Diethyl [benzyl­amino­(1,3-diphenyl-1H-pyrazol-4-­yl)meth­yl]phospho­nate

G Jagadeesan; G Suresh; B Nandakumar; P T Perumal; S Aravindhan

doi:10.1107/S1600536811032776

. 2011 Aug 27;67(Pt 9):o2376. doi: 10.1107/S1600536811032776

Diethyl [benzylamino(1,3-diphenyl-1H-pyrazol-4-yl)methyl]phosphonate

G Jagadeesan ^a, G Suresh ^a, B Nandakumar ^b, P T Perumal ^b, S Aravindhan ^a,^*

PMCID: PMC3200952 PMID: 22065814

Abstract

In the title compound, C₂₇H₃₀N₃O₃P, the pyrazole ring is essentially planar [maximum deviation = 0.002 (2) Å] and it forms dihedral angles of 9.3 (1) and 40.2 (1)°, respectively, with the phenyl rings attached to the N and C atoms. In the crystal, pairs of centrosymmetrically related molecules are linked into dimers by N—H⋯O hydrogen bonds.

Related literature

For the bioactivities of pyrazole derivatives, see: Sullivan et al. (2006 ▶); Patel et al. (2010 ▶); Siu et al. (2008 ▶).

Experimental

Crystal data

C₂₇H₃₀N₃O₃P
M _r = 475.51
Monoclinic,
a = 10.9534 (4) Å
b = 9.3777 (3) Å
c = 25.0690 (8) Å
β = 101.233 (2)°
V = 2525.70 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.14 mm⁻¹
T = 293 K
0.2 × 0.2 × 0.2 mm

Data collection

Oxford Diffraction Xcalibur-S diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.980, T _max = 0.990
28506 measured reflections
6292 independent reflections
4220 reflections with I > 2σ(I)
R _int = 0.031

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.124
S = 1.03
6292 reflections
403 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811032776/ci5195sup1.cif

e-67-o2376-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811032776/ci5195Isup2.hkl

e-67-o2376-Isup2.hkl^{(301.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811032776/ci5195Isup3.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
N7—H7⋯O2ⁱ	0.89 (2)	2.16 (2)	2.9891 (19)	155 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

SA thanks the UGC, India, for financial support.

supplementary crystallographic information

Comment

Pyrazoles exhibit a variety of pharmacological properties for e.g antibacterial and anti-inflammatory activities (Sullivan et al., 2006; Patel et al., 2010). One of the pyrazole derivatives shows nucleosidase inhibitory activity against Staphylococcus aureus (Siu et al., 2008). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented here.

The molecular structure of the title compound is shown in Fig. 1. The pyrazole ring is planar; the phenyl ring attached to N3 is almost coplanar [dihedral angle 9.3 (1)°] with it whereas the phenyl attached to C21 is tilted by 40.2 (1)°. Ester substitutions at the P atom lie anti to bulky substitutions at atom C6 [O1—P—C6—N7 = 169.2 (1)° and O3—P—C6—C5 = 175.2 (1)°].

In the crystal, pairs of centrosymmetrically related molecules are linked into dimers by N—H···O hydrogen bonds (Fig. 2).

Experimental

A mixture of 3-diphenyl-1H-pyrazole-4-carbaldehyde (1 mmol), benzyl amine (1 mmol), diethyl phosphate (1.5 mmol) and pottasium hydrogen sulfate (20 mol%) under neat condition was stirred at room temperature. After completion of the reaction as indicated by TLC, it was poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated under vacuum. The crude product was chromatographed. Single crystals were grown by slow evaporation an ethyl acetate-petroleum ether solution.