Crystal structure of N′-di­phenyl­methyl­idene-5-methyl-1H-pyrazole-3-carbo­hydrazide

Khalid Karrouchi; M’hammed Ansar; Smaail Radi; Mohamed Saadi; Lahcen El Ammari

doi:10.1107/S2056989015020071

. 2015 Oct 28;71(Pt 11):o890–o891. doi: 10.1107/S2056989015020071

Crystal structure of N′-diphenylmethylidene-5-methyl-1H-pyrazole-3-carbohydrazide

Khalid Karrouchi ^a,^b,^*, M’hammed Ansar ^a, Smaail Radi ^b, Mohamed Saadi ^c, Lahcen El Ammari ^c

PMCID: PMC4645091 PMID: 26594583

Abstract

In the title compound, C₁₈H₁₆N₄O, the planes of the phenyl rings are approximately perpendicular to each other [dihedral angle = 78.07 (8)°] and form dihedral angles of 56.43 (8) and 24.59 (8)° with the pyrazole ring. In the crystal, molecules are linked by N—H⋯O hydrogen bonds to form one-dimensional chains parallel to the [010] direction.

Keywords: crystal structure, pyrazole derivatives, biological activity, agrochemical applications, pharmaceutical applications

Related literature

For the biological activities of pyrazole derivatives, see: Zhang et al. (2015 ▸); Özdemir et al. (2015 ▸); El-Sabbagh et al. (2009 ▸); Farag et al. (2010 ▸); Karrouchi et al. (2014 ▸); Mert et al. (2014 ▸); Alegaon et al. (2014 ▸). For the applications in agrochemical and pharmaceutical industries of pyrazole derivatives, see: Patel et al. (2004 ▸). For the structure of a related compound, see: Karrouchi et al. (2013 ▸).

Experimental

Crystal data

C₁₈H₁₆N₄O
M _r = 304.35
Orthorhombic
a = 11.0299 (2) Å
b = 14.1131 (2) Å
c = 20.2211 (3) Å
V = 3147.74 (9) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.40 × 0.32 × 0.25 mm

Data collection

Bruker X8 APEX diffractometer
31259 measured reflections
3766 independent reflections
3117 reflections with I > 2σ(I)
R _int = 0.029

Refinement

R[F ² > 2σ(F ²)] = 0.047
wR(F ²) = 0.136
S = 1.04
3766 reflections
208 parameters
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▸); cell refinement: SAINT-Plus (Bruker, 2009 ▸); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸) and publCIF (Westrip, 2010 ▸).

Supplementary Material

Crystal structure: contains datablock(s) I. DOI: 10.1107/S2056989015020071/rz5174sup1.cif

e-71-0o890-sup1.cif^{(1.3MB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015020071/rz5174Isup2.hkl

e-71-0o890-Isup2.hkl^{(300.7KB, hkl)}

Click here for additional data file.^{(6.1KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015020071/rz5174Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015020071/rz5174fig1.tif

The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are represented as small circles.

Click here for additional data file.^{(1.2MB, tif)}

b . DOI: 10.1107/S2056989015020071/rz5174fig2.tif

Partial crystal packing of the title compound, showing molecules linked by N–H⋯O hydrogen bonds (dashed lines) into a chain parallel to the b axis.

CCDC reference: 1432912

Additional supporting information: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (, ).

DHA	DH	HA	D A	DHA
N1H1NO1ⁱ	0.86	2.02	2.8740(15)	172

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Mohammed V, Rabat, Morocco, for financial support.

supplementary crystallographic information

S1. Comment

Compounds containing the pyrazole moiety are known to exhibit a wide range of biological properties such as anticancer (Zhang et al., 2015), anticonvulsant (Özdemir et al., 2015), antiviral (El-Sabbagh et al., 2009), anti-tumor (Farag et al., 2010), analgesic, sedative (Karrouchi et al., 2014), antimicrobial (Mert et al., 2014), and anti-inflammatory activities (Alegaon et al., 2014). In addition, pyrazoles have a wide variety of applications in the agrochemical and pharmaceutical industries (Patel et al., 2004). Recently we have reported the synthesis of substituted pyrazoles (Karrouchi et al., 2013). As an extension of our work on the structural characterization of pyrazoles, the title compound was prepared and analysed by single-crystal X-ray diffraction.

The molecule of the title compound is build up from two phenyl rings linked to a pyrazole ring through the carbohydrazide group as shown in Fig. 1. The phenyl rings C7–C12 and C13–C18) are nearly approximately as indicated by the dihedral angle of 78.07 (8)° between them, and form makes dihedral angles of 56.43 (8)° and 24.59 (8)°, respectively, with the pyrazole ring. In the crystal, the molecules held together by N1–H1N···O1 hydrogen bonds and form one-dimensional chains along the [0 1 0] direction.

S2. Experimental

To a solution of 5-methyl-1H-pyrazole-3-carbohydrazide (1 mmol) in 10 ml of ethanol, an equimolar amount of the benzophenon was added in the presence of acetic acid. The mixture was maintained under reflux for 2 h, then the precipitate formed was filtered out washed with ethanol and recrystallized from ethanol. Single crystals of the title compound were obtained on slow evaporation of the solvent (yield 87%; m. p. 595 K).

IR (KBr, ν(cm^-1)): 3241 (NH), 1655 (C=O), 1592 (N=CH). ¹H-NMR (300 MHz, DMSO-d6, δ (p.p.m.)): δ = 2.19 (s, 3H, –CH3), 6.46 (s, 1H, Pz—H), 7.37–7.56 (m, 10H, Ar—H), 9.80 (s, 1H, N=CH), 11.23 (s, 1H, CONH), 12.99 (s, 1H, Pz—NH). MS: m/z = 304.9 (M—H+).