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

Li-Jun Zhang; Bing-Zhu Yin

doi:10.1107/S1600536811010944

. 2011 Apr 13;67(Pt 5):o1107. doi: 10.1107/S1600536811010944

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

Li-Jun Zhang ^a, Bing-Zhu Yin ^a,^*

PMCID: PMC3089128 PMID: 21754425

Abstract

The asymmetric unit of the title compound, C₁₄H₁₇N₃O₃, contains two independent molecules with different conformations of the ethyl groups. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules into ribbons extending along the a axis.

Related literature

For the bioactivity and chemiluminescence of coumarin derivatives, see: Munasinghe et al. (2007 ▶). For a related structure, see: Yu et al. (2009 ▶). For details of the synthesis, see: Ma et al. (2010 ▶).

Experimental

Crystal data

C₁₄H₁₇N₃O₃
M _r = 275.31
Triclinic,
a = 9.3438 (19) Å
b = 12.771 (3) Å
c = 12.978 (3) Å
α = 95.17 (3)°
β = 110.13 (3)°
γ = 106.18 (3)°
V = 1366.4 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 290 K
0.14 × 0.12 × 0.11 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.987, T _max = 0.990
13506 measured reflections
6186 independent reflections
3402 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.045
wR(F ²) = 0.117
S = 1.01
6186 reflections
383 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Data collection: RAPID-AUTO (Rigaku Corporation, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku Corporation, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010944/cv5061sup1.cif

e-67-o1107-sup1.cif^{(23.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010944/cv5061Isup2.hkl

e-67-o1107-Isup2.hkl^{(302.8KB, hkl)}

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
N2—H2⋯O2	0.86 (3)	2.01 (2)	2.7098 (18)	137 (2)
N5—H5⋯O5	0.87 (3)	2.03 (2)	2.733 (2)	138 (2)
N6—H6B⋯O3	0.86 (3)	2.30 (1)	3.131 (2)	164 (2)
N3—H3A⋯O3ⁱ	0.87 (3)	2.20 (1)	3.002 (2)	155 (2)
N3—H3B⋯O6ⁱⁱ	0.87 (3)	2.23 (1)	3.039 (2)	154 (2)

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

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

Coumarin derivatives have received considerable attention since their diverse bioactivities and chemiluminescence (Munasinghe et al. 2007). Herein, we report the crystal structure of the title compound, an important organic intermediate and a fluorescent tagging agent for chemosensors.

In the title compound, all bond lengths and angles are normal and comparable to those observed in the related struture (Yu et al., 2009). There are two independent molecules in the asymmetric unit with different conformation of the ethyl groups (Fig. 1). Except for four terminal carbon atoms, the other non-hydrogen atoms are nearly coplanar for two components [mean deviations from the mean planes are 0.065 (1) and 0.07 (1), respectively] and form an angle of 19.39 (4) °. Intermolecuar N—H···O hydrogen bonds (Table 1) link the molecules into ribbons extended along axis a.

Experimental

The title compound was prepared according to the literature (Ma et al., 2010). Single crystals suitable for X-ray diffraction were prepared by slow evaporation a mixture of dichloromethane and petroleum (60–90 °C) at room temperature.