(3E)-3-[(2E)-3-(4-Meth­oxy­phen­yl)prop-2-enyl­idene]-2,3-di­hydro-4H-chromen-4-one

Biruntha, K.; Reuben Jonathan, D.; Mohamooda Sumaya, U.; Dravida Thendral, E.R.A.; Usha, G.

doi:10.1107/S2414314618008295

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 3| Part 6| June 2018| x180829

https://doi.org/10.1107/S2414314618008295

Open

access

(3E)-3-[(2E)-3-(4-Methoxyphenyl)prop-2-enylidene]-2,3-dihydro-4H-chromen-4-one

K. Biruntha,^a D. Reuben Jonathan,^b U. Mohamooda Sumaya,^a E. R. A. Dravida Thendral ^c and G. Usha ^c ^*

^aDepartment of Physics, Bharathi Women's College, Chennai-108, Tamilnadu, India, ^bDepartment of Chemistry, Madras Christian College, Chennai-59, Tamilnadu, India, and ^cPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 29 May 2018; accepted 5 June 2018; online 8 June 2018)

In the title compound, C₁₉H₁₆O₃, the dihedral angle between the chromanone moiety and the methoxy phenyl ring is 16.47 (1)°. In the crystal, the molecules are linked by pairs of C—H⋯O hydrogen bonds, generating R₂²(14) inversion dimers; further C—H⋯O hydrogen bonds connect the dimers into [100] double chains.

Keywords: crystal structure; chalcone derivative; hydrogen bonds.

CCDC reference: 1842509

Structure description

A large number of naturally occurring chalcones are polyhydroxylated in the aryl rings (Jasinski et al., 2010 ). The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using these compounds or chalcone-rich plant extracts as drugs or food preservatives (Dhar, 1981 ). As part of our studies in this area, we now describe the synthesis and structure of the title compound (Fig. 1).

Figure 1
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

The tetrahydro-4H-pyran-4-one ring adopts a sofa conformation with the methylene group (atom C12) displaced from the other atoms. The C—O and C=O distances in the chromanone moiety are typical of those in previously reported structures (Gopaul et al., 2012 ). The dihedral angle between the the methoxy phenyl ring and chromanone ring system (all atoms) is 16.47 (1)°.

In the crystal, the molecules are linked by C—H⋯O hydrogen bonds (Table 1). Inversion dimers featuring $[R_{2}^{2}]$ (14) loops arise from the very weak C8—H8⋯O2 bonds and the dimers are linked into [100] double chains by the C17—H17⋯O3 bonds (Figs. 2 and 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O2ⁱ	0.93	2.59	3.362 (5)	141
C17—H17⋯O3ⁱⁱ	0.93	2.53	3.342 (5)	146
Symmetry codes: (i) -x+2, -y, -z+1; (ii) x+1, y, z.

Figure 2
The packing of the molecules in the crystal structure. The dashed lines indicate hydrogen bonds.

Figure 3
A partial view of the packing of the title compound showing the hydrogen bonds as dashed lines.

Synthesis and crystallization

In a 250 ml round-bottomed flask, a mixture of 4-chromanone (1.4 g, 0.010 mol) and methoxy cinnamaldehyde (1.5 g, 0.010 mol) was added to absolute alcohol and stirred for five minutes. Then, a solution of NaOH (0.3 g, 10 ml) was added and stirred for 2 h. The mixture was kept overnight at room temperature and then dumped into crushed ice, leading to a precipitate of the title compound, which was isolated by filtration and washed with distilled water several times to remove any trace of NaOH remaining in the product. The crude chalcone derivative was recrystallized twice from ethyl methylketone solution to give colourless blocks of the title compound (yield: 80%; mp: 135°C).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₆O₃
M_r	292.32
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	6.8573 (12), 7.4073 (14), 15.550 (3)
α, β, γ (°)	87.843 (6), 78.892 (5), 72.347 (5)
V (Å³)	738.4 (2)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.15 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXIII CMOS
Absorption correction	Multi-scan (SADABS)
T_min, T_max	0.987, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	20521, 2589, 1609
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.080, 0.251, 1.12
No. of reflections	2580
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.25
Computer programs: APEX3 and SAINT (Bruker, 2016 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1842509

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008295/hb4235sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618008295/hb4235Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314618008295/hb4235Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015b).

(3E)-3-[(2E)-3-(4-Methoxyphenyl)prop-2-enylidene]-2,3-dihydro-4H-chromen-4-one top

Crystal data top

C₁₉H₁₆O₃	Z = 2
M_r = 292.32	F(000) = 308
Triclinic, P1	D_x = 1.315 Mg m⁻³
a = 6.8573 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 7.4073 (14) Å	Cell parameters from 7704 reflections
c = 15.550 (3) Å	θ = 3.2–26.7°
α = 87.843 (6)°	µ = 0.09 mm⁻¹
β = 78.892 (5)°	T = 296 K
γ = 72.347 (5)°	Block, colourless
V = 738.4 (2) Å³	0.15 × 0.15 × 0.10 mm

Data collection top

Bruker APEXIII CMOS diffractometer	1609 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.092
Absorption correction: multi-scan (SADABS)	θ_max = 25.0°, θ_min = 2.9°
T_min = 0.987, T_max = 0.991	h = −8→8
20521 measured reflections	k = −8→8
2589 independent reflections	l = −18→18

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.080	w = 1/[σ²(F_o²) + (0.0879P)² + 0.7561P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.251	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.24 e Å⁻³
2580 reflections	Δρ_min = −0.25 e Å⁻³
201 parameters	Extinction correction: SHELXL2014 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.09 (3)
Primary atom site location: structure-invariant direct methods

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. H atoms were positioned geometrically and treated as riding on their parent atoms and refined with, C—H distance of 0.93–0.97 Å, with U_iso(H)= 1.5 U_eq(c-methyl),and U_iso(H)= 1.2Ueq(C) for other H atom.

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

	x	y	z	U_iso*/U_eq
C1	−0.3016 (8)	0.3018 (7)	0.8572 (3)	0.0924 (15)
H1A	−0.2325	0.3744	0.8833	0.139*
H1B	−0.2454	0.1701	0.8693	0.139*
H1C	−0.4481	0.3440	0.8814	0.139*
C2	−0.0725 (6)	0.2889 (5)	0.7197 (3)	0.0597 (10)
C3	−0.0532 (6)	0.3314 (5)	0.6320 (3)	0.0628 (10)
H3	−0.1725	0.3833	0.6085	0.075*
C4	0.1369 (6)	0.2990 (5)	0.5794 (3)	0.0605 (10)
H4	0.1451	0.3291	0.5205	0.073*
C5	0.3203 (6)	0.2214 (5)	0.6116 (2)	0.0539 (9)
C8	0.5250 (6)	0.1928 (5)	0.5585 (3)	0.0596 (10)
H8	0.6378	0.1365	0.5855	0.072*
C9	0.5699 (6)	0.2387 (5)	0.4746 (3)	0.0593 (10)
H9	0.4594	0.2937	0.4462	0.071*
C10	0.7755 (6)	0.2092 (5)	0.4260 (3)	0.0567 (10)
H10	0.8838	0.1566	0.4560	0.068*
C11	0.8297 (5)	0.2488 (5)	0.3421 (2)	0.0524 (9)
C19	1.0486 (6)	0.2170 (5)	0.3014 (3)	0.0555 (10)
C18	1.0927 (5)	0.2306 (5)	0.2055 (2)	0.0537 (9)
C17	1.2938 (6)	0.2108 (6)	0.1601 (3)	0.0682 (11)
H17	1.4000	0.1982	0.1913	0.082*
C16	1.3383 (8)	0.2095 (7)	0.0702 (3)	0.0831 (13)
H16	1.4731	0.1976	0.0405	0.100*
C15	1.1807 (9)	0.2259 (8)	0.0246 (3)	0.0949 (16)
H15	1.2105	0.2234	−0.0363	0.114*
C7	0.1057 (7)	0.2083 (5)	0.7534 (3)	0.0651 (11)
H7	0.0958	0.1757	0.8120	0.078*
C6	0.2986 (6)	0.1764 (5)	0.6996 (3)	0.0629 (11)
H6	0.4177	0.1230	0.7230	0.076*
C14	0.9823 (8)	0.2457 (8)	0.0671 (3)	0.0875 (14)
H14	0.8775	0.2567	0.0353	0.105*
C13	0.9370 (6)	0.2496 (6)	0.1575 (3)	0.0635 (10)
C12	0.6740 (6)	0.3353 (6)	0.2856 (3)	0.0693 (11)
H12A	0.5441	0.3102	0.3106	0.083*
H12B	0.6476	0.4715	0.2862	0.083*
O1	−0.2702 (5)	0.3267 (5)	0.7659 (2)	0.0835 (10)
O2	1.1894 (4)	0.1790 (4)	0.3435 (2)	0.0788 (10)
O3	0.7373 (4)	0.2668 (4)	0.19599 (18)	0.0742 (9)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.100 (4)	0.077 (3)	0.083 (3)	−0.016 (3)	0.006 (3)	0.005 (3)
C2	0.061 (2)	0.050 (2)	0.070 (3)	−0.0191 (17)	−0.0130 (19)	−0.0013 (18)
C3	0.060 (2)	0.055 (2)	0.076 (3)	−0.0138 (17)	−0.024 (2)	0.0037 (19)
C4	0.063 (2)	0.054 (2)	0.067 (2)	−0.0182 (18)	−0.0183 (19)	0.0042 (18)
C5	0.060 (2)	0.0371 (18)	0.069 (2)	−0.0184 (16)	−0.0165 (18)	−0.0016 (16)
C8	0.063 (2)	0.044 (2)	0.077 (3)	−0.0185 (17)	−0.0219 (19)	0.0022 (18)
C9	0.058 (2)	0.043 (2)	0.079 (3)	−0.0128 (16)	−0.0227 (19)	−0.0006 (18)
C10	0.056 (2)	0.0421 (19)	0.074 (3)	−0.0129 (16)	−0.0214 (18)	−0.0018 (17)
C11	0.055 (2)	0.0378 (18)	0.068 (2)	−0.0145 (15)	−0.0211 (17)	−0.0020 (16)
C19	0.054 (2)	0.0365 (18)	0.082 (3)	−0.0156 (15)	−0.0239 (19)	0.0010 (16)
C18	0.056 (2)	0.0395 (18)	0.071 (2)	−0.0181 (15)	−0.0192 (18)	0.0013 (16)
C17	0.068 (3)	0.059 (2)	0.086 (3)	−0.0256 (19)	−0.023 (2)	0.004 (2)
C16	0.078 (3)	0.090 (3)	0.086 (3)	−0.037 (3)	−0.008 (2)	0.002 (3)
C15	0.100 (4)	0.120 (4)	0.073 (3)	−0.047 (3)	−0.014 (3)	0.005 (3)
C7	0.083 (3)	0.057 (2)	0.062 (2)	−0.029 (2)	−0.019 (2)	0.0067 (18)
C6	0.071 (3)	0.049 (2)	0.075 (3)	−0.0195 (18)	−0.028 (2)	0.0075 (18)
C14	0.088 (3)	0.112 (4)	0.075 (3)	−0.039 (3)	−0.029 (3)	0.006 (3)
C13	0.061 (2)	0.062 (2)	0.074 (3)	−0.0238 (18)	−0.020 (2)	0.0042 (19)
C12	0.058 (2)	0.070 (3)	0.081 (3)	−0.0162 (19)	−0.021 (2)	0.001 (2)
O1	0.074 (2)	0.090 (2)	0.080 (2)	−0.0201 (16)	−0.0068 (16)	0.0035 (16)
O2	0.0637 (18)	0.090 (2)	0.087 (2)	−0.0200 (15)	−0.0310 (15)	0.0082 (16)
O3	0.0652 (18)	0.092 (2)	0.0743 (19)	−0.0280 (15)	−0.0279 (14)	0.0066 (15)

Geometric parameters (Å, º) top

C1—O1	1.408 (5)	C11—C12	1.492 (5)
C1—H1A	0.9600	C19—O2	1.227 (4)
C1—H1B	0.9600	C19—C18	1.469 (5)
C1—H1C	0.9600	C18—C13	1.386 (5)
C2—O1	1.357 (5)	C18—C17	1.390 (5)
C2—C3	1.378 (5)	C17—C16	1.373 (6)
C2—C7	1.380 (6)	C17—H17	0.9300
C3—C4	1.356 (5)	C16—C15	1.376 (7)
C3—H3	0.9300	C16—H16	0.9300
C4—C5	1.395 (5)	C15—C14	1.360 (6)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.386 (5)	C7—C6	1.380 (5)
C5—C8	1.444 (5)	C7—H7	0.9300
C8—C9	1.337 (5)	C6—H6	0.9300
C8—H8	0.9300	C14—C13	1.380 (6)
C9—C10	1.421 (5)	C14—H14	0.9300
C9—H9	0.9300	C13—O3	1.354 (4)
C10—C11	1.334 (5)	C12—O3	1.439 (5)
C10—H10	0.9300	C12—H12A	0.9700
C11—C19	1.462 (5)	C12—H12B	0.9700

O1—C1—H1A	109.5	C13—C18—C17	118.3 (4)
O1—C1—H1B	109.5	C13—C18—C19	120.5 (3)
H1A—C1—H1B	109.5	C17—C18—C19	121.0 (3)
O1—C1—H1C	109.5	C16—C17—C18	121.1 (4)
H1A—C1—H1C	109.5	C16—C17—H17	119.4
H1B—C1—H1C	109.5	C18—C17—H17	119.4
O1—C2—C3	116.0 (3)	C17—C16—C15	119.1 (4)
O1—C2—C7	125.1 (4)	C17—C16—H16	120.5
C3—C2—C7	118.9 (4)	C15—C16—H16	120.5
C4—C3—C2	121.2 (4)	C14—C15—C16	121.2 (5)
C4—C3—H3	119.4	C14—C15—H15	119.4
C2—C3—H3	119.4	C16—C15—H15	119.4
C3—C4—C5	121.5 (4)	C2—C7—C6	119.7 (4)
C3—C4—H4	119.3	C2—C7—H7	120.1
C5—C4—H4	119.3	C6—C7—H7	120.1
C6—C5—C4	116.8 (4)	C7—C6—C5	122.0 (4)
C6—C5—C8	120.2 (3)	C7—C6—H6	119.0
C4—C5—C8	123.0 (4)	C5—C6—H6	119.0
C9—C8—C5	127.0 (4)	C15—C14—C13	119.7 (4)
C9—C8—H8	116.5	C15—C14—H14	120.1
C5—C8—H8	116.5	C13—C14—H14	120.1
C8—C9—C10	124.4 (4)	O3—C13—C14	116.9 (4)
C8—C9—H9	117.8	O3—C13—C18	122.5 (4)
C10—C9—H9	117.8	C14—C13—C18	120.6 (4)
C11—C10—C9	127.0 (4)	O3—C12—C11	114.2 (3)
C11—C10—H10	116.5	O3—C12—H12A	108.7
C9—C10—H10	116.5	C11—C12—H12A	108.7
C10—C11—C19	121.0 (3)	O3—C12—H12B	108.7
C10—C11—C12	122.8 (3)	C11—C12—H12B	108.7
C19—C11—C12	116.1 (3)	H12A—C12—H12B	107.6
O2—C19—C11	123.0 (4)	C2—O1—C1	119.0 (4)
O2—C19—C18	121.0 (3)	C13—O3—C12	116.3 (3)
C11—C19—C18	116.0 (3)

O1—C2—C3—C4	−179.8 (3)	C18—C17—C16—C15	−0.8 (7)
C7—C2—C3—C4	−1.3 (6)	C17—C16—C15—C14	0.8 (8)
C2—C3—C4—C5	0.0 (6)	O1—C2—C7—C6	179.9 (3)
C3—C4—C5—C6	1.0 (5)	C3—C2—C7—C6	1.6 (6)
C3—C4—C5—C8	−177.1 (3)	C2—C7—C6—C5	−0.6 (6)
C6—C5—C8—C9	−176.1 (3)	C4—C5—C6—C7	−0.8 (5)
C4—C5—C8—C9	2.0 (6)	C8—C5—C6—C7	177.4 (3)
C5—C8—C9—C10	179.1 (3)	C16—C15—C14—C13	0.0 (8)
C8—C9—C10—C11	178.7 (3)	C15—C14—C13—O3	−179.1 (4)
C9—C10—C11—C19	177.7 (3)	C15—C14—C13—C18	−0.9 (7)
C9—C10—C11—C12	0.6 (6)	C17—C18—C13—O3	179.0 (3)
C10—C11—C19—O2	−10.5 (5)	C19—C18—C13—O3	3.7 (5)
C12—C11—C19—O2	166.8 (3)	C17—C18—C13—C14	1.0 (6)
C10—C11—C19—C18	168.7 (3)	C19—C18—C13—C14	−174.3 (4)
C12—C11—C19—C18	−14.0 (4)	C10—C11—C12—O3	−143.7 (3)
O2—C19—C18—C13	171.7 (3)	C19—C11—C12—O3	39.0 (5)
C11—C19—C18—C13	−7.5 (5)	C3—C2—O1—C1	−174.7 (4)
O2—C19—C18—C17	−3.5 (5)	C7—C2—O1—C1	7.0 (6)
C11—C19—C18—C17	177.3 (3)	C14—C13—O3—C12	−159.3 (4)
C13—C18—C17—C16	−0.2 (6)	C18—C13—O3—C12	22.6 (5)
C19—C18—C17—C16	175.2 (4)	C11—C12—O3—C13	−43.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O2ⁱ	0.93	2.59	3.362 (5)	141
C17—H17···O3ⁱⁱ	0.93	2.53	3.342 (5)	146

Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1, y, z.

Acknowledgements

The authors thank the Central Instrumentation Facility, Queen Mary's College, Chennai-4 for providing computing facilities and SAIF, IIT, Madras, for the X-ray data collection.

References

Bruker (2016). APEX3, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. New York: John Wiley. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gopaul, K., Shaikh, M. M., Koorbanally, N. A., Ramjugernath, D. & Omondi, B. (2012). Acta Cryst. E68, o1972. CSD CrossRef IUCr Journals Google Scholar
Jasinski, J. P., Pek, A. E., Narayana, B., Kamath, P. K. & Yathirajan, H. S. (2010). Acta Cryst. E66, o1995. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.