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

Abdel-Wahab, B.F.; Mohamed, H.A.; Farahat, A.A.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536813004893

Volume 69
Part 3
Page o437
March 2013

Received 14 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.054
wR = 0.153
Data-to-parameter ratio = 16.4
Details

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 and Edward R. T. Tiekink ^c ^*

^aApplied Organic Chemistry Department, National Research Centre, Dokki, 12622 Giza, Egypt,^bDepartment of Pharmaceutical Organic Chemistry, Faculty of Pharmacy, Mansoura University, Mansoura 35516, Egypt,^cDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^dChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: edward.tiekink@gmail.com

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-HO and C-H [pi] interactions.

Related literature

For background to the biological activity exhibited by pyrroles and pyranopyrroles, see: Amer et al. (2008, 2009).

Experimental

Crystal data

C₁₄H₁₃N₃O₃
M_r = 271.27
Monoclinic, P 2₁ /c
a = 12.7408 (14) Å
b = 7.8520 (9) Å
c = 14.4194 (18) Å
= 115.163 (14)°
V = 1305.6 (3) Å³
Z = 4
Mo K radiation
= 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 > 2(I)
R_int = 0.040

Refinement

R[F² > 2(F²)] = 0.054
wR(F²) = 0.153
S = 1.04
3020 reflections
184 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.17 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C6-H6AO2ⁱ	0.96	2.54	3.397 (3)	149
C12-H12O1ⁱⁱ	0.93	2.54	3.384 (3)	151
C5-H5BCg1ⁱⁱⁱ	0.96	2.94	3.848 (3)	158
C6-H6BCg1^iv	0.96	3.00	3.781 (3)	140
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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 data and figures for this paper are available from the IUCr electronic archives (Reference: HB7042 ).

Acknowledgements

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

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Amer, F. A.-K., Hammouda, M., El-Ahl, A.-A. S. & Abdel-Wahab, B. F. (2008). J. Heterocycl. Chem. 45, 1549-1569.
Amer, F. A.-K., Hammouda, M., El-Ahl, A. A. S. & Abdel-Wahab, B. F. (2009). Synth. Commun. 39, 416-425.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds