7H-Chromeno[3,2-h]quinolin-7-one methanol monosolvate

Qin, J.-K.; Yang, Z.-M.; Zeng, M.-H.; Ng, S.W.

doi:10.1107/S160053680903534X

Volume 65
Part 10
Page o2368
October 2009

Received 1 September 2009
Accepted 1 September 2009
Online 9 September 2009

Key indicators
Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R = 0.046
wR = 0.147
Data-to-parameter ratio = 13.8
Details

7H-Chromeno[3,2-h]quinolin-7-one methanol monosolvate

Jiang-Ke Qin,^a Zheng-Min Yang,^a Ming-Hua Zeng ^a and Seik Weng Ng ^b ^*

^aKey Laboratory for the Chemistry & Molecular Engineering of Medicinal Resources, (Ministry of Education of China), School of Chemistry & Chemical Engineering, Guangxi Normal University, 541004 Guilin 541004, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The four-ring system in the title compound, C₁₆H₉NO₂·CH₃OH, is planar (r.m.s deviation = 0.03 Å); the methanol solvent molecule forms a hydrogen bond to the quinoline N atom.

Related literature

The compound in this study was synthesized from the cyclization of 2-(quinolin-8-yloxy)benzoic acid; for the synthesis of this acid, see: Chen et al. (2007). For the synthesis by the Skraup reaction of amino-9H-xanthene-9-one, see: Fujiwara & Okabayashi (1994).

Experimental

Crystal data

C₁₆H₉NO₂·CH₄O
M_r = 279.28
Triclinic, $[P \overline 1]$
a = 8.102 (2) Å
b = 8.791 (3) Å
c = 10.150 (3) Å
= 102.172 (3)°
= 108.760 (3)°
= 93.532 (3)°
V = 662.6 (3) Å³
Z = 2
Mo K radiation
= 0.10 mm^-1
T = 295 K
0.41 × 0.30 × 0.18 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: none
3838 measured reflections
2655 independent reflections
1456 reflections with I > 2(I)
R_int = 0.016

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.147
S = 1.02
2655 reflections
192 parameters
H-atom parameters constrained
_max = 0.22 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3N1	0.82	2.07	2.852 (2)	160

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU2605 ).

Acknowledgements

This work was supported by the Guangxi Natural Science Foundation (No.0639030), the Guangxi Normal University Foundation and the University of Malaya.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2004). APEX2 and SAINT. Bruker AXS inc., Madison, Wisconsin, USA.
Chen, Q., Qin, J.-K., Zeng, M.-H. & Ng, S. W. (2007). Acta Cryst. E63, o453-o454.
Fujiwara, H. & Okabayashi, I. (1994). Heterocycles, 38, 541-550.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2009). publCIF. In preparation.

organic compounds

7H-Chromeno[3,2-h]quinolin-7-one methanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References