1-[3-(Anthracen-9-yl)-5-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Shi-Lu Zhang; Kun Huang; Da-Bin Qin

doi:10.1107/S160053681201505X

. 2012 Apr 13;68(Pt 5):o1370. doi: 10.1107/S160053681201505X

1-[3-(Anthracen-9-yl)-5-(pyridin-2-yl)-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Shi-Lu Zhang ^a, Kun Huang ^b, Da-Bin Qin ^a,^*

PMCID: PMC3344501 PMID: 22590263

Abstract

In the title compound, C₂₄H₁₉N₃O, the pyrazoline ring adopts an envelope conformation with the C atom linking to the pyridine ring as the flap. The mean plane of the pyrazoline ring makes dihedral angles of 85.54 (4) and 81.66 (3)° with the pyridine ring and the anthracene ring system, respectively. In the crystal, molecules are linked by C—H⋯O hydrogen bonds. In addition, weak π–π interactions [centroid–centroid distances = 3.695 (3)–3.850 (7) Å] are observed.

Related literature

For applications of pyrazoline derivitives, see: Amir et al. (2008 ▶); Stell (2005 ▶). For the synthesis of the title compound, see: Lévai & Jekó (2006 ▶). For a related structure, see: Liu et al. (2008 ▶).

Experimental

Crystal data

C₂₄H₁₉N₃O
M _r = 365.42
Monoclinic,
a = 10.1768 (8) Å
b = 23.6035 (18) Å
c = 7.9994 (7) Å
β = 109.134 (3)°
V = 1815.4 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.28 × 0.26 × 0.24 mm

Data collection

Rigaku Saturn diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2004 ▶) T _min = 0.977, T _max = 0.980
10313 measured reflections
3544 independent reflections
3081 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.102
S = 1.02
3544 reflections
254 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Data collection: CrystalClear (Rigaku/MSC, 2004 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681201505X/hb6687sup1.cif

e-68-o1370-sup1.cif^{(21.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201505X/hb6687Isup2.hkl

e-68-o1370-Isup2.hkl^{(173.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681201505X/hb6687Isup3.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
C12—H12⋯O1ⁱ	0.93	2.42	3.2745 (16)	153
C24—H24A⋯O1ⁱⁱ	0.96	2.58	3.5265 (16)	167

Open in a new tab

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

Acknowledgments

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003).

supplementary crystallographic information

Comment

Nowdays pyrazoline and its derivatives attract much attention of scientists due to its application in medication and coordination chemistry. (Amir et al., 2008; Stell, 2005). Herein we report on the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The mean plane of the Pyrzoline ring makes dihedral angles with the mean planes of the pyridine and anthracene rings of 85.54 (4)° and 81.66 (3)°, respectively.

In the crystal there are weak π–π interactions involving the pyridine, Pyrazoline and anthracene rings with centroid-centroid distances, Cg1···Cg2ⁱ, Cg2···Cg3ⁱⁱ and Cg2···Cg4ⁱⁱ of 3.695 (3), 3.768 (0) and 3.850 (7) Å, respectively [symmetry codes: (i) x, y, z; (ii) 1-X,-Y,-Z. Cg1 centroid of the Pyrazoline ring (N1, N2, C15—C17); Cg2 centroid of the pyridine ring(N3,C18—C22,); Cg3 centroid of ring (C1—C6); Cg3 centroid of ring (C1/C6/c7/c8/c13/c14)]. In addition, weak C—H···O hydrogen bonds interactions are observed (Table 1 and Fig. 2).

Experimental

The title compound was prepared according to the reported procedures (Lévai et al., 2006). Colourless prisms were obtained by recrystallization from ethyl acetate and petroleum ether (v:v = 1:1) solutoion.