3-(3-Nitro­benz­yl)-4H-chromen-4-one

Gopaul, K.; Koorbanally, N.A.; Shaikh, M.; Su, H.; Ramjugernath, D.

doi:10.1107/S1600536813003589

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 (C-C) = 0.002 Å
R = 0.047
wR = 0.138
Data-to-parameter ratio = 22.3
Details

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

Kaalin Gopaul,^a Neil Anthony Koorbanally,^a ^* Mahidansha Shaikh,^a Hong Su ^b and Deresh Ramjugernath ^c

^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-HO hydrogen bonds link the molecules into a three-dimensional network.

Related literature

For the preparation, see: Valkonen et al. (2012). For related structures, see: Sievänen et al. (2010); Gopaul et al. (2012); Valkonen et al. (2012). For general background to homoisoflavoinoids, see: Shaikh et al. (2011); du Toit et al. (2010).

Experimental

Crystal data

C₁₆H₁₁NO₄
M_r = 281.26
Monoclinic, P 2₁ /c
a = 4.6082 (3) Å
b = 10.4219 (6) Å
c = 26.4468 (17) Å
= 90.428 (1)°
V = 1270.10 (14) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.956, T_max = 0.996
16973 measured reflections
4246 independent reflections
3069 reflections with I > 2(I)
R_int = 0.030

Refinement

R[F² > 2(F²)] = 0.047
wR(F²) = 0.138
S = 1.04
4246 reflections
190 parameters
H-atom parameters constrained
_max = 0.44 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C2-H2O2	0.95	2.32	3.2663 (15)	171
C7-H7O3ⁱ	0.95	2.65	3.5614 (19)	160
C8-H8O3ⁱⁱ	0.95	2.54	3.3071 (18)	138
C14-H14O4ⁱⁱⁱ	0.95	2.50	3.4380 (17)	172
C15-H15O1^iv	0.95	2.62	3.5569 (15)	170
C16-H16O2^v	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); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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.
Gopaul, K., Shaikh, M. M., Koorbanally, N. A., Ramjugernath, D. & Omondi, B. (2012). Acta Cryst. E68, o1972.
Shaikh, M., Petzold, K., Kruger, H. & du Toit, K. (2011). Struct. Chem. 22, 161-166.
Sheldrick, G. M. (1997). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Valkonen, A., Laihia, K., Kolehmainen, E., Kauppinen, R. & Perjési, P. (2012). Struct. Chem. 23, 209-217.

organic compounds