Crystal structure of the chalcone (E)-3-(furan-2-yl)-1-phenylprop-2-en-1-one

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.

Key indicators

• Single-crystal X-ray study
• T = 130 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.045
• wR factor = 0.115
• Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O2      ..       2.62 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      3.921 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT910_ALERT_3_G Missing # of FCF Reflection(s) Below Th(Min) ...          4 Report
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600        304 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   3 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. 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) (see scheme). 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-di­aryl­prop-2-en-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 inhibitors of mono­amine oxidase (MAO); 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 test their biological activity (Robinson et al., 2013; Shaikh et al., 2014; Sharma et al., 2013; Zheng et al., 2011). In the view of the varied biological and pharmacological applications, we report herein on the synthesis and the molecular and supra­molecular structure of (E)-3-(furan-2-yl)-1-phenyl­prop-2-en-1-one, synthesized by a conventional base-catalysed Claisen–Schmidt condensation reaction.

S2. Structural commentary

The symmetry-independent molecule adopts an E configuration 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.

S3. 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 R₂¹(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 R₂²(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).

S4. 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—H_alk), 3035 (C—H_arom), 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.

S5. 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 U_iso(H) = 1.2U_eq(C).

Related literature

(type here to add)

For related literature, see: Bernstein et al. (1995); Boeck et al. (2006); Chimenti et al. (2010); Elarfi & Al-Difar (2012); Ghosh & Das (2014); Gilli & Gilli (2009); Hamada & Sharshira (2011); Harrison et al. (2006); Hsieh et al. (2000); Kumar et al. (2003); Mahé et al. (2012); Ocak Iskeleli, Isik, Ozdemir & Bilgin (2005a, 2005b); Qiu et al. (2006); Robinson et al. (2013); Shaikh et al. (2014); Sharma et al. (2013); Steiner (2002); Tiwari et al. (2010); Zheng et al. (2011).

Computing details

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008, 2015); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006); software used to prepare material for publication: DIAMOND (Brandenburg, 2012) and WinGX (Farrugia, 2012).

Figures

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound, showing the hydrogen-bonded supramolecular assembly via C—H···O interactions (blue dashed lines).
	Fig. 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.

(E)-3-(Furan-2-yl)-1-phenylprop-2-en-1-one

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) Å^3	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 F^2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.045	H-atom parameters constrained
wR(F^2) = 0.115	w = 1/[σ^2(Fo^2) + (0.0462P)^2 + 0.1328P] where P = (Fo^2 + 2Fc^2)/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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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···O2^i	0.95	2.51	3.457 (2)	151
C9—H9···O2^ii	0.95	2.62	3.416 (1)	142
C11—H11···O2^ii	0.95	2.51	3.277 (2)	138
C6—H6···Cg1^iii	0.95	2.88	3.687 (2)	144
C13—H13···Cg2^iv	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.