3′,6′-Bis(diethyl­amino)-2-[(E)-2-(4-hy­droxy-3-meth­oxy­benzyl­idene­amino)­eth­yl]spiro­[isoindoline-1,9′-xanthen]-3-one ethanol monosolvate

Zhen Wei; Jinlong Guo; Xujun Zheng; Shunwei Chen; Qun Wan

doi:10.1107/S1600536812016741

. 2012 Apr 21;68(Pt 5):o1479. doi: 10.1107/S1600536812016741

3′,6′-Bis(diethylamino)-2-[(E)-2-(4-hydroxy-3-methoxybenzylideneamino)ethyl]spiro[isoindoline-1,9′-xanthen]-3-one ethanol monosolvate

Zhen Wei ^a,^*, Jinlong Guo ^a, Xujun Zheng ^a, Shunwei Chen ^a, Qun Wan ^a

PMCID: PMC3344589 PMID: 22590351

Abstract

In the title compound, C₃₈H₄₂N₄O₄·C₂H₆O, prepared via a spirolactam ring-formation reaction in a rhodamine dye, the xanthene ring system is approximately planar (r.m.s. deviation = 0.0014Å) and subtends dihedral angles of 88.10 (3) and 86.92 (4)° with the spirolactam (r.m.s. deviations = 0.0012 Å) and benzene rings, respectively. The crystal structure consists of chains parallel to [-101], formed via O—H⋯O interactions.

Related literature

For related structures and background to rhodamine-based dyes, see: Xu et al.(2010a ▶,b ▶); Zhang et al. (2008 ▶); Tian & Peng (2008 ▶); Kwon et al. (2005 ▶); Wu et al.(2007 ▶).

Experimental

Crystal data

C₃₈H₄₂N₄O₄·C₂H₆O
M _r = 664.82
Monoclinic,
a = 16.674 (4) Å
b = 12.197 (3) Å
c = 17.936 (4) Å
β = 96.445 (4)°
V = 3624.5 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 113 K
0.20 × 0.12 × 0.10 mm

Data collection

Rigaku Saturn724+ diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2008 ▶) T _min = 0.984, T _max = 0.992
45486 measured reflections
8576 independent reflections
7385 reflections with I > 2σ(I)
R _int = 0.043

Refinement

R[F ² > 2σ(F ²)] = 0.049
wR(F ²) = 0.119
S = 1.10
8576 reflections
450 parameters
H-atom parameters constrained
Δρ_max = 0.32 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: CrystalClear (Rigaku, 2008 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku, 2008 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812016741/bg2444sup1.cif

e-68-o1479-sup1.cif^{(31.8KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812016741/bg2444Isup2.hkl

e-68-o1479-Isup2.hkl^{(411.1KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812016741/bg2444Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O5ⁱ	0.84	1.96	2.7052 (15)	148
O5—H5A⋯O2	0.84	1.93	2.7552 (14)	166

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank the Science Development Committee of Tianjin Agricultural University (research grant No. 2009 N02).

supplementary crystallographic information

Comment

Rhodamine-based dyes have been widely used for conjugation with biomolecules, owing to their excellent spectroscopic properties such as large molar extinction coefficient and high fluorescence quantum yields. Moreover, it is well known that many derivatives of Rhodamine undergo equilibrium between spirolactam and an open ring amide, and both conformations behave with different spectroscopic properties, for what Rhodamine-based dyes have been widely used as sensing materials (Kwon et al., 2005). Detailed information on their molecular and crystal structures is necessary to understand their photophysical and photochemical properties. In the title compound [(C₃₈H₄₂N₄O₄)], the xanthene and the spirolactam rings are almost planar (r.m.s. deviations from the mean plane, 0.0014Å and 0.0012 Å, respectively), with the former ring forming dihedral angles of 88.10 (3)° to the spirolactam ring and 86.92 (4)°. to the benzene ring. The crystal structure consists of one-dimensional chains parallel to [101], formed via O3—H3···O5, O5—H5A···O2 interactions (Table 1).

Experimental

N-(rhodamine-6 G)lactam-ethylenediamine (5m mol) was dissolved in 50 ml of ethanol, followed by addition of 3-methoxy-4-hydroxybenzaldehyde(5m mol). The solution was stirred and refluxed for 10 h. The white precipitate was filtrated and disolved in ethanol. Single crystals suitable for X-ray measurements were obtained at room temperature by slow evaporation of this solution.