Crystal structure of 3-(4-meth­oxy­phen­yl)-2,3-di­hydro-1H-naphtho­[2,1-b]pyran-1-one

R Vasanthi; D Reuben Jonathan; K S Elizhlarasi; B K Revathi; G Usha

doi:10.1107/S2056989015007082

. 2015 Apr 22;71(Pt 5):o332. doi: 10.1107/S2056989015007082

Crystal structure of 3-(4-methoxyphenyl)-2,3-dihydro-1H-naphtho[2,1-b]pyran-1-one

R Vasanthi ^a, D Reuben Jonathan ^b, K S Elizhlarasi ^a, B K Revathi ^a, G Usha ^a,^*

PMCID: PMC4420115 PMID: 25995933

Abstract

In the title compound, C₂₀H₁₆O₃, the hydropyran ring adopts a distorted half-chair conformation with the methine C atom and the ring O atom displaced by −0.554 (2) and 0.158 (1) Å, respectively, from the plane of the other four atoms (r.m.s. deviation = 0.020 Å). Its mean plane (all atoms) is inclined to the naphthalene ring system at a dihedral angle of 11.67 (1)°. The dihedral angle between the napthalene ring system and the phenyl ring is 71.84 (1)°. In the crystal, no diectional interactions beyond van der Waals contacts could be identified.

Keywords: crystal structure, hydropyran, flavone derivative

Related literature

For the biological activity of flavone derivatives, see: Thomas et al. (2013 ▸); Kumar et al. (2014 ▸); Lee et al. (2014 ▸). For further synthetic details, see: Vasanthi et al. (2014 ▸).

Experimental

Crystal data

C₂₀H₁₆O₃
M _r = 304.33
Monoclinic,
a = 7.3612 (3) Å
b = 17.8540 (9) Å
c = 11.9465 (6) Å
β = 105.697 (2)°
V = 1511.54 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T _min = 0.974, T _max = 0.982
33755 measured reflections
3548 independent reflections
2297 reflections with I > 2σ(I)
R _int = 0.035

Refinement

R[F ² > 2σ(F ²)] = 0.048
wR(F ²) = 0.171
S = 1.00
3548 reflections
209 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: SAINT (Bruker, 2004 ▸); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015007082/hb7401sup1.cif

e-71-0o332-sup1.cif^{(24.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015007082/hb7401Isup2.hkl

e-71-0o332-Isup2.hkl^{(169.2KB, hkl)}

Click here for additional data file.^{(6KB, cml)}

Supporting information file. DOI: 10.1107/S2056989015007082/hb7401Isup3.cml

Click here for additional data file.^{(1.1MB, tif)}

. DOI: 10.1107/S2056989015007082/hb7401fig1.tif

The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Click here for additional data file.^{(1.3MB, tif)}

. DOI: 10.1107/S2056989015007082/hb7401fig2.tif

The packing of the molecules in the crystal structure. The dashed lines indicate the hydrogen bonds.

CCDC reference: 1058707

Additional supporting information: crystallographic information; 3D view; checkCIF report

Acknowledgments

The authors thank SAIF (IIT Madras) for collecting the intensity data.

supplementary crystallographic information

S1. Synthesis and crystallization

The procedure (Vasanthi et al., 2014) adopted in the synthesis of the compound 3-(4-methoxyphenyl)-2,3-dihydro-1H-benzo(f)chromen-1-one is represented here. In a 250 ml round-bottomed flask 2-hydroxy-1-acetonaphthone (0.05 mol) and 4-methoxyoxybenzaldehyde (0.05mol) were placed to which about 100 ml of absolute alcohol was added and stirred at room temperature for a time span of 5 minutes. Then about 10 ml of 40% sodium hydroxide solution was added and the mixture was stirred for 6 hours. On adding ice cold water a precipitate was generated which was filtered, washed with sufficient quantity of distilled water and dried. The crude product was recrystallized twice from chloroform (yield = 86%).

S2. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1. H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H distance of 0.93-0.97Å with Uiso(H)= 1.5 Ueq(c-methyl) and Uiso(H)= 1.2Ueq(C) for other H atom.