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Volume 68 
Part 1 
Pages o180-o181  
January 2012  

Received 23 November 2011
Accepted 12 December 2011
Online 21 December 2011

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.073
wR = 0.232
Data-to-parameter ratio = 12.0
Details
Open access

6-Ethyl-N-methyl-3-nitro-4-nitromethyl-4H-chromen-2-amine

aCentre for Bioinformatics, Pondicherry University, Puducherry 605 014, India, and bDepartment of Chemistry, Pondicherry University, Puducherry 605 014, India
Correspondence e-mail: krishstrucbio@gmail.com

In the title compound, C13H15N3O5, the O and N atoms of the nitromethyl group and the methyl C atom of the ethyl group are disordered over two sets of sites with refined occupancies of 0.629 (7):0.371 (7) and 0.533 (8):0.467 (8), respectively. The dihydropyran ring has an extremely flattened conformation. An intramolecular N-H...O hydrogen bond occurs. In the crystal, pairs of N-H...O hydrogen bonds link molecules, forming inversion dimers. In addition, weak intermolecular C-H...O hydrogen bonds are also present.

Related literature

For the biological and pharmacological importance of 4H-chromene derivatives, see: Cai (2007[Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.], 2008[Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.]); Cai et al. (2006[Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.]); Gabor (1988[Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.]); Brooks (1998[Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.]); Hyana & Saimoto (1987[Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.]); Tang et al. (2007[Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.]). For related structures, see: Muthukumaran et al. (2011a[Muthukumaran, J., Parthiban, A., Rao, H. S. P. & Krishna, R. (2011c). J. Chem. Crystallogr. 41, 1927-1934.],b[Muthukumaran, J., Parthiban, A., Kannan, M., Rao, H. S. P. & Krishna, R. (2011a). Acta Cryst. E67, o898-o899.],c[Muthukumaran, J., Parthiban, A., Manivel, P., Rao, H. S. P. & Krishna, R. (2011b). Acta Cryst. E67, o1276-o1277.]); Gayathri et al. (2006[Gayathri, D., Velmurugan, D., Ravikumar, K., Geetha, K. & Surya Prakash Rao, H. (2006). Acta Cryst. E62, o1961-o1963.]); Bhaskaran et al. (2006[Bhaskaran, S., Velmurugan, D., Ravikumar, K., Geetha, K. & Surya Prakash Rao, H. (2006). Acta Cryst. E62, o188-o190.]).

[Scheme 1]

Experimental

Crystal data
  • C13H15N3O5

  • Mr = 293.28

  • Triclinic, [P \overline 1]

  • a = 8.2538 (10) Å

  • b = 9.0431 (9) Å

  • c = 10.3323 (12) Å

  • [alpha] = 73.484 (9)°

  • [beta] = 71.728 (11)°

  • [gamma] = 83.234 (9)°

  • V = 701.75 (14) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.4 × 0.35 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Eos diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.958, Tmax = 0.979

  • 4281 measured reflections

  • 2463 independent reflections

  • 1520 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.232

  • S = 1.06

  • 2463 reflections

  • 205 parameters

  • 122 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.40 e Å-3

  • [Delta][rho]min = -0.34 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.86 1.97 2.600 (3) 129
N1-H1...O2i 0.86 2.21 2.943 (4) 143
C11-H11A...O3ii 0.97 2.58 3.258 (4) 128
C12-H12A...O2iii 0.97 2.55 3.457 (5) 156
Symmetry codes: (i) -x+1, -y+1, -z+3; (ii) -x+2, -y+1, -z+2; (iii) x, y, z-1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, 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, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5388 ).


Acknowledgements

JM thanks the Council for Scientific and Industrial Research (CSIR) for a Senior Research Fellowship (SRF). RK thanks the Centre for Bioinformatics (funded by the Department of Biotechnology and Department of Information Technology, New Delhi, India), Pondicherry University, for providing the computational facilities to carry out this research work. AP thanks Pondicherry University for a fellowship. HSPR thanks the UGC (University Grant Commission) for the Special Assistance Programme (SAP) and the Department of Science and Technology (DST) for the Fund for Improvement of Science and Technology Infrastructure in Universities and Higher Educational Institutions (FIST).

References

Bhaskaran, S., Velmurugan, D., Ravikumar, K., Geetha, K. & Surya Prakash Rao, H. (2006). Acta Cryst. E62, o188-o190.  [CrossRef] [details]
Brooks, G. T. (1998). Pestic. Sci. 22, 41-50.  [CrossRef]
Cai, S. X. (2007). Recent Patents Anticancer Drug Discov. 2, 79-101.
Cai, S. X. (2008). Bioorg. Med. Chem. Lett. 18, 603-607.  [PubMed]
Cai, S. X., Drewe, J. & Kasibhatla, S. (2006). Curr. Med. Chem. 13, 2627-2644.  [ISI] [PubMed] [ChemPort]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Gabor, M. (1988). The Pharmacology of Benzopyrone Derivatives and Related Compounds, pp. 91-126. Budapest: Akademiai Kiado.
Gayathri, D., Velmurugan, D., Ravikumar, K., Geetha, K. & Surya Prakash Rao, H. (2006). Acta Cryst. E62, o1961-o1963.  [CrossRef] [details]
Hyana, T. & Saimoto, H. (1987). Jpn Patent JP 621 812 768.
Muthukumaran, J., Parthiban, A., Kannan, M., Rao, H. S. P. & Krishna, R. (2011a). Acta Cryst. E67, o898-o899.  [CSD] [CrossRef] [ChemPort] [details]
Muthukumaran, J., Parthiban, A., Manivel, P., Rao, H. S. P. & Krishna, R. (2011b). Acta Cryst. E67, o1276-o1277.  [CSD] [CrossRef] [ChemPort] [details]
Muthukumaran, J., Parthiban, A., Rao, H. S. P. & Krishna, R. (2011c). J. Chem. Crystallogr. 41, 1927-1934.  [CSD] [CrossRef] [ChemPort]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Tang, Q.-G., Wu, W.-Y., He, W., Sun, H.-S. & Guo, C. (2007). Acta Cryst. E63, o1437-o1438.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o180-o181   [ doi:10.1107/S1600536811053554 ]

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