(E)-1-(2-Hy-droxy-phen-yl)-3-(2,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title chalcone derivative, C(18)H(18)O(5), the dihedral angle between the hy-droxy-substituted benzene ring and the trimeth-oxy-substituted benzene ring is 16.3 (1)°. The three meth-oxy groups are essentially coplanar with the benzene ring to which they are attached, with an r.m.s. deviation of 0.0208 Å. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, weak C-H⋯O inter-actions link mol-ecules into helical chains along the b axis. These chains are connected into sheets parallel to the bc plane by further weak C-H⋯O inter-actions.

Related literature

For background to and applications of chalcones, see: Boeck et al. (2006 ▶); Cheng et al. (2008 ▶); Hatayama et al. (2010 ▶); Jung et al. (2008 ▶); Lee et al. (2006 ▶); Liu et al. (2011 ▶); Nerya et al. (2004 ▶); Patil & Dharmaprakash (2008 ▶); Saydam et al. (2003 ▶); Tewtrakul et al. (2003 ▶). For related structures, see: Suwunwong et al. (2009 ▶); Fun et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C18H18O5

M = 314.32

Orthorhombic,

a = 4.2891 (2) Å

b = 17.3341 (9) Å

c = 20.5732 (10) Å

V = 1529.57 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.56 × 0.16 × 0.14 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.946, T max = 0.986

16077 measured reflections

2392 independent reflections

1946 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.095

S = 1.08

2392 reflections

280 parameters

All H-atom parameters refined

Δρmax = 0.25 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811031382/lh5295sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811031382/lh5295Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811031382/lh5295Isup3.cml

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

C18H18O5	Dx = 1.365 Mg m−3
Mr = 314.32	Melting point = 404–405 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2392 reflections
a = 4.2891 (2) Å	θ = 2.0–29.0°
b = 17.3341 (9) Å	µ = 0.10 mm−1
c = 20.5732 (10) Å	T = 100 K
V = 1529.57 (13) Å3	Block, yellow
Z = 4	0.56 × 0.16 × 0.14 mm
F(000) = 664

Bruker APEXII CCD area-detector diffractometer	2392 independent reflections
Radiation source: sealed tube	1946 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 29.0°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −5→5
Tmin = 0.946, Tmax = 0.986	k = −23→17
16077 measured reflections	l = −24→27

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	All H-atom parameters refined
S = 1.08	w = 1/[σ2(Fo2) + (0.0466P)2 + 0.2277P] where P = (Fo2 + 2Fc2)/3
2392 reflections	(Δ/σ)max = 0.001
280 parameters	Δρmax = 0.25 e Å−3
0 restraints	Δρmin = −0.20 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 120.0 (1) K.

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
O1	−0.2483 (4)	0.67956 (9)	0.11729 (7)	0.0294 (4)
O2	0.0456 (4)	0.56059 (8)	0.15537 (6)	0.0277 (4)
O3	0.5147 (4)	0.34185 (8)	0.25185 (6)	0.0239 (4)
O4	0.3357 (4)	0.08107 (8)	0.17331 (7)	0.0241 (4)
O5	−0.0186 (4)	0.13159 (7)	0.08358 (6)	0.0228 (4)
C1	−0.3401 (5)	0.63667 (11)	0.06566 (9)	0.0205 (5)
C2	−0.5266 (6)	0.67134 (12)	0.01880 (10)	0.0245 (5)
C3	−0.6134 (6)	0.63167 (13)	−0.03616 (11)	0.0267 (5)
C4	−0.5151 (6)	0.55587 (12)	−0.04557 (10)	0.0254 (5)
C5	−0.3396 (5)	0.52027 (12)	0.00162 (10)	0.0214 (5)
C6	−0.2498 (5)	0.55849 (11)	0.05878 (9)	0.0181 (4)
C7	−0.0708 (5)	0.52102 (11)	0.11099 (9)	0.0194 (4)
C8	−0.0393 (6)	0.43673 (11)	0.11163 (9)	0.0189 (4)
C9	0.1472 (5)	0.40085 (12)	0.15445 (10)	0.0197 (5)
C10	0.1985 (5)	0.31843 (11)	0.16063 (9)	0.0178 (4)
C11	0.3882 (5)	0.28887 (11)	0.21024 (9)	0.0188 (4)
C12	0.4385 (5)	0.20945 (12)	0.21658 (9)	0.0197 (5)
C13	0.3018 (5)	0.15894 (11)	0.17306 (9)	0.0183 (4)
C14	0.1069 (5)	0.18730 (11)	0.12307 (9)	0.0178 (4)
C15	0.0587 (5)	0.26522 (11)	0.11777 (9)	0.0174 (4)
C16	0.7030 (6)	0.31494 (14)	0.30485 (10)	0.0256 (5)
C17	0.5405 (6)	0.04847 (13)	0.22131 (12)	0.0267 (5)
C18	−0.2027 (6)	0.15760 (14)	0.03089 (11)	0.0236 (5)
H2A	−0.586 (6)	0.7230 (14)	0.0249 (10)	0.033 (7)*
H3A	−0.739 (7)	0.6549 (13)	−0.0687 (10)	0.029 (6)*
H4A	−0.557 (6)	0.5303 (12)	−0.0823 (10)	0.021 (6)*
H5A	−0.280 (6)	0.4677 (13)	−0.0057 (10)	0.029 (6)*
H8A	−0.163 (6)	0.4083 (11)	0.0806 (9)	0.015 (5)*
H9A	0.258 (6)	0.4335 (12)	0.1827 (9)	0.022 (6)*
H12A	0.568 (6)	0.1911 (12)	0.2488 (9)	0.019 (6)*
H15A	−0.079 (6)	0.2835 (12)	0.0829 (9)	0.020 (6)*
H16A	0.766 (7)	0.3640 (14)	0.3280 (10)	0.036 (7)*
H16B	0.890 (6)	0.2889 (13)	0.2889 (10)	0.028 (6)*
H16C	0.574 (7)	0.2787 (14)	0.3348 (10)	0.033 (6)*
H17A	0.467 (7)	0.0620 (13)	0.2662 (11)	0.040 (7)*
H17B	0.757 (7)	0.0676 (13)	0.2147 (11)	0.031 (7)*
H17C	0.539 (6)	−0.0083 (13)	0.2145 (9)	0.027 (6)*
H18A	−0.274 (6)	0.1128 (13)	0.0074 (9)	0.023 (6)*
H18B	−0.088 (6)	0.1914 (12)	0.0019 (10)	0.021 (6)*
H18C	−0.394 (7)	0.1848 (14)	0.0468 (10)	0.032 (7)*
H1O1	−0.123 (7)	0.6493 (15)	0.1401 (11)	0.042 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0418 (10)	0.0179 (8)	0.0286 (8)	0.0059 (8)	−0.0036 (9)	−0.0062 (7)
O2	0.0388 (10)	0.0186 (7)	0.0257 (7)	0.0033 (8)	−0.0077 (8)	−0.0047 (6)
O3	0.0308 (9)	0.0202 (7)	0.0207 (7)	−0.0013 (8)	−0.0069 (7)	−0.0022 (6)
O4	0.0311 (9)	0.0154 (7)	0.0256 (7)	0.0029 (7)	−0.0058 (7)	0.0032 (6)
O5	0.0307 (9)	0.0168 (7)	0.0208 (7)	0.0004 (7)	−0.0068 (7)	−0.0008 (5)
C1	0.0220 (11)	0.0172 (10)	0.0222 (10)	−0.0009 (9)	0.0066 (9)	0.0001 (8)
C2	0.0265 (12)	0.0155 (10)	0.0316 (11)	0.0015 (10)	0.0039 (10)	0.0023 (9)
C3	0.0269 (13)	0.0248 (12)	0.0283 (12)	0.0010 (10)	−0.0028 (11)	0.0085 (9)
C4	0.0311 (13)	0.0229 (11)	0.0221 (10)	−0.0027 (11)	−0.0029 (11)	0.0003 (9)
C5	0.0263 (12)	0.0151 (10)	0.0226 (10)	0.0002 (10)	0.0029 (10)	0.0003 (8)
C6	0.0188 (11)	0.0149 (10)	0.0206 (9)	−0.0012 (9)	0.0045 (9)	0.0019 (8)
C7	0.0211 (11)	0.0182 (10)	0.0189 (9)	−0.0001 (9)	0.0050 (9)	−0.0012 (8)
C8	0.0225 (11)	0.0167 (10)	0.0176 (9)	−0.0014 (9)	0.0023 (9)	−0.0011 (8)
C9	0.0223 (11)	0.0189 (10)	0.0178 (9)	−0.0022 (9)	0.0045 (9)	−0.0028 (8)
C10	0.0207 (10)	0.0181 (10)	0.0146 (9)	0.0022 (9)	0.0026 (9)	0.0001 (8)
C11	0.0204 (11)	0.0195 (10)	0.0164 (9)	−0.0009 (9)	0.0036 (9)	−0.0020 (8)
C12	0.0206 (11)	0.0228 (11)	0.0156 (9)	0.0023 (9)	−0.0003 (9)	0.0030 (8)
C13	0.0208 (11)	0.0153 (10)	0.0188 (9)	0.0013 (9)	0.0037 (9)	0.0034 (8)
C14	0.0205 (11)	0.0168 (10)	0.0162 (9)	−0.0006 (9)	0.0027 (9)	−0.0014 (8)
C15	0.0190 (10)	0.0193 (10)	0.0139 (9)	0.0015 (9)	0.0008 (9)	0.0021 (8)
C16	0.0287 (13)	0.0278 (13)	0.0202 (11)	−0.0017 (11)	−0.0052 (10)	0.0018 (9)
C17	0.0314 (14)	0.0196 (12)	0.0291 (12)	0.0059 (11)	−0.0038 (12)	0.0066 (9)
C18	0.0266 (13)	0.0217 (12)	0.0226 (11)	0.0003 (11)	−0.0066 (11)	−0.0003 (9)

O1—C1	1.355 (2)	C8—C9	1.343 (3)
O1—H1O1	0.89 (3)	C8—H8A	0.96 (2)
O2—C7	1.246 (2)	C9—C10	1.451 (3)
O3—C11	1.368 (2)	C9—H9A	0.94 (2)
O3—C16	1.435 (3)	C10—C11	1.402 (3)
O4—C13	1.358 (2)	C10—C15	1.410 (3)
O4—C17	1.437 (3)	C11—C12	1.400 (3)
O5—C14	1.372 (2)	C12—C13	1.383 (3)
O5—C18	1.415 (3)	C12—H12A	0.92 (2)
C1—C2	1.389 (3)	C13—C14	1.413 (3)
C1—C6	1.417 (3)	C14—C15	1.371 (3)
C2—C3	1.375 (3)	C15—H15A	0.98 (2)
C2—H2A	0.94 (2)	C16—H16A	1.01 (2)
C3—C4	1.394 (3)	C16—H16B	0.98 (3)
C3—H3A	0.95 (2)	C16—H16C	1.04 (2)
C4—C5	1.375 (3)	C17—H17A	1.00 (2)
C4—H4A	0.89 (2)	C17—H17B	1.00 (3)
C5—C6	1.404 (3)	C17—H17C	0.99 (2)
C5—H5A	0.96 (2)	C18—H18A	0.96 (2)
C6—C7	1.471 (3)	C18—H18B	0.97 (2)
C7—C8	1.467 (3)	C18—H18C	1.00 (3)
C1—O1—H1O1	105.5 (16)	O3—C11—C12	122.76 (18)
C11—O3—C16	118.72 (16)	O3—C11—C10	116.12 (17)
C13—O4—C17	117.32 (16)	C12—C11—C10	121.11 (19)
C14—O5—C18	116.65 (16)	C13—C12—C11	119.82 (19)
O1—C1—C2	118.27 (18)	C13—C12—H12A	120.2 (13)
O1—C1—C6	121.59 (19)	C11—C12—H12A	119.9 (13)
C2—C1—C6	120.13 (19)	O4—C13—C12	125.57 (18)
C3—C2—C1	120.7 (2)	O4—C13—C14	114.32 (17)
C3—C2—H2A	120.9 (14)	C12—C13—C14	120.11 (17)
C1—C2—H2A	118.4 (14)	C15—C14—O5	125.95 (18)
C2—C3—C4	120.3 (2)	C15—C14—C13	119.32 (18)
C2—C3—H3A	121.4 (14)	O5—C14—C13	114.72 (17)
C4—C3—H3A	118.3 (14)	C14—C15—C10	122.06 (19)
C5—C4—C3	119.4 (2)	C14—C15—H15A	117.9 (12)
C5—C4—H4A	118.9 (15)	C10—C15—H15A	120.1 (12)
C3—C4—H4A	121.6 (14)	O3—C16—H16A	103.7 (14)
C4—C5—C6	122.0 (2)	O3—C16—H16B	111.0 (13)
C4—C5—H5A	117.5 (13)	H16A—C16—H16B	109 (2)
C6—C5—H5A	120.5 (13)	O3—C16—H16C	110.3 (14)
C5—C6—C1	117.40 (18)	H16A—C16—H16C	111.9 (18)
C5—C6—C7	123.12 (18)	H16B—C16—H16C	111 (2)
C1—C6—C7	119.48 (17)	O4—C17—H17A	110.4 (16)
O2—C7—C8	120.31 (18)	O4—C17—H17B	110.2 (14)
O2—C7—C6	120.05 (17)	H17A—C17—H17B	110 (2)
C8—C7—C6	119.61 (18)	O4—C17—H17C	106.8 (14)
C9—C8—C7	121.5 (2)	H17A—C17—H17C	111.1 (18)
C9—C8—H8A	121.7 (12)	H17B—C17—H17C	108 (2)
C7—C8—H8A	116.9 (12)	O5—C18—H18A	107.7 (13)
C8—C9—C10	127.1 (2)	O5—C18—H18B	112.3 (14)
C8—C9—H9A	115.3 (13)	H18A—C18—H18B	109.8 (17)
C10—C9—H9A	117.5 (13)	O5—C18—H18C	110.9 (13)
C11—C10—C15	117.57 (18)	H18A—C18—H18C	107 (2)
C11—C10—C9	120.77 (18)	H18B—C18—H18C	109.4 (19)
C15—C10—C9	121.66 (18)
O1—C1—C2—C3	176.7 (2)	C16—O3—C11—C10	178.07 (19)
C6—C1—C2—C3	−3.1 (3)	C15—C10—C11—O3	−178.60 (18)
C1—C2—C3—C4	0.0 (3)	C9—C10—C11—O3	0.9 (3)
C2—C3—C4—C5	2.2 (3)	C15—C10—C11—C12	0.5 (3)
C3—C4—C5—C6	−1.4 (3)	C9—C10—C11—C12	179.9 (2)
C4—C5—C6—C1	−1.6 (3)	O3—C11—C12—C13	179.56 (19)
C4—C5—C6—C7	177.9 (2)	C10—C11—C12—C13	0.6 (3)
O1—C1—C6—C5	−176.0 (2)	C17—O4—C13—C12	−2.5 (3)
C2—C1—C6—C5	3.9 (3)	C17—O4—C13—C14	177.65 (18)
O1—C1—C6—C7	4.4 (3)	C11—C12—C13—O4	179.0 (2)
C2—C1—C6—C7	−175.7 (2)	C11—C12—C13—C14	−1.2 (3)
C5—C6—C7—O2	168.3 (2)	C18—O5—C14—C15	3.1 (3)
C1—C6—C7—O2	−12.2 (3)	C18—O5—C14—C13	−176.94 (19)
C5—C6—C7—C8	−13.8 (3)	O4—C13—C14—C15	−179.32 (19)
C1—C6—C7—C8	165.8 (2)	C12—C13—C14—C15	0.9 (3)
O2—C7—C8—C9	−8.8 (3)	O4—C13—C14—O5	0.7 (3)
C6—C7—C8—C9	173.2 (2)	C12—C13—C14—O5	−179.08 (19)
C7—C8—C9—C10	179.7 (2)	O5—C14—C15—C10	−179.87 (19)
C8—C9—C10—C11	−176.5 (2)	C13—C14—C15—C10	0.2 (3)
C8—C9—C10—C15	2.9 (3)	C11—C10—C15—C14	−0.8 (3)
C16—O3—C11—C12	−1.0 (3)	C9—C10—C15—C14	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.89 (3)	1.73 (3)	2.541 (2)	152 (2)
C5—H5A···O5i	0.96 (2)	2.57 (2)	3.254 (3)	129.0 (18)
C16—H16C···O1ii	1.04 (3)	2.42 (3)	3.446 (3)	167.5 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.89 (3)	1.73 (3)	2.541 (2)	152 (2)
C5—H5A⋯O5i	0.96 (2)	2.57 (2)	3.254 (3)	129.0 (18)
C16—H16C⋯O1ii	1.04 (3)	2.42 (3)	3.446 (3)	167.5 (18)

Symmetry codes: (i) ; (ii) .