3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile

Hatem A Abdel-Aziz; Hazem A Ghabbour; Suchada Chantrapromma; Hoong-Kun Fun

doi:10.1107/S1600536812010938

. 2012 Mar 17;68(Pt 4):o1095–o1096. doi: 10.1107/S1600536812010938

3-Acetyl-1,5-diphenyl-1H-pyrazole-4-carbonitrile

Hatem A Abdel-Aziz ^a, Hazem A Ghabbour ^a, Suchada Chantrapromma ^b,^‡, Hoong-Kun Fun ^c,^*,^§

PMCID: PMC3344048 PMID: 22589957

Abstract

The title compound, C₁₈H₁₃N₃O, has a butterfly-like structure, in which the pyrazole ring forms dihedral angles of 59.31 (8) and 57.24 (8)° with the two phenyl rings. The dihedral angle between the two phenyl rings is 64.03 (8)°. The pyrazole ring and the C—C=O plane of the acetyl group are twisted slightly, making a dihedral angle of 7.95 (18)°. In the crystal, molecules are linked through weak C—H⋯N and C—H⋯O interactions into a helical chain along the a-axis direction.

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For background to and the bioactivity of pyrazole derivatives, see: Abdel-Aziz et al. (2009 ▶, 2010 ▶); Abdel-Wahab et al. (2009 ▶); Bharate et al. (2008 ▶); Dawood et al. (2003 ▶); Fu et al. (2010 ▶); Thumar & Patel (2011 ▶). For a related structure, see: Abdel-Aziz et al. (2011 ▶).

Experimental

Crystal data

C₁₈H₁₃N₃O
M _r = 287.31
Orthorhombic,
a = 6.8322 (2) Å
b = 16.8974 (5) Å
c = 25.7968 (6) Å
V = 2978.15 (14) Å³
Z = 8
Cu Kα radiation
μ = 0.66 mm⁻¹
T = 296 K
0.56 × 0.35 × 0.23 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.708, T _max = 0.863
10678 measured reflections
2782 independent reflections
2338 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.116
S = 1.08
2782 reflections
201 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 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/S1600536812010938/is5091sup1.cif

e-68-o1095-sup1.cif^{(24.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010938/is5091Isup2.hkl

e-68-o1095-Isup2.hkl^{(136.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812010938/is5091Isup3.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
C6—H6A⋯N3ⁱ	0.93	2.53	3.432 (2)	165
C16—H16A⋯O1ⁱⁱ	0.93	2.59	3.3758 (19)	142

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

Acknowledgments

The authors thank the Deanship of Scientific Research and the Research Center, College of Pharmacy, King Saud University, and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160. HKF also thanks King Saud University, Riyadh, Saudi Arabia, for the award of a visiting Professorship (December 23rd 2011 to January 14th 2012).

supplementary crystallographic information

Comment

Owing to the various biological properties of pyrazole derivatives such as anti-cancer (Fu et al., 2010), anti-inflammatory (Bharate et al., 2008) and antimicrobial activities (Thumar & Patel, 2011), we have during the course of our medicinal chemistry research reported the synthesis and bioactivity of pyrazole derivatives (Abdel-Aziz et al., 2009, 2010; Abdel-Wahab et al., 2009). The title compound (I) was synthesized and characterized in order to study the structure activity relationship of this class of compounds.

The molecule of (I), C₁₈H₁₃N₃O, has a butterfly-like structure. The pyrazole ring forms the dihedral angles of 59.31 (8) and 57.24 (8)°, respectively, with the C5–C10 and C11–C16 phenyl rings, whereas the dihedral angle between these two rings is 64.03 (8)°. The cabonitrile substituent lies on the same plane with the pyrazole ring with an r.m.s. 0.0027 (1) Å for the seven non-H atoms (C1–C4/N1–N3), whereas the acetyl group is slightly deviated with the torsion angles N2–C1–C17–C18 = 8.3 (2)° and N2–C1–C17–O1 = -171.47 (13)°. The bond distances in (I) are within normal ranges (Allen et al., 1987) and comparable to the related structure (Abdel-Aziz et al., 2011). The crystal packing of (I) is stabilized by weak C—H···N and C—H···O interactions (Table 1). Figure 2 shows the molecular a helical chain along the [1 0 0] linked by these interactions.

Experimental

The title compound was prepared according to the reported method (Dawood et al., 2003). Single crystals of the title compound suitable for X-ray structure determination were recrystallized from ethanol by the slow evaporation of the solvent at room temperature after several days.