3,6-Dihydr­oxy-2′-[(2-hydr­oxy-1-naphth­yl)methyl­eneamino]xanthene-9-spiro-1′-isoindolin-3′-one acetonitrile solvate

Wang, P.-S.; Wu, G.-H.

doi:10.1107/S1600536808000974

Volume 64
Part 2
Page o442
February 2008

Received 9 January 2008
Accepted 10 January 2008
Online 16 January 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.099
Data-to-parameter ratio = 12.3
Details

3,6-Dihydroxy-2'-[(2-hydroxy-1-naphthyl)methyleneamino]xanthene-9-spiro-1'-isoindolin-3'-one acetonitrile solvate

Pei-San Wang ^a,^b and Gen-Hua Wu ^a ^*

^aAnhui Key Laboratory of Functional Coordination Compounds, School of Chemistry and Chemical Engineering, Anqing Normal College, Anqing 246003, People's Republic of China, and ^bSchool of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000, People's Republic of China
Correspondence e-mail: liugx@live.com

The title compound, C₃₁H₂₀N₂O₅·C₂H₃N, was synthesized by the reaction of fluorescein hydrazide and excess 2-hydroxy-1-naphthaldehyde in acetonitrile. The spirolactam ring is planar and is nearly at right angles to the two benzene rings of the xanthene system. The dihedral angle between the two benzene rings of the xanthene system is 9.92 (4)°. In the crystal structure, the molecules are linked into extended two-dimensional networks by intermolecular hydrogen bonding. Acetonitrile molecules are located in the voids between the two-dimensional networks.

Related literature

For general background, see: Chen et al., (2006). For related literature, see: Wu et al., (2007).

Experimental

Crystal data

C₃₁H₂₀N₂O₅·C₂H₃N
M_r = 541.54
Monoclinic, P 2₁ /c
a = 18.729 (5) Å
b = 15.572 (4) Å
c = 9.021 (2) Å
= 98.495 (4)°
V = 2601.9 (11) Å³
Z = 4
Mo K radiation
= 0.10 mm^-1
T = 293 (2) K
0.26 × 0.22 × 0.16 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000) T_min = 0.976, T_max = 0.985
12963 measured reflections
4627 independent reflections
3272 reflections with I > 2(I)
R_int = 0.047

Refinement

R[F² > 2(F²)] = 0.037
wR(F²) = 0.098
S = 1.03
4627 reflections
375 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4N1	0.82	1.83	2.5600 (16)	147
O3-H6N3ⁱ	0.82	2.08	2.882 (2)	165
O1-H1O4ⁱⁱ	0.82	1.94	2.7484 (16)	170
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1997); cell refinement: SAINT-Plus (Bruker, 1997); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP (Bruker, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: AT2535 ).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Project No. 20775003) and the Natural Science Foundation of the Education Committee of Anhui Province, China (Project No. 2002 K J201).

References

Bruker (1997). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2000). XP. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, X. Q. & Ma, H. M. (2006). Anal. Chim. Acta, 575, 217-222.
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wu, D. Y., Huang, W., Duan, C. Y., Li, Z. & Meng, Q. J. (2007). Inorg. Chem. 46, 1538-1544.

organic compounds