1-Benzoyl-3-(pyridin-2-yl)-1H-pyrazole

Alexander H Shelton; Andrew Stephenson; Michael D Ward; Mohammad B Kassim

doi:10.1107/S1600536811033368

. 2011 Aug 27;67(Pt 9):o2445. doi: 10.1107/S1600536811033368

1-Benzoyl-3-(pyridin-2-yl)-1H-pyrazole

Alexander H Shelton ^a, Andrew Stephenson ^a, Michael D Ward ^a, Mohammad B Kassim ^b,^c,^*

PMCID: PMC3200672 PMID: 22059016

Abstract

In the title compound, C₁₅H₁₁N₃O, the dihedral angle betwen the heterocyclic rings is 9.23 (5)° and the dihedral angle between the benzoyl and pyrazole rings is 58.64 (5)°. In the crystal, inversion dimers linked by pairs of C—H⋯O hydrogen bonds generate R ₂ ²(10) loops. The dimers stack into a column running parallel to the b-axis direction.

Related literature

For related structures and background, see: Jones et al. (1997 ▶); Adams et al. (2006 ▶); Al-abbasi & Kassim (2011 ▶). For reference bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₅H₁₁N₃O
M _r = 249.27
Monoclinic,
a = 10.6325 (11) Å
b = 5.7775 (6) Å
c = 19.572 (2) Å
β = 98.426 (6)°
V = 1189.3 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T _min = 0.982, T _max = 0.991
10450 measured reflections
2735 independent reflections
2532 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.035
wR(F ²) = 0.097
S = 1.00
2735 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811033368/hb6370sup1.cif

e-67-o2445-sup1.cif^{(19.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033368/hb6370Isup2.hkl

e-67-o2445-Isup2.hkl^{(134.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033368/hb6370Isup3.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
C8—H8⋯O1ⁱ	0.93	2.44	3.3720 (13)	175

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors gratefully acknowledge Universiti Kebangsaan Malaysia for the UKM-GUP-BTT-07–30–190 and UKM-OUP-TK-16–73/2010 & 2011 grants and sabbatical leave for MBK at the University of Sheffield. They also thank the RSC, UK, for financial support from the Leverhulme trust.

supplementary crystallographic information

Comment

The starting material, 3-(2-pyridyl)pyrazole, is a bidentate ligand which is commonly used in coordination chemistry (Jones et al. 1997 & Adams et al. 2006). The title compound is made up of a 3-(2-pyridyl)pyrazole and benzoyl fragments. This new compound has a potential to be applied as a tridentate ligand (ONN) involving the O atom on the carbonyl group and the N atom on the pyrazole and pyridine rings.

In the crystal structure, the mean planes of acetamide (O1/N1/C1/C7) and the benzene (C1/C2/C3/C4/C5/C6) fragments make a dihedral angle of 49.54 (5)° with each other. The mean planes of the pyrazole and pyridyl rings are slightly twisted and make a dihedral 9.23 (5)°. The C7—O1 bond length 1.2117 (12) is slightly longer that of the C=O found in another benzoyl derivative, 1-ethyl-1-methyl-3-(2-nitrobenzoyl)thiourea (Al-abbasi & Kassim, 2011). Other bond lengths and angles within the compounds are in the normal ranges (Allen et al. 1987).

A C—H···O intermolecular hydrogen bond links adjacent molecules into centrosymmetric dimers forming a one dimensional column parallel to the b-axis.

Experimental

3-(2-pyridyl)pyrazole (0.728 g, 5.0 mmol) was deprotonated by reacting with NaH (60% in mineral oil) in 30 ml of dry THF under N₂ at room temperature for 2 h. Then, benzoyl chloride (0.702 g, 5.0 mmol) was added slowly to the mixture and the temperature was brought to reflux and left stirring for 4 hrs. The solvent was removed and the residue was re-dissolved in a minimum volume of DCM, washed 3 times with 30 ml of distilled water. The organic fraction was collected and dried with MgSO₄, filtered and the solvent was removed in vacuo. Slow evaporation of acetone/DCM solution of the residue afforded colourless blocks of (I). Yield 78%.