(E)-1-(2-Hy-droxy-4,6-dimeth-oxy-phen-yl)-3-(4-meth-oxy-phen-yl)prop-2-en-1-one from Kaempferia rotunda Val.

The planar -CH=CHC(=O)- fragment (r.m.s. deviation = 0.074 Å) in the title compound, C(18)H(18)O(5), connects the planar hy-droxy-dimeth-oxy-phenyl (r.m.s. deviation = 0.039 Å) and meth-oxy-lphenyl (r.m.s. deviation = 0.021 Å) parts. The central fragment forms a dihedral angle of 13.7 (1)° with the hy-droxy-dimeth-oxy-phenyl part and 32.0 (1)° with the meth-oxy-phenyl part. The hy-droxy group forms an intra-molecular hydrogen bond to the carbonyl O atom.

Related literature

For the isolation of the compound from Kaempferia rotunda, see: Sirat et al. (2001 ▶); Stevenson et al. (2007 ▶).

Experimental

Crystal data

C18H18O5

M = 314.32

Monoclinic,

a = 12.8502 (8) Å

b = 8.3226 (5) Å

c = 14.1865 (9) Å

β = 97.765 (1)°

V = 1503.29 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.45 × 0.40 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

13992 measured reflections

3464 independent reflections

2989 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.101

S = 1.01

3464 reflections

215 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.32 e Å−3

Δρmin = −0.23 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: X-SEED (Barbour, 2001 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042674/bt5385sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042674/bt5385Isup2.hkl

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

C18H18O5	F(000) = 664
Mr = 314.32	Dx = 1.389 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5893 reflections
a = 12.8502 (8) Å	θ = 2.3–28.2°
b = 8.3226 (5) Å	µ = 0.10 mm−1
c = 14.1865 (9) Å	T = 100 K
β = 97.765 (1)°	Irregular block, yellow
V = 1503.29 (16) Å3	0.45 × 0.40 × 0.05 mm
Z = 4

Bruker SMART APEX diffractometer	2989 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.027
graphite	θmax = 27.5°, θmin = 2.0°
ω scans	h = −16→15
13992 measured reflections	k = −10→10
3464 independent reflections	l = −18→18

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0545P)2 + 0.5468P] where P = (Fo2 + 2Fc2)/3
3464 reflections	(Δ/σ)max = 0.001
215 parameters	Δρmax = 0.32 e Å−3
1 restraint	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
O1	0.71889 (6)	0.58291 (10)	0.67517 (6)	0.02051 (19)
H1	0.7343 (14)	0.536 (2)	0.6242 (9)	0.049 (5)*
O2	0.44911 (7)	0.93407 (10)	0.74558 (6)	0.0224 (2)
O3	0.45229 (6)	0.75473 (10)	0.42926 (5)	0.01955 (19)
O4	0.72544 (6)	0.50207 (10)	0.50890 (6)	0.02089 (19)
O5	0.61863 (7)	0.54719 (10)	−0.08390 (5)	0.01985 (19)
C1	0.63266 (9)	0.66965 (13)	0.64416 (8)	0.0166 (2)
C2	0.58866 (9)	0.75693 (13)	0.71251 (8)	0.0181 (2)
H2	0.6199	0.7560	0.7771	0.022*
C3	0.49855 (9)	0.84502 (13)	0.68446 (8)	0.0176 (2)
C4	0.45027 (9)	0.84618 (14)	0.58972 (8)	0.0177 (2)
H4	0.3869	0.9041	0.5724	0.021*
C5	0.49567 (9)	0.76227 (13)	0.52174 (8)	0.0163 (2)
C6	0.59130 (8)	0.67424 (13)	0.54579 (7)	0.0160 (2)
C7	0.49545 (11)	0.93606 (16)	0.84345 (8)	0.0257 (3)
H7A	0.4487	0.9924	0.8815	0.039*
H7B	0.5632	0.9917	0.8491	0.039*
H7C	0.5061	0.8255	0.8665	0.039*
C8	0.35464 (9)	0.83628 (15)	0.40224 (8)	0.0210 (2)
H8A	0.3332	0.8236	0.3337	0.032*
H8B	0.3632	0.9507	0.4176	0.032*
H8C	0.3008	0.7903	0.4370	0.032*
C9	0.64968 (9)	0.59271 (13)	0.47819 (8)	0.0170 (2)
C10	0.62915 (9)	0.61886 (14)	0.37466 (8)	0.0180 (2)
H10	0.5914	0.7110	0.3497	0.022*
C11	0.66420 (9)	0.51130 (14)	0.31598 (8)	0.0179 (2)
H11	0.6976	0.4182	0.3446	0.022*
C12	0.65630 (8)	0.52262 (14)	0.21240 (8)	0.0170 (2)
C13	0.67036 (9)	0.38511 (14)	0.15961 (8)	0.0194 (2)
H13	0.6880	0.2870	0.1922	0.023*
C14	0.65939 (9)	0.38694 (14)	0.06058 (8)	0.0191 (2)
H14	0.6686	0.2912	0.0262	0.023*
C15	0.63480 (8)	0.53098 (14)	0.01267 (8)	0.0166 (2)
C16	0.62576 (9)	0.67210 (14)	0.06464 (8)	0.0192 (2)
H16	0.6127	0.7714	0.0322	0.023*
C17	0.63562 (9)	0.66808 (14)	0.16271 (8)	0.0183 (2)
H17	0.6284	0.7645	0.1971	0.022*
C18	0.63148 (10)	0.40641 (15)	−0.13935 (8)	0.0219 (2)
H18A	0.6141	0.4319	−0.2071	0.033*
H18B	0.5847	0.3215	−0.1222	0.033*
H18C	0.7045	0.3696	−0.1267	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0192 (4)	0.0242 (4)	0.0175 (4)	0.0058 (3)	0.0000 (3)	0.0029 (3)
O2	0.0276 (5)	0.0221 (4)	0.0174 (4)	0.0066 (3)	0.0027 (3)	−0.0003 (3)
O3	0.0168 (4)	0.0253 (4)	0.0156 (4)	0.0041 (3)	−0.0011 (3)	0.0016 (3)
O4	0.0204 (4)	0.0229 (4)	0.0191 (4)	0.0052 (3)	0.0017 (3)	0.0024 (3)
O5	0.0246 (4)	0.0197 (4)	0.0156 (4)	0.0016 (3)	0.0042 (3)	0.0000 (3)
C1	0.0150 (5)	0.0154 (5)	0.0188 (5)	−0.0015 (4)	0.0007 (4)	0.0041 (4)
C2	0.0200 (6)	0.0183 (5)	0.0152 (5)	−0.0012 (4)	−0.0001 (4)	0.0025 (4)
C3	0.0200 (5)	0.0147 (5)	0.0185 (5)	−0.0016 (4)	0.0044 (4)	0.0006 (4)
C4	0.0166 (5)	0.0172 (5)	0.0191 (5)	0.0017 (4)	0.0018 (4)	0.0037 (4)
C5	0.0168 (5)	0.0159 (5)	0.0156 (5)	−0.0025 (4)	0.0002 (4)	0.0032 (4)
C6	0.0160 (5)	0.0157 (5)	0.0160 (5)	−0.0013 (4)	0.0016 (4)	0.0023 (4)
C7	0.0348 (7)	0.0229 (6)	0.0188 (6)	0.0044 (5)	0.0013 (5)	−0.0027 (5)
C8	0.0170 (5)	0.0242 (6)	0.0207 (5)	0.0033 (4)	−0.0019 (4)	0.0034 (4)
C9	0.0161 (5)	0.0156 (5)	0.0189 (5)	−0.0026 (4)	0.0013 (4)	0.0021 (4)
C10	0.0162 (5)	0.0194 (5)	0.0184 (5)	0.0002 (4)	0.0023 (4)	0.0038 (4)
C11	0.0173 (5)	0.0180 (5)	0.0181 (5)	−0.0008 (4)	0.0011 (4)	0.0031 (4)
C12	0.0142 (5)	0.0198 (6)	0.0171 (5)	0.0005 (4)	0.0022 (4)	0.0012 (4)
C13	0.0199 (6)	0.0167 (5)	0.0211 (6)	0.0025 (4)	0.0011 (4)	0.0030 (4)
C14	0.0187 (5)	0.0179 (6)	0.0206 (5)	0.0021 (4)	0.0024 (4)	−0.0014 (4)
C15	0.0131 (5)	0.0210 (6)	0.0160 (5)	−0.0005 (4)	0.0030 (4)	0.0003 (4)
C16	0.0207 (6)	0.0167 (5)	0.0205 (5)	0.0021 (4)	0.0039 (4)	0.0027 (4)
C17	0.0191 (5)	0.0169 (6)	0.0190 (5)	0.0008 (4)	0.0035 (4)	−0.0005 (4)
C18	0.0253 (6)	0.0220 (6)	0.0193 (5)	−0.0011 (5)	0.0060 (4)	−0.0033 (4)

O1—C1	1.3457 (13)	C8—H8A	0.9800
O1—H1	0.867 (9)	C8—H8B	0.9800
O2—C3	1.3615 (14)	C8—H8C	0.9800
O2—C7	1.4349 (14)	C9—C10	1.4728 (15)
O3—C5	1.3558 (13)	C10—C11	1.3411 (16)
O3—C8	1.4326 (13)	C10—H10	0.9500
O4—C9	1.2618 (14)	C11—C12	1.4623 (15)
O5—C15	1.3644 (13)	C11—H11	0.9500
O5—C18	1.4331 (14)	C12—C13	1.3927 (16)
C1—C2	1.3913 (16)	C12—C17	1.4079 (16)
C1—C6	1.4250 (15)	C13—C14	1.3929 (16)
C2—C3	1.3828 (16)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.3932 (16)
C3—C4	1.4023 (15)	C14—H14	0.9500
C4—C5	1.3820 (16)	C15—C16	1.3999 (16)
C4—H4	0.9500	C16—C17	1.3804 (16)
C5—C6	1.4318 (15)	C16—H16	0.9500
C6—C9	1.4619 (15)	C17—H17	0.9500
C7—H7A	0.9800	C18—H18A	0.9800
C7—H7B	0.9800	C18—H18B	0.9800
C7—H7C	0.9800	C18—H18C	0.9800
C1—O1—H1	103.7 (12)	O4—C9—C6	119.43 (10)
C3—O2—C7	117.01 (9)	O4—C9—C10	117.29 (10)
C5—O3—C8	117.88 (9)	C6—C9—C10	123.16 (10)
C15—O5—C18	117.20 (9)	C11—C10—C9	119.37 (10)
O1—C1—C2	116.51 (10)	C11—C10—H10	120.3
O1—C1—C6	121.08 (10)	C9—C10—H10	120.3
C2—C1—C6	122.39 (10)	C10—C11—C12	126.67 (10)
C3—C2—C1	118.66 (10)	C10—C11—H11	116.7
C3—C2—H2	120.7	C12—C11—H11	116.7
C1—C2—H2	120.7	C13—C12—C17	117.82 (10)
O2—C3—C2	123.37 (10)	C13—C12—C11	119.40 (10)
O2—C3—C4	115.00 (10)	C17—C12—C11	122.77 (10)
C2—C3—C4	121.63 (10)	C12—C13—C14	122.04 (10)
C5—C4—C3	119.44 (10)	C12—C13—H13	119.0
C5—C4—H4	120.3	C14—C13—H13	119.0
C3—C4—H4	120.3	C15—C14—C13	119.13 (10)
O3—C5—C4	122.78 (10)	C15—C14—H14	120.4
O3—C5—C6	115.74 (10)	C13—C14—H14	120.4
C4—C5—C6	121.46 (10)	O5—C15—C14	124.66 (10)
C1—C6—C5	116.20 (10)	O5—C15—C16	115.70 (10)
C1—C6—C9	118.26 (10)	C14—C15—C16	119.64 (10)
C5—C6—C9	125.53 (10)	C17—C16—C15	120.50 (10)
O2—C7—H7A	109.5	C17—C16—H16	119.7
O2—C7—H7B	109.5	C15—C16—H16	119.7
H7A—C7—H7B	109.5	C16—C17—C12	120.72 (10)
O2—C7—H7C	109.5	C16—C17—H17	119.6
H7A—C7—H7C	109.5	C12—C17—H17	119.6
H7B—C7—H7C	109.5	O5—C18—H18A	109.5
O3—C8—H8A	109.5	O5—C18—H18B	109.5
O3—C8—H8B	109.5	H18A—C18—H18B	109.5
H8A—C8—H8B	109.5	O5—C18—H18C	109.5
O3—C8—H8C	109.5	H18A—C18—H18C	109.5
H8A—C8—H8C	109.5	H18B—C18—H18C	109.5
H8B—C8—H8C	109.5
O1—C1—C2—C3	−178.53 (10)	C5—C6—C9—O4	−170.97 (10)
C6—C1—C2—C3	3.23 (17)	C1—C6—C9—C10	−165.63 (10)
C7—O2—C3—C2	0.85 (16)	C5—C6—C9—C10	13.18 (17)
C7—O2—C3—C4	179.78 (10)	O4—C9—C10—C11	22.06 (16)
C1—C2—C3—O2	179.81 (10)	C6—C9—C10—C11	−162.02 (11)
C1—C2—C3—C4	0.96 (17)	C9—C10—C11—C12	−176.23 (10)
O2—C3—C4—C5	178.59 (10)	C10—C11—C12—C13	−162.90 (11)
C2—C3—C4—C5	−2.46 (17)	C10—C11—C12—C17	17.58 (18)
C8—O3—C5—C4	−0.74 (16)	C17—C12—C13—C14	−3.23 (17)
C8—O3—C5—C6	177.90 (10)	C11—C12—C13—C14	177.23 (10)
C3—C4—C5—O3	178.40 (10)	C12—C13—C14—C15	0.76 (18)
C3—C4—C5—C6	−0.17 (17)	C18—O5—C15—C14	−2.19 (16)
O1—C1—C6—C5	176.25 (10)	C18—O5—C15—C16	177.52 (10)
C2—C1—C6—C5	−5.59 (16)	C13—C14—C15—O5	−177.73 (10)
O1—C1—C6—C9	−4.83 (16)	C13—C14—C15—C16	2.57 (17)
C2—C1—C6—C9	173.33 (10)	O5—C15—C16—C17	176.90 (10)
O3—C5—C6—C1	−174.67 (9)	C14—C15—C16—C17	−3.38 (17)
C4—C5—C6—C1	4.00 (16)	C15—C16—C17—C12	0.84 (17)
O3—C5—C6—C9	6.50 (16)	C13—C12—C17—C16	2.41 (17)
C4—C5—C6—C9	−174.84 (11)	C11—C12—C17—C16	−178.06 (11)
C1—C6—C9—O4	10.22 (16)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4	0.87 (1)	1.65 (1)	2.465 (1)	156 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4	0.87 (1)	1.65 (1)	2.465 (1)	156 (2)