Flavokavain B from the rhizome of Alpinia mutica Roxb.

THE TITLE COMPOUND [SYSTEMATIC NAME: (E)-1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylprop-2-en-1-one], C(17)H(16)O(4), has an aromatic ring at both ends of the -CH= CH-C(=O)- fragment with the -CH=CH- bond in a trans configuration. The phenyl ring is nearly coplanar with this fragment [dihedral angle 4.8 (3) °] as is the hy-droxy-ldimeth-oxy-lphenyl unit [dihedral angle 6.3 (3) °]. The hy-droxy group is the donor in an intra-molecular hydrogen bond to the double-bonded O atom.

Related literature

For the isolation and spectroscopic characterization of the title compound, see: Flores et al. (2007 ▶); Xuan et al. (2008 ▶).

Experimental

Crystal data

C17H16O4

M = 284.30

Orthorhombic,

a = 4.9668 (10) Å

b = 12.305 (3) Å

c = 22.552 (5) Å

V = 1378.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.40 × 0.10 × 0.05 mm

Data collection

Bruker SMART APEX diffractometer

10723 measured reflections

1449 independent reflections

1162 reflections with I > 2σ(I)

R int = 0.089

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.128

S = 1.09

1449 reflections

197 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.27 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/S1600536810041395/fl2321sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041395/fl2321Isup2.hkl

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

C17H16O4	F(000) = 600
Mr = 284.30	Dx = 1.370 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1135 reflections
a = 4.9668 (10) Å	θ = 3.2–21.7°
b = 12.305 (3) Å	µ = 0.10 mm−1
c = 22.552 (5) Å	T = 100 K
V = 1378.3 (5) Å3	Prism, faint yellow
Z = 4	0.40 × 0.10 × 0.05 mm

Bruker SMART APEX diffractometer	1162 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.089
graphite	θmax = 25.0°, θmin = 1.8°
ω scans	h = −5→5
10723 measured reflections	k = −14→14
1449 independent reflections	l = −26→25

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)] = 0.049	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.128	w = 1/[σ2(Fo2) + (0.0736P)2 + 0.021P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
1449 reflections	Δρmax = 0.20 e Å−3
197 parameters	Δρmin = −0.26 e Å−3
1 restraint	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (5)

	x	y	z	Uiso*/Ueq
O1	0.5688 (6)	0.96830 (19)	0.22125 (11)	0.0250 (7)
O2	0.3291 (6)	0.9379 (2)	0.12751 (11)	0.0260 (7)
H2	0.440 (7)	0.958 (4)	0.1541 (14)	0.048 (15)*
O3	−0.3912 (5)	0.68445 (19)	0.12028 (10)	0.0245 (7)
O4	0.0995 (6)	0.72577 (18)	0.29718 (11)	0.0272 (7)
C1	0.7327 (8)	0.9257 (3)	0.40417 (17)	0.0228 (9)
C2	0.5796 (9)	0.8616 (3)	0.44201 (16)	0.0283 (10)
H2A	0.4369	0.8191	0.4262	0.034*
C3	0.6311 (10)	0.8586 (3)	0.50210 (18)	0.0349 (10)
H3	0.5230	0.8150	0.5274	0.042*
C4	0.8406 (9)	0.9191 (3)	0.52537 (17)	0.0323 (11)
H4	0.8762	0.9177	0.5668	0.039*
C5	0.9976 (9)	0.9815 (3)	0.48823 (18)	0.0310 (10)
H5	1.1418	1.0229	0.5042	0.037*
C6	0.9476 (9)	0.9846 (3)	0.42798 (17)	0.0279 (10)
H6	1.0594	1.0267	0.4027	0.034*
C7	0.6751 (8)	0.9328 (3)	0.34039 (17)	0.0257 (9)
H7	0.7994	0.9723	0.3167	0.031*
C8	0.4658 (8)	0.8891 (3)	0.31275 (16)	0.0256 (9)
H8	0.3381	0.8493	0.3354	0.031*
C9	0.4237 (8)	0.8998 (3)	0.24859 (16)	0.0230 (9)
C10	0.2169 (8)	0.8393 (3)	0.21647 (16)	0.0196 (8)
C11	0.1737 (8)	0.8639 (3)	0.15591 (16)	0.0208 (9)
C12	−0.0285 (8)	0.8174 (3)	0.12220 (16)	0.0230 (9)
H12	−0.0586	0.8392	0.0823	0.028*
C13	−0.1857 (8)	0.7377 (3)	0.14850 (16)	0.0213 (9)
C14	−0.1454 (8)	0.7058 (3)	0.20702 (16)	0.0221 (8)
H14	−0.2544	0.6504	0.2238	0.027*
C15	0.0513 (8)	0.7543 (3)	0.24038 (15)	0.0211 (9)
C16	−0.0619 (9)	0.6404 (3)	0.32205 (16)	0.0298 (10)
H16A	−0.0115	0.6292	0.3636	0.045*
H16B	−0.0320	0.5731	0.2998	0.045*
H16C	−0.2525	0.6606	0.3197	0.045*
C17	−0.4398 (9)	0.7113 (3)	0.05989 (15)	0.0287 (10)
H17A	−0.5907	0.6679	0.0449	0.043*
H17B	−0.2783	0.6957	0.0364	0.043*
H17C	−0.4839	0.7887	0.0567	0.043*

	U11	U22	U33	U12	U13	U23
O1	0.0269 (15)	0.0177 (12)	0.0304 (15)	−0.0032 (12)	0.0027 (13)	0.0014 (11)
O2	0.0313 (17)	0.0199 (13)	0.0266 (16)	−0.0038 (13)	0.0000 (14)	0.0034 (12)
O3	0.0254 (15)	0.0218 (13)	0.0263 (14)	−0.0010 (12)	−0.0042 (13)	−0.0008 (11)
O4	0.0393 (17)	0.0180 (12)	0.0243 (14)	−0.0075 (13)	−0.0017 (13)	0.0058 (11)
C1	0.026 (2)	0.0154 (19)	0.027 (2)	0.0059 (17)	−0.0030 (18)	−0.0031 (16)
C2	0.031 (2)	0.0254 (19)	0.028 (2)	−0.006 (2)	−0.002 (2)	−0.0019 (17)
C3	0.038 (3)	0.037 (2)	0.030 (2)	−0.006 (2)	0.001 (2)	0.0001 (19)
C4	0.044 (3)	0.026 (2)	0.027 (2)	0.001 (2)	−0.006 (2)	0.0006 (17)
C5	0.035 (3)	0.021 (2)	0.037 (2)	−0.0020 (19)	−0.006 (2)	−0.0040 (17)
C6	0.032 (2)	0.0211 (19)	0.031 (2)	−0.0026 (19)	−0.0017 (19)	0.0021 (17)
C7	0.028 (2)	0.0173 (18)	0.032 (2)	−0.0015 (18)	0.005 (2)	0.0007 (17)
C8	0.030 (2)	0.0205 (19)	0.026 (2)	−0.0034 (17)	−0.0005 (19)	−0.0006 (16)
C9	0.024 (2)	0.0154 (16)	0.029 (2)	0.0021 (17)	0.0054 (19)	−0.0024 (16)
C10	0.022 (2)	0.0140 (17)	0.023 (2)	0.0009 (15)	0.0026 (17)	−0.0038 (15)
C11	0.025 (2)	0.0115 (17)	0.025 (2)	0.0016 (16)	0.0052 (18)	0.0015 (15)
C12	0.030 (2)	0.0202 (19)	0.0191 (19)	0.0022 (17)	−0.0020 (18)	−0.0002 (15)
C13	0.024 (2)	0.0159 (17)	0.025 (2)	0.0029 (16)	−0.0010 (17)	−0.0036 (15)
C14	0.022 (2)	0.0158 (16)	0.029 (2)	0.0009 (16)	0.0002 (18)	0.0005 (15)
C15	0.030 (2)	0.0139 (16)	0.0197 (18)	0.0015 (16)	0.0000 (18)	−0.0011 (14)
C16	0.043 (3)	0.0207 (18)	0.026 (2)	−0.0075 (19)	−0.002 (2)	0.0089 (16)
C17	0.036 (3)	0.027 (2)	0.024 (2)	−0.001 (2)	−0.001 (2)	−0.0043 (16)

O1—C9	1.269 (4)	C7—C8	1.326 (5)
O2—C11	1.354 (4)	C7—H7	0.9500
O2—H2	0.85 (1)	C8—C9	1.468 (5)
O3—C13	1.370 (5)	C8—H8	0.9500
O3—C17	1.422 (4)	C9—C10	1.461 (5)
O4—C15	1.349 (4)	C10—C11	1.415 (5)
O4—C16	1.436 (4)	C10—C15	1.436 (5)
C1—C2	1.389 (5)	C11—C12	1.384 (5)
C1—C6	1.397 (5)	C12—C13	1.386 (5)
C1—C7	1.469 (5)	C12—H12	0.9500
C2—C3	1.380 (5)	C13—C14	1.391 (5)
C2—H2A	0.9500	C14—C15	1.370 (5)
C3—C4	1.383 (6)	C14—H14	0.9500
C3—H3	0.9500	C16—H16A	0.9800
C4—C5	1.378 (6)	C16—H16B	0.9800
C4—H4	0.9500	C16—H16C	0.9800
C5—C6	1.382 (5)	C17—H17A	0.9800
C5—H5	0.9500	C17—H17B	0.9800
C6—H6	0.9500	C17—H17C	0.9800
C11—O2—H2	103 (3)	C11—C10—C15	115.5 (3)
C13—O3—C17	117.4 (3)	C11—C10—C9	118.4 (3)
C15—O4—C16	117.5 (3)	C15—C10—C9	126.0 (3)
C2—C1—C6	118.5 (4)	O2—C11—C12	115.6 (3)
C2—C1—C7	121.9 (4)	O2—C11—C10	120.9 (4)
C6—C1—C7	119.6 (4)	C12—C11—C10	123.5 (3)
C3—C2—C1	121.1 (4)	C11—C12—C13	117.8 (3)
C3—C2—H2A	119.4	C11—C12—H12	121.1
C1—C2—H2A	119.4	C13—C12—H12	121.1
C2—C3—C4	119.8 (4)	O3—C13—C12	124.0 (3)
C2—C3—H3	120.1	O3—C13—C14	114.4 (3)
C4—C3—H3	120.1	C12—C13—C14	121.6 (4)
C5—C4—C3	119.7 (4)	C15—C14—C13	120.0 (4)
C5—C4—H4	120.2	C15—C14—H14	120.0
C3—C4—H4	120.2	C13—C14—H14	120.0
C4—C5—C6	120.7 (4)	O4—C15—C14	122.3 (3)
C4—C5—H5	119.6	O4—C15—C10	116.4 (3)
C6—C5—H5	119.6	C14—C15—C10	121.3 (3)
C5—C6—C1	120.1 (4)	O4—C16—H16A	109.5
C5—C6—H6	120.0	O4—C16—H16B	109.5
C1—C6—H6	120.0	H16A—C16—H16B	109.5
C8—C7—C1	126.1 (4)	O4—C16—H16C	109.5
C8—C7—H7	117.0	H16A—C16—H16C	109.5
C1—C7—H7	117.0	H16B—C16—H16C	109.5
C7—C8—C9	122.6 (4)	O3—C17—H17A	109.5
C7—C8—H8	118.7	O3—C17—H17B	109.5
C9—C8—H8	118.7	H17A—C17—H17B	109.5
O1—C9—C10	119.8 (3)	O3—C17—H17C	109.5
O1—C9—C8	117.2 (4)	H17A—C17—H17C	109.5
C10—C9—C8	122.9 (3)	H17B—C17—H17C	109.5
C6—C1—C2—C3	2.3 (6)	C15—C10—C11—C12	5.5 (5)
C7—C1—C2—C3	−177.9 (4)	C9—C10—C11—C12	−175.4 (3)
C1—C2—C3—C4	−0.8 (6)	O2—C11—C12—C13	177.2 (3)
C2—C3—C4—C5	−0.4 (6)	C10—C11—C12—C13	−4.0 (5)
C3—C4—C5—C6	0.2 (6)	C17—O3—C13—C12	1.6 (5)
C4—C5—C6—C1	1.3 (6)	C17—O3—C13—C14	−178.6 (3)
C2—C1—C6—C5	−2.5 (6)	C11—C12—C13—O3	−179.6 (3)
C7—C1—C6—C5	177.7 (4)	C11—C12—C13—C14	0.7 (5)
C2—C1—C7—C8	6.2 (6)	O3—C13—C14—C15	−178.9 (3)
C6—C1—C7—C8	−173.9 (4)	C12—C13—C14—C15	0.8 (6)
C1—C7—C8—C9	−179.8 (4)	C16—O4—C15—C14	0.8 (5)
C7—C8—C9—O1	−12.0 (5)	C16—O4—C15—C10	−179.6 (3)
C7—C8—C9—C10	170.8 (4)	C13—C14—C15—O4	−179.6 (3)
O1—C9—C10—C11	−3.8 (5)	C13—C14—C15—C10	0.9 (6)
C8—C9—C10—C11	173.4 (3)	C11—C10—C15—O4	176.6 (3)
O1—C9—C10—C15	175.3 (3)	C9—C10—C15—O4	−2.5 (5)
C8—C9—C10—C15	−7.5 (6)	C11—C10—C15—C14	−3.8 (5)
C15—C10—C11—O2	−175.9 (3)	C9—C10—C15—C14	177.1 (4)
C9—C10—C11—O2	3.3 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1	0.85 (1)	1.65 (2)	2.455 (4)	157 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1	0.85 (1)	1.65 (2)	2.455 (4)	157 (4)