The crystal packing of the compound is described by an intermolecular arrangement with the molecules as interlaced layers in a zigzag fashion, denoting interacting self-complementary dimers mainly by the localization of weak hydrogen bonds in a head-to-tail arrangement.
Keywords: crystal structure, Claisen–Schmidt reaction, chalcone derivative, hydrogen bonding, biological activity, zigzag fashion.
Abstract
The title chalcone derivative, C13H10O2, adopts an E conformation about the C=C double bond. The molecule is composed of a furanyl and a phenyl ring, bridged by an α,β-unsaturated carbonyl system, which are inclined to one another by 24.07 (7)°. In the crystal, molecules are connected by weak C—H⋯O hydrogen bonds involving the carbonyl O atom acting as a trifurcated acceptor and C—H⋯π interactions, forming ribbons extending along the c-axis direction.
Chemical context
The Claisen–Schmidt condensation reaction between substituted acetophenones and aryl aldehydes under basic conditions has been widely used to synthesize chalcone derivatives (Ghosh & Das, 2014 ▸; Robinson et al., 2013 ▸; Sharma et al., 2013 ▸; Tiwari et al., 2010 ▸). Chalcones, belonging to the flavonoid family, are an important class of natural products with widespread distribution in fruits, vegetables, spices and tea. These compounds are also often used as the precursors for the synthesis of various heterocyclic compounds (Chimenti et al., 2010 ▸; Elarfi & Al-Difar, 2012 ▸; Ghosh & Das, 2014 ▸; Hamada & Sharshira, 2011 ▸; Mahé et al., 2012 ▸; Sharma et al., 2013 ▸). Chemically, chalcones are 1,3-diaryl-2-propen-1-ones in which two aromatic rings, mainly benzene groups, are joined by a three-carbon bridge having a carbonyl moiety and α,β-unsaturation.
Many studies have shown that chalcone derivatives exhibit a wide range of pharmacological activities, such as potential cytotoxic, antimicrobial, antiviral, anti-inflammatory, anti-oxidant, anaesthetic, antimalarial, antileishmanial, antitubercular, antitumor and anticancer activities (Boeck et al., 2006 ▸; Chimenti et al., 2010 ▸; Elarfi & Al-Difar, 2012 ▸; Hamada & Sharshira, 2011 ▸; Hsieh et al., 2000 ▸; Kumar et al., 2003 ▸; Sharma et al., 2013 ▸). These versatile compounds and their furan derivatives are often used as intermediates in the syntheses of monoamine oxidase (MAO) inhibitors; moreover, the chalcones themselves have MAO inhibitory activity. Since the furan moiety represents a high π-electron density that contributes to the interaction with the flavin nucleus of the co-factor in the inhibition of MAO, some furan-substituted chalcones, where an electron-rich heterocyclic oxygen replaces the benzene ring, have been synthesized to investigate their biological activity (Robinson et al., 2013 ▸; Shaikh et al., 2014 ▸; Sharma et al., 2013 ▸; Zheng et al., 2011 ▸). In view of the varied biological and pharmacological applications, we report herein on the synthesis and the molecular and supramolecular structure of the title compound, synthesized by a conventional base-catalysed Claisen–Schmidt condensation reaction.
Structural commentary
The symmetry-independent molecule adopts an E conformation corresponding to an α,β-unsaturated non-planar structure, which bridges the pair of aromatic groups (Fig. 1 ▸). The two main planar groups, the furanyl and the phenyl rings, form a dihedral angle of 24.07 (7)°. In this context, the molecular structure can be considered, for descriptive purposes, as two fragments basically described by the furanyl acryloyl and the benzoyl moieties. The benzoyl group shows a non-planar structure and presents rotation when observing the C2—C1—C7—O2 torsion angle of 19.4 (2)°, denoting a marked deviation from planarity at the C1—C7 bond, a single bond with rotational freedom. This deviation from planarity has also been reported previously in the crystal structure of an (E)-3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)-prop-2-en-1-one derivative, when observing the analogous reported interplanar angle shown in the respectively 4-methoxybenzoyl moiety (Qiu et al., 2006 ▸). In the same manner, the furanyl acryloyl entity presents a quasi-planar structure indicated by the two small torsion angles O2—C7—C8—C9 [−5.4 (2)°] and C7—C8—C9—C10 [−176.31 (13)°], similar to the structure of the difuranyl chalcone derivative (E)-1,3-di(2-furyl)-2-propen-1-one (Ocak Iskeleli et al., 2005b ▸). On the other hand, the molecule interatomic linkage coincides with similar reported structures, specifically in the α,β-unsaturated entity of the title crystal (Harrison et al., 2006 ▸; Ocak Iskeleli et al., 2005a ▸,b ▸). As a result, the interatomic distances are in agreement with the conjugative nature, which is additionally supported by other described types of different weak interactions (vide infra) and also define the characteristic quasi-planar structure of chalcone derivatives.
Figure 1.
The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
Supramolecular features
The crystal packing does not present geometrical parameters corresponding to classical hydrogen bonding (Gilli & Gilli, 2009 ▸; Steiner, 2002 ▸), neither intra- nor intermolecular. In the crystal, centrosymmetrically related molecules interact through a pair of weak hydrogen contacts (Table 1 ▸) with the C9 and C11 carbon atoms as donors and the O2 oxygen atom as a bifurcated acceptor, generating a ring with an 
(6) graph-set motif (Bernstein et al., 1995 ▸). The reciprocal interactions with the corresponding molecule positioned in a head-to-tail mode generate the same ring motif and, as a consequence, an 
(10) ring is formed, describing a three-fused-ring system (Fig. 2 ▸). In addition, a weak hydrogen contact is present involving the C3 carbon atom as H-donor and the O2 oxygen atom acting, in this way, as a trifurcated acceptor. The propagation of this interaction generates a ribbon along the c-axis direction (Fig. 2 ▸). The supramolecular assembly is additionally supported by weak C—H⋯π interactions, implicating the phenyl and furanyl π systems (Fig. 3 ▸).
Table 1. Hydrogen-bond geometry (, ).
Cg1 and Cg2 are the centroids of the O1/C10C13 furanyl ring and the C1C6 phenyl ring, respectively.
| DHA | DH | HA | D A | DHA |
|---|---|---|---|---|
| C3H3O2i | 0.95 | 2.51 | 3.457(2) | 151 |
| C9H9O2ii | 0.95 | 2.62 | 3.416(1) | 142 |
| C11H11O2ii | 0.95 | 2.51 | 3.277(2) | 138 |
| C6H6Cg1iii | 0.95 | 2.88 | 3.687(2) | 144 |
| C13H13Cg2iv | 0.95 | 2.71 | 3.519(9) | 143 |
Symmetry codes: (i) 
; (ii) 
; (iii) 
; (iv) 
.
Figure 2.
A partial packing diagram of the title compound, showing the hydrogen-bonded supramolecular assembly via C—H⋯O interactions (blue dashed lines).
Figure 3.
A partial packing diagram of the title compound, showing the C—H⋯π stacking interactions, depicted as blue and purple dotted lines for the C6—H6⋯Cg1 and C13—H13⋯Cg2 contacts, respectively. H atoms not involved in hydrogen-bonding interactions have been omitted for clarity.
Synthesis and crystallization
To a solution of NaOH (2.18 g, 55 mmol) in H2O/EtOH (30 ml, 2:1 v/v) was added pure acetophenone (5.2 g, 43 mmol), and stirring started; furfuraldehyde (4.6 g, 43 mmol) was then added at once. The reaction mixture was stirred for two hours and then kept in a refrigerator overnight. The resulting product was separated and then distilled under vacuum. The title compound was obtained as a yellow solid in 82% yield. Single-crystals suitable for X-ray determination were obtained by evaporation of an ethyl ether solution. M.p. 311–313 K; IR (ν, cm−1): 3123 (C—Halk), 3035 (C—Harom), 1658 (C=O), 1594, 1545, 1474 (C=C). 1H NMR (400 MHz, CDCl3, δ, p.p.m.): 8.04 (2H, dd), 7.61 (1H, d), 7.58 (1H, tt), 7.52 (2H, dd), 7.49 (1H, dd), 7.47 (1H, d), 6.72 (1H, dd), 6.51 (1H, dd). 13C NMR (100 MHz, CDCl3, δ, p.p.m.): 189.85 (C7), 151.69 (C10), 144.98 (C13), 138.16 (C1), 132.82 (C4), 130.72 (C9), 128.65 (C2,6), 128.47 (C3,5), 119.30 (C8), 116.33 (C11), 112.74 (C12). MS m/z: 199 (M +1); Analysis calculated for C13H10O2: C, 78.78; H, 5.05. Found: 78.80; H, 5.09.
Refinement details
Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. H atoms attached to C atoms were placed in geometrically idealized positions and refined as riding on their parent atoms, with C—H = 0.95 Å and with Uiso(H) = 1.2Ueq(C).
Table 2. Experimental details.
| Crystal data | |
| Chemical formula | C13H10O2 |
| M r | 198.21 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 130 |
| a, b, c () | 9.5296(7), 10.1383(7), 11.1595(7) |
| () | 103.922(6) |
| V (3) | 1046.49(13) |
| Z | 4 |
| Radiation type | Mo K |
| (mm1) | 0.08 |
| Crystal size (mm) | 0.50 0.45 0.32 |
| Data collection | |
| Diffractometer | Agilent Xcalibur Atlas Gemini |
| Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2011 ▸) |
| T min, T max | 0.781, 1 |
| No. of measured, independent and observed [I > 2(I)] reflections | 8114, 2553, 1755 |
| R int | 0.019 |
| (sin /)max (1) | 0.691 |
| Refinement | |
| R[F 2 > 2(F 2)], wR(F 2), S | 0.045, 0.115, 1.04 |
| No. of reflections | 2553 |
| No. of parameters | 136 |
| H-atom treatment | H-atom parameters constrained |
| max, min (e 3) | 0.11, 0.17 |
Supplementary Material
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500047X/rz5145sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500047X/rz5145Isup2.hkl
Supporting information file. DOI: 10.1107/S205698901500047X/rz5145Isup3.cml
CCDC reference: 1042952
Additional supporting information: crystallographic information; 3D view; checkCIF report
Acknowledgments
The authors thank Claudio Andrade-Silva for his contribution to the laboratory work.
supplementary crystallographic information
Crystal data
| C13H10O2 | F(000) = 416 |
| Mr = 198.21 | Dx = 1.258 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 2252 reflections |
| a = 9.5296 (7) Å | θ = 3.8–29.4° |
| b = 10.1383 (7) Å | µ = 0.08 mm−1 |
| c = 11.1595 (7) Å | T = 130 K |
| β = 103.922 (6)° | Prism, colorless |
| V = 1046.49 (13) Å3 | 0.50 × 0.45 × 0.32 mm |
| Z = 4 |
Data collection
| Agilent Xcalibur Atlas Gemini diffractometer | 2553 independent reflections |
| Graphite monochromator | 1755 reflections with I > 2σ(I) |
| Detector resolution: 10.4685 pixels mm-1 | Rint = 0.019 |
| ω scans | θmax = 29.4°, θmin = 3.8° |
| Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) | h = −12→11 |
| Tmin = 0.781, Tmax = 1 | k = −13→14 |
| 8114 measured reflections | l = −14→14 |
Refinement
| Refinement on F2 | 0 restraints |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.045 | H-atom parameters constrained |
| wR(F2) = 0.115 | w = 1/[σ2(Fo2) + (0.0462P)2 + 0.1328P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 2553 reflections | Δρmax = 0.11 e Å−3 |
| 136 parameters | Δρmin = −0.17 e Å−3 |
Special details
| Experimental. Absorption correction: CrysAlisPro, Agilent Technologies (Agilent, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. |
| 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
| x | y | z | Uiso*/Ueq | ||
| O1 | 0.96039 (10) | 0.15914 (10) | 0.09922 (8) | 0.0619 (3) | |
| C1 | 0.65936 (13) | −0.05129 (13) | 0.39220 (11) | 0.0465 (3) | |
| O2 | 0.50969 (10) | −0.03589 (12) | 0.19207 (8) | 0.0724 (3) | |
| C7 | 0.62831 (14) | −0.01269 (13) | 0.25976 (11) | 0.0499 (3) | |
| C9 | 0.72460 (14) | 0.06998 (13) | 0.09060 (12) | 0.0498 (3) | |
| H9 | 0.6322 | 0.049 | 0.0396 | 0.06* | |
| C8 | 0.74268 (14) | 0.04814 (14) | 0.21095 (11) | 0.0516 (3) | |
| H8 | 0.8312 | 0.0724 | 0.2662 | 0.062* | |
| C10 | 0.82803 (14) | 0.12119 (13) | 0.02963 (11) | 0.0477 (3) | |
| C11 | 0.82469 (15) | 0.13668 (14) | −0.09089 (12) | 0.0549 (3) | |
| H11 | 0.7452 | 0.1182 | −0.1585 | 0.066* | |
| C6 | 0.76975 (15) | 0.00494 (14) | 0.48148 (12) | 0.0551 (4) | |
| H6 | 0.8309 | 0.0694 | 0.4587 | 0.066* | |
| C12 | 0.96066 (16) | 0.18535 (14) | −0.09817 (13) | 0.0587 (4) | |
| H12 | 0.991 | 0.2057 | −0.1711 | 0.07* | |
| C2 | 0.57275 (16) | −0.14617 (15) | 0.42759 (13) | 0.0605 (4) | |
| H2 | 0.4966 | −0.1857 | 0.3675 | 0.073* | |
| C13 | 1.03802 (17) | 0.19718 (16) | 0.01731 (14) | 0.0649 (4) | |
| H13 | 1.1349 | 0.2281 | 0.0399 | 0.078* | |
| C5 | 0.79115 (17) | −0.03262 (17) | 0.60379 (13) | 0.0674 (4) | |
| H5 | 0.8662 | 0.0069 | 0.6649 | 0.081* | |
| C4 | 0.70484 (19) | −0.12620 (19) | 0.63691 (15) | 0.0745 (5) | |
| H4 | 0.72 | −0.1517 | 0.721 | 0.089* | |
| C3 | 0.59661 (19) | −0.18335 (18) | 0.54951 (16) | 0.0740 (5) | |
| H3 | 0.5375 | −0.2492 | 0.573 | 0.089* |
Atomic displacement parameters (Å2)
| U11 | U22 | U33 | U12 | U13 | U23 | |
| O1 | 0.0544 (6) | 0.0759 (7) | 0.0512 (5) | −0.0135 (5) | 0.0044 (4) | 0.0031 (5) |
| C1 | 0.0452 (7) | 0.0491 (7) | 0.0454 (7) | 0.0025 (5) | 0.0115 (5) | −0.0024 (5) |
| O2 | 0.0504 (6) | 0.1151 (9) | 0.0482 (6) | −0.0173 (6) | 0.0049 (4) | −0.0038 (6) |
| C7 | 0.0457 (7) | 0.0577 (8) | 0.0448 (7) | −0.0021 (6) | 0.0080 (5) | −0.0071 (6) |
| C9 | 0.0469 (7) | 0.0538 (8) | 0.0471 (7) | −0.0012 (6) | 0.0085 (5) | −0.0031 (6) |
| C8 | 0.0476 (7) | 0.0602 (8) | 0.0455 (7) | −0.0060 (6) | 0.0081 (5) | −0.0030 (6) |
| C10 | 0.0470 (7) | 0.0475 (7) | 0.0468 (7) | −0.0015 (5) | 0.0078 (5) | −0.0010 (5) |
| C11 | 0.0556 (8) | 0.0610 (8) | 0.0473 (7) | −0.0025 (7) | 0.0110 (6) | −0.0014 (6) |
| C6 | 0.0585 (8) | 0.0595 (8) | 0.0467 (7) | −0.0017 (6) | 0.0113 (6) | −0.0054 (6) |
| C12 | 0.0610 (9) | 0.0609 (9) | 0.0582 (8) | 0.0001 (7) | 0.0217 (7) | 0.0050 (7) |
| C2 | 0.0546 (8) | 0.0661 (9) | 0.0605 (9) | −0.0038 (7) | 0.0129 (6) | 0.0034 (7) |
| C13 | 0.0533 (8) | 0.0721 (10) | 0.0702 (10) | −0.0104 (7) | 0.0164 (7) | 0.0086 (8) |
| C5 | 0.0675 (10) | 0.0847 (11) | 0.0461 (8) | 0.0074 (8) | 0.0060 (7) | −0.0061 (8) |
| C4 | 0.0788 (11) | 0.0943 (13) | 0.0523 (9) | 0.0182 (10) | 0.0193 (8) | 0.0168 (9) |
| C3 | 0.0742 (11) | 0.0777 (11) | 0.0742 (11) | 0.0007 (8) | 0.0256 (9) | 0.0199 (9) |
Geometric parameters (Å, º)
| O1—C13 | 1.3627 (17) | C11—H11 | 0.95 |
| O1—C10 | 1.3678 (15) | C6—C5 | 1.3840 (19) |
| C1—C2 | 1.3855 (19) | C6—H6 | 0.95 |
| C1—C6 | 1.3857 (18) | C12—C13 | 1.327 (2) |
| C1—C7 | 1.4882 (17) | C12—H12 | 0.95 |
| O2—C7 | 1.2218 (15) | C2—C3 | 1.377 (2) |
| C7—C8 | 1.4664 (18) | C2—H2 | 0.95 |
| C9—C8 | 1.3308 (17) | C13—H13 | 0.95 |
| C9—C10 | 1.4236 (18) | C5—C4 | 1.364 (2) |
| C9—H9 | 0.95 | C5—H5 | 0.95 |
| C8—H8 | 0.95 | C4—C3 | 1.366 (2) |
| C10—C11 | 1.3468 (18) | C4—H4 | 0.95 |
| C11—C12 | 1.407 (2) | C3—H3 | 0.95 |
| C13—O1—C10 | 105.91 (10) | C5—C6—H6 | 119.9 |
| C2—C1—C6 | 118.81 (12) | C1—C6—H6 | 119.9 |
| C2—C1—C7 | 118.43 (11) | C13—C12—C11 | 106.25 (13) |
| C6—C1—C7 | 122.76 (12) | C13—C12—H12 | 126.9 |
| O2—C7—C8 | 120.74 (12) | C11—C12—H12 | 126.9 |
| O2—C7—C1 | 119.78 (12) | C3—C2—C1 | 120.25 (14) |
| C8—C7—C1 | 119.44 (11) | C3—C2—H2 | 119.9 |
| C8—C9—C10 | 127.34 (12) | C1—C2—H2 | 119.9 |
| C8—C9—H9 | 116.3 | C12—C13—O1 | 111.18 (13) |
| C10—C9—H9 | 116.3 | C12—C13—H13 | 124.4 |
| C9—C8—C7 | 121.16 (12) | O1—C13—H13 | 124.4 |
| C9—C8—H8 | 119.4 | C4—C5—C6 | 120.22 (15) |
| C7—C8—H8 | 119.4 | C4—C5—H5 | 119.9 |
| C11—C10—O1 | 109.34 (12) | C6—C5—H5 | 119.9 |
| C11—C10—C9 | 131.84 (12) | C5—C4—C3 | 120.17 (14) |
| O1—C10—C9 | 118.76 (11) | C5—C4—H4 | 119.9 |
| C10—C11—C12 | 107.32 (12) | C3—C4—H4 | 119.9 |
| C10—C11—H11 | 126.3 | C4—C3—C2 | 120.40 (16) |
| C12—C11—H11 | 126.3 | C4—C3—H3 | 119.8 |
| C5—C6—C1 | 120.15 (14) | C2—C3—H3 | 119.8 |
| C2—C1—C7—O2 | 19.4 (2) | C9—C10—C11—C12 | −176.65 (14) |
| C6—C1—C7—O2 | −159.66 (14) | C2—C1—C6—C5 | −0.7 (2) |
| C2—C1—C7—C8 | −158.15 (13) | C7—C1—C6—C5 | 178.37 (13) |
| C6—C1—C7—C8 | 22.74 (19) | C10—C11—C12—C13 | −0.29 (17) |
| C10—C9—C8—C7 | −176.31 (13) | C6—C1—C2—C3 | 0.0 (2) |
| O2—C7—C8—C9 | −5.4 (2) | C7—C1—C2—C3 | −179.11 (14) |
| C1—C7—C8—C9 | 172.14 (12) | C11—C12—C13—O1 | −0.03 (18) |
| C13—O1—C10—C11 | −0.50 (16) | C10—O1—C13—C12 | 0.33 (17) |
| C13—O1—C10—C9 | 177.07 (12) | C1—C6—C5—C4 | 0.8 (2) |
| C8—C9—C10—C11 | 173.72 (14) | C6—C5—C4—C3 | −0.1 (2) |
| C8—C9—C10—O1 | −3.2 (2) | C5—C4—C3—C2 | −0.7 (3) |
| O1—C10—C11—C12 | 0.49 (16) | C1—C2—C3—C4 | 0.7 (3) |
Hydrogen-bond geometry (Å, º)
Cg1 and Cg2 are the centroids of the O1/C10–C13 furanyl ring and the C1–C6 phenyl ring, respectively.
| D—H···A | D—H | H···A | D···A | D—H···A |
| C3—H3···O2i | 0.95 | 2.51 | 3.457 (2) | 151 |
| C9—H9···O2ii | 0.95 | 2.62 | 3.416 (1) | 142 |
| C11—H11···O2ii | 0.95 | 2.51 | 3.277 (2) | 138 |
| C6—H6···Cg1iii | 0.95 | 2.88 | 3.687 (2) | 144 |
| C13—H13···Cg2iv | 0.95 | 2.71 | 3.519 (9) | 143 |
Symmetry codes: (i) x, −y−1/2, z+1/2; (ii) −x+1, −y, −z; (iii) x, −y+1/2, z+1/2; (iv) −x−2, y+1/2, −z+1/2.
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Associated Data
This section collects any data citations, data availability statements, or supplementary materials included in this article.
Supplementary Materials
Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S205698901500047X/rz5145sup1.cif
Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500047X/rz5145Isup2.hkl
Supporting information file. DOI: 10.1107/S205698901500047X/rz5145Isup3.cml
CCDC reference: 1042952
Additional supporting information: crystallographic information; 3D view; checkCIF report