(E)-3-(2-Fur­yl)-1-(2-hydroxy­phen­yl)prop-2-en-1-one

Kong, L.; Liu, Y.

doi:10.1107/S1600536808031644

organic compounds

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ISSN: 2056-9890

Volume 64| Part 11| November 2008| Page o2161

doi:10.1107/S1600536808031644

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(E)-3-(2-Furyl)-1-(2-hydroxyphenyl)prop-2-en-1-one

Lingqian Kong ^a ^* and Yanhong Liu ^b

^aDongchang College, Liaocheng University, Liaocheng 250059, People's Republic of China, and ^bLiaocheng No.3 Middle School, Liaocheng, People's Republic of China
^*Correspondence e-mail: konglingqian08@163.com

(Received 13 September 2008; accepted 30 September 2008; online 22 October 2008)

In the title molecule, C₁₃H₁₀O₃, an intramolecular O—H⋯O hydrogen bond influences the molecular conformation, and the benzene and furan rings form a dihedral angle of 8.35 (7)°. Weak intermolecular C—H⋯O hydrogen bonds link molecules into sheets parallel to the bc plane.

Related literature

For a related crystal structure, see: Li et al. (1992 ).

Experimental

Crystal data

C₁₃H₁₀O₃
M_r = 214.21
Monoclinic, P 2₁ /c
a = 3.8560 (5) Å
b = 15.6565 (14) Å
c = 17.309 (2) Å
β = 95.065 (2)°
V = 1040.9 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.27 × 0.25 × 0.07 mm

Data collection

Siemens SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.974, T_max = 0.993
5153 measured reflections
1848 independent reflections
668 reflections with I > 2σ(I)
R_int = 0.126

Refinement

R[F² > 2σ(F²)] = 0.067
wR(F²) = 0.184
S = 0.81
1848 reflections
146 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O2	0.82	1.84	2.544 (4)	144
C1—H1⋯O2ⁱ	0.93	2.59	3.400 (5)	146
C3—H3A⋯O3ⁱⁱ	0.93	2.59	3.504 (5)	169
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: SMART (Siemens, 1996 ); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808031644/cv2448sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808031644/cv2448Isup2.hkl

checkCIF report

Comment top

In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis, we describe in this paper a user-friendly, solvent-free protocol for the synthesis of chalcones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method, which can be considered as a a general method for the synthesis of chalcones, we obtained the title compound, (I). We present here its crystal structure.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in related compound (Li et al., 1992). The benzene and furan rings form a dihedral angle of 8.35 (7)°. In the crystal, weak intermolecular C—H···O hydrogen bonds (Table 1) link the molecules into sheets parallel to bc plane.

Related literature top

For a related crystal structure, see: Li et al. (1992).

Experimental top

Furan-2-carbaldehyde (0.3 mmol) and 2-hydroxylacetophenone (0.3 mmol), NaOH (0.3 mmol) were mixed in 50 ml flash under sovlent-free conditions After stirring for 5 min at 373 K, the mixture was soilden slowly and afforded the title compound, then recrystallized from ethanol, affording the title compound as a colourless crystalline solid. Elemental analysis: calculated for C₁₃H₁₀O₃: C 72.90, H 4.71%; found: C 72.88, H 4.65%.

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I) showing the atomic numbering and 40% probability displacement ellipsoids.

(E)-3-(2-Furyl)-1-(2-hydroxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₃H₁₀O₃	F(000) = 448
M_r = 214.21	D_x = 1.367 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 3.8560 (5) Å	Cell parameters from 438 reflections
b = 15.6565 (14) Å	θ = 2.4–18.4°
c = 17.309 (2) Å	µ = 0.10 mm⁻¹
β = 95.065 (2)°	T = 298 K
V = 1040.9 (2) Å³	Block, colourless
Z = 4	0.27 × 0.25 × 0.07 mm

Data collection top

Siemens SMART CCD area-detector diffractometer	1848 independent reflections
Radiation source: fine-focus sealed tube	668 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.126
Detector resolution: ϕ and ω pixels mm^-1	θ_max = 25.0°, θ_min = 1.8°
ϕ and ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −7→18
T_min = 0.974, T_max = 0.993	l = −20→20
5153 measured reflections

Refinement top

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 0.81	w = 1/[σ²(F_o²) + (0.0721P)²] where P = (F_o² + 2F_c²)/3
1848 reflections	(Δ/σ)_max < 0.001
146 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₁₃H₁₀O₃	V = 1040.9 (2) Å³
M_r = 214.21	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 3.8560 (5) Å	µ = 0.10 mm⁻¹
b = 15.6565 (14) Å	T = 298 K
c = 17.309 (2) Å	0.27 × 0.25 × 0.07 mm
β = 95.065 (2)°

Data collection top

Siemens SMART CCD area-detector diffractometer	1848 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	668 reflections with I > 2σ(I)
T_min = 0.974, T_max = 0.993	R_int = 0.126
5153 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 0.81	Δρ_max = 0.22 e Å⁻³
1848 reflections	Δρ_min = −0.19 e Å⁻³
146 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1	1.0561 (7)	0.73465 (16)	0.48262 (15)	0.0794 (9)
O2	0.8017 (8)	0.83794 (18)	0.74522 (15)	0.0885 (11)
O3	0.5477 (10)	0.9672 (2)	0.80912 (17)	0.1030 (12)
H3	0.6546	0.9220	0.8087	0.154*
C1	1.1454 (12)	0.6735 (3)	0.4327 (2)	0.0842 (15)
H1	1.1472	0.6811	0.3794	0.101*
C2	1.2297 (11)	0.6018 (3)	0.4699 (3)	0.0769 (13)
H2	1.3018	0.5510	0.4485	0.092*
C3	1.1887 (11)	0.6177 (3)	0.5478 (2)	0.0748 (13)
H3A	1.2271	0.5788	0.5882	0.090*
C4	1.0842 (10)	0.6991 (2)	0.5544 (2)	0.0584 (10)
C5	0.9983 (9)	0.7493 (2)	0.6177 (2)	0.0608 (11)
H5	1.0222	0.7240	0.6665	0.073*
C6	0.8860 (10)	0.8300 (2)	0.6137 (2)	0.0598 (11)
H6	0.8676	0.8578	0.5661	0.072*
C7	0.7918 (10)	0.8754 (2)	0.6822 (2)	0.0600 (11)
C8	0.6700 (9)	0.9648 (2)	0.6757 (2)	0.0553 (10)
C9	0.5559 (11)	1.0064 (3)	0.7399 (2)	0.0690 (12)
C10	0.4467 (12)	1.0901 (3)	0.7358 (3)	0.0835 (14)
H10	0.3697	1.1170	0.7790	0.100*
C11	0.4529 (13)	1.1329 (3)	0.6679 (3)	0.0930 (16)
H11	0.3769	1.1893	0.6649	0.112*
C12	0.5685 (12)	1.0951 (3)	0.6033 (3)	0.0839 (14)
H12	0.5747	1.1256	0.5573	0.101*
C13	0.6745 (11)	1.0117 (3)	0.6079 (2)	0.0702 (12)
H13	0.7518	0.9858	0.5642	0.084*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.111 (3)	0.0632 (19)	0.0648 (18)	0.0106 (16)	0.0132 (16)	−0.0022 (16)
O2	0.138 (3)	0.067 (2)	0.0625 (18)	0.0095 (18)	0.0190 (18)	0.0029 (15)
O3	0.150 (4)	0.087 (3)	0.076 (2)	0.010 (2)	0.033 (2)	−0.0105 (18)
C1	0.112 (4)	0.076 (3)	0.065 (3)	0.008 (3)	0.015 (3)	−0.014 (3)
C2	0.080 (4)	0.057 (3)	0.095 (3)	0.008 (2)	0.012 (3)	−0.016 (3)
C3	0.086 (4)	0.061 (3)	0.078 (3)	0.008 (2)	0.011 (2)	−0.004 (2)
C4	0.065 (3)	0.053 (2)	0.058 (2)	−0.002 (2)	0.010 (2)	−0.001 (2)
C5	0.063 (3)	0.059 (2)	0.061 (2)	0.001 (2)	0.010 (2)	0.004 (2)
C6	0.067 (3)	0.058 (2)	0.054 (2)	0.002 (2)	0.005 (2)	−0.003 (2)
C7	0.064 (3)	0.057 (3)	0.059 (2)	−0.005 (2)	0.004 (2)	0.001 (2)
C8	0.055 (3)	0.053 (2)	0.058 (2)	−0.0020 (19)	0.006 (2)	−0.001 (2)
C9	0.071 (3)	0.069 (3)	0.068 (3)	−0.001 (2)	0.009 (2)	−0.009 (2)
C10	0.080 (4)	0.073 (3)	0.095 (4)	0.008 (3)	0.001 (3)	−0.023 (3)
C11	0.093 (4)	0.061 (3)	0.122 (4)	0.014 (3)	−0.014 (3)	−0.013 (3)
C12	0.099 (4)	0.063 (3)	0.086 (3)	0.000 (3)	−0.008 (3)	0.007 (3)
C13	0.078 (3)	0.056 (3)	0.076 (3)	−0.004 (2)	0.007 (2)	−0.005 (2)

Geometric parameters (Å, º) top

O1—C1	1.354 (4)	C6—C7	1.455 (5)
O1—C4	1.357 (4)	C6—H6	0.9300
O2—C7	1.237 (4)	C7—C8	1.476 (5)
O3—C9	1.349 (4)	C8—C13	1.386 (5)
O3—H3	0.8200	C8—C9	1.393 (5)
C1—C2	1.321 (5)	C9—C10	1.377 (6)
C1—H1	0.9300	C10—C11	1.354 (5)
C2—C3	1.394 (5)	C10—H10	0.9300
C2—H2	0.9300	C11—C12	1.374 (6)
C3—C4	1.343 (5)	C11—H11	0.9300
C3—H3A	0.9300	C12—C13	1.368 (5)
C4—C5	1.413 (5)	C12—H12	0.9300
C5—C6	1.335 (5)	C13—H13	0.9300
C5—H5	0.9300

C1—O1—C4	106.9 (3)	O2—C7—C8	120.1 (4)
C9—O3—H3	109.5	C6—C7—C8	120.1 (3)
C2—C1—O1	110.8 (3)	C13—C8—C9	117.1 (4)
C2—C1—H1	124.6	C13—C8—C7	122.6 (3)
O1—C1—H1	124.6	C9—C8—C7	120.3 (4)
C1—C2—C3	106.0 (4)	O3—C9—C10	116.6 (4)
C1—C2—H2	127.0	O3—C9—C8	122.0 (4)
C3—C2—H2	127.0	C10—C9—C8	121.4 (4)
C4—C3—C2	108.2 (4)	C11—C10—C9	119.2 (4)
C4—C3—H3A	125.9	C11—C10—H10	120.4
C2—C3—H3A	125.9	C9—C10—H10	120.4
C3—C4—O1	108.2 (3)	C10—C11—C12	121.6 (4)
C3—C4—C5	133.3 (4)	C10—C11—H11	119.2
O1—C4—C5	118.5 (3)	C12—C11—H11	119.2
C6—C5—C4	125.7 (3)	C13—C12—C11	118.8 (4)
C6—C5—H5	117.1	C13—C12—H12	120.6
C4—C5—H5	117.1	C11—C12—H12	120.6
C5—C6—C7	121.6 (3)	C12—C13—C8	122.0 (4)
C5—C6—H6	119.2	C12—C13—H13	119.0
C7—C6—H6	119.2	C8—C13—H13	119.0
O2—C7—C6	119.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.84	2.544 (4)	144
C1—H1···O2ⁱ	0.93	2.59	3.400 (5)	146
C3—H3A···O3ⁱⁱ	0.93	2.59	3.504 (5)	169

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y−1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀O₃
M_r	214.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	3.8560 (5), 15.6565 (14), 17.309 (2)
β (°)	95.065 (2)
V (Å³)	1040.9 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.27 × 0.25 × 0.07

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.974, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	5153, 1848, 668
R_int	0.126
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.184, 0.81
No. of reflections	1848
No. of parameters	146
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.19

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2	0.82	1.84	2.544 (4)	143.8
C1—H1···O2ⁱ	0.93	2.59	3.400 (5)	145.7
C3—H3A···O3ⁱⁱ	0.93	2.59	3.504 (5)	168.8

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) −x+2, y−1/2, −z+3/2.

Acknowledgements

This project was supported by the Foundation of Dongchang College, Liaocheng University (grant No. LG0801).

References

Li, Z.-D., Huang, L.-Z., Su, G.-B. & Wang, H.-Y. (1992). Chin. J. Struct. Chem. 11, 1–4. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar