Ethyl 3,4-dimethyl-5-[(E)-(phenyl­imino)­meth­yl]-1H-pyrrole-2-carboxyl­ate

Wei-Na Wu; Lei Yang; Xiao-Xia Li; Bao-Feng Qin; Qiu-Fen Wang

doi:10.1107/S1600536810022051

. 2010 Jun 16;66(Pt 7):o1655. doi: 10.1107/S1600536810022051

Ethyl 3,4-dimethyl-5-[(E)-(phenylimino)methyl]-1H-pyrrole-2-carboxylate

Wei-Na Wu ^a,^*, Lei Yang ^a, Xiao-Xia Li ^b, Bao-Feng Qin ^c, Qiu-Fen Wang ^a

PMCID: PMC3006869 PMID: 21587883

Abstract

In the title compound, C₁₆H₁₈N₂O₂, the molecule adopts an E conformation about the C=N double bond. The dihedral angle between the pyrrole and phenyl rings is 41.55 (8)°. In the crystal structure, pairs of intermolecular N—H⋯O hydrogen bonds link the molecules into centrosymmetric dimers. In the dimer, the two pyrrole rings are almost coplanar and the two phenyl rings are parallel to each other.

Related literature

For the structure of 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate, see Wu et al. (2009 ▶). For the similar structure of ethyl 5-[(2,3-dimethyl-5-oxo-1-phenyl-2,5-dihydro-1H-pyrazol-4-yl)iminomethyl]-3,4-dimethyl-1H-pyrrole-2-carboxylate, see Wang et al. (2009 ▶). For the coordination abilities for metal ions of pyrrol-2-ylmethyleneamine ligands, see: Wang et al. (2010 ▶); Yang et al. (2003 ▶).

Experimental

Crystal data

C₁₆H₁₈N₂O₂
M _r = 270.32
Monoclinic,
a = 12.5463 (7) Å
b = 14.6525 (9) Å
c = 8.4490 (5) Å
β = 105.042 (3)°
V = 1500.00 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.35 × 0.26 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.975, T _max = 0.986
12405 measured reflections
3413 independent reflections
2078 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.044
wR(F ²) = 0.144
S = 1.01
3413 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.16 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/S1600536810022051/gw2080sup1.cif

e-66-o1655-sup1.cif^{(18.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810022051/gw2080Isup2.hkl

e-66-o1655-Isup2.hkl^{(167.4KB, 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
N2—H2A⋯O3ⁱ	0.86	2.06	2.8883 (18)	162

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors are grateful for financial support from the Doctoral Foundation of Henan Polytechnic University (B2009–65 648359 and B2009–70 648364).

supplementary crystallographic information

Comment

Pyrrol-2-ylmethyleneamine ligands have attracted much recent attention due to their excellent coordination abilities for metal ions (Yang et al., 2006 & Wang et al., 2010). As part of our ongoing search for a biologically active material, the title compound was synthesized and characterized by X-ray diffraction.

In the title compound, all the bond lengths are comparable with those observed in the other similar compound (Wang et al., 2009). The molecule adopts an E configuration at the C=N double bond. The dihedral angle between pyrrole ring (N2/C8–C11, r.m.s. deviation 0.0035 Å) and phenyl ring (C1–C6, r.m.s. deviation 0.0036 Å) is 41.55 (8)°. In the crystal, the molecules are linked into a centrosymmetric dimer by two intermolecular N—H···O hydrogen bonds, forming a R₂²(10) ring motif (Table1, Fig. 2). In the dimer, the two pyrrole rings are almost coplanar (r.m.s. deviation 0.028 Å) and the two phenyl rings are parallel with each other. The crystal packing is further stabilized by the stacking between the C=N with the adjacent pyrrole ring, with centroid–centroid distances of 3.642 Å.

Experimental

A quantity of aniline (0.186 g, 2 mmol) was dissolved in ethanol (10 ml), then an ethanol solution (10 ml) containing ethyl 5-formyl-3,4-dimethyl-1H-pyrrole-2-carboxylate (0.39 g, 2 mmol) was added dropwise at room temperature. After stirring for 4 h, the mixture was filtered and set aside to crystallize at room temperature for several days, giving yellow block crystals.