organic compounds
(3E)-3-[(2E)-3-(4-Methoxyphenyl)prop-2-enylidene]-2,3-dihydro-4H-chromen-4-one
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
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 et al., 2010). The radical quenching properties of the phenolic groups present in many 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).
are polyhydroxylated in the aryl rings (JasinskiThe 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 (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).
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 .
details are summarized in Table 2Structural data
CCDC reference: 1842509
https://doi.org/10.1107/S2414314618008295/hb4235sup1.cif
contains datablock I. DOI: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
Data collection: APEX3 (Bruker, 2016); cell
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).C19H16O3 | Z = 2 |
Mr = 292.32 | F(000) = 308 |
Triclinic, P1 | Dx = 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 |
Bruker APEXIII CMOS diffractometer | 1609 reflections with I > 2σ(I) |
φ and ω scans | Rint = 0.092 |
Absorption correction: multi-scan (SADABS) | θmax = 25.0°, θmin = 2.9° |
Tmin = 0.987, Tmax = 0.991 | h = −8→8 |
20521 measured reflections | k = −8→8 |
2589 independent reflections | l = −18→18 |
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(Fo2) + (0.0879P)2 + 0.7561P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.251 | (Δ/σ)max < 0.001 |
S = 1.12 | Δρmax = 0.24 e Å−3 |
2580 reflections | Δρmin = −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 |
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 Uiso(H)= 1.5 Ueq(c-methyl),and Uiso(H)= 1.2Ueq(C) for other H atom. |
x | y | z | Uiso*/Ueq | ||
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) |
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) |
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) |
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.