organic compounds
(E)-3-(4-Heptyloxyphenyl)-1-phenylprop-2-en-1-one
aDepartment of Chemistry, North Carolina A&T State University, Greensboro, NC 27411, USA
*Correspondence e-mail: mafranks@ncat.edu
In the title compound, C22H26O2, the aromatic rings are inclined to one another by 8.39 (9)° and the molecule has an E conformation about the C=C bond. In the crystal, molecules stack head-to-tail along the b-axis direction. They are linked by very weak C—H⋯O contacts, forming C(4) chains along [100]. Two chains are linked by a pair of very weak C—H⋯O contacts, enclosing inversion-dimeric R22(8) ring motifs. There are also C—H⋯π interactions present, which link the double-stranded chains, forming a two-dimensional network.
CCDC reference: 978369
Related literature
For general background to et al. (1998); Indira et al. (2002); Treadwell (2006). For their various biological properties, see: Avila et al. (2008); ElSohly et al. (2001); Gafner et al. (1996); Akihisa et al. (2003); Szliszka et al. (2009); Xia et al. (2000); Lahtchev et al. (2008); Bandgar et al. (2010). For their enhanced cytotoxicity towards certain cancers, see: Won et al. (2005). For examples of with general formula Ar—CH–CH—CO—Ar, with molecular pairing involving π–π interactions and hydrogen-bonding, see: Wang et al. (2005). For related halogen derivatives, see: Dutkiewicz et al. (2010); Qiu et al. (2006).
see: UchidaExperimental
Crystal data
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Data collection: SMART (Bruker, 2005; cell SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: JMol (Hanson, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
CCDC reference: 978369
10.1107/S1600536813034429/zp2008sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536813034429/zp2008Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536813034429/zp2008Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536813034429/zp2008Isup4.cml
The title compound was obtained by mixing acetophenone (0.150 g, 1.22 mmol), 4-(heptyloxy)benzaldehyde (0.269 g, 1.22 mmol), a 10% solution of NaOH and ethanol at 273 K for 18 h, after which it was acidified with 1 N HCl. The crude product obtained was recrystallized from ethanol yielding yellow plate-like crystals.
Chalcones along with their derivatives can easily be obtained by means of isolation from natural products or synthesized by classic scientific methods. These compounds are interesting in the medical field because of their antibacterial (Avila et al., 2008), antifungal (ElSohly et al., 2001; Gafner et al., 1996), antitumor (Akihisa et al., 2003; Szliszka et al., 2009; Xia et al., 2000; Lahtchev et al., 2008) and anti-inflammatory properties (Bandgar et al., 2010). These compounds have also shown enhanced cytotoxicity towards certain cancers (Won et al., 2005). Synthetically α,β-unsaturated carbonyl system, and we report herein on its crystal structure.
are derived through an aldol condensation which involves the reaction between an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a strong base (hydroxide or alkoxide). The resulting compound contains two aromatic rings joined by a three carbonThe molecular structure of the title molecule is illustrated in Fig. 1. The two aromatic rings (C4–C9 and C17–C22) are inclined to one another by 8.39 (9)° and the molecule has an E conformation about the C2═C3 bond.
In the crystal, the molecules stack head-to-tail along the b axis. They molecules are linked by very weak C-H···O and C-H···π interactions (Table 1). Atom O1 of the carbonyl group interacts with the H atom, H2, of the C2═ C3 double bond in a C═O···HC═C fashion, resulting in the formation of C(4) chains along the a-axis direction. In addition, the O atom, O2, of the ether moiety is also involved in a weak hydrogen bond with the central phenyl group of an inversion related neighboring molecule. The two molecules are arranged head-to-tail, which induces formation of an inversion dimeric unit and an eight-membered R22(8) ring containing a pair of very weak C-H···O hydrogen bonds (Table 1).
As a result of the head-to-tail flipping, there is no ring alignment within the structure, hence the system lacks any significant π–π interactions but there are C—H···π contacts present (Table 1) which link the double stranded chains to form a two-dimensional network.
For general background to π–π interactions and hydrogen-bonding, see: Wang et al. (2005). For related halogen derivatives, see: Dutkiewicz et al. (2010); Qiu et al. (2006).
see: Uchida et al. (1998); Indira et al. (2002); Treadwell (2006). For their various biological properties, see: Avila et al. (2008); ElSohly et al. (2001); Gafner et al. (1996); Akihisa et al. (2003); Szliszka et al. (2009); Xia et al. (2000); Lahtchev et al. (2008); Bandgar et al. (2010). For their enhanced cytotoxicity towards certain cancers, see: Won et al. (2005). For examples of with general formula Ar—CH–CH—CO—Ar, with molecular pairing involvingData collection: SMART (Bruker, 2005; cell
SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: JMol (Hanson, 2010); software used to prepare material for publication: publCIF (Westrip, 2010).Fig. 1. A view of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. |
C22H26O2 | Z = 2 |
Mr = 322.43 | F(000) = 348 |
Triclinic, P1 | Dx = 1.157 Mg m−3 |
a = 5.6069 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 7.7822 (13) Å | Cell parameters from 2314 reflections |
c = 22.864 (4) Å | θ = 0.9–25.1° |
α = 81.101 (5)° | µ = 0.07 mm−1 |
β = 85.571 (5)° | T = 200 K |
γ = 69.879 (4)° | Plate, yellow |
V = 925.2 (3) Å3 | 0.50 × 0.26 × 0.16 mm |
Bruker X2S diffractometer | 3149 independent reflections |
Radiation source: fine-focus sealed tube | 2314 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
automatic scans | θmax = 25.1°, θmin = 0.9° |
Absorption correction: multi-scan (SADABS, Bruker, 2005) | h = −6→6 |
Tmin = 0.965, Tmax = 0.989 | k = −9→9 |
5754 measured reflections | l = −27→27 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | All H-atom parameters refined |
wR(F2) = 0.152 | w = 1/[σ2(Fo2) + (0.0807P)2 + 0.0136P] where P = (Fo2 + 2Fc2)/3 |
S = 1.09 | (Δ/σ)max = 0.001 |
3149 reflections | Δρmax = 0.44 e Å−3 |
322 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.055 (8) |
C22H26O2 | γ = 69.879 (4)° |
Mr = 322.43 | V = 925.2 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.6069 (9) Å | Mo Kα radiation |
b = 7.7822 (13) Å | µ = 0.07 mm−1 |
c = 22.864 (4) Å | T = 200 K |
α = 81.101 (5)° | 0.50 × 0.26 × 0.16 mm |
β = 85.571 (5)° |
Bruker X2S diffractometer | 3149 independent reflections |
Absorption correction: multi-scan (SADABS, Bruker, 2005) | 2314 reflections with I > 2σ(I) |
Tmin = 0.965, Tmax = 0.989 | Rint = 0.044 |
5754 measured reflections |
R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
wR(F2) = 0.152 | All H-atom parameters refined |
S = 1.09 | Δρmax = 0.44 e Å−3 |
3149 reflections | Δρmin = −0.24 e Å−3 |
322 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 | 0.0523 (3) | 0.7906 (2) | 0.72962 (7) | 0.0430 (4) | |
C2 | 0.2373 (3) | 0.7615 (2) | 0.77569 (7) | 0.0400 (4) | |
C3 | 0.1563 (3) | 0.7911 (2) | 0.83070 (7) | 0.0387 (4) | |
C4 | 0.3023 (3) | 0.7649 (2) | 0.88344 (7) | 0.0364 (4) | |
C5 | 0.1749 (3) | 0.8252 (2) | 0.93499 (7) | 0.0413 (4) | |
C6 | 0.2981 (3) | 0.8036 (2) | 0.98702 (8) | 0.0416 (4) | |
C7 | 0.5591 (3) | 0.7171 (2) | 0.98833 (7) | 0.0351 (4) | |
C8 | 0.6904 (3) | 0.6503 (2) | 0.93778 (7) | 0.0390 (4) | |
C9 | 0.5660 (3) | 0.6753 (2) | 0.88623 (7) | 0.0382 (4) | |
C10 | 0.5762 (3) | 0.7608 (2) | 1.08943 (7) | 0.0402 (4) | |
C11 | 0.7707 (3) | 0.7139 (2) | 1.13640 (7) | 0.0417 (4) | |
C12 | 0.6526 (3) | 0.7708 (2) | 1.19529 (7) | 0.0434 (5) | |
C13 | 0.8447 (4) | 0.7246 (2) | 1.24366 (8) | 0.0449 (5) | |
C14 | 0.7285 (4) | 0.7721 (2) | 1.30362 (8) | 0.0471 (5) | |
C15 | 0.9149 (4) | 0.7081 (3) | 1.35305 (9) | 0.0608 (6) | |
C16 | 0.7959 (7) | 0.7512 (4) | 1.41297 (10) | 0.0790 (7) | |
C17 | 0.3892 (4) | 0.6901 (3) | 0.64939 (8) | 0.0485 (5) | |
C18 | 0.4548 (4) | 0.6707 (3) | 0.59057 (9) | 0.0582 (5) | |
C19 | 0.2705 (4) | 0.7373 (3) | 0.54822 (9) | 0.0596 (6) | |
C20 | 0.0207 (4) | 0.8227 (3) | 0.56481 (8) | 0.0580 (6) | |
C21 | −0.0447 (4) | 0.8401 (3) | 0.62334 (8) | 0.0492 (5) | |
C22 | 0.1388 (3) | 0.7733 (2) | 0.66679 (7) | 0.0403 (4) | |
O1 | −0.1746 (2) | 0.8262 (2) | 0.74253 (5) | 0.0659 (5) | |
O2 | 0.7021 (2) | 0.68945 (15) | 1.03686 (5) | 0.0435 (3) | |
H2 | 0.421 (4) | 0.718 (2) | 0.7647 (7) | 0.049 (5)* | |
H3 | −0.021 (4) | 0.828 (2) | 0.8379 (7) | 0.047 (5)* | |
H5 | −0.003 (3) | 0.881 (2) | 0.9330 (7) | 0.044 (5)* | |
H6 | 0.206 (3) | 0.843 (2) | 1.0227 (8) | 0.051 (5)* | |
H8 | 0.867 (3) | 0.587 (2) | 0.9416 (7) | 0.040 (4)* | |
H9 | 0.660 (3) | 0.629 (2) | 0.8518 (7) | 0.043 (4)* | |
H10A | 0.444 (3) | 0.700 (2) | 1.1034 (7) | 0.053 (5)* | |
H10B | 0.496 (3) | 0.895 (2) | 1.0810 (7) | 0.044 (4)* | |
H11A | 0.898 (3) | 0.775 (2) | 1.1222 (7) | 0.049 (5)* | |
H11B | 0.860 (3) | 0.578 (2) | 1.1418 (7) | 0.042 (4)* | |
H12A | 0.534 (4) | 0.700 (2) | 1.2111 (8) | 0.059 (5)* | |
H12B | 0.563 (3) | 0.899 (3) | 1.1912 (8) | 0.052 (5)* | |
H13A | 0.967 (4) | 0.790 (2) | 1.2316 (8) | 0.058 (5)* | |
H13B | 0.938 (4) | 0.588 (3) | 1.2473 (8) | 0.059 (5)* | |
H14A | 0.644 (3) | 0.901 (3) | 1.3017 (7) | 0.051 (5)* | |
H14B | 0.601 (4) | 0.711 (3) | 1.3149 (8) | 0.064 (6)* | |
H15A | 1.048 (4) | 0.763 (3) | 1.3422 (8) | 0.070 (6)* | |
H15B | 0.994 (4) | 0.571 (3) | 1.3551 (9) | 0.076 (6)* | |
H16A | 0.719 (4) | 0.880 (3) | 1.4161 (9) | 0.078 (7)* | |
H16B | 0.917 (5) | 0.698 (4) | 1.4446 (13) | 0.119 (10)* | |
H16C | 0.656 (5) | 0.692 (4) | 1.4224 (12) | 0.121 (10)* | |
H17 | 0.517 (3) | 0.644 (2) | 0.6772 (8) | 0.048 (5)* | |
H18 | 0.630 (4) | 0.611 (2) | 0.5772 (8) | 0.064 (6)* | |
H19 | 0.319 (4) | 0.725 (3) | 0.5065 (9) | 0.068 (6)* | |
H20 | −0.115 (4) | 0.867 (3) | 0.5363 (9) | 0.067 (6)* | |
H21 | −0.219 (4) | 0.898 (3) | 0.6362 (8) | 0.060 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0374 (11) | 0.0448 (9) | 0.0462 (10) | −0.0142 (8) | −0.0048 (8) | −0.0014 (7) |
C2 | 0.0357 (11) | 0.0423 (9) | 0.0413 (10) | −0.0133 (8) | −0.0032 (8) | −0.0020 (7) |
C3 | 0.0334 (10) | 0.0376 (8) | 0.0438 (10) | −0.0111 (7) | −0.0014 (8) | −0.0036 (7) |
C4 | 0.0374 (10) | 0.0317 (8) | 0.0400 (9) | −0.0119 (7) | −0.0008 (7) | −0.0044 (7) |
C5 | 0.0318 (10) | 0.0410 (9) | 0.0486 (11) | −0.0074 (8) | 0.0003 (8) | −0.0111 (7) |
C6 | 0.0393 (11) | 0.0432 (9) | 0.0406 (10) | −0.0095 (8) | 0.0040 (8) | −0.0135 (7) |
C7 | 0.0373 (10) | 0.0312 (7) | 0.0350 (9) | −0.0095 (7) | −0.0003 (7) | −0.0041 (6) |
C8 | 0.0325 (10) | 0.0401 (9) | 0.0399 (9) | −0.0072 (8) | 0.0010 (8) | −0.0046 (7) |
C9 | 0.0366 (10) | 0.0397 (8) | 0.0351 (9) | −0.0094 (7) | 0.0032 (8) | −0.0057 (7) |
C10 | 0.0432 (11) | 0.0379 (9) | 0.0368 (9) | −0.0094 (8) | 0.0036 (8) | −0.0091 (7) |
C11 | 0.0459 (11) | 0.0386 (9) | 0.0380 (10) | −0.0109 (8) | −0.0013 (8) | −0.0052 (7) |
C12 | 0.0455 (11) | 0.0410 (9) | 0.0403 (10) | −0.0096 (8) | −0.0023 (8) | −0.0066 (7) |
C13 | 0.0493 (11) | 0.0390 (9) | 0.0425 (10) | −0.0088 (8) | −0.0060 (8) | −0.0059 (7) |
C14 | 0.0545 (12) | 0.0414 (10) | 0.0426 (10) | −0.0120 (9) | −0.0046 (9) | −0.0055 (8) |
C15 | 0.0751 (15) | 0.0541 (12) | 0.0495 (12) | −0.0130 (11) | −0.0172 (11) | −0.0088 (9) |
C16 | 0.119 (2) | 0.0727 (16) | 0.0472 (13) | −0.0301 (16) | −0.0154 (14) | −0.0122 (11) |
C17 | 0.0422 (12) | 0.0569 (10) | 0.0458 (11) | −0.0149 (9) | −0.0054 (9) | −0.0073 (8) |
C18 | 0.0522 (13) | 0.0721 (13) | 0.0516 (12) | −0.0205 (10) | 0.0036 (10) | −0.0159 (10) |
C19 | 0.0697 (15) | 0.0743 (13) | 0.0412 (11) | −0.0317 (12) | 0.0002 (10) | −0.0105 (10) |
C20 | 0.0625 (15) | 0.0695 (13) | 0.0449 (12) | −0.0264 (11) | −0.0144 (10) | −0.0007 (9) |
C21 | 0.0446 (12) | 0.0557 (11) | 0.0475 (11) | −0.0181 (9) | −0.0078 (9) | −0.0022 (8) |
C22 | 0.0438 (11) | 0.0398 (9) | 0.0404 (9) | −0.0186 (8) | −0.0052 (8) | −0.0028 (7) |
O1 | 0.0394 (9) | 0.1036 (11) | 0.0515 (8) | −0.0195 (7) | −0.0026 (6) | −0.0110 (7) |
O2 | 0.0394 (7) | 0.0494 (7) | 0.0347 (7) | −0.0047 (5) | −0.0026 (5) | −0.0088 (5) |
C1—O1 | 1.228 (2) | C12—H12A | 1.014 (18) |
C1—C2 | 1.473 (2) | C12—H12B | 0.940 (18) |
C1—C22 | 1.491 (2) | C13—C14 | 1.515 (2) |
C2—C3 | 1.331 (2) | C13—H13A | 0.986 (18) |
C2—H2 | 0.991 (19) | C13—H13B | 1.005 (19) |
C3—C4 | 1.459 (2) | C14—C15 | 1.506 (3) |
C3—H3 | 0.944 (18) | C14—H14A | 0.947 (19) |
C4—C5 | 1.389 (2) | C14—H14B | 0.99 (2) |
C4—C9 | 1.403 (2) | C15—C16 | 1.510 (3) |
C5—C6 | 1.380 (2) | C15—H15A | 0.98 (2) |
C5—H5 | 0.944 (18) | C15—H15B | 1.00 (2) |
C6—C7 | 1.385 (2) | C16—H16A | 0.95 (2) |
C6—H6 | 0.963 (18) | C16—H16B | 0.97 (3) |
C7—O2 | 1.3659 (19) | C16—H16C | 1.03 (3) |
C7—C8 | 1.393 (2) | C17—C18 | 1.384 (3) |
C8—C9 | 1.370 (2) | C17—C22 | 1.385 (3) |
C8—H8 | 0.945 (18) | C17—H17 | 0.934 (18) |
C9—H9 | 0.959 (17) | C18—C19 | 1.380 (3) |
C10—O2 | 1.4343 (19) | C18—H18 | 0.98 (2) |
C10—C11 | 1.504 (2) | C19—C20 | 1.379 (3) |
C10—H10A | 1.019 (17) | C19—H19 | 0.982 (19) |
C10—H10B | 0.977 (17) | C20—C21 | 1.375 (3) |
C11—C12 | 1.514 (2) | C20—H20 | 0.97 (2) |
C11—H11A | 0.992 (17) | C21—C22 | 1.395 (2) |
C11—H11B | 0.995 (17) | C21—H21 | 0.966 (19) |
C12—C13 | 1.519 (2) | ||
O1—C1—C2 | 120.52 (15) | H12A—C12—H12B | 110.1 (16) |
O1—C1—C22 | 119.01 (15) | C14—C13—C12 | 114.23 (15) |
C2—C1—C22 | 120.45 (15) | C14—C13—H13A | 108.9 (10) |
C3—C2—C1 | 119.86 (16) | C12—C13—H13A | 109.1 (11) |
C3—C2—H2 | 121.6 (10) | C14—C13—H13B | 108.6 (10) |
C1—C2—H2 | 118.5 (10) | C12—C13—H13B | 107.0 (10) |
C2—C3—C4 | 129.51 (17) | H13A—C13—H13B | 108.9 (15) |
C2—C3—H3 | 116.6 (10) | C15—C14—C13 | 114.37 (17) |
C4—C3—H3 | 113.8 (10) | C15—C14—H14A | 109.2 (10) |
C5—C4—C9 | 117.15 (15) | C13—C14—H14A | 110.3 (10) |
C5—C4—C3 | 118.98 (15) | C15—C14—H14B | 106.2 (11) |
C9—C4—C3 | 123.82 (15) | C13—C14—H14B | 108.9 (10) |
C6—C5—C4 | 122.69 (17) | H14A—C14—H14B | 107.6 (16) |
C6—C5—H5 | 120.8 (10) | C14—C15—C16 | 114.0 (2) |
C4—C5—H5 | 116.5 (10) | C14—C15—H15A | 107.9 (12) |
C5—C6—C7 | 118.98 (16) | C16—C15—H15A | 111.3 (12) |
C5—C6—H6 | 121.5 (11) | C14—C15—H15B | 107.1 (12) |
C7—C6—H6 | 119.5 (11) | C16—C15—H15B | 108.3 (11) |
O2—C7—C6 | 124.38 (14) | H15A—C15—H15B | 108.1 (18) |
O2—C7—C8 | 116.11 (14) | C15—C16—H16A | 114.9 (13) |
C6—C7—C8 | 119.51 (15) | C15—C16—H16B | 112.3 (17) |
C9—C8—C7 | 120.79 (16) | H16A—C16—H16B | 107 (2) |
C9—C8—H8 | 123.0 (9) | C15—C16—H16C | 108.7 (15) |
C7—C8—H8 | 116.2 (9) | H16A—C16—H16C | 107 (2) |
C8—C9—C4 | 120.84 (16) | H16B—C16—H16C | 106 (2) |
C8—C9—H9 | 119.5 (10) | C18—C17—C22 | 120.81 (18) |
C4—C9—H9 | 119.7 (10) | C18—C17—H17 | 118.4 (11) |
O2—C10—C11 | 108.43 (13) | C22—C17—H17 | 120.8 (11) |
O2—C10—H10A | 108.8 (9) | C19—C18—C17 | 120.1 (2) |
C11—C10—H10A | 109.4 (10) | C19—C18—H18 | 117.5 (11) |
O2—C10—H10B | 109.6 (9) | C17—C18—H18 | 122.4 (11) |
C11—C10—H10B | 109.8 (10) | C20—C19—C18 | 119.71 (19) |
H10A—C10—H10B | 110.8 (14) | C20—C19—H19 | 120.7 (12) |
C10—C11—C12 | 112.39 (14) | C18—C19—H19 | 119.6 (12) |
C10—C11—H11A | 108.4 (10) | C21—C20—C19 | 120.16 (19) |
C12—C11—H11A | 110.8 (9) | C21—C20—H20 | 118.0 (12) |
C10—C11—H11B | 108.5 (9) | C19—C20—H20 | 121.8 (12) |
C12—C11—H11B | 108.7 (9) | C20—C21—C22 | 120.95 (19) |
H11A—C11—H11B | 107.9 (14) | C20—C21—H21 | 121.8 (11) |
C11—C12—C13 | 113.55 (15) | C22—C21—H21 | 117.3 (11) |
C11—C12—H12A | 110.2 (10) | C17—C22—C21 | 118.26 (16) |
C13—C12—H12A | 104.3 (10) | C17—C22—C1 | 123.77 (15) |
C11—C12—H12B | 110.4 (11) | C21—C22—C1 | 117.95 (15) |
C13—C12—H12B | 108.2 (11) | C7—O2—C10 | 118.10 (12) |
Cg1 and Cg2 are the centroids of rings C4–C9 and C17–C22, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.99 (2) | 2.67 (2) | 3.513 (2) | 143.3 (12) |
C8—H8···O2ii | 0.95 (2) | 2.64 (2) | 3.545 (2) | 159.3 (13) |
C10—H10B···Cg1iii | 0.98 (2) | 2.972 (15) | 3.8279 (18) | 146.6 (13) |
C16—H16A···Cg2iii | 0.97 (3) | 2.97 (2) | 3.792 (3) | 144.5 (18) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+2, −z+2. |
Cg1 and Cg2 are the centroids of rings C4–C9 and C17–C22, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C2—H2···O1i | 0.99 (2) | 2.67 (2) | 3.513 (2) | 143.3 (12) |
C8—H8···O2ii | 0.95 (2) | 2.64 (2) | 3.545 (2) | 159.3 (13) |
C10—H10B···Cg1iii | 0.98 (2) | 2.972 (15) | 3.8279 (18) | 146.6 (13) |
C16—H16A···Cg2iii | 0.97 (3) | 2.97 (2) | 3.792 (3) | 144.5 (18) |
Symmetry codes: (i) x+1, y, z; (ii) −x+2, −y+1, −z+2; (iii) −x+1, −y+2, −z+2. |
Acknowledgements
Support from the National Science Foundation (CHE-0959406) for the purchase of the X-ray diffractometer is gratefully acknowledged.
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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.
Chalcones along with their derivatives can easily be obtained by means of isolation from natural products or synthesized by classic scientific methods. These compounds are interesting in the medical field because of their antibacterial (Avila et al., 2008), antifungal (ElSohly et al., 2001; Gafner et al., 1996), antitumor (Akihisa et al., 2003; Szliszka et al., 2009; Xia et al., 2000; Lahtchev et al., 2008) and anti-inflammatory properties (Bandgar et al., 2010). These compounds have also shown enhanced cytotoxicity towards certain cancers (Won et al., 2005). Synthetically chalcones are derived through an aldol condensation which involves the reaction between an aromatic aldehyde with an aliphatic aldehyde or ketone in the presence of a strong base (hydroxide or alkoxide). The resulting compound contains two aromatic rings joined by a three carbon α,β-unsaturated carbonyl system, and we report herein on its crystal structure.
The molecular structure of the title molecule is illustrated in Fig. 1. The two aromatic rings (C4–C9 and C17–C22) are inclined to one another by 8.39 (9)° and the molecule has an E conformation about the C2═C3 bond.
In the crystal, the molecules stack head-to-tail along the b axis. They molecules are linked by very weak C-H···O and C-H···π interactions (Table 1). Atom O1 of the carbonyl group interacts with the H atom, H2, of the C2═ C3 double bond in a C═O···HC═C fashion, resulting in the formation of C(4) chains along the a-axis direction. In addition, the O atom, O2, of the ether moiety is also involved in a weak hydrogen bond with the central phenyl group of an inversion related neighboring molecule. The two molecules are arranged head-to-tail, which induces formation of an inversion dimeric unit and an eight-membered R22(8) ring containing a pair of very weak C-H···O hydrogen bonds (Table 1).
As a result of the head-to-tail flipping, there is no ring alignment within the structure, hence the system lacks any significant π–π interactions but there are C—H···π contacts present (Table 1) which link the double stranded chains to form a two-dimensional network.