4-[(Anthracen-9-yl­methyl­idene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Abdullah M Asiri; Salman A Khan; M Nawaz Tahir

doi:10.1107/S1600536811029126

. 2011 Jul 30;67(Pt 8):o2163. doi: 10.1107/S1600536811029126

4-[(Anthracen-9-ylmethylidene)amino]-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one

Abdullah M Asiri ^a, Salman A Khan ^a, M Nawaz Tahir ^b,^*

PMCID: PMC3213599 PMID: 22091176

Abstract

In the title compound, C₂₆H₂₁N₃O, the phenyl ring of the 4-aminoantipyrine group and the heterocyclic five-membered ring along with its substituents, except for the N-bound methyl group (r.m.s. deviation = 0.0027 Å), form a dihedral angle of 54.20 (5)°. Two S(6) ring motifs are formed due to intramolecular C—H⋯N and C—H⋯O hydrogen bonds. In the crystal, molecules are linked into supramolecular chains along the a-axis direction via C—H⋯O contacts.

Related literature

For background to pyrazol-3-ones, see: Asiri & Khan (2010 ▶); Crane et al. (1985 ▶); Desai et al. (2010 ▶); Rai et al. (2009 ▶); Takagi et al. (1987 ▶); Yao et al. (2007 ▶); Zhang et al. (2005 ▶); For related crystal structures, see: Li & Zhang (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₆H₂₁N₃O
M _r = 391.46
Monoclinic,
a = 7.6603 (3) Å
b = 16.4549 (6) Å
c = 15.8849 (6) Å
β = 95.243 (1)°
V = 1993.91 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.32 × 0.24 × 0.22 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.975, T _max = 0.980
14673 measured reflections
3593 independent reflections
2791 reflections with I > 2σ(I)
R _int = 0.039

Refinement

R[F ² > 2σ(F ²)] = 0.039
wR(F ²) = 0.109
S = 1.06
3593 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811029126/tk2768sup1.cif

e-67-o2163-sup1.cif^{(29.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811029126/tk2768Isup2.hkl

e-67-o2163-Isup2.hkl^{(172.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811029126/tk2768Isup3.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
C5—H5a⋯O1ⁱ	0.96	2.59	3.530 (2)	167
C5—H5c⋯O1ⁱⁱ	0.96	2.57	3.5305 (19)	177
C12—H12⋯O1	0.93	2.37	3.0375 (19)	128
C15—H15⋯N1	0.93	2.42	3.024 (2)	123

Open in a new tab

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

Acknowledgments

The authors would like to thank the Chemistry Department, King Abdulaziz University, Jeddah, Saudi Arabia, for providing research facilities.

supplementary crystallographic information

Comment

Pyrazol-3-one rings are key substructures in a large variety of compounds of therapeutic importance (Zhang et al., 2005). Compounds containing this ring system are known to display diverse pharmacological activities such as analgesic (Takagi et al., 1987), antidepressant (Yao et al., 2007), antibacterial (Rai et al., 2009), plant growth regulatory (Crane et al., 1985) and anti-inflammatory (Desai et al., 2010). Pyrazol-3-one containing Schiff base derivatives dramatically increase the biological activity of the original pyrazol-3-one (Asiri & Khan, 2010). The title compound (I, Fig. 1) has been prepared as a pharmaceutical intermediate. The crystal structures of 1,5-dimethy-4-((2-nitrobenzylidene)amino)-2-phenyl- 1H-pyrazol-3(4H)-one which is related to (I) has been published (Li & Zhang, 2006).

In (I), the group A (C1/C2/C3/C4/N1/N2/N3/O1) and the benzene ring B (C6—C11) of 4-aminoantipyrine moiety are planar with a r.m.s. deviations of 0.0577 and 0.0027 Å, respectively. The group C (C12—C26) of anthracene-9-carbaldehyde moiety is also planar with an r.m.s. deviation of 0.0665 Å. The dihedral angles between A/B, A/C and B/C are 54.20 (5), 64.07 (2) and 44.43 (5) °, respectively. The methyl group attached at the N atom lies at a distance of 0.5611 (21) Å from the mean plane of A. Intramolecular H-bonding of the type C—H···N and C—H···O complete S(6) ring (Fig. 2 & Table 1) motifs (Bernstein et al., 1995). Intermolecular H-bonding of the type C—H···O sees methyl-H bridging the O atoms to connect molecules into a surpramolecular chain along the a axis (Table 1).

Experimental

A mixture of anthracene-9-carbaldehyde (0.50 g, 2.40 mmol) and 4-aminoantipyrine (0.49 g, 2.40 mmol) in ethanol (15 ml) was heated for 3 h. The progress of the reaction was monitored by TLC. The solid that separated from the cooled mixture was collected and recrystallized from a methanol-chloroform mixture (8:2) to give the yellow prisms of the title compound (I). Yield: 87%; M.pt. 404–405 K. IR (KBr) ν_max cm^-1: 3027 (Ar—H), 2874 (C—H), 1636 (C═O), 1580 (HC═N), 1138 (C—N). ¹H NMR (600 MHz, CDCl₃) (δ p.p.m.): 11.06 (s, CH_olefinic), 8.98–7.36 (m,14H, Ar—H) 3.23 (s, CH₃), 2.19 (s, CH₃).