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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 [sigma](C-C) = 0.003 Å
R = 0.054
wR = 0.153
Data-to-parameter ratio = 16.4
Details
Open access

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

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-H...O and C-H...[pi] interactions.

Related literature

For background to the biological activity exhibited by pyrroles and pyranopyrroles, see: Amer et al. (2008[Amer, F. A.-K., Hammouda, M., El-Ahl, A.-A. S. & Abdel-Wahab, B. F. (2008). J. Heterocycl. Chem. 45, 1549-1569.], 2009[Amer, F. A.-K., Hammouda, M., El-Ahl, A. A. S. & Abdel-Wahab, B. F. (2009). Synth. Commun. 39, 416-425.]).

[Scheme 1]

Experimental

Crystal data
  • C14H13N3O3

  • Mr = 271.27

  • Monoclinic, P 21 /c

  • a = 12.7408 (14) Å

  • b = 7.8520 (9) Å

  • c = 14.4194 (18) Å

  • [beta] = 115.163 (14)°

  • V = 1305.6 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]) Tmin = 0.869, Tmax = 1.000

  • 8113 measured reflections

  • 3020 independent reflections

  • 1772 reflections with I > 2[sigma](I)

  • Rint = 0.040

Refinement
  • R[F2 > 2[sigma](F2)] = 0.054

  • wR(F2) = 0.153

  • S = 1.04

  • 3020 reflections

  • 184 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.20 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

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...Cg1iv 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[Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort]
Amer, F. A.-K., Hammouda, M., El-Ahl, A. A. S. & Abdel-Wahab, B. F. (2009). Synth. Commun. 39, 416-425.  [ISI] [CrossRef] [ChemPort]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o437  [ doi:10.1107/S1600536813004893 ]

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