3-{1-[2-(2-Chloro­phen­yl)hydrazinyl­idene]-2,2,2-trifluoro­eth­yl}-7-diethyl­amino-2H-chromen-2-one

Hao Chen; Li Cai; Chaochao Yu; Hongqi Li

doi:10.1107/S1600536811031916

. 2011 Aug 17;67(Pt 9):o2344. doi: 10.1107/S1600536811031916

3-{1-[2-(2-Chlorophenyl)hydrazinylidene]-2,2,2-trifluoroethyl}-7-diethylamino-2H-chromen-2-one

Hao Chen ^a, Li Cai ^a, Chaochao Yu ^a, Hongqi Li ^a,^*

PMCID: PMC3200584 PMID: 22058963

Abstract

The title compound, C₂₁H₁₉ClF₃N₃O₂, has a structure related to other coumarin derivatives that have been used as fluorescent probes of metal ions. The dihedral angle between the coumarin ring system and the chlorobenzene ring is 42.99 (9)°. Intramolecular hydrogen bonding occurs via N—H⋯O and N—H⋯Cl interactions, generating S(7) and S(5) rings, respectively. The crystal packing is stabilized by weak C—H⋯O hydrogen bonds.

Related literature

For applications of coumarins and coumarin derivatives, see: Trenor et al. (2004 ▶); Starcevic et al. (2011 ▶); Danko et al. (2011 ▶). For the synthesis of the title compound and related structures, see: Li et al. (2011 ▶).

Experimental

Crystal data

C₂₁H₁₉ClF₃N₃O₂
M _r = 437.84
Orthorhombic,
a = 7.940 (6) Å
b = 12.602 (9) Å
c = 20.233 (15) Å
V = 2025 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 296 K
0.20 × 0.20 × 0.18 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T _min = 0.954, T _max = 0.958
10369 measured reflections
3576 independent reflections
3162 reflections with I > 2σ(I)
R _int = 0.023

Refinement

R[F ² > 2σ(F ²)] = 0.032
wR(F ²) = 0.078
S = 1.03
3576 reflections
273 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ▶), 1511 Friedel pairs
Flack parameter: −0.09 (6)

Data collection: APEX2 (Bruker, 2003 ▶); cell refinement: SAINT-Plus (Bruker, 2003 ▶); data reduction: SAINT-Plus; 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: SHELXTL.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811031916/lr2022sup1.cif

e-67-o2344-sup1.cif^{(22.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031916/lr2022Isup2.hkl

e-67-o2344-Isup2.hkl^{(175.4KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811031916/lr2022Isup3.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
N3—H3A⋯Cl1	0.86	2.57	2.960 (2)	109
N3—H3A⋯O2	0.86	2.22	2.761 (3)	121
C14—H14⋯O2ⁱ	0.93	2.55	3.316 (3)	140

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Symmetry code: (i) Inline graphic .

Acknowledgments

Financial support by the Fundamental Research Funds for the Central Universities was acknowledged.

supplementary crystallographic information

Comment

Because the structure of benzopyrone has many advantages including high fluorescence quantum yield, large Stokes shift, excellent light stability, and less toxicity coumairns have been widely used in the fields of biology, medicine (Starcevic et al., 2011), perfumes, cosmetics (Trenor et al., 2004), and fluorescent dyes (Danko et al., 2011). We have synthesized a series of novel coumarin derivatives and found that one of them 3-(2-benzoylhydrazonotrifluoroethyl)-7- (N,N-diethylamino)coumarin can be used as fluorescent probes of Cu(II) and Ni(II) (Li et al., 2011). Herein we report the single-crystal structure of 3-(2-Chlorophenylhydrazonotrifluoroethyl)-7-(N,N- diethylamino)coumarin, which may be a good candidate for fluorescent probe of metal ions.

Experimental

The title compound was prepared as reported in the literature (Li et al., 2011). Red orange single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from a 1:1 petroleum ether and ethyl acetate mixture.