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Volume 69 
Part 3 
Page o364  
March 2013  

Received 31 January 2013
Accepted 5 February 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.138
Data-to-parameter ratio = 22.3
Details
Open access

3-(3-Nitrobenzyl)-4H-chromen-4-one

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Private Bag X54001, Durban 4000, South Africa,bChemistry Department, University of Cape Town, Rondebosch 7701, South Africa, and cSchool of Chemical Engineering, University of KwaZulu-Natal, Durban 4041, South Africa
Correspondence e-mail: koorbanally@ukzn.ac.za

In the title compound, C16H11NO4, the dihedral angle between the 10-membered coplanar chromone ring system and the benzene ring is 77.83 (3)°. In the crystal, weak C-H...O hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For the preparation, see: Valkonen et al. (2012[Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjési, P. (2012). Struct. Chem. 23, 209-217.]). For related structures, see: Sievänen et al. (2010[Sievänen, E., Tousek, J., Lunerová, K., Marek, J., Jankovská, D., Dvorská, M. & Marek, R. (2010). J. Mol. Struct. 979, 172-179.]); Gopaul et al. (2012[Gopaul, K., Shaikh, M. M., Koorbanally, N. A., Ramjugernath, D. & Omondi, B. (2012). Acta Cryst. E68, o1972.]); Valkonen et al. (2012[Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjési, P. (2012). Struct. Chem. 23, 209-217.]). For general background to homoisoflavoinoids, see: Shaikh et al. (2011[Shaikh, M., Petzold, K., Kruger, H. & du Toit, K. (2011). Struct. Chem. 22, 161-166.]); du Toit et al. (2010[Toit, K. du, Drewes, S. E. & Bodenstein, J. (2010). Nat. Prod. Res. 24, 457-490.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11NO4

  • Mr = 281.26

  • Monoclinic, P 21 /c

  • a = 4.6082 (3) Å

  • b = 10.4219 (6) Å

  • c = 26.4468 (17) Å

  • [beta] = 90.428 (1)°

  • V = 1270.10 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.42 × 0.22 × 0.04 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1997[Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.]) Tmin = 0.956, Tmax = 0.996

  • 16973 measured reflections

  • 4246 independent reflections

  • 3069 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.138

  • S = 1.04

  • 4246 reflections

  • 190 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.44 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O2 0.95 2.32 3.2663 (15) 171
C7-H7...O3i 0.95 2.65 3.5614 (19) 160
C8-H8...O3ii 0.95 2.54 3.3071 (18) 138
C14-H14...O4iii 0.95 2.50 3.4380 (17) 172
C15-H15...O1iv 0.95 2.62 3.5569 (15) 170
C16-H16...O2v 0.95 2.46 3.3764 (15) 163
Symmetry codes: (i) [-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) -x+1, -y+2, -z+1; (iv) [-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (v) x+1, y, z.

Data collection: APEX2 (Bruker, 2006[Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2006[Bruker (2006). APEX2 and SAINT. 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 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2097 ).


Acknowledgements

We thank the University of KwaZulu-Natal and the South Africa Research Chairs initiative of the Department of Science and Technology for financial support and the National Research Foundation of South Africa for a bursary for KG.

References

Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gopaul, K., Shaikh, M. M., Koorbanally, N. A., Ramjugernath, D. & Omondi, B. (2012). Acta Cryst. E68, o1972.  [CSD] [CrossRef] [details]
Shaikh, M., Petzold, K., Kruger, H. & du Toit, K. (2011). Struct. Chem. 22, 161-166.  [ISI] [CrossRef] [ChemPort]
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sievänen, E., Tousek, J., Lunerová, K., Marek, J., Jankovská, D., Dvorská, M. & Marek, R. (2010). J. Mol. Struct. 979, 172-179.
Toit, K. du, Drewes, S. E. & Bodenstein, J. (2010). Nat. Prod. Res. 24, 457-490.  [ISI] [PubMed]
Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjési, P. (2012). Struct. Chem. 23, 209-217.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o364  [ doi:10.1107/S1600536813003589 ]

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