4-Hy­droxy-3-[(E)-3-phenyl­prop-2-eno­yl]-2H-chromen-2-one

Ghouili, A.; Ben Hassen, R.

doi:10.1107/S1600536811029801

organic compounds

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Volume 67| Part 8| August 2011| Page o2209

doi:10.1107/S1600536811029801

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4-Hydroxy-3-[(E)-3-phenylprop-2-enoyl]-2H-chromen-2-one

Afef Ghouili ^a and Rached Ben Hassen ^a ^*

^aUnité de chimie des Matériaux, ISSBAT, Université de Tunis-ElManar, 9 Avenue Dr Zoheir SAFI, 1006 Tunis, Tunisia
^*Correspondence e-mail: rached.benhassen@fss.rnu.tn

(Received 21 June 2011; accepted 22 July 2011; online 30 July 2011)

In the title molecule, C₁₈H₁₂O₄, the phenyl ring is twisted by 23.2 (1)° from the mean plane of the chromene system. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules into zigzag chains extending in the [010] direction. An intramolecular O—H⋯O hydrogen bond is also present.

Related literature

For related structures, see: Traven et al. (2000 ); Sun & Cui (2008 ); Mechi et al. (2009 ); Hamdi et al. (2010 ); Asad et al. (2010 ). For the synthesis of coumarin chalcones, see: Claisen & Claparede (1881 ).

Experimental

Crystal data

C₁₈H₁₂O₄
M_r = 292.28
Monoclinic, P 2₁ /c
a = 11.8040 (5) Å
b = 3.8860 (5) Å
c = 29.7190 (5) Å
β = 97.164 (5)°
V = 1352.58 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.3 × 0.14 × 0.06 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: numerical (SADABS; Bruker, 2003 ) T_min = 0.861, T_max = 0.865
11154 measured reflections
2983 independent reflections
1404 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.300
S = 1.04
2983 reflections
203 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.54 e Å⁻³
Δρ_min = −0.69 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3ⁱ	0.93	2.57	3.350 (5)	142
O1—H2⋯O2	0.99 (7)	1.51 (7)	2.413 (4)	149 (6)
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811029801/cv5125sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811029801/cv5125Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811029801/cv5125Isup3.cml

checkCIF report

Comment top

In continuation of our structural and biological studies of coumarin derivatives (Mechi et al., 2009; Hamdi et al., 2010), we present the crystal structure of the title compound (I) - a new chalcone of the coumarin.

In (I) (Fig. 1), all bond lengths and angles are normal and correspond to those observed in related structures (Mechi et al., 2009; Asad et al., 2010). The presence of α, β-unsaturated ketone is indicated by the short O2–C10 and C11–C12 bond lengths of 1.289 (5)Å and 1.327 (5) Å, respectively, and the O2–C10–C11 and C10–C11–C12 bond angles of 118.2 (4) ° and 121.8 (4) °, respectively. The structure exhibits intramolecular hydrogen bonding between the hydroxyl oxygen and the ketonic oxygen in the coumarin group (Table 1). The chromen-2-one is twisted out of the plane of the phenyl ring (C13– C14) at 23.2 (1) °. The linkage between the coumarin system and phenyl ring is quite conjugated with bond lengths C10–C11 = 1.457 (5) Å, C11–C12 = 1.327 (5) Å, and C12–C13 = 1.440 (5) Å, suggesting that all non-hydrogen atoms between the electron-donors and acceptors are highly conjugated, leading to a π-bridge for the charge transfer from phenyl ring to coumarin system. Similar geometry has been observed in coumarin chalcone analogues (Mechi et al., 2009; Sun & Cui, 2008). Consequently, the C10–O2 = 1.289 (5) Å is elongated as compared with its mean value found in 3-acetyl-4hydroxycoumarin (1.253 Å) (Traven et al., 2000) owing to the localization of the hydroxyl hydrogen (H2) between the O2 ketonic oxygen and the hydroxyl oxygen O1. The O1–H2 distance (0.99 (7) Å) in (I) is shorter than that in related compounds - C₁₈H₁₀O₇ (1.22 (7) Å) (Mechi et al., 2009) and C₁₈H₁₀Cl₂O₄ (1.27 (2) Å) (Asad et al., 2010). It should be noted that the C9–O4 bond length (1.198 (5) Å) is less than that (1.210 Å) observed in 3-acetyl-4hydroxycoumarin (Traven et al., 2000). It was concluded that it was a substantial difference for stabilizing the H atom of the hydroxyl group when we changed the nature of the substituted R group (from H to Cl and to OCH3).

In the crystal structure, weak intermolecular C– H···O hydrogen bonds (Table 1) link molecules into zigzag chains extended in [010].

Related literature top

For related structures, see: Traven et al. (2000); Sun & Cui (2008); Mechi et al. (2009); Hamdi et al. (2010); Asad et al. (2010). For the synthesis of coumarin chalcone, see: Claisen & Claparede (1881).

Experimental top

The new chalcone (I) was synthesized using the Claisen Schmidt reaction (Claisen & Claparede, 1881), by the condensation of 3-acetyl-4hydroxycoumarin (1g, 4.9 mmol) and aromatic benzaldehyde (6.4 mmol, 0.5 ml) in chloroform (5 ml) in the presence of one drop of piperidine. The mixture was refluxed in a water bath for 2 h. After cooling at room temperature, a yellow solid was obtained in good yield, filtered, washed with ethanol, and dried in air. Yellow block-shaped single crystals of the title compound, suitable for X-ray structure determination, were recrystalized by slow evaporation of dichloromethane (CH₂Cl₂) at room temperature after several days. Yield: 1.1 g (80%). mp= 499K. IR: ν 3468 (OH), 1690(s) (>C=O), 1578 (C= C), 1272(s) (sym) (C-O-C); 1HNMR: δppm: 7.4-8.1 (m, 10H, Ar-H+ Hethyl), 16.1(s,1H,OH). 13C NMR (ppm): 192.6(CO); 181.56 (C2); 160.22 (C9); 100.8 (C8), 116.32-147.368 (C arom); 124.39 (Cethyl1), 154.79 (Cethyl2),

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 1999); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids and the atomic numbering. Dashed line denotes hydrogen bond.

4-Hydroxy-3-[(E)-3-phenylprop-2-enoyl]-2H-chromen-2-one top

Crystal data top

C₁₈H₁₂O₄	F(000) = 608
M_r = 292.28	D_x = 1.435 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 489 K
Hall symbol: -P2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 11.8040 (5) Å	Cell parameters from 203 reflections
b = 3.8860 (5) Å	µ = 0.10 mm⁻¹
c = 29.7190 (5) Å	T = 296 K
β = 97.164 (5)°	Plate, yellow
V = 1352.58 (18) Å³	0.3 × 0.14 × 0.06 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	2983 independent reflections
Radiation source: fine-focus sealed tube	1404 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ϕ and ω scans	θ_max = 27.2°, θ_min = 1.4°
Absorption correction: numerical (SADABS; Bruker, 2003)	h = −15→14
T_min = 0.861, T_max = 0.865	k = −4→4
11154 measured reflections	l = −38→37

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.300	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.1616P)²] where P = (F_o² + 2F_c²)/3
2983 reflections	(Δ/σ)_max < 0.001
203 parameters	Δρ_max = 0.54 e Å⁻³
0 restraints	Δρ_min = −0.69 e Å⁻³

Crystal data top

C₁₈H₁₂O₄	V = 1352.58 (18) Å³
M_r = 292.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.8040 (5) Å	µ = 0.10 mm⁻¹
b = 3.8860 (5) Å	T = 296 K
c = 29.7190 (5) Å	0.3 × 0.14 × 0.06 mm
β = 97.164 (5)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2983 independent reflections
Absorption correction: numerical (SADABS; Bruker, 2003)	1404 reflections with I > 2σ(I)
T_min = 0.861, T_max = 0.865	R_int = 0.070
11154 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.300	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.54 e Å⁻³
2983 reflections	Δρ_min = −0.69 e Å⁻³
203 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	0.0403 (2)	0.2994 (9)	0.14926 (11)	0.0562 (9)
O2	0.0632 (2)	0.0415 (9)	0.07711 (9)	0.0559 (9)
C1	0.1298 (4)	0.5245 (10)	0.23674 (14)	0.0449 (11)
H1	0.0526	0.5667	0.2281	0.054*
C2	0.1481 (3)	0.2566 (10)	0.16162 (13)	0.0372 (9)
C10	0.1719 (3)	0.0080 (10)	0.08756 (13)	0.0403 (10)
C3	0.1795 (4)	0.6154 (11)	0.27952 (14)	0.0531 (12)
H3	0.1357	0.7162	0.2999	0.064*
C14	0.1811 (4)	−0.5082 (11)	−0.06124 (13)	0.0473 (11)
H12	0.1031	−0.5413	−0.0610	0.057*
C12	0.1891 (4)	−0.2364 (10)	0.01330 (13)	0.0418 (10)
H6	0.1098	−0.2428	0.0093	0.050*
C7	0.1950 (3)	0.3694 (9)	0.20651 (12)	0.0362 (9)
C8	0.2206 (3)	0.1046 (10)	0.13289 (12)	0.0363 (9)
C15	0.2328 (4)	−0.6146 (11)	−0.09835 (14)	0.0546 (13)
H11	0.1895	−0.7214	−0.1227	0.065*
C11	0.2385 (4)	−0.1217 (10)	0.05304 (13)	0.0421 (10)
H7	0.3177	−0.1241	0.0590	0.050*
C4	0.2948 (4)	0.5566 (11)	0.29212 (14)	0.0532 (12)
H4	0.3282	0.6208	0.3209	0.064*
C6	0.3095 (3)	0.3138 (10)	0.22020 (12)	0.0379 (9)
C9	0.3401 (4)	0.0457 (11)	0.14931 (13)	0.0445 (10)
C16	0.3483 (4)	−0.5624 (11)	−0.09925 (14)	0.0536 (12)
H10	0.3824	−0.6308	−0.1244	0.064*
C5	0.3595 (4)	0.4068 (11)	0.26304 (14)	0.0507 (11)
H5	0.4368	0.3669	0.2718	0.061*
O3	0.3791 (2)	0.1608 (8)	0.19242 (9)	0.0485 (8)
C17	0.4132 (4)	−0.4082 (12)	−0.06275 (15)	0.0538 (12)
H9	0.4912	−0.3759	−0.0630	0.065*
O4	0.4098 (3)	−0.0973 (11)	0.12993 (11)	0.0753 (12)
C18	0.3610 (4)	−0.3021 (11)	−0.02576 (13)	0.0471 (11)
H8	0.4046	−0.1954	−0.0015	0.057*
C13	0.2453 (4)	−0.3519 (10)	−0.02429 (13)	0.0386 (9)
H2	0.022 (6)	0.181 (17)	0.120 (2)	0.13 (2)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0409 (18)	0.085 (2)	0.0422 (18)	0.0068 (16)	0.0031 (14)	−0.0133 (17)
O2	0.0428 (18)	0.083 (2)	0.0404 (17)	0.0022 (16)	−0.0005 (14)	−0.0144 (16)
C1	0.056 (3)	0.040 (2)	0.041 (2)	0.0013 (19)	0.017 (2)	0.0005 (18)
C2	0.040 (2)	0.038 (2)	0.034 (2)	−0.0007 (17)	0.0080 (17)	0.0014 (17)
C10	0.045 (2)	0.040 (2)	0.037 (2)	−0.0008 (18)	0.0070 (19)	0.0017 (18)
C3	0.086 (4)	0.044 (2)	0.034 (2)	−0.002 (2)	0.021 (2)	−0.0042 (18)
C14	0.053 (3)	0.049 (2)	0.038 (2)	0.005 (2)	0.001 (2)	0.0004 (19)
C12	0.048 (2)	0.044 (2)	0.034 (2)	0.0010 (19)	0.0072 (19)	−0.0007 (18)
C7	0.045 (2)	0.036 (2)	0.028 (2)	−0.0032 (17)	0.0103 (17)	0.0047 (16)
C8	0.042 (2)	0.038 (2)	0.029 (2)	−0.0014 (17)	0.0038 (17)	0.0021 (16)
C15	0.084 (4)	0.047 (3)	0.030 (2)	0.011 (2)	0.001 (2)	−0.0057 (19)
C11	0.046 (2)	0.047 (2)	0.033 (2)	0.0025 (19)	0.0059 (18)	−0.0005 (18)
C4	0.076 (3)	0.050 (3)	0.032 (2)	−0.010 (2)	0.000 (2)	−0.0010 (19)
C6	0.043 (2)	0.041 (2)	0.030 (2)	−0.0036 (18)	0.0080 (17)	0.0012 (17)
C9	0.043 (2)	0.056 (3)	0.034 (2)	0.008 (2)	0.0060 (19)	−0.0003 (19)
C16	0.078 (4)	0.052 (3)	0.034 (2)	0.018 (2)	0.016 (2)	0.003 (2)
C5	0.055 (3)	0.055 (3)	0.041 (2)	−0.009 (2)	−0.002 (2)	0.000 (2)
O3	0.0369 (16)	0.072 (2)	0.0357 (16)	0.0048 (15)	0.0014 (12)	−0.0042 (14)
C17	0.060 (3)	0.056 (3)	0.047 (3)	0.007 (2)	0.014 (2)	0.003 (2)
O4	0.053 (2)	0.123 (3)	0.050 (2)	0.032 (2)	0.0068 (17)	−0.021 (2)
C18	0.060 (3)	0.047 (2)	0.033 (2)	0.001 (2)	0.005 (2)	0.0004 (18)
C13	0.052 (2)	0.035 (2)	0.029 (2)	0.0043 (18)	0.0049 (18)	0.0029 (16)

Geometric parameters (Å, º) top

O1—C2	1.290 (5)	C7—C6	1.379 (5)
O1—H2	0.99 (7)	C8—C9	1.452 (5)
O2—C10	1.289 (5)	C15—C16	1.383 (7)
C1—C3	1.378 (6)	C15—H11	0.9300
C1—C7	1.391 (5)	C11—H7	0.9300
C1—H1	0.9300	C4—C5	1.354 (6)
C2—C8	1.411 (5)	C4—H4	0.9300
C2—C7	1.447 (5)	C6—O3	1.371 (4)
C10—C8	1.447 (5)	C6—C5	1.383 (5)
C10—C11	1.457 (5)	C9—O4	1.198 (5)
C3—C4	1.385 (7)	C9—O3	1.381 (5)
C3—H3	0.9300	C16—C17	1.384 (6)
C14—C15	1.388 (6)	C16—H10	0.9300
C14—C13	1.394 (6)	C5—H5	0.9300
C14—H12	0.9300	C17—C18	1.388 (6)
C12—C11	1.327 (5)	C17—H9	0.9300
C12—C13	1.440 (5)	C18—C13	1.385 (6)
C12—H6	0.9300	C18—H8	0.9300

C2—O1—H2	107 (4)	C12—C11—C10	121.8 (4)
C3—C1—C7	120.0 (4)	C12—C11—H7	119.1
C3—C1—H1	120.0	C10—C11—H7	119.1
C7—C1—H1	120.0	C5—C4—C3	120.8 (4)
O1—C2—C8	122.2 (4)	C5—C4—H4	119.6
O1—C2—C7	118.3 (3)	C3—C4—H4	119.6
C8—C2—C7	119.5 (4)	O3—C6—C7	122.0 (3)
O2—C10—C8	117.8 (4)	O3—C6—C5	116.7 (4)
O2—C10—C11	118.2 (4)	C7—C6—C5	121.4 (4)
C8—C10—C11	124.0 (4)	O4—C9—O3	115.3 (4)
C1—C3—C4	119.9 (4)	O4—C9—C8	127.5 (4)
C1—C3—H3	120.1	O3—C9—C8	117.3 (3)
C4—C3—H3	120.1	C15—C16—C17	120.0 (4)
C15—C14—C13	120.4 (4)	C15—C16—H10	120.0
C15—C14—H12	119.8	C17—C16—H10	120.0
C13—C14—H12	119.8	C4—C5—C6	119.4 (4)
C11—C12—C13	127.0 (4)	C4—C5—H5	120.3
C11—C12—H6	116.5	C6—C5—H5	120.3
C13—C12—H6	116.5	C6—O3—C9	122.9 (3)
C6—C7—C1	118.6 (4)	C16—C17—C18	119.5 (5)
C6—C7—C2	118.2 (3)	C16—C17—H9	120.3
C1—C7—C2	123.2 (4)	C18—C17—H9	120.3
C2—C8—C10	118.1 (4)	C13—C18—C17	121.4 (4)
C2—C8—C9	120.0 (3)	C13—C18—H8	119.3
C10—C8—C9	121.9 (3)	C17—C18—H8	119.3
C16—C15—C14	120.3 (4)	C18—C13—C14	118.5 (4)
C16—C15—H11	119.9	C18—C13—C12	122.1 (4)
C14—C15—H11	119.9	C14—C13—C12	119.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.57	3.350 (5)	142
O1—H2···O2	0.99 (7)	1.51 (7)	2.413 (4)	149 (6)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₂O₄
M_r	292.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	11.8040 (5), 3.8860 (5), 29.7190 (5)
β (°)	97.164 (5)
V (Å³)	1352.58 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.3 × 0.14 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Numerical (SADABS; Bruker, 2003)
T_min, T_max	0.861, 0.865
No. of measured, independent and observed [I > 2σ(I)] reflections	11154, 2983, 1404
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.644

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.300, 1.04
No. of reflections	2983
No. of parameters	203
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.54, −0.69

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 1999), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3ⁱ	0.93	2.57	3.350 (5)	142.4
O1—H2···O2	0.99 (7)	1.51 (7)	2.413 (4)	149 (6)

Symmetry code: (i) −x+1, y+1/2, −z+1/2.

Acknowledgements

Professor A. Ben Salah is acknowledged for his contribution to the X-ray diffraction data collection at the Laboratory of Materials Science and the Environment, University of Sfax, Tunisia.

References

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