(E)-1-(2-Hy­droxy-4,6-dimeth­oxy­phen­yl)-3-(4-meth­oxy­phen­yl)prop-2-en-1-one from Kaempferia rotunda Val.

Sirat, H.M.; Feng, Y.S.; Hazni, H.; Awang, K.; Ng, S.W.

doi:10.1107/S1600536810042674

(E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one from Kaempferia rotunda Val.

H. M. Sirat, Y. S. Feng, H. Hazni, K. Awang and S. W. Ng

The planar -CH=CHC(=O)- fragment (r.m.s. deviation = 0.074 Å) in the title compound, C₁₈H₁₈O₅, connects the planar hydroxydimethoxyphenyl (r.m.s. deviation = 0.039 Å) and methoxylphenyl (r.m.s. deviation = 0.021 Å) parts. The central fragment forms a dihedral angle of 13.7 (1)° with the hydroxydimethoxyphenyl part and 32.0 (1)° with the methoxyphenyl part. The hydroxy group forms an intramolecular hydrogen bond to the carbonyl O atom.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810042674/bt5385sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536810042674/bt5385Isup2.hkl Contains datablock I

CCDC reference: 799698

checkCIF report

Key indicators

Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R factor = 0.036
wR factor = 0.101
Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level G
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1
PLAT128_ALERT_4_G Alternate Setting of Space-group P21/c   .......      P21/n

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Kaempferia rotunda is one of the four Malaysian Kaempferia of the Zingiberaceae family; among the constitutents isolated is 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one (Scheme I) (Sirat et al., 2001; Stevenson et al., 2007). The planar –CH═CHC(═O)– fragment (r.m.s. deviation 0.074 Å) connects the planar hydroxyldimethoxyphenyl (r.m.s. deviation 0.039 Å) and methoxylphenyl (r.m.s. deviation 0.021 Å) parts. The fragment is aligned at 13.7 (1) ° with the hydroxydimethoxyphenyl part and at 32.0 (1) ° with the methoxyphenyl part. The hydroxy group forms an intramolecular hydrogen bond to the carbonyl oxygen atom of the fragment (Fig. 1).

Related literature top

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

Experimental top

Kaempferia rotunda rhizomes were purchased from a market in Kempas, Johor. The rhizomes were dried and then grounded. The grounded rhizomes were extracted with n-hexane (4.5 L), ethyl acetate (4.5 L) and methanol (4.5 L) in a soxhlet extractor for 16 h. The extracts were concentrated to give a dark brown semi-solid from the n-hexane extract (2.32 g), a dark brown oil from the ethyl acetate extract (6.80 g) and a dark brown viscous liquid from the methanol extract (15.27 g). The n-hexane extract was purified by column chromatography (93.0 g, column size: 4.5 × 45.0 cm) with n-hexane:ether (99:1, 98:2 and 97:3) as eluents to give 20 fractions. Fractions 13 (0.08 g) and 14 (0.02 g) were combined and recrystallized by from an n-hexane: ether mixture to afford the title compound (6.9 mg) as yellow crystals.

Structure description top

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

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of C₁₈H₁₈O₅ at the 70% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

(E)-1-(2-Hydroxy-4,6-dimethoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₈H₁₈O₅	F(000) = 664
M_r = 314.32	D_x = 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

Data collection top

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

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)] = 0.036	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(F_o²) + (0.0545P)² + 0.5468P] where P = (F_o² + 2F_c²)/3
3464 reflections	(Δ/σ)_max = 0.001
215 parameters	Δρ_max = 0.32 e Å⁻³
1 restraint	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₁₈H₁₈O₅	V = 1503.29 (16) Å³
M_r = 314.32	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 12.8502 (8) Å	µ = 0.10 mm⁻¹
b = 8.3226 (5) Å	T = 100 K
c = 14.1865 (9) Å	0.45 × 0.40 × 0.05 mm
β = 97.765 (1)°

Data collection top

Bruker SMART APEX diffractometer	2989 reflections with I > 2σ(I)
13992 measured reflections	R_int = 0.027
3464 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	1 restraint
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.32 e Å⁻³
3464 reflections	Δρ_min = −0.23 e Å⁻³
215 parameters

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₈H₁₈O₅
M_r	314.32
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	12.8502 (8), 8.3226 (5), 14.1865 (9)
β (°)	97.765 (1)
V (Å³)	1503.29 (16)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.45 × 0.40 × 0.05

Data collection
Diffractometer	Bruker SMART APEX
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13992, 3464, 2989
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.036, 0.101, 1.01
No. of reflections	3464
No. of parameters	215
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.23

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).