4-Dimethyl­amino-1-(4-meth­oxy­phen­yl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

Bakr F Abdel-Wahab; Hanan A Mohamed; Abdelbasset A Farahat; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536813004893

. 2013 Feb 23;69(Pt 3):o437. doi: 10.1107/S1600536813004893

4-Dimethylamino-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile

Bakr F Abdel-Wahab ^a,^‡, Hanan A Mohamed ^a, Abdelbasset A Farahat ^b, Seik Weng Ng ^c,^d, Edward R T Tiekink ^c,^*

PMCID: PMC3588536 PMID: 23476607

Abstract

In the title compound, C₁₄H₁₃N₃O₃, a twist occurs, as seen in the dihedral angle of 53.60 (12)° between the pyrrole and benzene rings. A three-dimensional architecture is formed in the crystal whereby layers of molecules in the ac plane are connected by C—H⋯O and C—H⋯π interactions.

Related literature

For background to the biological activity exhibited by pyrroles and pyranopyrroles, see: Amer et al. (2008 ▶, 2009 ▶). graphic file with name e-69-0o437-scheme1.jpg

Experimental

Crystal data

C₁₄H₁₃N₃O₃
M _r = 271.27
Monoclinic,
a = 12.7408 (14) Å
b = 7.8520 (9) Å
c = 14.4194 (18) Å
β = 115.163 (14)°
V = 1305.6 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 295 K
0.40 × 0.20 × 0.10 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.869, T _max = 1.000
8113 measured reflections
3020 independent reflections
1772 reflections with I > 2σ(I)
R _int = 0.040

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.153
S = 1.04
3020 reflections
184 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2011 ▶); 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 for Windows (Farrugia, 2012 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Click here for additional data file.^{(18.3KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813004893/hb7042sup1.cif

e-69-0o437-sup1.cif^{(18.3KB, cif)}

Click here for additional data file.^{(148.2KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813004893/hb7042Isup2.hkl

e-69-0o437-Isup2.hkl^{(148.2KB, hkl)}

Click here for additional data file.^{(5.3KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813004893/hb7042Isup3.cml

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

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

Cg1 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6A⋯O2ⁱ	0.96	2.54	3.397 (3)	149
C12—H12⋯O1ⁱⁱ	0.93	2.54	3.384 (3)	151
C5—H5B⋯Cg1ⁱⁱⁱ	0.96	2.94	3.848 (3)	158
C6—H6B⋯Cg1^iv	0.96	3.00	3.781 (3)	140

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

Acknowledgments

We thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR-MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound (I) was investigated owing to the biological activities exhibited pyrroles and pyranopyrrole analogues (Amer et al. 2009; Amer et al. 2008). Herein, its crystal structure determination is described.

Crystallography shows that fusion of 1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile with excess 1,1-dimethoxy-N,N-dimethylmethanamine afforded 4-(dimethylamino)-1-(4-methoxyphenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrole-3-carbonitrile (I) not the expected 2-((dimethylamino)methylene)-1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile (II).

In (I), Fig. 1, the dihedral angle of 53.60 (12)° between the pyrrole (r.m.s. deviation = 0.005 Å) and benzene rings indicates a significant twist in the molecule. The methoxy substituent is twisted out of the plane of the ring to which it is attached as seen in the value of the C14—O3—C11—C10 torsion angle of -13.9 (4)°. The dimethylamino group is also slightly twisted out of the plane through the pyrrole ring to which it is attached; the C5—N2—C2—C1 torsion angle is 8.7 (3)°.

The three-dimensional architecture of (I) is consolidated by C—H···O interactions, involving both carbonyl-O atoms, as well as C—H···π interactions whereby the benzene ring serves as a bridge between molecules, Fig. 2 and Table 1.

Experimental

A mixture of 1-(4-methoxyphenyl)-4-oxopyrrolidine-3-carbonitrile (0.22 g, 0.001 M) and excess 1,1-dimethoxy-N,N-dimethylmethanamine (0.2 ml) was heated under reflux for about 1.5 h on water bath. The resultant solid was filtered and dried. Re-crystallization was by slow evaporation of its DMF solution which yielded yellow prisms in 28% yield. M.pt. 482–483 K.