Ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)imino­meth­yl]-3,4-dimethyl-1H-pyrrole-2-carboxyl­ate

Yuan Wang; Wei-Na Wu; Qiu-Fen Wang

doi:10.1107/S1600536809027780

. 2009 Jul 18;65(Pt 8):o1933. doi: 10.1107/S1600536809027780

Ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)iminomethyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate

Yuan Wang ^a, Wei-Na Wu ^a,^*, Qiu-Fen Wang ^a

PMCID: PMC2977180 PMID: 21583616

Abstract

In the title compound, C₂₁H₂₄N₄O₃, the molecule has an E configuration about the imine C=N double bond. Intermolecular N—H⋯O hydrogen bonds assemble molecules into centrosymmetric dimers.

Related literature

For studies on the complexes of bis(pyrrol-2-yl-methyleneamine) ligands, see: Wang et al. (2008 ▶); Yang et al. (2003 ▶). For the structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate, see: Wu et al. (2009 ▶).

Experimental

Crystal data

C₂₁H₂₄N₄O₃
M _r = 380.44
Monoclinic,
a = 13.421 (2) Å
b = 20.141 (3) Å
c = 7.5477 (13) Å
β = 96.147 (2)°
V = 2028.5 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.30 × 0.21 × 0.08 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T _min = 0.979, T _max = 0.993
23826 measured reflections
4717 independent reflections
2622 reflections with I > 2σ(I)
R _int = 0.051

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.149
S = 1.01
4717 reflections
258 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809027780/gk2222sup1.cif

e-65-o1933-sup1.cif^{(21.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809027780/gk2222Isup2.hkl

e-65-o1933-Isup2.hkl^{(231.1KB, hkl)}

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
N1—H1D⋯O2ⁱ	0.86	2.05	2.880 (2)	163

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Symmetry code: (i) Inline graphic .

supplementary crystallographic information

Comment

Due to the excellent fluorescent properties and good solubilities of their complexes, linear spaced bis(pyrrol-2-yl-methyleneamine) ligands have attracted much recent attention (Yang et al., 2003). As part of our ongoing studies of pyrrol-2-yl-methyleneamine ligand (Wu et al., 2008), the title compound was synthesized and characterized by X-ray diffraction.

In the title compound (Fig. 1), the molecule adopts an E configuration at the C=N double bond. The dihedral angle between dihydropyrazole ring (N3,4/C11–C13, r.m.s. deviation 0.026 Å) and pyrrole ring (N1/C4–C7, r.m.s. deviation 0.002 Å) is 9.6 (2)°. The phenyl ring (C16–C20) makes the dihedral angle of 42.4 (1)° with dihydropyrazole ring. In the crystal, th molecules are linked into a centrosymmetric dimer by two intermolecular N—H···O hydrogen bonds, forming a R₂²(10) ring motif (Table1, Fig. 2). The dimers stack alternately like letter "V" (Fig. 3) and the dihedral angle of the adjacent phenyl rings is 37.1 (3)°. Intermolecular C14—H14A···π (N1/C4–C7) interaction (C14-centroid distance 3.4992 Å). is also present.

Experimental

4-Amino-1,2-dihydro-2,3-dimethyl-1-phenylpyrazol-5-one (0.203 g, 1 mmol) was dissolved in ethanol (10 ml), then an ethanol solution (10 ml) containing ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate (0.195 g, 1 mmol) was added dropwise at room temperature. After stirring for 24 h, the precipitate was separated from the solution by suction filtration, washed with ethanol, and dried in a vacuum to yield the title compound 0.198 g (52%).Yellow blocks of the title compound were obtained by slow evaporation of an ethanol/THF (1:1) solution.