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Volume 69 
Part 9 
Pages o1380-o1381  
September 2013  

Received 23 July 2013
Accepted 30 July 2013
Online 3 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.126
Data-to-parameter ratio = 13.7
Details
Open access

(4S*)-2-Methylamino-3-nitro-4-(4-nitrophenyl)-5,6,7,8-tetrahydro-4H-chromen-5-one

aDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India, and bOrganic Chemistry Division, Central Leather Research Institute, Adyar, Chennai 600 020, India
Correspondence e-mail: ksethusankar@yahoo.co.in

The title compound, C16H15N3O6, is asymmetric with a chiral centre located in the pyran ring and crystallizes as a racemate. The six-membered carbocyclic ring adopts an envelope conformation with the central CH2 C atom as the flap. The amine N atom deviates from the mean plane of the pyran ring by 0.1365 (15) Å. The nitrophenyl ring is almost orthogonal to the pyran ring and the mean plane of the six-membered carbocyclic ring, the dihedral angle between their mean planes being 88.30 (7) and 87.61 (8)°, respectively. The molecular structure is stabilized by an intramolecular N-H...O hydrogen bond, which generates an S(6) ring motif. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming infinite bands lying parallel to (-110) and composed of alternate R22(24) and R24(12) graph-set ring motifs. The crystal structure is further stabilized by C-H...[pi] interactions, forming a three-dimensional structure.

Related literature

For the uses and biological importance of chromene, see: Ercole et al. (2009[Ercole, F., Davis, T. P. & Evans, R. A. (2009). Macromolecules, 42, 1500-1511.]); Geen et al. (1996[Geen, G. R., Evans, J. M. & Vong, A. K. (1996). Comprehensive Heterocyclic Chemistry, 1st ed., edited by A. R. Katrizky, Vol. 3, pp. 469-500. New York: Pergamon.]); Khan et al. (2010[Khan, K. M., Ambreen, N., Mughal, U. R., Jalil, S., Perveen, S. & Choudhary, M. I. (2010). Eur. J. Med. Chem. 45, 4058-4064.]); Raj et al. (2010[Raj, T., Bhatia, R. K., Kapur, A., Sharma, M., Saxena, A. K. & Ishar, M. P. S. (2010). Eur. J. Med. Chem. 45, 790-794.]). For related structures, see: Narayanan et al. (2013a[Narayanan, P., Kamalraja, J., Perumal, P. T. & Sethusankar, K. (2013a). Acta Cryst. E69, o931-o932.],b[Narayanan, P., Kamalraja, J., Perumal, P. T. & Sethusankar, K. (2013b). Acta Cryst. E69, o1053-o1054.]). For graph-set notation, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15N3O6

  • Mr = 345.31

  • Triclinic, [P \overline 1]

  • a = 8.2587 (3) Å

  • b = 8.7679 (4) Å

  • c = 10.9346 (5) Å

  • [alpha] = 101.616 (2)°

  • [beta] = 90.426 (2)°

  • [gamma] = 91.930 (2)°

  • V = 775.05 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.12 mm-1

  • T = 296 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.966, Tmax = 0.977

  • 10840 measured reflections

  • 3161 independent reflections

  • 2633 reflections with I > 2[sigma](I)

  • Rint = 0.026

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.126

  • S = 1.04

  • 3161 reflections

  • 230 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1-C6 ring.

D-H...A D-H H...A D...A D-H...A
N1-H1A...O3 0.90 (3) 1.89 (3) 2.601 (2) 134 (2)
C11-H11A...O6i 0.97 2.54 3.352 (2) 141
C11-H11B...O5ii 0.97 2.54 3.186 (2) 124
C10-H10A...Cg1iii 0.97 2.90 3.515 (2) 135
C16-H16B...Cg1iv 0.96 2.90 3.577 (3) 142
Symmetry codes: (i) -x+1, -y+2, -z; (ii) x-1, y-1, z; (iii) -x, -y+2, -z; (iv) -x+1, -y+2, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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 Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and 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: SU2627 ).


Acknowledgements

The authors thank Mr T. Srinivasan and Dr D. Velmurugan, Head of the CAS in Crystallography and Biophysics, University of Madras, Chennai, India, for the data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Ercole, F., Davis, T. P. & Evans, R. A. (2009). Macromolecules, 42, 1500-1511.  [ISI] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Geen, G. R., Evans, J. M. & Vong, A. K. (1996). Comprehensive Heterocyclic Chemistry, 1st ed., edited by A. R. Katrizky, Vol. 3, pp. 469-500. New York: Pergamon.
Khan, K. M., Ambreen, N., Mughal, U. R., Jalil, S., Perveen, S. & Choudhary, M. I. (2010). Eur. J. Med. Chem. 45, 4058-4064.  [ISI] [CrossRef] [ChemPort] [PubMed]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Narayanan, P., Kamalraja, J., Perumal, P. T. & Sethusankar, K. (2013a). Acta Cryst. E69, o931-o932.  [CSD] [CrossRef] [ChemPort] [details]
Narayanan, P., Kamalraja, J., Perumal, P. T. & Sethusankar, K. (2013b). Acta Cryst. E69, o1053-o1054.  [CrossRef] [ChemPort] [details]
Raj, T., Bhatia, R. K., Kapur, A., Sharma, M., Saxena, A. K. & Ishar, M. P. S. (2010). Eur. J. Med. Chem. 45, 790-794.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1380-o1381   [ doi:10.1107/S1600536813021181 ]

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