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BY-NC-ND 3.0 license Open Access Published by De Gruyter (O) December 15, 2016

Crystal structure of (E)-2-(4-hydroxy-3-methoxybenzylidene)-6-methoxy-3,4-dihydronaphthalen-1(2H)-one, C19H18O4

  • Nahed N.E. El-Sayed , Norah M. Almaneai , Hazem A. Ghabbour EMAIL logo and Ahmed M. Alafeefy

Abstract

C19H18O4, orthorhombic, Pbcn, a = 21.1472(8) Å, b = 9.7978(4) Å, c = 14.5181(6) Å, V = 3008.1(2) Å3, Z = 8, Rgt(F) = 0.0520, wRref(F2) = 0.1194, T = 100(2).

CCDC no.:: 1459326

The asymmetric unit of the title crystal structure is shown in the figure. Tables 1 and 2 contain details on crystal structure and measurement conditions and a list of the atoms including atomic coordinates and displacement parameters.

Table 1

Data collection and handling.

Crystal:Orange plate
Size:0.56 × 0.17 × 0.09 mm
Wavelength:Mo Kα radiation (0.71073 Å)
μ:1.0 cm−1
Diffractometer, scan mode:Bruker APEX-II, φ and ω
2θmax, completeness:55°, >99%
N(hkl)measured, N(hkl)unique, Rint:39151, 3461, 0.134
Criterion for Iobs, N(hkl)gt:Iobs > 2 σ(Iobs), 2466
N(param)refined:214
Programs:SHELX [22], Bruker programs [23]
Table 2

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

AtomxyzUiso*/Ueq
O10.45468(6)0.82075(12)−0.11321(9)0.0172(3)
O20.72991(6)1.06912(13)−0.11627(9)0.0207(3)
O30.36151(6)0.37388(14)0.36125(9)0.0197(3)
O40.28832(6)0.58164(13)0.31800(9)0.0232(3)
C10.49596(9)0.81438(17)−0.05242(12)0.0142(4)
C20.55753(9)0.88251(17)−0.06542(12)0.0147(4)
C30.57352(9)0.93631(17)−0.15192(12)0.0155(4)
H3A0.54460.9309−0.20000.019*
C40.63112(9)0.99665(19)−0.16657(13)0.0173(4)
H4A0.64141.0304−0.22450.021*
C50.67441(9)1.00737(18)−0.09393(13)0.0167(4)
C60.65949(9)0.95551(18)−0.00765(13)0.0155(4)
H6A0.68820.96330.04050.019*
C70.60138(9)0.89180(17)0.00671(12)0.0150(4)
C80.58494(9)0.83213(19)0.09932(13)0.0179(4)
H8A0.56190.89920.13520.021*
H8B0.62350.81010.13230.021*
C90.54469(9)0.70305(19)0.08894(13)0.0178(4)
H9A0.56920.63250.05860.021*
H9B0.53250.66970.14930.021*
C100.48615(9)0.73407(17)0.03296(13)0.0155(4)
C110.42684(9)0.69864(17)0.05672(12)0.0158(4)
H11A0.39430.73510.02130.019*
C120.40819(9)0.60866(18)0.13255(12)0.0158(4)
C130.44199(9)0.49039(18)0.15217(13)0.0180(4)
H13A0.47630.46630.11560.022*
C14.0.42482(9)0.40813(18)0.22580(13)0.0168(4)
H14A0.44690.32760.23680.020*
C150.37567(9)0.44399(18)0.28277(13)0.0154(4)
C160.33833(9)0.55846(18)0.26053(13)0.0160(4)
C170.35452(9)0.63824(18)0.18579(13)0.0164(4)
H17A0.32940.71280.17050.020*
C180.77579(10)1.0899(2)−0.04455(14)0.0247(5)
H18A0.81321.1303−0.07020.037*
H18B0.78631.0037−0.01710.037*
H18C0.75851.14940.00150.037*
C190.24712(10)0.6916(2)0.29427(15)0.0257(5)
H19A0.21210.69370.33630.039*
H19B0.23170.67890.23270.039*
H19C0.26980.77630.29790.039*
H1O30.3905(12)0.308(3)0.3694(17)0.049(8)*

Source of material

To a stirred solution of 6-methoxy-1-tetralone (5 g, 0.0028 mol) in conc. HCl (28 mL) and glacial acetic acid (28 mL) at 0 °C, vanillin (4.3 g, 0.0028 mol) was added. The resulting mixture was further stirred at this temperature for 3 h, then at room temperature for 18 h. Diethyl ether was added and the ethereal layer was discarded. The remaining residue was treated with a water/ice mixture. The separated solid was filtered off and recrystallized from ethanol/ petroleum ether to afford the title compound (50%) as red crystals, m.p. 110–115 °C; γmaxIR (KBr)/cm−1 3431, 3177, 2940, 2838, 1638, 1597, 1559, 1520, 1443, 1425, 1390, 1317, 1253, 1165; 1H-NMR (400 MHz; CDCl3) δH: 2.92 (2 H, t, J 6.0, CH2), 3.13 (2 H, app. td, J 6.0, 1.7, CH2), 3.87 (3H, s, OCH3), 3.92 (3H, s, OCH3), 6.70 (1H, d, J 2.6, CH—Ph-tetralone), 6.87 (1H, dd, J 8.5, 2.6, CH—Ph-tetralone), 6.96–6.95 (2H, m, 2 × CH—Ph-vanillin), 7.02(1H, dd, J 7.7, 1.7, CH—Ph-vanillin), 7.78 (1H, s, CH = CqCO), 8.10 (1H, d, J 8.5, CH—Ph-tetralone); 13C-NMR (100 MHz; CDCl3) δH: 27.28 (CH2), 29.18 (CH2), 55.40 (OCH3), 55.94 (OCH3), 112.21, 112.73, 113.21, 114.39, 123.64, 127.14, 128.32, 130.66, 133.70, 136.33, 145.51, 146.24, 163.46 (6 × CH—Ph-tetralone and CH—Ph, 6 × Cq-Ph-tetralone and Cq-Ph), 186.71 (C = O); δC (100 MHz; CDCl3) 27.28 (CH2), 29.18 (CH2), 55.40 (OCH3), 55.94 (OCH3), 112.21, 112.73, 113.21, 114.39, 123.64, 127.14, 128.32, 130.66, 133.70, 136.33, 145.51, 146.24, 163.46 (14 × CH-Ar, Cq-Ar and CH = Cq CO), 186.71 (C = O).

Experimental details

Carbon-bound H atoms were placed in calculated positions and were included in the refinement in the riding model approximation, with Uiso(H) set to 1.2Ueq(C) except for methyl hydrogen atoms. The H atoms of the methyl group were allowed to rotate with a fixed angle around the C—C bond to best fit the experimental electron density with Uiso(H) set to 1.5Ueq(C).

Discussion

2-Arylidene-1-tetralones contain the α,β-unsaturated enone fragment. This moiety is a characteristic functionality of biologically and synthetically important compounds known as chalcones. This synthon is considered as a versatile building block that can be used to construct heterocyclic rings having one or more heteroatoms and of different ring sizes such as 2-pyrazoline [1], pyrimidine [2, 3] , pyran, and isooxazoline [4]. Generally chalcones and their analogs are prepared by Claisen-Schmidt reactions under basic conditions using bases such as sodium hydroxide or potassium hydroxide [5], lithium hydroxide [6] and piperidine [7]. Acid catalyzed synthesis is also well established using p-toluene sulfonic acid under focused microwave irradiation [8], thionyl chloride [9], dry hydrochloric acid and borontrifluoride-etherate [10]. Some chalcones are known for their biological activities as they exhibit cytotoxic [11], antibacterial [12], antifungal [13], antimalarial and antitubercular [14], anti-inflammatory [15], antimalarial [16], antiviral [17], tyrosinase inhibitor [18], antiallergenic [19], antioxidant [20] and antihyperglycemic [21] activities.

The asymmetric unit cell of the titled compound contains one independent molecule. The bond length of C10—C11 is 1.346(3) Å, which are typical C = C double bond and the configuration around this double bond is trans. The molecules are connected in the crystal via intermolecular hydrogen bonds: O3—H1O3⋯O1i, symmetry code: (i) x, − y + 1, z + 1/2 forming chains along the c axis of the choosen unit cell. Additionally, non-classical hydrogen bonds may contribute to the stability of the packing.

Acknowledgements

The authors would like to extend their sincere appreciation to the Deanship of Scientific Research at King Saud University for its funding this Research Group No. RG-1435-083.

References

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Received: 2016-6-19
Accepted: 2016-11-8
Published Online: 2016-12-15
Published in Print: 2017-3-1

©2016 Nahed N. E. El-Sayed et al., published by De Gruyter.

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 3.0 License.

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