7-Diethyl­amino-2-oxo-2H-chromene-3-carbaldehyde

Hong-Da Li; Bing-Zhu Yin

doi:10.1107/S160053681102294X

. 2011 Jun 18;67(Pt 7):o1713. doi: 10.1107/S160053681102294X

7-Diethylamino-2-oxo-2H-chromene-3-carbaldehyde

Hong-Da Li ^a, Bing-Zhu Yin ^a,^*

PMCID: PMC3151821 PMID: 21837106

Abstract

In the title compound, C₁₄H₁₅NO₃, all non-H atoms except for those of the methyl and the disordered ethyl groupare approximately co-planar, the largest deviation from the mean plane being 0.0223 (13) Å at the N atom. In the crystal, the packing of molecules through weak intermolecular C—H⋯O hydrogen-bonding interactions leads to the formation of layers parallel to bc plane. Within these layers, there exist slipped π–π stacking interactions between symmetry-related fused rings [centroid–centroid distances = 3.527 (3) and 3.554 (3), slippage = 0.988 and 1.011 Å, respectively]. One ethyl group is disordered over two sets of sites with site-occupation factors of 0.54 and 0.46.

Related literature

For background to the title compound, an organic intermediate and a fluorescent probe for cyanide and amino acids, see: Kim et al. (2010 ▶). For electronic and photonic applications of coumarins, see: Murray et al. (1982 ▶). For the synthesis, see: Wu et al. (2007 ▶).

Experimental

Crystal data

C₁₄H₁₅NO₃
M _r = 245.27
Monoclinic,
a = 25.488 (17) Å
b = 7.844 (6) Å
c = 12.599 (12) Å
β = 92.39 (3)°
V = 2517 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.41 × 0.39 × 0.21 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.963, T _max = 0.981
11514 measured reflections
2850 independent reflections
1724 reflections with I > 2σ(I)
R _int = 0.033

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.144
S = 1.06
2850 reflections
184 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S160053681102294X/dn2698sup1.cif

e-67-o1713-sup1.cif^{(22.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681102294X/dn2698Isup2.hkl

e-67-o1713-Isup2.hkl^{(140KB, hkl)}

Supplementary material file. DOI: 10.1107/S160053681102294X/dn2698Isup3.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
C8—H8⋯O3ⁱ	0.93	2.58	3.367 (4)	143
C9—H9⋯O1ⁱⁱ	0.93	2.55	3.432 (3)	158
C13—H13B⋯O2ⁱⁱⁱ	0.97	2.53	3.388 (3)	147

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

The authors acknowledge financial support from the National Natural Science Foundation of China (grant No. 21062022) and the Open Project of the State Key Laboratory of Supramolecular Structure and Materials, Jilin University.

supplementary crystallographic information

Comment

Coumarins are an important class of naturally occurring and synthetic compounds, which have been extentively investigated for electronic and photonic applications (Murray et al., 1982). Herein, we reported the crystal structure of the title compound, an important organic intermediate and a fluorescent probe for cyanide and amino acids (Kim et al., 2010).

The molecule of title compound formed by two fused rings is mainly planar with the exception of the methyl and disordered ethyl group (Fig. 1). The weak intermolcular C—H···O hydrogen bonds (Table 1) link the molecules into layers parallel to the (100) plane. Futhermore, slipped π-π stacking occurs between symetry related fused rings within the layers (Table 2)

Experimental

The title compound was prepared according to the literature (Wu et al., 2007). Single crystals suitable for X-ray diffraction were prepared by recrystallization from mixture of dichloromethane and petroleum (60–90 °C).