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

Vázquez-Vuelvas, O.F.; Enríquez-Figueroa, R.A.; García-Ortega, H.; Flores-Alamo, M.; Pineda-Contreras, A.

doi:10.1107/S205698901500047X

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ISSN: 2056-9890

Volume 71| Part 2| February 2015| Pages 161-164

doi:10.1107/S205698901500047X

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

Oscar F. Vázquez-Vuelvas,^a ‡ René A. Enríquez-Figueroa,^a Héctor García-Ortega,^b Marcos Flores-Alamo ^b and Armando Pineda-Contreras ^a ^*

^aFacultad de Ciencias Químicas, Universidad de Colima, Km 9 Carr. Colima-Coquimatlán s/n, Coquimatlán, Colima 28400, Mexico, and ^bFacultad de Química, Universidad Nacional Autónoma de México, Ciudad Universitaria, México, DF 04510, Mexico
^*Correspondence e-mail: armandop@ucol.mx

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 16 December 2014; accepted 9 January 2015; online 17 January 2015)

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.

Keywords: crystal structure; Claisen–Schmidt reaction; chalcone derivative; hydrogen bonding; biological activity; zigzag fashion..

CCDC reference: 1042952

1. Chemical context

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.

2. 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.

3. 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).

Table 1
Hydrogen-bond geometry (Å, °)

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⋯Cg2^iv	0.95	2.71	3.519 (9)	143
Symmetry codes: (i) $[x, -y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x+1, -y, -z; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iv) $[-x-2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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.

4. 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.

5. 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).

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 (Å)	9.5296 (7), 10.1383 (7), 11.1595 (7)
β (°)	103.922 (6)
V (Å³)	1046.49 (13)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	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 > 2σ(I)] reflections	8114, 2553, 1755
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.691

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.04
No. of reflections	2553
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.17
Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS2013 and SHELXL2013 (Sheldrick, 2008 , 2015 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ), Mercury (Macrae et al., 2006 ) and DIAMOND (Brandenburg, 2012 ).

Supporting information

CCDC reference: 1042952

Crystal structure: contains datablocks global, I. DOI: 10.1107/S205698901500047X/rz5145sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901500047X/rz5145Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901500047X/rz5145Isup3.cml

checkCIF report

Chemical context top

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.

Structural commentary top

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.

Supramolecular features top

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).

Synthesis and crystallization top

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.

Refinement details top

Related literature top

(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 top

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 top

	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 top

Crystal data top

C₁₃H₁₀O₂	F(000) = 416
M_r = 198.21	D_x = 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 top

Agilent Xcalibur Atlas Gemini diffractometer	2553 independent reflections
Graphite monochromator	1755 reflections with I > 2σ(I)
Detector resolution: 10.4685 pixels mm^-1	R_int = 0.019
ω scans	θ_max = 29.4°, θ_min = 3.8°
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	h = −12→11
T_min = 0.781, T_max = 1	k = −13→14
8114 measured reflections	l = −14→14

Refinement top

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(F_o²) + (0.0462P)² + 0.1328P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
2553 reflections	Δρ_max = 0.11 e Å⁻³
136 parameters	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₃H₁₀O₂	V = 1046.49 (13) Å³
M_r = 198.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.5296 (7) Å	µ = 0.08 mm⁻¹
b = 10.1383 (7) Å	T = 130 K
c = 11.1595 (7) Å	0.50 × 0.45 × 0.32 mm
β = 103.922 (6)°

Data collection top

Agilent Xcalibur Atlas Gemini diffractometer	2553 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	1755 reflections with I > 2σ(I)
T_min = 0.781, T_max = 1	R_int = 0.019
8114 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.04	Δρ_max = 0.11 e Å⁻³
2553 reflections	Δρ_min = −0.17 e Å⁻³
136 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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) top

	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) top

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) top

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···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.

Hydrogen-bond geometry (Å, º) top

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)	150.5
C9—H9···O2ⁱⁱ	0.95	2.62	3.416 (1)	141.9
C11—H11···O2ⁱⁱ	0.95	2.51	3.277 (2)	137.9
C6—H6···Cg1ⁱⁱⁱ	0.95	2.88	3.687 (2)	144.0
C13—H13···Cg2^iv	0.95	2.71	3.519 (9)	143.2

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.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀O₂
M_r	198.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	130
a, b, c (Å)	9.5296 (7), 10.1383 (7), 11.1595 (7)
β (°)	103.922 (6)
V (Å³)	1046.49 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.45 × 0.32

Data collection
Diffractometer	Agilent Xcalibur Atlas Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.781, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	8114, 2553, 1755
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.691

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.115, 1.04
No. of reflections	2553
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.11, −0.17

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS2013 (Sheldrick, 2008, 2015), SHELXL2013 (Sheldrick, 2008, 2015), ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2006), DIAMOND (Brandenburg, 2012) and WinGX (Farrugia, 2012).

Footnotes

‡Additional correspondence author, e-mail: oscar_vazquez@ucol.mx.

Acknowledgements

The authors thank Claudio Andrade-Silva for his contribution to the laboratory work.

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Volume 71| Part 2| February 2015| Pages 161-164

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