2-[5-(4-Meth­oxy­phen­yl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothia­zole

Hoong-Kun Fun; Suhana Arshad; M Himaja; D Munirajasekhar; B K Sarojini

doi:10.1107/S1600536811033666

. 2011 Aug 27;67(Pt 9):o2412. doi: 10.1107/S1600536811033666

2-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]-6-methyl-1,3-benzothiazole

Hoong-Kun Fun ^a,^*,^‡, Suhana Arshad ^a, M Himaja ^b, D Munirajasekhar ^b, B K Sarojini ^c

PMCID: PMC3200767 PMID: 22065664

Abstract

In the title compound, C₂₄H₂₁N₃OS, the pyrazole ring makes dihedral angles of 5.40 (7) and 6.72 (8)° with the benzo[d]thiazole ring system and the benzene ring, respectively, and a dihedral angle of 85.72 (8)° with the methoxy-substituted benzene ring. In the crystal structure, the molecules are linked by C—H⋯π interactions.

Related literature

For background to the properties and applications of pyrazolines, see: Taylor et al. (1992 ▶); Rajendera Prasad et al. (2005 ▶). For reference bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₂₄H₂₁N₃OS
M _r = 399.50
Orthorhombic,
a = 22.632 (3) Å
b = 11.1961 (12) Å
c = 16.1137 (18) Å
V = 4083.1 (8) Å³
Z = 8
Mo Kα radiation
μ = 0.18 mm⁻¹
T = 296 K
0.37 × 0.24 × 0.19 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.936, T _max = 0.967
25081 measured reflections
5949 independent reflections
3835 reflections with I > 2σ(I)
R _int = 0.041

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.123
S = 1.00
5949 reflections
264 parameters
H-atom parameters constrained
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.29 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/S1600536811033666/hb6368sup1.cif

e-67-o2412-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811033666/hb6368Isup2.hkl

e-67-o2412-Isup2.hkl^{(291.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811033666/hb6368Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1, Cg2 and Cg3 are the centroids of the S1/C17/N1/C18/C23, C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cg1ⁱ	0.93	2.91	3.6318 (17)	138
C22—H22A⋯Cg2ⁱ	0.93	2.89	3.6438 (18)	140
C2—H2A⋯Cg3ⁱⁱ	0.93	2.74	3.4884 (18)	138

Open in a new tab

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

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). SA thanks the Malaysian government and USM for the award of a research scholarship.

supplementary crystallographic information

Comment

Pyrazolines are an important class of heterocyclic compounds, some of which exhibit important pharmacological activities such as antitumor (Taylor et al., 1992) and antidepressant (Rajendera Prasad et al., 2005) agents. The title compound, (I), was synthesized by the condensation of 1-(6-methylbenzo[d]thiazol-2-yl)hydrazine with (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one in presence of ethanol and its crystal structure is now described.

In the molecular structure (Fig 1), the pyrazole ring (N2/N3/C7–C9) is approximately planar with the benzo[d]thiozole ring system (S1/N1/C17–C23) and the benzene ring (C1–C6) with dihedral angles of 5.40 (7)° and 6.72 (8)°, respectively. On the other hand, the pyrazole ring (N2/N3/C7–C9) is approximately perpendicular to the methoxy substituted benzene ring (C10–C15) with dihedral angle of 85.72 (8)°. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

The crystal packing is shown in Fig. 2. The crystal structure is stabilized by the intermolecular C15–H15A···Cg1, C22—H22A···Cg2 and C2—H2A···Cg3 (Table 1) interactions (Cg1, Cg2 and Cg3 are the centroids of S1/C17/N1/C18/C23, C1—C6 and C10—C15 rings, respectively).

Experimental

A mixture of (E)-3-(4-methoxyphenyl)-1-phenylprop-2-en-1-one (5 mmol) and 1-(6-methylbenzo[d]thiazol-2-yl)hydrazine (5 mmol) was refluxed for 16 h in ethanol (20 ml). After completion of the reaction, the reaction mixture was poured into cold water. The precipitate obtained was filtered and washed with cold water. The product was recrystalized from ethanol to yield colourless blocks of (I) and dried. m.p. 131–132 °C, HRMS Calcd for C₂₄H₂₁N₃OS 399.5080 found 399.5079.