the plane of the pyrazolone ring. Intramolecular N—H⋯O hydrogen bonds occur. In the crystal, the ethanol solvent molecule links adjacent molecules through N—H⋯O—H⋯O hydrogen bonds, leading to an infinite chain along the c-axis direction. The ethyl group of the ethanol solvent molecule is disordered over two set of sites in a 0.762 (5):0.238 (5) ratio.

Related literature

For a related structure, see: Idemudia et al. (2012 ▶).

Experimental

Crystal data

C₂₃H₁₈N₆O₅·C₂H₆O
M _r = 504.50
Monoclinic,
a = 12.8289 (4) Å
b = 14.3247 (4) Å
c = 14.4213 (4) Å
β = 111.347 (1)°
V = 2468.38 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 200 K
0.61 × 0.43 × 0.39 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: numerical (SADABS; Bruker, 2008 ▶) T _min = 0.89, T _max = 0.96
23873 measured reflections
6124 independent reflections
5136 reflections with I > 2σ(I)
R _int = 0.014

Refinement

R[F ² > 2σ(F ²)] = 0.042
wR(F ²) = 0.116
S = 1.04
6124 reflections
368 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶) and SHELXLE (Hübschle et al., 2011 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(32.9KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812044935/ng5294sup1.cif

e-68-o3380-sup1.cif^{(32.9KB, cif)}

Click here for additional data file.^{(299.8KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812044935/ng5294Isup2.hkl

e-68-o3380-Isup2.hkl^{(299.8KB, hkl)}

Click here for additional data file.^{(4.8KB, cdx)}

Supplementary material file. DOI: 10.1107/S1600536812044935/ng5294Isup3.cdx

Click here for additional data file.^{(9.5KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536812044935/ng5294Isup4.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
N4—H4N⋯O1	0.915 (17)	2.023 (17)	2.8261 (13)	145.6 (14)
N4—H4N⋯O2	0.915 (17)	2.040 (17)	2.6497 (14)	122.8 (13)
N2—H2N⋯O6ⁱ	0.936 (18)	1.711 (18)	2.6464 (14)	177.4 (16)
O6—H6⋯O1	0.89 (2)	1.72 (2)	2.5863 (14)	167 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors would like to thank the Department of Chemistry and Govan Mbeki Research and Development Centre (GMRDC) both of the University of Fort Hare for their support.

supplementary crystallographic information

Comment

Acylpyrazolone derived heterocycles have received considerable research interest due to their versatile reactivity and enormous applications. So have phenylhydrazine Schiff bases and its derivatives. We have reported the crystal structure of a phenyl hydrazone with 4-benzoyl-3-methyl-1-phenyl-2-pyrazolin-5-one (Idemudia et al., 2012). Presented herein is the crystal structure report of an acylpyrazolone based dinitrophenyl hydrazone in continuation of our probe on acylpyrazolone Schiff bases.

In the titled compound the least square plane of the pyrazolone ring makes a dihedral angle of 53.56 (3) ° with the least square plane of all the phenyl rings C11–C16, C21–C26, and C31–C36. The largest deviation distance from the phenyl ring plane is C14 at 0.2688 (16) Å. The dihedral angles with the individual least square planes through the phenyl rings with the pyrazolone plane are 45.87 (7) °, 58.29 (7) ° and 55.84 (7) ° repectively. The ethyl group of the ethanol solvent molecule is disordered over two set of sites [occupancy ratio 0.762 (5):0.238 (5)].

H4N, the hydrogen on N4, has two intra molecular contacts of 2.023 (17) Å and 2.040 (17) Å with O1 and O2 respectievly (Table 1). A C36—H36···N3 intra molecular contact of 2.34 Å also occurs. Molecules of the title compound are stacked in the c axis direction and linked via the ethanol solvent molecule with N2—H2N···O6 and O6—H6···O1 inter molecular contacts of length 1.711 (18) Å and 1.72 (2) Å respectively (Figure 2). Adjacent molecules have a C26—H26···O5 interaction of 2.43 Å (Table 1).

Experimental

An equimolar mixture of 2,4-dinitrophenyl hydrazine and 4-benzoyl-3-methyl-1-phenyl-2-pyrazoline-5-one in ethanol stirred under reflux for 4 h, afforded a precipitate of the titled compound. Slow evaporation at room temperature of an ethanolic solution of it, gave red single crystals suitable for X-ray diffraction with a melting point of 233–236 °C after a few days.