2-Amino-4-(4-meth­oxy­phen­yl)-5-oxo-5,6,7,8-tetra­hydro-4H-chromene-3-carbonitrile

Lingqian Kong; Xiuping Ju; Yan Qiao; Jidong Zhang; Zhiqing Gao

doi:10.1107/S1600536811043674

. 2011 Oct 29;67(Pt 11):o3100. doi: 10.1107/S1600536811043674

2-Amino-4-(4-methoxyphenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile

Lingqian Kong ^a,^b,^*, Xiuping Ju ^a, Yan Qiao ^a, Jidong Zhang ^a, Zhiqing Gao ^a

PMCID: PMC3247486 PMID: 22220104

Abstract

The title compound, C₁₇H₁₆N₂O₃, crystallizes with two independent molecules in the asymmetric unit. In both molecules, the fused cyclohexenone ring adopts a sofa conformation. In the crystal, N—H⋯N and N—H⋯O hydrogen bonds link the molecules into corrugated layers parallel to the (101) plane.

Related literature

For the crystal structures of related compounds, see: Nesterov et al. (2004 ▶); Wang & Zhu (2007 ▶). For applications of benzopyran derivatives, see: O’Callaghan et al. (1995 ▶).

Experimental

Crystal data

C₁₇H₁₆N₂O₃
M _r = 296.32
Monoclinic,
a = 31.973 (3) Å
b = 8.7750 (8) Å
c = 22.6861 (2) Å
β = 106.766 (1)°
V = 6094.4 (8) Å³
Z = 16
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.43 × 0.42 × 0.38 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T _min = 0.962, T _max = 0.967
14893 measured reflections
5361 independent reflections
2215 reflections with I > 2σ(I)
R _int = 0.066

Refinement

R[F ² > 2σ(F ²)] = 0.052
wR(F ²) = 0.160
S = 1.01
5361 reflections
399 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; 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) I, global. DOI: 10.1107/S1600536811043674/cv5173sup1.cif

e-67-o3100-sup1.cif^{(23.6KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043674/cv5173Isup2.hkl

e-67-o3100-Isup2.hkl^{(262.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536811043674/cv5173Isup3.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
N1—H1A⋯N4	0.86	2.19	3.035 (5)	168
N3—H3AA⋯N2	0.86	2.23	3.083 (5)	173
N1—H1C⋯O5ⁱ	0.86	2.03	2.877 (4)	167
N3—H3BA⋯O2ⁱⁱ	0.86	2.27	3.029 (4)	148

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

Acknowledgments

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

supplementary crystallographic information

Comment

Benzopyran derivatives are useful starting materials for the preparation of polyheterocyclic compounds (O'Callaghan et al., 1995), so much interest has still been paid to the design of polyfunctionalized substituted pyran derivatives (Wang & Zhu, 2007). We obtained the title compound, (I), and report here its crystal structure.

The asymmetric unit of (I) contains two independent molecules (Fig. 1). The bond lengths and angles are normal and correspond to those observed in 2-amino- 4-(1-naphthyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3- carbonitrile (Nesterov et al., 2004). In one independent molecule, the pyran ring adopts a half-chair conformation. The O3/C9/C10/C11/C12 plane forms an angle of 82.69 (11 )° with the benzene ring C2-C7. In another independent molecule, the O6/C26/C27/C28/C29 plane and the benzen ring C19-C24 forms an angle of 89.24(11 )°. The triple bond lengths in nitrile groups are typical [N2≡C17 1.147 (4) Å, N4≡C34 1.142 (5)Å ].

In the crystal structure, intermolecular N—H···N and N—H···O hydrogen bonds (Table 1) link the molecules into corrugated layers parallel to (101) plane.

Experimental

Malononitrile (5 mmol), 1,3-cyclohexanedione (5 mmol),and 4-methoxybenzaldehyde (5 mmol)was dissolved in 20ml ethanol ml in a round-bottom flask. The mixture was warmed, with agitation, to 363 K over a period of 3 h. The resulting solution was cooled. Crystal of (I) suitable for X-ray diffraction analysis were obtained by slow evaporation.