4-Hy-droxy-3-[(E)-3-phenyl-prop-2-eno-yl]-2H-chromen-2-one.

In the title mol-ecule, C(18)H(12)O(4), the phenyl ring is twisted by 23.2 (1)° from the mean plane of the chromene system. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into zigzag chains extending in the [010] direction. An intra-molecular 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 = 292.28

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.300

S = 1.04

2983 reflections

203 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.54 e Å−3

Δρmin = −0.69 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811029801/cv5125sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536811029801/cv5125Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H12O4	F(000) = 608
Mr = 292.28	Dx = 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

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

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(Fo2) + (0.1616P)2] where P = (Fo2 + 2Fc2)/3
2983 reflections	(Δ/σ)max < 0.001
203 parameters	Δρmax = 0.54 e Å−3
0 restraints	Δρmin = −0.69 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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)

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)

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) .