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Volume 69 
Part 4 
Page o513  
April 2013  

Received 20 February 2013
Accepted 4 March 2013
Online 9 March 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.050
wR = 0.154
Data-to-parameter ratio = 17.3
Details
Open access

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

aSchool of Chemistry and Physics, University of KwaZulu-Natal, Durban 4000, South Africa,bSchool of Chemical Engineering, University of KwaZulu-Natal, Durban, South Africa, and cChemistry Department, University of Cape Town, Rondebosch 7701, South Africa
Correspondence e-mail: koorbanally@ukzn.ac.za

In the title compound, C16H11NO4, the dihedral angle between the ten-membered chromen-4-one ring system (r.m.s. deviation = 0.0095 Å) and the benzene ring is 86.16 (5)°. In the crystal, molecules are linked into a three-dimensional network by weak C-H...O hydrogen bonds. The crystal studied was a non-merohedral twin, with the minor twin component refining to 0.093 (1).

Related literature

For the preparation, see: Desideri et al. (2011[Desideri, N., Bolasco, A., Fioravanti, R., Proietti Monaco, L., Orallo, F., Yáñez, M., Ortuso, F. & Alcaro, S. (2011). J. Med. Chem. 54, 2155-2164.]); Valkonen et al. (2012[Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjési, P. (2012). Struct. Chem. 23, 209-217.]). For related structures, see: Valkonen et al. (2012[Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjési, P. (2012). Struct. Chem. 23, 209-217.]); Gopaul et al. (2013[Gopaul, K., Koorbanally, N. A., Shaikh, M., Su, H. & Ramjugernath, D. (2013). Acta Cryst. E69, o364.]). For the biological activity of homoisoflavonoids, see: Abegaz et al. (2007[Abegaz, B. M., Mutanyatta-Comar, J. & Nindi, M. (2007). Nat. Prod. Commun. 2, 475-498.]).

[Scheme 1]

Experimental

Crystal data
  • C16H11NO4

  • Mr = 281.26

  • Monoclinic, P 21 /n

  • a = 4.9246 (9) Å

  • b = 10.0160 (19) Å

  • c = 25.907 (5) Å

  • [beta] = 92.845 (4)°

  • V = 1276.3 (4) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 173 K

  • 0.35 × 0.09 × 0.08 mm

Data collection
  • Bruker Kappa DUO APEXII diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 1997[Sheldrick, G. M. (1997). TWINABS. University of Göttingen, Germany.]) Tmin = 0.964, Tmax = 0.992

  • 87638 measured reflections

  • 3303 independent reflections

  • 2887 reflections with I > 2[sigma](I)

  • Rint = 0.063

Refinement
  • R[F2 > 2[sigma](F2)] = 0.050

  • wR(F2) = 0.154

  • S = 1.09

  • 3303 reflections

  • 191 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.25 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2...O2i 0.95 2.38 3.322 (3) 170
C7-H7...O3ii 0.95 2.56 3.491 (3) 166
C9-H9...O4iii 0.95 2.42 3.355 (3) 167
C13-H13...O3iv 0.95 2.53 3.382 (3) 149
C16-H16...O2v 0.95 2.46 3.378 (3) 163
Symmetry codes: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iv) -x+1, -y+1, -z+1; (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 for Windows (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: FJ2618 ).


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

Abegaz, B. M., Mutanyatta-Comar, J. & Nindi, M. (2007). Nat. Prod. Commun. 2, 475-498.  [ChemPort]
Bruker (2006). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Desideri, N., Bolasco, A., Fioravanti, R., Proietti Monaco, L., Orallo, F., Yáñez, M., Ortuso, F. & Alcaro, S. (2011). J. Med. Chem. 54, 2155-2164.  [ISI] [CrossRef] [ChemPort] [PubMed]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gopaul, K., Koorbanally, N. A., Shaikh, M., Su, H. & Ramjugernath, D. (2013). Acta Cryst. E69, o364.  [CrossRef] [details]
Sheldrick, G. M. (1997). TWINABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjési, P. (2012). Struct. Chem. 23, 209-217.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o513  [ doi:10.1107/S1600536813006119 ]

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