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Volume 69 
Part 7 
Pages o1053-o1054  
July 2013  

Received 4 May 2013
Accepted 27 May 2013
Online 8 June 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.042
wR = 0.119
Data-to-parameter ratio = 12.8
Details
Open access

rac-4-(4-Chlorophenyl)-2-methylamino-3-nitro-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, C16H15ClN2O4, contains a chiral centre and crystallizes as a racemate. The methylene group [beta]-positioned to the carbonyl group is partially (21%) disordered. It flips to the opposite sides of the corresponding six-membered carbocycle by -0.304 (3) and 0.197 (11) Å, producing alternative envelope conformations. The planes of the pyran and chlorophenyl rings form a dihedral angle of 86.25 (9)°. The molecular structure is characterized by an intramolecular N-H...O interaction, which generates an S(6) ring motif. The corresponding amino N atom deviates from the plane of the pyran ring by 0.1634 (19) Å. In the crystal, molecules are linked via C-H...O hydrogen bonds, forming C(8) chains running parallel to the b-axis direction. The crystal structure also features C-H...[pi] interactions.

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: Sun et al., (2012[Sun, R., Wang, K., Wu, D.-D., Huang, W. & Ou, Y.-B. (2012). Acta Cryst. E68, o824.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C16H15ClN2O4

  • Mr = 334.75

  • Monoclinic, P 21 /n

  • a = 8.0285 (4) Å

  • b = 10.8460 (5) Å

  • c = 18.2337 (9) Å

  • [beta] = 94.067 (2)°

  • V = 1583.74 (13) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 296 K

  • 0.35 × 0.30 × 0.30 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 = 0.912, Tmax = 0.924

  • 11848 measured reflections

  • 2786 independent reflections

  • 2208 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.119

  • S = 1.09

  • 2786 reflections

  • 218 parameters

  • 4 restraints

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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the pyran ring C7/C8/C13/O1/C14/C15.

D-H...A D-H H...A D...A D-H...A
N2-H2A...O3 0.90 (2) 1.86 (2) 2.599 (2) 137 (2)
C2-H2...O4i 0.93 2.53 3.420 (3) 160
C10-H10A...Cg1ii 0.97 2.75 3.515 (2) 136
C16-H16B...Cg1iii 0.96 2.76 3.577 (3) 144
Symmetry codes: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) -x+2, -y+2, -z; (iii) -x+1, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2; data reduction: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); 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: LD2104 ).


Acknowledgements

PN and KS thank Dr Babu Varghese, Senior Scientific Officer, SAIF, IIT Madras, Chennai, India, for the X-ray intensity data collection.

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Ercole, F., Davis, T. P. & Evans, R. A. (2009). Macromolecules, 42, 1500-1511.  [Web of Science] [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
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.  [Web of Science] [CrossRef] [ChemPort] [PubMed]
Raj, T., Bhatia, R. K., Kapur, A., Sharma, M., Saxena, A. K. & Ishar, M. P. S. (2010). Eur. J. Med. Chem. 45, 790-794.  [Web of Science] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sun, R., Wang, K., Wu, D.-D., Huang, W. & Ou, Y.-B. (2012). Acta Cryst. E68, o824.  [CSD] [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1053-o1054   [ doi:10.1107/S1600536813014530 ]

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