1-(2,6-Dihydr-oxy-4-methoxy-phen-yl)-3-phenyl-propan-1-one.

The title compound, C(16)H(16)O(4), a dihydro-chalcone, was isolated from the rhizomes of Etlingera littoralis. The mol-ecule is twisted with a dihedral angle of 71.69 (6)° between the two aromatic rings. The propanone unit makes dihedral angles of 4.07 (6) and 73.56 (7)°, respectively, with the 2,6-dihydroxy-4-methoxyphenyl and phenyl rings. The meth-oxy group is approximately coplanar with the attached benzene ring with a dihedral angle of 1.74 (10)°. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, inter-molecular O-H⋯O hydrogen bonds link the mol-ecules into chains along [201]. A π-π inter-action with a centroid-centroid distance of 3.5185 (6) Å is also observed.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to dihydro­chalcones and their activities, see: Nilsson (1961 ▶); Nowakowska (2007 ▶); Portet et al. (2007 ▶). For Zingiberaceae plants, see: Chuakul & Boonpleng (2003 ▶); Reanmongkol et al. (2006 ▶); Sirirugsa (1999 ▶); Tewtrakul, Subhadhirasakul & Kummee (2003 ▶); Tewtrakul, Subhadhirasakul, Puripattanavong & Panphadung (2003 ▶). For a related structure, see: Ng et al. (2005 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H16O4

M = 272.29

Monoclinic,

a = 7.2142 (6) Å

b = 30.522 (2) Å

c = 6.5587 (5) Å

β = 107.267 (2)°

V = 1379.09 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.46 × 0.34 × 0.18 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.958, T max = 0.983

17744 measured reflections

3044 independent reflections

2940 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.097

S = 1.08

3044 reflections

186 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.40 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810013590/is2537sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013590/is2537Isup2.hkl

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

C16H16O4	F(000) = 576
Mr = 272.29	Dx = 1.311 Mg m−3
Monoclinic, Cc	Melting point: 443 K
Hall symbol: C -2yc	Mo Kα radiation, λ = 0.71073 Å
a = 7.2142 (6) Å	Cell parameters from 3044 reflections
b = 30.522 (2) Å	θ = 2.7–35.0°
c = 6.5587 (5) Å	µ = 0.09 mm−1
β = 107.267 (2)°	T = 100 K
V = 1379.09 (18) Å3	Block, yellow
Z = 4	0.46 × 0.34 × 0.18 mm

Bruker APEX DUO CCD area-detector diffractometer	3044 independent reflections
Radiation source: sealed tube	2940 reflections with I > 2σ(I)
graphite	Rint = 0.025
φ and ω scans	θmax = 35.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.958, Tmax = 0.983	k = −49→48
17744 measured reflections	l = −10→10

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0648P)2 + 0.1812P] where P = (Fo2 + 2Fc2)/3
3044 reflections	(Δ/σ)max = 0.001
186 parameters	Δρmax = 0.34 e Å−3
2 restraints	Δρmin = −0.40 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.57929 (10)	0.09273 (3)	0.16110 (12)	0.01772 (14)
O2	0.40256 (10)	0.02283 (2)	0.09183 (12)	0.01659 (14)
H1O2	0.4212	0.0494	0.0997	0.025*
O3	0.76008 (12)	−0.11076 (2)	0.22402 (13)	0.01827 (13)
O4	1.09458 (10)	0.02313 (2)	0.35682 (12)	0.01540 (13)
H1O4	1.186 (4)	0.0088 (8)	0.419 (4)	0.043 (6)*
C1	0.57479 (11)	0.00170 (3)	0.15654 (13)	0.01230 (14)
C2	0.56979 (13)	−0.04392 (3)	0.15433 (14)	0.01400 (15)
H2A	0.4524	−0.0589	0.1102	0.017*
C3	0.74533 (14)	−0.06642 (3)	0.21997 (15)	0.01307 (13)
C4	0.92225 (13)	−0.04409 (3)	0.28721 (14)	0.01272 (14)
H4A	1.0381	−0.0597	0.3298	0.015*
C5	0.92521 (11)	0.00137 (3)	0.29051 (12)	0.01140 (13)
C6	0.75073 (14)	0.02604 (3)	0.22318 (15)	0.01112 (13)
C7	0.74075 (13)	0.07385 (3)	0.21838 (14)	0.01271 (13)
C8	0.91965 (13)	0.10221 (3)	0.27702 (14)	0.01421 (14)
H8A	1.0023	0.0936	0.1911	0.017*
H8B	0.9911	0.0971	0.4255	0.017*
C9	0.87479 (16)	0.15107 (3)	0.24454 (17)	0.01880 (16)
H9A	0.7893	0.1559	0.1013	0.023*
H9B	0.8081	0.1608	0.3448	0.023*
C10	1.05757 (16)	0.17743 (3)	0.27659 (18)	0.01983 (18)
C11	1.1302 (2)	0.20381 (4)	0.4562 (2)	0.0303 (2)
H11A	1.0662	0.2049	0.5601	0.036*
C12	1.2988 (3)	0.22868 (4)	0.4815 (3)	0.0440 (4)
H12A	1.3455	0.2463	0.6013	0.053*
C13	1.3961 (2)	0.22708 (5)	0.3287 (3)	0.0453 (4)
H13A	1.5074	0.2438	0.3455	0.054*
C14	1.3276 (2)	0.20066 (5)	0.1517 (3)	0.0396 (3)
H14A	1.3938	0.1992	0.0499	0.048*
C15	1.15876 (19)	0.17616 (4)	0.1255 (2)	0.0273 (2)
H15A	1.1128	0.1587	0.0049	0.033*
C16	0.58350 (17)	−0.13568 (3)	0.16199 (18)	0.0230 (2)
H16A	0.6136	−0.1664	0.1775	0.034*
H16B	0.5142	−0.1294	0.0157	0.034*
H16C	0.5046	−0.1279	0.2513	0.034*

	U11	U22	U33	U12	U13	U23
O1	0.0124 (3)	0.0166 (3)	0.0227 (3)	0.0027 (2)	0.0030 (2)	0.0000 (3)
O2	0.0085 (3)	0.0182 (3)	0.0212 (3)	0.0004 (2)	0.0016 (2)	−0.0017 (2)
O3	0.0201 (3)	0.0120 (3)	0.0216 (3)	−0.0026 (2)	0.0044 (2)	−0.0005 (2)
O4	0.0072 (2)	0.0147 (3)	0.0221 (3)	−0.0008 (2)	0.0010 (2)	0.0007 (2)
C1	0.0087 (3)	0.0161 (3)	0.0118 (3)	−0.0003 (3)	0.0025 (2)	−0.0004 (3)
C2	0.0119 (3)	0.0157 (3)	0.0139 (3)	−0.0030 (3)	0.0030 (3)	−0.0011 (3)
C3	0.0144 (3)	0.0129 (3)	0.0116 (3)	−0.0014 (3)	0.0034 (2)	−0.0004 (3)
C4	0.0111 (3)	0.0132 (3)	0.0134 (3)	0.0002 (3)	0.0029 (2)	0.0002 (3)
C5	0.0089 (3)	0.0135 (3)	0.0114 (3)	−0.0005 (3)	0.0025 (2)	0.0002 (3)
C6	0.0087 (3)	0.0128 (3)	0.0114 (3)	−0.0007 (3)	0.0022 (2)	−0.0004 (3)
C7	0.0117 (3)	0.0137 (3)	0.0124 (3)	0.0003 (3)	0.0032 (2)	−0.0002 (3)
C8	0.0130 (3)	0.0125 (3)	0.0161 (3)	−0.0013 (3)	0.0028 (3)	−0.0007 (3)
C9	0.0179 (4)	0.0126 (3)	0.0242 (4)	0.0011 (3)	0.0036 (3)	−0.0009 (3)
C10	0.0203 (4)	0.0112 (3)	0.0232 (4)	−0.0016 (3)	−0.0010 (3)	0.0012 (3)
C11	0.0361 (6)	0.0168 (4)	0.0293 (5)	−0.0027 (4)	−0.0035 (4)	−0.0040 (4)
C12	0.0459 (8)	0.0190 (5)	0.0472 (8)	−0.0115 (5)	−0.0170 (6)	0.0002 (5)
C13	0.0297 (6)	0.0271 (6)	0.0637 (10)	−0.0136 (5)	−0.0098 (6)	0.0190 (6)
C14	0.0266 (5)	0.0360 (7)	0.0532 (8)	−0.0074 (5)	0.0073 (6)	0.0202 (6)
C15	0.0251 (5)	0.0238 (5)	0.0308 (5)	−0.0043 (4)	0.0052 (4)	0.0054 (4)
C16	0.0263 (5)	0.0178 (4)	0.0227 (4)	−0.0090 (4)	0.0040 (4)	−0.0014 (3)

O1—C7	1.2531 (11)	C8—H8B	0.9700
O2—C1	1.3516 (11)	C9—C10	1.5052 (14)
O2—H1O2	0.8200	C9—H9A	0.9700
O3—C3	1.3574 (11)	C9—H9B	0.9700
O3—C16	1.4349 (13)	C10—C11	1.3943 (15)
O4—C5	1.3445 (10)	C10—C15	1.3951 (17)
O4—H1O4	0.79 (3)	C11—C12	1.401 (2)
C1—C2	1.3928 (13)	C11—H11A	0.9300
C1—C6	1.4230 (12)	C12—C13	1.384 (3)
C2—C3	1.3917 (14)	C12—H12A	0.9300
C2—H2A	0.9300	C13—C14	1.379 (3)
C3—C4	1.3978 (13)	C13—H13A	0.9300
C4—C5	1.3877 (12)	C14—C15	1.3956 (18)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.4201 (12)	C15—H15A	0.9300
C6—C7	1.4607 (11)	C16—H16A	0.9600
C7—C8	1.5061 (13)	C16—H16B	0.9600
C8—C9	1.5276 (13)	C16—H16C	0.9600
C8—H8A	0.9700
C1—O2—H1O2	109.5	C10—C9—C8	111.21 (8)
C3—O3—C16	117.72 (9)	C10—C9—H9A	109.4
C5—O4—H1O4	115.4 (18)	C8—C9—H9A	109.4
O2—C1—C2	117.08 (8)	C10—C9—H9B	109.4
O2—C1—C6	120.02 (8)	C8—C9—H9B	109.4
C2—C1—C6	122.90 (8)	H9A—C9—H9B	108.0
C3—C2—C1	118.14 (8)	C11—C10—C15	118.14 (11)
C3—C2—H2A	120.9	C11—C10—C9	121.36 (11)
C1—C2—H2A	120.9	C15—C10—C9	120.50 (9)
O3—C3—C2	123.84 (9)	C10—C11—C12	120.52 (15)
O3—C3—C4	114.90 (9)	C10—C11—H11A	119.7
C2—C3—C4	121.26 (7)	C12—C11—H11A	119.7
C5—C4—C3	120.05 (8)	C13—C12—C11	120.27 (14)
C5—C4—H4A	120.0	C13—C12—H12A	119.9
C3—C4—H4A	120.0	C11—C12—H12A	119.9
O4—C5—C4	120.48 (8)	C14—C13—C12	119.88 (13)
O4—C5—C6	118.37 (7)	C14—C13—H13A	120.1
C4—C5—C6	121.15 (8)	C12—C13—H13A	120.1
C5—C6—C1	116.50 (7)	C13—C14—C15	119.88 (16)
C5—C6—C7	124.74 (8)	C13—C14—H14A	120.1
C1—C6—C7	118.76 (8)	C15—C14—H14A	120.1
O1—C7—C6	120.09 (8)	C10—C15—C14	121.29 (13)
O1—C7—C8	117.52 (7)	C10—C15—H15A	119.4
C6—C7—C8	122.38 (8)	C14—C15—H15A	119.4
C7—C8—C9	113.30 (7)	O3—C16—H16A	109.5
C7—C8—H8A	108.9	O3—C16—H16B	109.5
C9—C8—H8A	108.9	H16A—C16—H16B	109.5
C7—C8—H8B	108.9	O3—C16—H16C	109.5
C9—C8—H8B	108.9	H16A—C16—H16C	109.5
H8A—C8—H8B	107.7	H16B—C16—H16C	109.5
O2—C1—C2—C3	179.91 (8)	C5—C6—C7—O1	−178.29 (8)
C6—C1—C2—C3	−0.16 (14)	C1—C6—C7—O1	1.64 (14)
C16—O3—C3—C2	−1.66 (15)	C5—C6—C7—C8	2.74 (15)
C16—O3—C3—C4	178.47 (8)	C1—C6—C7—C8	−177.33 (8)
C1—C2—C3—O3	−179.62 (8)	O1—C7—C8—C9	−3.30 (12)
C1—C2—C3—C4	0.24 (14)	C6—C7—C8—C9	175.70 (8)
O3—C3—C4—C5	−179.79 (8)	C7—C8—C9—C10	−172.32 (8)
C2—C3—C4—C5	0.34 (14)	C8—C9—C10—C11	−108.05 (11)
C3—C4—C5—O4	179.38 (7)	C8—C9—C10—C15	72.21 (12)
C3—C4—C5—C6	−1.01 (14)	C15—C10—C11—C12	0.83 (17)
O4—C5—C6—C1	−179.33 (7)	C9—C10—C11—C12	−178.92 (11)
C4—C5—C6—C1	1.05 (13)	C10—C11—C12—C13	−0.5 (2)
O4—C5—C6—C7	0.60 (14)	C11—C12—C13—C14	−0.4 (2)
C4—C5—C6—C7	−179.02 (8)	C12—C13—C14—C15	1.0 (2)
O2—C1—C6—C5	179.46 (8)	C11—C10—C15—C14	−0.27 (17)
C2—C1—C6—C5	−0.46 (14)	C9—C10—C15—C14	179.47 (11)
O2—C1—C6—C7	−0.47 (13)	C13—C14—C15—C10	−0.6 (2)
C2—C1—C6—C7	179.60 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1	0.82	1.71	2.4576 (11)	150
O4—H1O4···O2i	0.80 (3)	1.90 (3)	2.6920 (10)	175 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1	0.82	1.71	2.4576 (11)	150
O4—H1O4⋯O2i	0.80 (3)	1.90 (3)	2.6920 (10)	175 (3)

Symmetry code: (i) .