(E)-1-(4-Decyl-oxyphen-yl)-3-(2-hy-droxy-phen-yl)prop-2-en-1-one.

In the title compound, C(25)H(32)O(3), the enone group adopts an s-cis conformation. The alk-oxy chain is in an all-trans conformation. The dihedral angle between the benzene rings is 7.86 (5)°. In the crystal, mol-ecules are connected by pairs of O-H⋯O hydrogen bonds, forming inversion dimers and giving R(2) (2)(10) rings. Within these dimers, weak C-H⋯O hydrogen bonds form two R(2) (2)(7) rings. In the crystal, the approximately planar mol-ecules [largest deviation for an atom being 0.4737 (12) Å for the terminal C atom of the alk-oxy chain] are arranged in sheets parallel to (20-1). Weak C-H⋯π inter-actions are also observed.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Won et al. (2005 ▶); Zhao et al. (2005 ▶); Satyanarayana et al. (2004 ▶). For related structures, see: Razak et al. (2009 ▶); Ngaini et al. (2010 ▶, 2011 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶). 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 ▶).

Experimental

Crystal data

C25H32O3

M = 380.51

Triclinic,

a = 8.6674 (13) Å

b = 10.9865 (17) Å

c = 12.1352 (19) Å

α = 74.405 (3)°

β = 72.891 (3)°

γ = 85.981 (4)°

V = 1063.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.62 × 0.15 × 0.14 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.990

30192 measured reflections

8434 independent reflections

6213 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.160

S = 1.02

8434 reflections

258 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.20 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 datablock(s) global, I. DOI: 10.1107/S160053681203872X/lh5525sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681203872X/lh5525Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681203872X/lh5525Isup3.cml

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

C25H32O3	Z = 2
Mr = 380.51	F(000) = 412
Triclinic, P1	Dx = 1.188 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6674 (13) Å	Cell parameters from 7111 reflections
b = 10.9865 (17) Å	θ = 2.5–33.7°
c = 12.1352 (19) Å	µ = 0.08 mm−1
α = 74.405 (3)°	T = 100 K
β = 72.891 (3)°	Block, yellow
γ = 85.981 (4)°	0.62 × 0.15 × 0.14 mm
V = 1063.7 (3) Å3

Bruker APEXII DUO CCD area-detector diffractometer	8434 independent reflections
Radiation source: fine-focus sealed tube	6213 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
φ and ω scans	θmax = 33.9°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.955, Tmax = 0.990	k = −17→17
30192 measured 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0957P)2 + 0.086P] where P = (Fo2 + 2Fc2)/3
8434 reflections	(Δ/σ)max < 0.001
258 parameters	Δρmax = 0.63 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 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	0.97173 (10)	0.64655 (7)	0.51189 (7)	0.03236 (17)
O2	0.94280 (8)	0.34433 (6)	0.29484 (6)	0.02528 (14)
O3	0.72670 (9)	0.27611 (6)	−0.13495 (6)	0.02605 (15)
C1	0.83637 (12)	0.82610 (8)	0.26041 (8)	0.02406 (17)
H1A	0.8087	0.8127	0.1961	0.029*
C2	0.82611 (13)	0.94641 (9)	0.27668 (9)	0.0290 (2)
H2A	0.7910	1.0128	0.2241	0.035*
C3	0.86846 (12)	0.96808 (9)	0.37210 (9)	0.02815 (19)
H3A	0.8630	1.0493	0.3825	0.034*
C4	0.91859 (11)	0.86906 (8)	0.45150 (9)	0.02482 (17)
H4A	0.9466	0.8836	0.5152	0.030*
C5	0.92699 (11)	0.74707 (8)	0.43560 (8)	0.02130 (16)
C6	0.88752 (10)	0.72389 (8)	0.33845 (7)	0.01911 (15)
C7	0.89920 (10)	0.59575 (8)	0.32398 (8)	0.02062 (16)
H7A	0.9260	0.5326	0.3836	0.025*
C8	0.87499 (11)	0.56017 (8)	0.23288 (8)	0.02137 (16)
H8A	0.8464	0.6213	0.1727	0.026*
C9	0.89166 (10)	0.42876 (8)	0.22394 (7)	0.01902 (15)
C10	0.84626 (10)	0.39669 (8)	0.12615 (7)	0.01838 (15)
C11	0.87712 (10)	0.27355 (8)	0.11183 (8)	0.02067 (16)
H11A	0.9258	0.2158	0.1626	0.025*
C12	0.83636 (11)	0.23708 (8)	0.02362 (8)	0.02239 (16)
H12A	0.8581	0.1555	0.0151	0.027*
C13	0.76235 (10)	0.32268 (8)	−0.05314 (7)	0.02090 (16)
C14	0.73151 (11)	0.44598 (8)	−0.04146 (8)	0.02183 (16)
H14A	0.6834	0.5036	−0.0927	0.026*
C15	0.77373 (10)	0.48127 (8)	0.04772 (7)	0.02078 (16)
H15A	0.7532	0.5633	0.0554	0.025*
C16	0.66227 (11)	0.35667 (9)	−0.22515 (8)	0.02424 (17)
H16A	0.7379	0.4242	−0.2752	0.029*
H16B	0.5613	0.3935	−0.1892	0.029*
C17	0.63573 (12)	0.27105 (9)	−0.29722 (8)	0.02506 (17)
H17A	0.5556	0.2074	−0.2455	0.030*
H17B	0.7358	0.2277	−0.3235	0.030*
C18	0.58040 (11)	0.33829 (9)	−0.40639 (8)	0.02417 (17)
H18A	0.4746	0.3743	−0.3809	0.029*
H18B	0.6551	0.4066	−0.4560	0.029*
C19	0.57271 (12)	0.24580 (9)	−0.47838 (8)	0.02537 (18)
H19A	0.5075	0.1735	−0.4251	0.030*
H19B	0.6809	0.2157	−0.5082	0.030*
C20	0.50411 (11)	0.29821 (9)	−0.58370 (8)	0.02291 (16)
H20A	0.3978	0.3323	−0.5557	0.027*
H20B	0.5730	0.3666	−0.6408	0.027*
C21	0.49168 (11)	0.19692 (9)	−0.64525 (8)	0.02409 (17)
H21A	0.4292	0.1263	−0.5861	0.029*
H21B	0.5993	0.1665	−0.6763	0.029*
C22	0.41473 (11)	0.24020 (8)	−0.74698 (8)	0.02339 (17)
H22A	0.4848	0.3026	−0.8115	0.028*
H22B	0.3129	0.2806	−0.7190	0.028*
C23	0.38450 (12)	0.13207 (9)	−0.79502 (8)	0.02553 (18)
H23A	0.4858	0.0898	−0.8200	0.031*
H23B	0.3116	0.0712	−0.7310	0.031*
C24	0.31312 (12)	0.17379 (10)	−0.89953 (9)	0.02908 (19)
H24A	0.3923	0.2250	−0.9676	0.035*
H24B	0.2199	0.2261	−0.8785	0.035*
C25	0.26215 (14)	0.06325 (11)	−0.93513 (10)	0.0364 (2)
H25A	0.2134	0.0949	−0.9987	0.055*
H25B	0.1857	0.0109	−0.8676	0.055*
H25C	0.3552	0.0143	−0.9615	0.055*
H1O1	0.9937 (19)	0.6709 (15)	0.5747 (15)	0.054 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0556 (5)	0.0212 (3)	0.0321 (4)	0.0096 (3)	−0.0303 (3)	−0.0091 (3)
O2	0.0347 (3)	0.0214 (3)	0.0252 (3)	0.0039 (2)	−0.0166 (3)	−0.0073 (2)
O3	0.0373 (4)	0.0246 (3)	0.0235 (3)	0.0037 (3)	−0.0170 (3)	−0.0099 (2)
C1	0.0322 (4)	0.0187 (4)	0.0236 (4)	0.0014 (3)	−0.0130 (3)	−0.0042 (3)
C2	0.0410 (5)	0.0178 (4)	0.0316 (5)	0.0032 (3)	−0.0178 (4)	−0.0049 (3)
C3	0.0368 (5)	0.0178 (4)	0.0343 (5)	0.0028 (3)	−0.0164 (4)	−0.0082 (3)
C4	0.0310 (4)	0.0204 (4)	0.0287 (4)	0.0026 (3)	−0.0143 (3)	−0.0100 (3)
C5	0.0247 (4)	0.0178 (3)	0.0240 (4)	0.0031 (3)	−0.0112 (3)	−0.0058 (3)
C6	0.0220 (4)	0.0171 (3)	0.0198 (3)	0.0004 (3)	−0.0084 (3)	−0.0047 (3)
C7	0.0249 (4)	0.0171 (3)	0.0216 (4)	0.0016 (3)	−0.0092 (3)	−0.0055 (3)
C8	0.0273 (4)	0.0179 (3)	0.0209 (4)	−0.0003 (3)	−0.0104 (3)	−0.0045 (3)
C9	0.0203 (3)	0.0191 (3)	0.0188 (3)	−0.0006 (3)	−0.0068 (3)	−0.0052 (3)
C10	0.0205 (3)	0.0181 (3)	0.0172 (3)	−0.0011 (3)	−0.0063 (3)	−0.0044 (3)
C11	0.0247 (4)	0.0188 (3)	0.0207 (4)	0.0014 (3)	−0.0100 (3)	−0.0054 (3)
C12	0.0291 (4)	0.0196 (4)	0.0220 (4)	0.0021 (3)	−0.0114 (3)	−0.0073 (3)
C13	0.0240 (4)	0.0225 (4)	0.0182 (3)	−0.0006 (3)	−0.0076 (3)	−0.0066 (3)
C14	0.0259 (4)	0.0211 (4)	0.0206 (4)	0.0019 (3)	−0.0102 (3)	−0.0055 (3)
C15	0.0252 (4)	0.0187 (3)	0.0197 (3)	0.0007 (3)	−0.0083 (3)	−0.0052 (3)
C16	0.0285 (4)	0.0271 (4)	0.0210 (4)	0.0023 (3)	−0.0114 (3)	−0.0085 (3)
C17	0.0295 (4)	0.0281 (4)	0.0221 (4)	−0.0002 (3)	−0.0114 (3)	−0.0093 (3)
C18	0.0263 (4)	0.0281 (4)	0.0218 (4)	0.0012 (3)	−0.0100 (3)	−0.0093 (3)
C19	0.0302 (4)	0.0279 (4)	0.0216 (4)	0.0011 (3)	−0.0103 (3)	−0.0092 (3)
C20	0.0246 (4)	0.0263 (4)	0.0197 (4)	−0.0002 (3)	−0.0079 (3)	−0.0073 (3)
C21	0.0289 (4)	0.0260 (4)	0.0207 (4)	0.0016 (3)	−0.0110 (3)	−0.0077 (3)
C22	0.0264 (4)	0.0243 (4)	0.0219 (4)	0.0015 (3)	−0.0102 (3)	−0.0068 (3)
C23	0.0316 (4)	0.0254 (4)	0.0239 (4)	0.0023 (3)	−0.0144 (3)	−0.0070 (3)
C24	0.0330 (5)	0.0309 (5)	0.0279 (4)	0.0006 (4)	−0.0176 (4)	−0.0056 (4)
C25	0.0427 (6)	0.0421 (6)	0.0349 (5)	0.0011 (5)	−0.0217 (4)	−0.0156 (5)

O1—C5	1.3523 (10)	C16—C17	1.5146 (12)
O1—H1O1	0.943 (17)	C16—H16A	0.9700
O2—C9	1.2389 (10)	C16—H16B	0.9700
O3—C13	1.3485 (10)	C17—C18	1.5260 (13)
O3—C16	1.4363 (11)	C17—H17A	0.9700
C1—C2	1.3811 (13)	C17—H17B	0.9700
C1—C6	1.4000 (12)	C18—C19	1.5236 (12)
C1—H1A	0.9300	C18—H18A	0.9700
C2—C3	1.3938 (14)	C18—H18B	0.9700
C2—H2A	0.9300	C19—C20	1.5239 (13)
C3—C4	1.3846 (13)	C19—H19A	0.9700
C3—H3A	0.9300	C19—H19B	0.9700
C4—C5	1.3985 (12)	C20—C21	1.5228 (12)
C4—H4A	0.9300	C20—H20A	0.9700
C5—C6	1.4080 (12)	C20—H20B	0.9700
C6—C7	1.4579 (11)	C21—C22	1.5229 (12)
C7—C8	1.3414 (12)	C21—H21A	0.9700
C7—H7A	0.9300	C21—H21B	0.9700
C8—C9	1.4706 (12)	C22—C23	1.5250 (13)
C8—H8A	0.9300	C22—H22A	0.9700
C9—C10	1.4854 (11)	C22—H22B	0.9700
C10—C15	1.3998 (11)	C23—C24	1.5201 (13)
C10—C11	1.4072 (12)	C23—H23A	0.9700
C11—C12	1.3800 (12)	C23—H23B	0.9700
C11—H11A	0.9300	C24—C25	1.5252 (15)
C12—C13	1.3999 (12)	C24—H24A	0.9700
C12—H12A	0.9300	C24—H24B	0.9700
C13—C14	1.3988 (12)	C25—H25A	0.9600
C14—C15	1.3906 (12)	C25—H25B	0.9600
C14—H14A	0.9300	C25—H25C	0.9600
C15—H15A	0.9300
C5—O1—H1O1	110.9 (10)	C16—C17—H17A	108.6
C13—O3—C16	120.53 (7)	C18—C17—H17A	108.6
C2—C1—C6	121.51 (9)	C16—C17—H17B	108.6
C2—C1—H1A	119.2	C18—C17—H17B	108.6
C6—C1—H1A	119.2	H17A—C17—H17B	107.6
C1—C2—C3	119.86 (9)	C19—C18—C17	110.31 (8)
C1—C2—H2A	120.1	C19—C18—H18A	109.6
C3—C2—H2A	120.1	C17—C18—H18A	109.6
C4—C3—C2	120.20 (9)	C19—C18—H18B	109.6
C4—C3—H3A	119.9	C17—C18—H18B	109.6
C2—C3—H3A	119.9	H18A—C18—H18B	108.1
C3—C4—C5	119.80 (8)	C18—C19—C20	115.59 (8)
C3—C4—H4A	120.1	C18—C19—H19A	108.4
C5—C4—H4A	120.1	C20—C19—H19A	108.4
O1—C5—C4	122.25 (8)	C18—C19—H19B	108.4
O1—C5—C6	116.99 (8)	C20—C19—H19B	108.4
C4—C5—C6	120.76 (8)	H19A—C19—H19B	107.4
C1—C6—C5	117.86 (8)	C21—C20—C19	111.70 (8)
C1—C6—C7	122.86 (8)	C21—C20—H20A	109.3
C5—C6—C7	119.27 (7)	C19—C20—H20A	109.3
C8—C7—C6	126.24 (8)	C21—C20—H20B	109.3
C8—C7—H7A	116.9	C19—C20—H20B	109.3
C6—C7—H7A	116.9	H20A—C20—H20B	107.9
C7—C8—C9	122.90 (8)	C20—C21—C22	114.80 (8)
C7—C8—H8A	118.6	C20—C21—H21A	108.6
C9—C8—H8A	118.6	C22—C21—H21A	108.6
O2—C9—C8	122.21 (8)	C20—C21—H21B	108.6
O2—C9—C10	119.06 (7)	C22—C21—H21B	108.6
C8—C9—C10	118.72 (7)	H21A—C21—H21B	107.5
C15—C10—C11	117.94 (8)	C21—C22—C23	112.95 (7)
C15—C10—C9	124.00 (7)	C21—C22—H22A	109.0
C11—C10—C9	118.06 (7)	C23—C22—H22A	109.0
C12—C11—C10	121.04 (8)	C21—C22—H22B	109.0
C12—C11—H11A	119.5	C23—C22—H22B	109.0
C10—C11—H11A	119.5	H22A—C22—H22B	107.8
C11—C12—C13	120.15 (8)	C24—C23—C22	113.85 (8)
C11—C12—H12A	119.9	C24—C23—H23A	108.8
C13—C12—H12A	119.9	C22—C23—H23A	108.8
O3—C13—C14	125.19 (8)	C24—C23—H23B	108.8
O3—C13—C12	114.85 (8)	C22—C23—H23B	108.8
C14—C13—C12	119.96 (8)	H23A—C23—H23B	107.7
C15—C14—C13	119.15 (8)	C23—C24—C25	113.04 (8)
C15—C14—H14A	120.4	C23—C24—H24A	109.0
C13—C14—H14A	120.4	C25—C24—H24A	109.0
C14—C15—C10	121.76 (8)	C23—C24—H24B	109.0
C14—C15—H15A	119.1	C25—C24—H24B	109.0
C10—C15—H15A	119.1	H24A—C24—H24B	107.8
O3—C16—C17	104.98 (7)	C24—C25—H25A	109.5
O3—C16—H16A	110.8	C24—C25—H25B	109.5
C17—C16—H16A	110.8	H25A—C25—H25B	109.5
O3—C16—H16B	110.8	C24—C25—H25C	109.5
C17—C16—H16B	110.8	H25A—C25—H25C	109.5
H16A—C16—H16B	108.8	H25B—C25—H25C	109.5
C16—C17—C18	114.77 (8)
C6—C1—C2—C3	0.50 (15)	C9—C10—C11—C12	179.29 (7)
C1—C2—C3—C4	−0.91 (16)	C10—C11—C12—C13	−0.32 (13)
C2—C3—C4—C5	0.14 (15)	C16—O3—C13—C14	4.73 (13)
C3—C4—C5—O1	−178.52 (9)	C16—O3—C13—C12	−175.05 (8)
C3—C4—C5—C6	1.05 (14)	C11—C12—C13—O3	−179.37 (8)
C2—C1—C6—C5	0.65 (14)	C11—C12—C13—C14	0.84 (13)
C2—C1—C6—C7	179.81 (9)	O3—C13—C14—C15	179.56 (8)
O1—C5—C6—C1	178.17 (8)	C12—C13—C14—C15	−0.67 (13)
C4—C5—C6—C1	−1.42 (13)	C13—C14—C15—C10	−0.01 (13)
O1—C5—C6—C7	−1.02 (12)	C11—C10—C15—C14	0.51 (13)
C4—C5—C6—C7	179.39 (8)	C9—C10—C15—C14	−179.10 (8)
C1—C6—C7—C8	4.99 (14)	C13—O3—C16—C17	−179.02 (7)
C5—C6—C7—C8	−175.86 (9)	O3—C16—C17—C18	−175.00 (7)
C6—C7—C8—C9	179.01 (8)	C16—C17—C18—C19	174.72 (8)
C7—C8—C9—O2	−6.40 (14)	C17—C18—C19—C20	174.57 (8)
C7—C8—C9—C10	173.90 (8)	C18—C19—C20—C21	−176.48 (7)
O2—C9—C10—C15	173.99 (8)	C19—C20—C21—C22	176.53 (8)
C8—C9—C10—C15	−6.30 (12)	C20—C21—C22—C23	−172.41 (8)
O2—C9—C10—C11	−5.62 (12)	C21—C22—C23—C24	−177.98 (8)
C8—C9—C10—C11	174.09 (7)	C22—C23—C24—C25	−172.02 (9)
C15—C10—C11—C12	−0.34 (13)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.939 (18)	1.789 (18)	2.6867 (12)	159.0 (16)
C7—H7A···O1i	0.93	2.31	3.2169 (13)	164
C22—H22A···Cg1ii	0.97	2.85	3.6887 (12)	146

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.939 (18)	1.789 (18)	2.6867 (12)	159.0 (16)
C7—H7A⋯O1i	0.93	2.31	3.2169 (13)	164
C22—H22A⋯Cg1ii	0.97	2.85	3.6887 (12)	146

Symmetry codes: (i) ; (ii) .