3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

Hong, Z.; Jiang, H.-J.; Zhuang, Y.-G.; Guo, H.-C.

doi:10.1107/S1600536808009732

Volume 64
Part 5
Page o857
May 2008

Received 29 March 2008
Accepted 8 April 2008
Online 16 April 2008

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.058
wR = 0.144
Data-to-parameter ratio = 12.3
Details

3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

Zhi Hong,^a ^* Hua-Jiang Jiang,^a Yu-Guo Zhuang ^a and Hai-Chang Guo ^a

^aSchool of Pharmaceutical and Chemical Engineering, Taizhou University, Linhai 317000, People's Republic of China
Correspondence e-mail: hongxiuzhi@yahoo.com.cn

In the title compound, C₁₇H₁₂O₄, the chromene unit is approximately planar, the maximum deviation from the mean plane being 0.0166 Å. The attached phenyl ring makes a dihedral angle of 53.2 (1)° with the fused ring system. The packing of the molecules in the crystal structure is governed by C-HO and O-HO hydrogen-bonding interactions.

Related literature

For related literature, see: Uneyama et al. (1985); Ghoneim et al. (2007); Da Re (1960, 1968); Sianesi (1972).

Experimental

Crystal data

C₁₇H₁₂O₄
M_r = 280.27
Triclinic, $[P \overline 1]$
a = 7.2760 (8) Å
b = 9.6551 (10) Å
c = 11.3095 (12) Å
= 65.965 (2)°
= 79.748 (2)°
= 68.286 (2)°
V = 673.78 (12) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 298 (2) K
0.35 × 0.27 × 0.18 mm

Data collection

Bruker APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002) T_min = 0.969, T_max = 0.989
3569 measured reflections
2354 independent reflections
2086 reflections with I > 2(I)
R_int = 0.015

Refinement

R[F² > 2(F²)] = 0.058
wR(F²) = 0.144
S = 1.10
2354 reflections
192 parameters
H-atom parameters constrained
_max = 0.20 e Å^-3
_min = -0.25 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1O4ⁱ	0.82	1.86	2.615 (3)	154
C3-H3O1	0.93	2.35	2.683 (3)	101
C14-H14O2ⁱⁱ	0.93	2.57	3.347 (4)	141
C16-H16O2ⁱⁱⁱ	0.93	2.57	3.473 (5)	163
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+1, -z; (iii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2554 ).

Acknowledgements

The authors thank the Materia Medica Institute of Taizhou University for supporting this work.

References

Bruker (2002). SADABS, SAINT and SMART. Bruker AXS Inc., Madison, Winsonsin, USA.
Da Re, P. (1960). US Patent 2921070.
Da Re, P. (1968). US Patent 3350411.
Ghoneim, M. M., El-Attar, M. A. & Razeq, S. A. (2007). Cent. Eur. J. Chem. 5, 496-507.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sianesi, E. (1972). Ger. Patent 2059296.
Uneyama, K., Masatsugu, Y. & Torll, S. (1985). Bull. Chem. Soc. Jpn, 58, 2361-2365.

organic compounds

3-Methyl-4-oxo-2-phenyl-4H-chromene-8-carboxylic acid

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References