Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxyl­ate

Yuan-Hong Jiao; Qian Zhang; Fa-Yan Meng; Lei Teng; Jia Yuan; Seik Weng Ng

doi:10.1107/S1600536809008885

. 2009 Mar 14;65(Pt 4):o775. doi: 10.1107/S1600536809008885

Ethyl 3-amino-1-phenyl-1H-benzo[f]chromene-2-carboxylate

Yuan-Hong Jiao ^a, Qian Zhang ^a,^*, Fa-Yan Meng ^a, Lei Teng ^a, Jia Yuan ^a, Seik Weng Ng ^b

PMCID: PMC2969098 PMID: 21582501

Abstract

The pyranyl ring of the title compound, C₂₂H₁₉NO₃, adopts a flattened-boat conformation. The dihedral angle between naphthalene and phenyl rings is 78.3 (1)°The molecule also features an intramolecular N—H⋯O_carbonyl hydrogen bond. Adjacent molecules are linked by an intermolecular N—H⋯O_carbonyl hydrogen bond, forming a zigzag chain that runs along the c axis.

Related literature

For the crystal structures of other ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylate derivatives, see: Klokol et al. (1987 ▶); Shi et al. (2003a ▶,b ▶); Wang et al. (2003 ▶); Zhuang et al. (2003a ▶,b ▶).

Experimental

Crystal data

C₂₂H₁₉NO₃
M _r = 345.38
Monoclinic,
a = 13.7835 (5) Å
b = 14.6460 (4) Å
c = 8.8713 (2) Å
β = 99.551 (1)°
V = 1766.05 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 153 K
0.36 × 0.25 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T _min = 0.864, T _max = 0.988
8563 measured reflections
2029 independent reflections
1958 reflections with I > 2σ(I)
R _int = 0.016

Refinement

R[F ² > 2σ(F ²)] = 0.030
wR(F ²) = 0.078
S = 1.09
2029 reflections
244 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.27 e Å⁻³

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2009 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008885/zl2186sup1.cif

e-65-0o775-sup1.cif^{(20.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008885/zl2186Isup2.hkl

e-65-0o775-Isup2.hkl^{(99.8KB, 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
N1—H11⋯O3ⁱ	0.88 (1)	2.05 (1)	2.907 (2)	166 (2)
N1—H12⋯O3	0.88 (1)	2.07 (2)	2.707 (2)	129 (2)

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Symmetry code: (i) Inline graphic .

Acknowledgments

We thank the Huangshi Institute of Technology (grant No. 08yjz23B) and the University of Malaya for supporting this work.

supplementary crystallographic information

Comment

2-Naphthol, substituted benzaldehydes and ethyl 2-cyanoacetate react in the presence of a catalyst to form the ethyl 3-amino-1-aryl-1H-benzo[f]chromene-2-carboxylates; the compounds possess a primary amine group. The crystal structures of several 1-aryl derivatives have been reported (Klokol et al., 1987; Shi et al., 2003a; Shi et al., 2003b; Wang et al., 2003; Zhuang et al., 2003a; Zhuang et al., 2003b). Interestingly, the crystal structure of the unsubstituted 1-phenyl compound was not known, and its structure is reported here. The title compound (Scheme I, Fig. 1) exhibits a pyranyl ring in a flattened boat conformation. The molecule also features an intramolecular N–H···O_carbonyl bond. Adjacent molecules are linked by an intermolecular N—H···O_carbonyl hydrogen bond to furnish a zigzag chain that runs along the c-axis.

Experimental

2-Naphthol (1.4 g, 10 mmol), benzaldehyde (1.1 g, 10 mmol), ethyl 2-cyanoacetate (1.0 g, 10 mmol) and piperidine (1 ml) were dissolved in ethanol (30 ml). The solution was heated for 5 h. The solvent was removed under reduced pressure and and the residue recrystallized from dichloromethane/methanol (1:1/v:v) to give yellow crystals in 80% yield; m.p. 436–437 K.