organic compounds
(2E)-1-(3,5-Dihydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one
aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and bPG and Research Department of Chemistry, Presidency College, Chennai-5, Tamil Nadu, India
*Correspondence e-mail: guqmc@yahoo.com
In the title compound, C16H14O4, the benzene rings are inclined to one another by 4.91 (7)°. The conformation about the C=O and C=C bonds is trans and cis, respectively. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming inversion dimers with an R22(14) ring motif. The dimers are linked via O—H⋯O and C—H⋯O hydrogen bonds, forming undulating two-dimensional networks lying parallel to (10-1). These networks are linked by further C—H⋯O hydrogen bonds, forming a three-dimensional structure.
CCDC reference: 998945
Related literature
For the biological activity of chalcone derivatives, see: Shenvi et al. (2013); Sharma et al. (2012); Hsieh et al. (2012); Sashidhara et al. (2011). For related structures, see: Ahn et al. (2013); Jasinski et al. (2011). For standard bend lengths, see: Allen et al. (1987). For the synthesis, see: Shettigar et al. (2006); Patil et al. (2007). For graph-set notation, see: Bernstein et al. (1995).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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 and PLATON (Spek, 2009).
Supporting information
CCDC reference: 998945
10.1107/S1600536814009155/su2727sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814009155/su2727Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814009155/su2727Isup3.cml
The title compound was syntheized by the base catalyzed Claisen-Schmidt reaction according to the published procedures (Shettigar et al., 2006; Patil et al., 2007). In a 250 ml round-bottomed flask 3,5-hydroxyacetophenone (0.05 mol) and 4-methoxybenzaldehyde (0.05 mol) were placed and 120 ml of absolute alcohol were added. The mixture was stirred at room temperature for 5 min. Then 20 ml of 20% sodium hydroxide solution was added and the mixture was stirred for 2 h. The precipitate generated by adding a sufficient amount of dilute hydrochloric acid was filtered, washed with water and dried. The crude product was recrystallized twice from absolute alcohol yielding colourless block-like crystals (Yield 79%; M.p. 477 K).
H atoms were positioned geometrically and treated as riding atoms: O—H = 0.82 Å, C—H =0.93 – 0.96 Å, with Uiso(H)= 1.5Ueq(O and C-methyl) and = 1.2Ueq(C) for other H atom.
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level. | |
Fig. 2. The crystal packing of the title compound viewed along the a axis. The dashed lines indicate the hydrogen bonds (see Table 1 for details). |
C16H14O4 | F(000) = 568 |
Mr = 270.28 | Dx = 1.342 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 3402 reflections |
a = 9.1920 (9) Å | θ = 2.4–28.5° |
b = 13.8931 (13) Å | µ = 0.10 mm−1 |
c = 10.9299 (10) Å | T = 293 K |
β = 106.619 (2)° | Block, colourless |
V = 1337.5 (2) Å3 | 0.22 × 0.20 × 0.20 mm |
Z = 4 |
Bruker Kappa APEXII CCD diffractometer | 3402 independent reflections |
Radiation source: fine-focus sealed tube | 2617 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.032 |
ω and ϕ scan | θmax = 28.5°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −10→12 |
Tmin = 0.979, Tmax = 0.981 | k = −18→18 |
13378 measured reflections | l = −14→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.0868P)2 + 0.2822P] where P = (Fo2 + 2Fc2)/3 |
3384 reflections | (Δ/σ)max < 0.001 |
181 parameters | Δρmax = 0.22 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C16H14O4 | V = 1337.5 (2) Å3 |
Mr = 270.28 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 9.1920 (9) Å | µ = 0.10 mm−1 |
b = 13.8931 (13) Å | T = 293 K |
c = 10.9299 (10) Å | 0.22 × 0.20 × 0.20 mm |
β = 106.619 (2)° |
Bruker Kappa APEXII CCD diffractometer | 3402 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2617 reflections with I > 2σ(I) |
Tmin = 0.979, Tmax = 0.981 | Rint = 0.032 |
13378 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.22 e Å−3 |
3384 reflections | Δρmin = −0.17 e Å−3 |
181 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.24996 (15) | 0.22432 (10) | 0.12529 (12) | 0.0470 (3) | |
H1 | 0.2457 | 0.2550 | 0.1998 | 0.056* | |
C2 | 0.15728 (15) | 0.25425 (10) | 0.00768 (12) | 0.0447 (3) | |
C3 | 0.16469 (14) | 0.20929 (10) | −0.10413 (11) | 0.0429 (3) | |
H3 | 0.1017 | 0.2292 | −0.1827 | 0.051* | |
C4 | 0.26647 (14) | 0.13466 (9) | −0.09755 (11) | 0.0404 (3) | |
C5 | 0.35787 (15) | 0.10425 (10) | 0.01976 (11) | 0.0431 (3) | |
H5 | 0.4258 | 0.0538 | 0.0243 | 0.052* | |
C6 | 0.34818 (14) | 0.14885 (10) | 0.13033 (11) | 0.0427 (3) | |
C7 | 0.28664 (15) | 0.08504 (10) | −0.21300 (12) | 0.0455 (3) | |
C8 | 0.18574 (15) | 0.10638 (10) | −0.33903 (11) | 0.0440 (3) | |
H8 | 0.1070 | 0.1502 | −0.3473 | 0.053* | |
C9 | 0.20462 (15) | 0.06396 (10) | −0.44272 (12) | 0.0456 (3) | |
H9 | 0.2855 | 0.0212 | −0.4289 | 0.055* | |
C10 | 0.11515 (14) | 0.07605 (9) | −0.57409 (11) | 0.0414 (3) | |
C11 | 0.14639 (15) | 0.01784 (10) | −0.66808 (12) | 0.0461 (3) | |
H11 | 0.2250 | −0.0267 | −0.6448 | 0.055* | |
C12 | 0.06338 (16) | 0.02522 (10) | −0.79376 (12) | 0.0474 (3) | |
H12 | 0.0849 | −0.0147 | −0.8547 | 0.057* | |
C13 | −0.05233 (15) | 0.09213 (10) | −0.82969 (11) | 0.0423 (3) | |
C14 | −0.08502 (16) | 0.15125 (11) | −0.73877 (12) | 0.0477 (3) | |
H14 | −0.1623 | 0.1967 | −0.7627 | 0.057* | |
C15 | −0.00197 (16) | 0.14207 (10) | −0.61259 (12) | 0.0474 (3) | |
H15 | −0.0252 | 0.1812 | −0.5517 | 0.057* | |
C16 | −0.24683 (19) | 0.16157 (14) | −0.99921 (14) | 0.0642 (4) | |
H16A | −0.2893 | 0.1554 | −1.0899 | 0.096* | |
H16B | −0.2083 | 0.2257 | −0.9792 | 0.096* | |
H16C | −0.3240 | 0.1492 | −0.9578 | 0.096* | |
O1 | 0.39025 (14) | 0.02703 (10) | −0.19868 (9) | 0.0712 (4) | |
O2 | 0.43646 (11) | 0.11864 (8) | 0.24713 (8) | 0.0539 (3) | |
H2 | 0.4898 | 0.0736 | 0.2377 | 0.081* | |
O3 | 0.06007 (13) | 0.32813 (8) | 0.00670 (10) | 0.0626 (3) | |
H3A | 0.0110 | 0.3399 | −0.0671 | 0.094* | |
O4 | −0.12717 (12) | 0.09454 (8) | −0.95602 (9) | 0.0559 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0550 (7) | 0.0512 (8) | 0.0324 (6) | −0.0020 (6) | 0.0088 (5) | −0.0046 (5) |
C2 | 0.0490 (7) | 0.0439 (7) | 0.0394 (6) | −0.0002 (5) | 0.0098 (5) | −0.0002 (5) |
C3 | 0.0462 (6) | 0.0460 (7) | 0.0327 (6) | −0.0006 (5) | 0.0052 (5) | 0.0019 (5) |
C4 | 0.0452 (6) | 0.0422 (7) | 0.0303 (5) | −0.0040 (5) | 0.0051 (5) | −0.0014 (4) |
C5 | 0.0463 (6) | 0.0459 (7) | 0.0321 (6) | 0.0004 (5) | 0.0033 (5) | −0.0018 (5) |
C6 | 0.0462 (6) | 0.0480 (7) | 0.0290 (5) | −0.0075 (5) | 0.0027 (5) | −0.0010 (5) |
C7 | 0.0523 (7) | 0.0479 (7) | 0.0312 (6) | 0.0038 (5) | 0.0035 (5) | −0.0010 (5) |
C8 | 0.0495 (7) | 0.0465 (7) | 0.0312 (6) | 0.0022 (5) | 0.0036 (5) | 0.0003 (5) |
C9 | 0.0508 (7) | 0.0479 (7) | 0.0336 (6) | 0.0053 (5) | 0.0048 (5) | −0.0008 (5) |
C10 | 0.0479 (6) | 0.0437 (7) | 0.0302 (5) | 0.0002 (5) | 0.0073 (5) | −0.0022 (5) |
C11 | 0.0519 (7) | 0.0478 (7) | 0.0378 (6) | 0.0087 (6) | 0.0116 (5) | −0.0020 (5) |
C12 | 0.0592 (7) | 0.0504 (8) | 0.0337 (6) | 0.0040 (6) | 0.0149 (5) | −0.0068 (5) |
C13 | 0.0503 (7) | 0.0463 (7) | 0.0282 (5) | −0.0033 (5) | 0.0081 (5) | −0.0024 (5) |
C14 | 0.0536 (7) | 0.0487 (8) | 0.0366 (6) | 0.0107 (6) | 0.0062 (5) | −0.0043 (5) |
C15 | 0.0574 (8) | 0.0496 (7) | 0.0322 (6) | 0.0086 (6) | 0.0079 (5) | −0.0079 (5) |
C16 | 0.0666 (10) | 0.0746 (11) | 0.0406 (7) | 0.0090 (8) | −0.0018 (6) | 0.0036 (7) |
O1 | 0.0817 (8) | 0.0862 (9) | 0.0363 (5) | 0.0398 (7) | 0.0017 (5) | −0.0036 (5) |
O2 | 0.0619 (6) | 0.0627 (6) | 0.0286 (4) | 0.0080 (5) | −0.0006 (4) | −0.0031 (4) |
O3 | 0.0747 (7) | 0.0664 (7) | 0.0434 (5) | 0.0224 (5) | 0.0116 (5) | −0.0024 (5) |
O4 | 0.0678 (6) | 0.0644 (7) | 0.0293 (4) | 0.0076 (5) | 0.0036 (4) | −0.0044 (4) |
C1—C6 | 1.374 (2) | C10—C15 | 1.3850 (18) |
C1—C2 | 1.3873 (18) | C10—C11 | 1.4002 (17) |
C1—H1 | 0.9300 | C11—C12 | 1.3712 (17) |
C2—O3 | 1.3589 (16) | C11—H11 | 0.9300 |
C2—C3 | 1.3913 (18) | C12—C13 | 1.3823 (19) |
C3—C4 | 1.3846 (18) | C12—H12 | 0.9300 |
C3—H3 | 0.9300 | C13—O4 | 1.3555 (14) |
C4—C5 | 1.3829 (16) | C13—C14 | 1.3868 (18) |
C4—C7 | 1.4952 (18) | C14—C15 | 1.3780 (17) |
C5—C6 | 1.3835 (17) | C14—H14 | 0.9300 |
C5—H5 | 0.9300 | C15—H15 | 0.9300 |
C6—O2 | 1.3681 (14) | C16—O4 | 1.4152 (19) |
C7—O1 | 1.2230 (16) | C16—H16A | 0.9600 |
C7—C8 | 1.4542 (16) | C16—H16B | 0.9600 |
C8—C9 | 1.3320 (18) | C16—H16C | 0.9600 |
C8—H8 | 0.9300 | O2—H2 | 0.8200 |
C9—C10 | 1.4460 (16) | O3—H3A | 0.8200 |
C9—H9 | 0.9300 | ||
C6—C1—C2 | 119.21 (12) | C15—C10—C11 | 117.67 (11) |
C6—C1—H1 | 120.4 | C15—C10—C9 | 123.40 (11) |
C2—C1—H1 | 120.4 | C11—C10—C9 | 118.93 (12) |
O3—C2—C1 | 117.50 (12) | C12—C11—C10 | 121.31 (12) |
O3—C2—C3 | 121.97 (12) | C12—C11—H11 | 119.3 |
C1—C2—C3 | 120.53 (12) | C10—C11—H11 | 119.3 |
C4—C3—C2 | 119.52 (11) | C11—C12—C13 | 119.83 (12) |
C4—C3—H3 | 120.2 | C11—C12—H12 | 120.1 |
C2—C3—H3 | 120.2 | C13—C12—H12 | 120.1 |
C5—C4—C3 | 119.95 (12) | O4—C13—C12 | 115.54 (11) |
C5—C4—C7 | 116.91 (12) | O4—C13—C14 | 124.36 (12) |
C3—C4—C7 | 123.12 (11) | C12—C13—C14 | 120.10 (11) |
C4—C5—C6 | 119.95 (12) | C15—C14—C13 | 119.39 (12) |
C4—C5—H5 | 120.0 | C15—C14—H14 | 120.3 |
C6—C5—H5 | 120.0 | C13—C14—H14 | 120.3 |
O2—C6—C1 | 118.62 (11) | C14—C15—C10 | 121.69 (12) |
O2—C6—C5 | 120.56 (12) | C14—C15—H15 | 119.2 |
C1—C6—C5 | 120.82 (11) | C10—C15—H15 | 119.2 |
O1—C7—C8 | 121.19 (12) | O4—C16—H16A | 109.5 |
O1—C7—C4 | 118.41 (11) | O4—C16—H16B | 109.5 |
C8—C7—C4 | 120.40 (12) | H16A—C16—H16B | 109.5 |
C9—C8—C7 | 120.85 (12) | O4—C16—H16C | 109.5 |
C9—C8—H8 | 119.6 | H16A—C16—H16C | 109.5 |
C7—C8—H8 | 119.6 | H16B—C16—H16C | 109.5 |
C8—C9—C10 | 128.17 (13) | C6—O2—H2 | 109.5 |
C8—C9—H9 | 115.9 | C2—O3—H3A | 109.5 |
C10—C9—H9 | 115.9 | C13—O4—C16 | 118.40 (11) |
C6—C1—C2—O3 | 179.03 (12) | C4—C7—C8—C9 | 178.67 (13) |
C6—C1—C2—C3 | −0.8 (2) | C7—C8—C9—C10 | 179.53 (13) |
O3—C2—C3—C4 | 179.68 (12) | C8—C9—C10—C15 | 5.0 (2) |
C1—C2—C3—C4 | −0.6 (2) | C8—C9—C10—C11 | −174.38 (14) |
C2—C3—C4—C5 | 1.14 (19) | C15—C10—C11—C12 | −0.5 (2) |
C2—C3—C4—C7 | −177.38 (12) | C9—C10—C11—C12 | 178.91 (13) |
C3—C4—C5—C6 | −0.4 (2) | C10—C11—C12—C13 | 0.9 (2) |
C7—C4—C5—C6 | 178.19 (12) | C11—C12—C13—O4 | 179.54 (12) |
C2—C1—C6—O2 | −178.54 (12) | C11—C12—C13—C14 | −0.4 (2) |
C2—C1—C6—C5 | 1.5 (2) | O4—C13—C14—C15 | 179.57 (13) |
C4—C5—C6—O2 | 179.12 (12) | C12—C13—C14—C15 | −0.5 (2) |
C4—C5—C6—C1 | −0.9 (2) | C13—C14—C15—C10 | 0.9 (2) |
C5—C4—C7—O1 | −6.2 (2) | C11—C10—C15—C14 | −0.4 (2) |
C3—C4—C7—O1 | 172.31 (14) | C9—C10—C15—C14 | −179.79 (14) |
C5—C4—C7—C8 | 174.30 (12) | C12—C13—O4—C16 | −179.90 (14) |
C3—C4—C7—C8 | −7.1 (2) | C14—C13—O4—C16 | 0.0 (2) |
O1—C7—C8—C9 | −0.8 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.90 | 2.7196 (15) | 174 |
O3—H3A···O2ii | 0.82 | 2.03 | 2.8361 (14) | 167 |
C3—H3···O2ii | 0.93 | 2.59 | 3.2875 (17) | 132 |
C5—H5···O1i | 0.93 | 2.43 | 3.1498 (17) | 134 |
C12—H12···O4iii | 0.93 | 2.47 | 3.3926 (16) | 169 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y, −z−2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1i | 0.82 | 1.90 | 2.7196 (15) | 174 |
O3—H3A···O2ii | 0.82 | 2.03 | 2.8361 (14) | 167 |
C3—H3···O2ii | 0.93 | 2.59 | 3.2875 (17) | 132 |
C5—H5···O1i | 0.93 | 2.43 | 3.1498 (17) | 134 |
C12—H12···O4iii | 0.93 | 2.47 | 3.3926 (16) | 169 |
Symmetry codes: (i) −x+1, −y, −z; (ii) x−1/2, −y+1/2, z−1/2; (iii) −x, −y, −z−2. |
Acknowledgements
The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data-collection and computer facilities.
References
Ahn, S., Lee, H.-J., Lim, Y. & Koh, D. (2013). Acta Cryst. E69, o666. CSD CrossRef IUCr Journals Google Scholar
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343–350. CrossRef Web of Science IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hsieh, C.-T., Hsieh, T.-J., El-Shazly, M., Chuang, D.-W., Tsai, Y.-H., Yen, C.-T., Wu, S.-F., Wu, Y.-C. & Chang, F.-R. (2012). Bioorg. Med. Chem. Lett. 22, 3912–3915. Web of Science CrossRef CAS PubMed Google Scholar
Jasinski, J. P., Butcher, R. J., Musthafa Khaleel, V., Sarojini, B. K. & Yathirajan, H. S. (2011). Acta Cryst. E67, o845. Web of Science CSD CrossRef IUCr Journals Google Scholar
Patil, P. S., Dharmaprakash, S. M., Ramakrishna, V., Fun, H.-K., Kumar, R. S. S. & Rao, D. N. (2007). J. Cryst. Growth, 303, 520–524. Web of Science CrossRef CAS Google Scholar
Sashidhara, K. V., Kumar, M., Modukuri, R. M., Sonkar, R., Bhatia, G., Khanna, A. K., Rai, S. V. & Shukla, R. (2011). Bioorg. Med. Chem. Lett. 21, 4480–4484. Web of Science CrossRef CAS PubMed Google Scholar
Sharma, V., Singh, G., Kaur, H., Saxena, A. K. & Ishar, M. P. S. (2012). Bioorg. Med. Chem. Lett. 22, 6343–6346. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shenvi, S., Kumar, K., Hatti, K. S., Rijesh, K., Diwakar, L. & Reddy, G. C. (2013). Eur. J. Med. Chem. 62, 435–442. Web of Science CrossRef CAS PubMed Google Scholar
Shettigar, V., Patil, P. S., Naveen, S., Dharmaprakash, S. M., Sridhar, M. A. & Shashidhara, J. (2006). J. Cryst. Growth, 295, 44–49. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Chalcones are one of the secondary metabolites in plants and belong to a class of flavonoid. They have shown diverse biological activities including anticancer (Shenvi et al., 2013), antimicrobial (Sharma et al. 2012), antidiabetic (Hsieh et al., 2012) and antiinflammatory (Sashidhara et al., 2011). As part of our attempt to investigate how the substituent effects of chalcones effect the biological activities of various compounds, the title compound was synthesized and its crystal structure is reported herein.
The molecuar structure of the title compound is illustrated in Fig. 1. The bond lengths (Allen et al., 1987) and bond angles are within normal values. The benzene rings (C1-C6 and C10-C15) are inclined to one another by 4.91 (7) °. The torsion angles about the C7═O1 and C8═C9 bonds confirm the trans and cis conformations of the respective bonds. The C8═ C9 bond distance is 1.332 (2) Å, and is in good agreement with the value [1.329 (3) Å] reported for a similar structure (Ahn et al., 2013). The methoxy C atom and hydroxy O atoms are almost coplanar with the benezene ring to which they are attached. The bond angles C4—C7—C8 = 120.4 (1)° and C8—C9—C10 = 128.2 (1)° differ slightly from the normal values but are comparable with the values reported for a similar structure (Jasinski et al., 2011).
In the crystal, molecules are linked by O—H···O hydrogen bonds forming inversion dimers with a graph set motif of R22(14) [Bernstein et al., 1995]. The dimers are linked by O-H···O and C-H···O hydrogen bonds forming undulating two-dimensional networks lying parallel to (10-1) [Fig. 2 and Table 1]. These networks are linked by further C-H···O hydrogen bonds forming a three-dimensional structure (Table 1).