(E)-3-(2,3-Dimethoxyphenyl)-1-(2-hydroxy-4-methoxyphenyl)prop-2-en-1-one.

The mol-ecular conformation of the title compound, C(18)H(18)O(5), is stabilized by a strong intra-molecular hydrogen bond between the hydroxyl and carbonyl groups. The C=C double bond displays an E configuration while the carbonyl group shows an S-cis configuration relative to the double bond. The dihedral angle between the two rings is 15.0 (1)°.

Related literature

For related literature, see: Chu et al. (2004 ▶); Desiraju (2002 ▶); Fronczek et al. (1987 ▶); Radha Krishna et al. (2005 ▶); Rao et al. (2004 ▶); Shoja (1999 ▶); Subbiah Pandi et al. (2003 ▶); Usman et al. (2006 ▶); Wafo et al. (2005 ▶); Wallet et al. (1995 ▶); Wu et al. (2005 ▶).

Experimental

Crystal data

C18H18O5

M = 314.32

Monoclinic,

a = 4.8793 (5) Å

b = 24.283 (3) Å

c = 13.0770 (14) Å

β = 97.044 (2)°

V = 1537.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 150 (2) K

0.25 × 0.10 × 0.07 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1999 ▶) T min = 0.976, T max = 0.993

9482 measured reflections

2717 independent reflections

1522 reflections with I > 2σ(I)

R int = 0.080

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.139

S = 1.03

2717 reflections

212 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART-NT (Bruker, 2001 ▶); cell refinement: SAINT-NT (Bruker, 1999 ▶); data reduction: SAINT-NT; program(s) used to solve structure: SHELXTL-NT (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL-NT; molecular graphics: SHELXTL-NT; software used to prepare material for publication: SHELXTL-NT.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808026949/bx2172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808026949/bx2172Isup2.hkl

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

C18H18O5	F000 = 664
Mr = 314.32	Dx = 1.358 Mg m−3
Monoclinic, P21/c	Melting point: 98-101 οC K
Hall symbol: -P 2ybc	Mo Kα radiation λ = 0.71073 Å
a = 4.8793 (5) Å	Cell parameters from 935 reflections
b = 24.283 (3) Å	θ = 3.0–19.9º
c = 13.0770 (14) Å	µ = 0.10 mm−1
β = 97.044 (2)º	T = 150 (2) K
V = 1537.7 (3) Å3	Plate, orange
Z = 4	0.25 × 0.10 × 0.07 mm

Siemens SMART CCD area-detector diffractometer	2717 independent reflections
Radiation source: fine-focus sealed tube	1522 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.080
T = 150(2) K	θmax = 25.0º
phi and ω scans	θmin = 1.8º
Absorption correction: multi-scan(SADABS; Bruker, 1999)	h = −5→5
Tmin = 0.976, Tmax = 0.993	k = −28→28
9482 measured reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.064	H-atom parameters constrained
wR(F2) = 0.139	w = 1/[σ2(Fo2) + (0.0553P)2] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
2717 reflections	Δρmax = 0.21 e Å−3
212 parameters	Δρmin = −0.16 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. 0.3 ° between frames and 30 secs exposure (per frame)

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
C100	0.5970 (6)	0.41587 (14)	0.7398 (2)	0.0353 (8)
O1	0.6194 (4)	0.45867 (9)	0.68878 (17)	0.0458 (6)
C200	0.3714 (6)	0.37731 (13)	0.7078 (2)	0.0353 (8)
H200	0.3422	0.3473	0.7518	0.042*
C300	0.2072 (6)	0.38252 (12)	0.6203 (2)	0.0375 (8)
H300	0.2417	0.4132	0.5787	0.045*
C1	−0.0221 (6)	0.34652 (12)	0.5798 (2)	0.0334 (8)
C2	−0.1667 (6)	0.35684 (13)	0.4845 (2)	0.0330 (8)
O2	−0.0892 (4)	0.40002 (9)	0.42551 (16)	0.0438 (6)
C20	−0.2738 (7)	0.44601 (13)	0.4198 (3)	0.0514 (10)
H20A	−0.4614	0.4336	0.3951	0.077*
H20B	−0.2152	0.4735	0.3720	0.077*
H20C	−0.2713	0.4625	0.4883	0.077*
C3	−0.3817 (6)	0.32244 (13)	0.4428 (2)	0.0373 (8)
O3	−0.5036 (5)	0.33541 (9)	0.34667 (17)	0.0504 (7)
C30	−0.7260 (7)	0.30177 (15)	0.3026 (3)	0.0552 (10)
H30A	−0.6599	0.2640	0.2951	0.083*
H30B	−0.7987	0.3163	0.2347	0.083*
H30C	−0.8726	0.3018	0.3475	0.083*
C4	−0.4506 (6)	0.27696 (13)	0.4990 (3)	0.0409 (9)
H4	−0.5951	0.2530	0.4715	0.049*
C5	−0.3078 (6)	0.26662 (13)	0.5953 (3)	0.0397 (8)
H5	−0.3561	0.2357	0.6339	0.048*
C6	−0.0971 (6)	0.30068 (13)	0.6354 (3)	0.0386 (8)
H6	−0.0009	0.2931	0.7015	0.046*
C1'	0.7965 (6)	0.40449 (13)	0.8300 (2)	0.0314 (7)
C6'	0.8088 (7)	0.35443 (13)	0.8848 (2)	0.0381 (8)
H6'	0.6777	0.3265	0.8635	0.046*
C5'	1.0022 (6)	0.34452 (13)	0.9674 (2)	0.0387 (8)
H5'	1.0067	0.3100	1.0018	0.046*
C4'	1.1930 (6)	0.38540 (14)	1.0010 (2)	0.0377 (8)
O4	1.3722 (4)	0.37200 (9)	1.08503 (16)	0.0454 (6)
C40	1.5663 (6)	0.41353 (14)	1.1273 (3)	0.0490 (9)
H40A	1.6879	0.4235	1.0760	0.074*
H40B	1.6772	0.3990	1.1890	0.074*
H40C	1.4652	0.4462	1.1458	0.074*
C3'	1.1901 (6)	0.43537 (13)	0.9511 (2)	0.0362 (8)
H3'	1.3179	0.4634	0.9749	0.043*
C2'	0.9974 (6)	0.44402 (13)	0.8654 (2)	0.0351 (8)
O20	1.0090 (4)	0.49305 (9)	0.81665 (18)	0.0453 (6)
H20	0.8938	0.4933	0.7634	0.046 (11)*

	U11	U22	U33	U12	U13	U23
C100	0.0270 (18)	0.040 (2)	0.0400 (19)	0.0031 (15)	0.0089 (15)	−0.0042 (16)
O1	0.0407 (14)	0.0398 (15)	0.0549 (15)	−0.0023 (11)	−0.0017 (11)	0.0059 (12)
C200	0.0277 (18)	0.037 (2)	0.0410 (19)	−0.0003 (15)	0.0057 (15)	−0.0033 (16)
C300	0.0309 (19)	0.035 (2)	0.048 (2)	0.0034 (15)	0.0100 (16)	−0.0035 (16)
C1	0.0270 (18)	0.0325 (19)	0.0414 (19)	0.0058 (15)	0.0070 (15)	−0.0060 (15)
C2	0.0237 (18)	0.0351 (19)	0.041 (2)	0.0032 (14)	0.0085 (15)	−0.0037 (16)
O2	0.0394 (14)	0.0424 (14)	0.0498 (14)	−0.0008 (12)	0.0067 (11)	0.0088 (12)
C20	0.054 (2)	0.038 (2)	0.061 (2)	0.0044 (18)	0.0015 (19)	0.0061 (18)
C3	0.0296 (19)	0.045 (2)	0.037 (2)	0.0013 (16)	0.0043 (16)	−0.0064 (16)
O3	0.0408 (14)	0.0594 (17)	0.0487 (15)	−0.0070 (12)	−0.0038 (12)	−0.0063 (13)
C30	0.040 (2)	0.067 (3)	0.057 (2)	−0.009 (2)	−0.0025 (18)	−0.021 (2)
C4	0.033 (2)	0.041 (2)	0.051 (2)	−0.0035 (16)	0.0113 (17)	−0.0148 (17)
C5	0.0344 (19)	0.033 (2)	0.053 (2)	0.0007 (16)	0.0106 (17)	−0.0048 (16)
C6	0.033 (2)	0.0360 (19)	0.047 (2)	0.0051 (16)	0.0060 (16)	0.0003 (17)
C1'	0.0231 (17)	0.039 (2)	0.0342 (18)	−0.0007 (15)	0.0100 (14)	−0.0062 (15)
C6'	0.0313 (19)	0.039 (2)	0.046 (2)	−0.0031 (16)	0.0104 (17)	−0.0017 (16)
C5'	0.0308 (19)	0.043 (2)	0.043 (2)	−0.0002 (16)	0.0077 (16)	0.0013 (17)
C4'	0.0278 (19)	0.046 (2)	0.0392 (19)	0.0019 (16)	0.0048 (16)	−0.0034 (17)
O4	0.0364 (13)	0.0522 (15)	0.0457 (14)	−0.0042 (12)	−0.0020 (11)	0.0029 (12)
C40	0.034 (2)	0.060 (2)	0.051 (2)	−0.0078 (18)	−0.0034 (17)	−0.0113 (19)
C3'	0.0290 (19)	0.040 (2)	0.0400 (19)	−0.0036 (15)	0.0047 (16)	−0.0064 (17)
C2'	0.0337 (19)	0.035 (2)	0.039 (2)	0.0008 (15)	0.0133 (16)	−0.0006 (16)
O20	0.0411 (14)	0.0414 (15)	0.0516 (16)	−0.0057 (11)	−0.0021 (13)	0.0028 (11)

C100—O1	1.247 (4)	O4—C40	1.446 (3)
C100—C1'	1.461 (4)	C3'—C2'	1.388 (4)
C100—C200	1.467 (4)	C2'—O20	1.355 (3)
C200—C300	1.319 (4)	C200—H200	0.9500
C300—C1	1.467 (4)	C300—H300	0.9500
C1—C2	1.377 (4)	C20—H20A	0.9800
C1—C6	1.403 (4)	C20—H20B	0.9800
C2—O2	1.382 (3)	C20—H20C	0.9800
C2—C3	1.398 (4)	C30—H30A	0.9800
O2—C20	1.431 (4)	C30—H30B	0.9800
C3—O3	1.360 (4)	C30—H30C	0.9800
C3—C4	1.391 (4)	C4—H4	0.9500
O3—C30	1.423 (3)	C5—H5	0.9500
C4—C5	1.385 (4)	C6—H6	0.9500
C5—C6	1.372 (4)	C6'—H6'	0.9500
C1'—C6'	1.409 (4)	C5'—H5'	0.9500
C1'—C2'	1.409 (4)	C40—H40A	0.9800
C6'—C5'	1.366 (4)	C40—H40B	0.9800
C5'—C4'	1.394 (4)	C40—H40C	0.9800
C4'—O4	1.357 (3)	C3'—H3'	0.9500
C4'—C3'	1.377 (4)	O20—H20	0.8400
O1—C100—C1'	119.7 (3)	C200—C300—H300	116.1
O1—C100—C200	119.4 (3)	C1—C300—H300	116.1
C1'—C100—C200	120.8 (3)	O2—C20—H20A	109.5
C300—C200—C100	122.8 (3)	O2—C20—H20B	109.5
C200—C300—C1	127.7 (3)	H20A—C20—H20B	109.5
C2—C1—C6	118.4 (3)	O2—C20—H20C	109.5
C2—C1—C300	120.1 (3)	H20A—C20—H20C	109.5
C6—C1—C300	121.4 (3)	H20B—C20—H20C	109.5
C1—C2—O2	119.9 (3)	O3—C30—H30A	109.5
C1—C2—C3	121.4 (3)	O3—C30—H30B	109.5
O2—C2—C3	118.7 (3)	H30A—C30—H30B	109.5
C2—O2—C20	114.1 (2)	O3—C30—H30C	109.5
O3—C3—C4	124.5 (3)	H30A—C30—H30C	109.5
O3—C3—C2	116.4 (3)	H30B—C30—H30C	109.5
C4—C3—C2	119.1 (3)	C5—C4—H4	120.1
C3—O3—C30	117.8 (3)	C3—C4—H4	120.1
C5—C4—C3	119.8 (3)	C6—C5—H5	119.7
C6—C5—C4	120.5 (3)	C4—C5—H5	119.7
C5—C6—C1	120.7 (3)	C5—C6—H6	119.6
C6'—C1'—C2'	115.9 (3)	C1—C6—H6	119.6
C6'—C1'—C100	123.8 (3)	C5'—C6'—H6'	118.8
C2'—C1'—C100	120.3 (3)	C1'—C6'—H6'	118.8
C5'—C6'—C1'	122.4 (3)	C6'—C5'—H5'	120.2
C6'—C5'—C4'	119.6 (3)	C4'—C5'—H5'	120.2
O4—C4'—C3'	124.3 (3)	O4—C40—H40A	109.5
O4—C4'—C5'	115.0 (3)	O4—C40—H40B	109.5
C3'—C4'—C5'	120.7 (3)	H40A—C40—H40B	109.5
C4'—O4—C40	118.0 (3)	O4—C40—H40C	109.5
C4'—C3'—C2'	118.9 (3)	H40A—C40—H40C	109.5
O20—C2'—C3'	116.7 (3)	H40B—C40—H40C	109.5
O20—C2'—C1'	120.8 (3)	C4'—C3'—H3'	120.6
C3'—C2'—C1'	122.5 (3)	C2'—C3'—H3'	120.6
C300—C200—H200	118.6	C2'—O20—H20	109.5
C100—C200—H200	118.6
O1—C100—C200—C300	7.8 (5)	C2—C1—C6—C5	0.6 (4)
C1'—C100—C200—C300	−171.6 (3)	C300—C1—C6—C5	−178.4 (3)
C100—C200—C300—C1	179.4 (3)	O1—C100—C1'—C6'	−171.9 (3)
C200—C300—C1—C2	−177.5 (3)	C200—C100—C1'—C6'	7.5 (4)
C200—C300—C1—C6	1.5 (5)	O1—C100—C1'—C2'	6.2 (4)
C6—C1—C2—O2	−176.8 (3)	C200—C100—C1'—C2'	−174.4 (3)
C300—C1—C2—O2	2.3 (4)	C2'—C1'—C6'—C5'	0.2 (4)
C6—C1—C2—C3	−0.7 (4)	C100—C1'—C6'—C5'	178.4 (3)
C300—C1—C2—C3	178.4 (3)	C1'—C6'—C5'—C4'	1.2 (4)
C1—C2—O2—C20	−107.3 (3)	C6'—C5'—C4'—O4	178.5 (3)
C3—C2—O2—C20	76.5 (3)	C6'—C5'—C4'—C3'	−0.7 (5)
C1—C2—C3—O3	−177.7 (3)	C3'—C4'—O4—C40	2.4 (4)
O2—C2—C3—O3	−1.6 (4)	C5'—C4'—O4—C40	−176.8 (3)
C1—C2—C3—C4	0.1 (4)	O4—C4'—C3'—C2'	179.6 (3)
O2—C2—C3—C4	176.2 (3)	C5'—C4'—C3'—C2'	−1.3 (4)
C4—C3—O3—C30	3.2 (4)	C4'—C3'—C2'—O20	−177.7 (3)
C2—C3—O3—C30	−179.0 (3)	C4'—C3'—C2'—C1'	2.8 (4)
O3—C3—C4—C5	178.2 (3)	C6'—C1'—C2'—O20	178.2 (3)
C2—C3—C4—C5	0.5 (4)	C100—C1'—C2'—O20	0.0 (4)
C3—C4—C5—C6	−0.6 (5)	C6'—C1'—C2'—C3'	−2.3 (4)
C4—C5—C6—C1	0.0 (5)	C100—C1'—C2'—C3'	179.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O20—H20···O1	0.84	1.77	2.515 (3)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O20—H20⋯O1	0.84	1.77	2.515 (3)	147