(E)-3-[4-(Dec-yloxy)phen-yl]-1-(4-hydroxy-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 unit is nearly planar and is in a trans conformation. The two benzene rings make a dihedral angle of 18.87 (9)°. In the crystal structure, mol-ecules are linked into chains running along the a axis by inter-molecular O-H⋯O hydrogen bonds involving the hydr-oxy and keto groups. The chains are crosslinked along the b axis via C-H⋯O hydrogen bonds, forming a two-dimensional network parallel to the ab plane.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Satyanarayana et al. (2004 ▶); Lee et al. (2006 ▶). For related structures, see: Ng et al. (2006 ▶); Razak et al. (2009 ▶); Ngaini, Fadzillah et al. (2009 ▶); Ngaini, Rahman et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C25H32O3

M = 380.51

Orthorhombic,

a = 10.5192 (3) Å

b = 9.9839 (3) Å

c = 40.8415 (12) Å

V = 4289.3 (2) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.58 × 0.49 × 0.03 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.957, T max = 0.998

42832 measured reflections

4922 independent reflections

3526 reflections with I > 2σ(I)

R int = 0.082

Refinement

R[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.132

S = 1.10

4922 reflections

258 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.20 e Å−3

Δρmin = −0.22 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 datablocks global, I. DOI: 10.1107/S160053680901441X/ci2782sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680901441X/ci2782Isup2.hkl

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

C25H32O3	F(000) = 1648
Mr = 380.51	Dx = 1.178 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4176 reflections
a = 10.5192 (3) Å	θ = 2.2–23.9°
b = 9.9839 (3) Å	µ = 0.08 mm−1
c = 40.8415 (12) Å	T = 100 K
V = 4289.3 (2) Å3	Plate, colourless
Z = 8	0.58 × 0.49 × 0.03 mm

Bruker APEXII CCD area-detector diffractometer	4922 independent reflections
Radiation source: sealed tube	3526 reflections with I > 2σ(I)
graphite	Rint = 0.082
π and ω scans	θmax = 27.5°, θmin = 1.0°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.957, Tmax = 0.998	k = −12→12
42832 measured reflections	l = −53→52

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0368P)2 + 2.6345P] where P = (Fo2 + 2Fc2)/3
4922 reflections	(Δ/σ)max = 0.001
258 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.22 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 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	0.97999 (14)	0.70636 (15)	0.20018 (3)	0.0232 (3)
O2	0.66825 (13)	0.56794 (14)	0.32684 (3)	0.0228 (3)
O3	0.93786 (13)	−0.03516 (14)	0.45190 (3)	0.0227 (3)
C1	0.79176 (18)	0.6934 (2)	0.27426 (5)	0.0213 (4)
H1	0.7242	0.7397	0.2836	0.026*
C2	0.83983 (19)	0.7353 (2)	0.24449 (5)	0.0220 (4)
H2	0.8051	0.8096	0.2340	0.026*
C3	0.94058 (19)	0.6659 (2)	0.23015 (5)	0.0198 (4)
C4	0.9958 (2)	0.5589 (2)	0.24676 (5)	0.0224 (4)
H4	1.0655	0.5149	0.2378	0.027*
C5	0.94723 (18)	0.5179 (2)	0.27665 (5)	0.0219 (4)
H5	0.9847	0.4463	0.2875	0.026*
C6	0.84262 (18)	0.5826 (2)	0.29070 (4)	0.0193 (4)
C7	0.77760 (18)	0.5307 (2)	0.32020 (4)	0.0189 (4)
C8	0.84031 (19)	0.4306 (2)	0.34137 (4)	0.0206 (4)
H8	0.9248	0.4078	0.3377	0.025*
C9	0.77621 (19)	0.3725 (2)	0.36590 (4)	0.0204 (4)
H9	0.6932	0.4018	0.3690	0.024*
C10	0.82043 (18)	0.2687 (2)	0.38841 (4)	0.0204 (4)
C11	0.94097 (18)	0.2090 (2)	0.38649 (5)	0.0216 (4)
H11	0.9981	0.2378	0.3706	0.026*
C12	0.97590 (19)	0.1086 (2)	0.40773 (5)	0.0222 (5)
H12	1.0560	0.0698	0.4059	0.027*
C13	0.89207 (19)	0.0645 (2)	0.43198 (4)	0.0201 (4)
C14	0.77209 (18)	0.1205 (2)	0.43435 (5)	0.0213 (4)
H14	0.7153	0.0914	0.4503	0.026*
C15	0.73770 (19)	0.2212 (2)	0.41247 (4)	0.0223 (4)
H15	0.6567	0.2581	0.4139	0.027*
C16	0.85615 (19)	−0.0838 (2)	0.47766 (5)	0.0223 (5)
H16A	0.7759	−0.1141	0.4686	0.027*
H16B	0.8391	−0.0130	0.4933	0.027*
C17	0.92412 (19)	−0.1985 (2)	0.49413 (5)	0.0226 (5)
H17A	1.0055	−0.1674	0.5023	0.027*
H17B	0.9403	−0.2684	0.4782	0.027*
C18	0.84727 (19)	−0.2561 (2)	0.52231 (5)	0.0241 (5)
H18A	0.7647	−0.2837	0.5142	0.029*
H18B	0.8337	−0.1867	0.5386	0.029*
C19	0.91156 (19)	−0.3754 (2)	0.53860 (5)	0.0245 (5)
H19A	0.9968	−0.3496	0.5451	0.029*
H19B	0.9190	−0.4472	0.5227	0.029*
C20	0.84121 (19)	−0.4277 (2)	0.56855 (5)	0.0246 (5)
H20A	0.8313	−0.3552	0.5842	0.030*
H20B	0.7569	−0.4565	0.5620	0.030*
C21	0.9087 (2)	−0.5439 (2)	0.58526 (5)	0.0260 (5)
H21A	0.9129	−0.6187	0.5701	0.031*
H21B	0.9951	−0.5172	0.5903	0.031*
C22	0.8444 (2)	−0.5903 (2)	0.61656 (5)	0.0282 (5)
H22A	0.8427	−0.5161	0.6319	0.034*
H22B	0.7570	−0.6136	0.6116	0.034*
C23	0.90728 (19)	−0.7093 (2)	0.63310 (5)	0.0266 (5)
H23A	0.9130	−0.7823	0.6175	0.032*
H23B	0.9932	−0.6846	0.6393	0.032*
C24	0.8373 (2)	−0.7579 (2)	0.66318 (5)	0.0347 (6)
H24A	0.7505	−0.7799	0.6572	0.042*
H24B	0.8342	−0.6861	0.6792	0.042*
C25	0.8993 (2)	−0.8805 (3)	0.67877 (6)	0.0446 (7)
H25A	0.8492	−0.9095	0.6971	0.067*
H25B	0.9833	−0.8577	0.6861	0.067*
H25C	0.9043	−0.9513	0.6629	0.067*
H1O1	1.046 (3)	0.654 (3)	0.1909 (7)	0.078 (10)*

	U11	U22	U33	U12	U13	U23
O1	0.0271 (8)	0.0216 (8)	0.0209 (7)	0.0019 (7)	0.0033 (6)	0.0032 (6)
O2	0.0224 (7)	0.0248 (8)	0.0213 (7)	0.0034 (7)	0.0014 (6)	0.0005 (6)
O3	0.0228 (7)	0.0231 (8)	0.0222 (7)	0.0004 (6)	0.0017 (6)	0.0052 (6)
C1	0.0207 (10)	0.0187 (11)	0.0245 (10)	0.0008 (9)	0.0005 (8)	−0.0032 (9)
C2	0.0230 (10)	0.0175 (11)	0.0255 (11)	0.0006 (9)	0.0002 (8)	0.0024 (9)
C3	0.0239 (10)	0.0159 (11)	0.0195 (10)	−0.0047 (9)	−0.0001 (8)	0.0004 (8)
C4	0.0239 (10)	0.0195 (11)	0.0237 (10)	0.0032 (9)	0.0025 (8)	−0.0016 (9)
C5	0.0235 (10)	0.0186 (11)	0.0236 (10)	0.0005 (9)	−0.0006 (8)	0.0010 (9)
C6	0.0212 (10)	0.0169 (11)	0.0198 (10)	−0.0021 (9)	−0.0010 (8)	−0.0018 (8)
C7	0.0226 (10)	0.0152 (10)	0.0190 (10)	−0.0001 (9)	−0.0018 (8)	−0.0048 (8)
C8	0.0203 (10)	0.0213 (11)	0.0203 (10)	0.0004 (9)	−0.0006 (8)	−0.0017 (8)
C9	0.0228 (10)	0.0205 (11)	0.0178 (10)	−0.0004 (9)	−0.0012 (8)	−0.0029 (8)
C10	0.0231 (10)	0.0208 (11)	0.0171 (9)	−0.0012 (9)	−0.0002 (8)	−0.0028 (8)
C11	0.0222 (10)	0.0246 (12)	0.0178 (10)	−0.0032 (9)	0.0008 (8)	0.0019 (9)
C12	0.0187 (10)	0.0265 (12)	0.0215 (10)	0.0000 (9)	0.0002 (8)	−0.0016 (9)
C13	0.0238 (10)	0.0187 (11)	0.0179 (9)	−0.0012 (9)	−0.0023 (8)	0.0002 (8)
C14	0.0223 (10)	0.0199 (11)	0.0216 (10)	−0.0029 (9)	0.0038 (8)	0.0011 (9)
C15	0.0213 (10)	0.0235 (12)	0.0221 (10)	0.0021 (9)	0.0005 (8)	−0.0017 (9)
C16	0.0249 (10)	0.0212 (11)	0.0207 (10)	−0.0017 (9)	0.0021 (8)	0.0030 (8)
C17	0.0224 (10)	0.0209 (11)	0.0245 (10)	−0.0031 (9)	−0.0022 (8)	−0.0002 (9)
C18	0.0260 (10)	0.0233 (12)	0.0230 (10)	−0.0006 (10)	−0.0015 (8)	0.0036 (9)
C19	0.0279 (11)	0.0223 (12)	0.0234 (10)	0.0014 (10)	0.0018 (9)	0.0011 (9)
C20	0.0249 (11)	0.0235 (12)	0.0255 (11)	−0.0018 (10)	−0.0006 (9)	0.0032 (9)
C21	0.0272 (11)	0.0249 (12)	0.0261 (11)	0.0006 (10)	0.0009 (9)	0.0037 (9)
C22	0.0261 (11)	0.0269 (12)	0.0315 (12)	0.0029 (10)	0.0007 (9)	0.0071 (10)
C23	0.0260 (11)	0.0270 (12)	0.0268 (11)	0.0001 (10)	0.0005 (9)	0.0046 (9)
C24	0.0357 (13)	0.0337 (14)	0.0346 (12)	0.0097 (12)	0.0066 (10)	0.0125 (10)
C25	0.0445 (15)	0.0485 (17)	0.0408 (14)	0.0177 (13)	0.0110 (12)	0.0201 (13)

O1—C3	1.354 (2)	C16—C17	1.508 (3)
O1—H1O1	0.94 (3)	C16—H16A	0.97
O2—C7	1.239 (2)	C16—H16B	0.97
O3—C13	1.373 (2)	C17—C18	1.520 (3)
O3—C16	1.443 (2)	C17—H17A	0.97
C1—C2	1.382 (3)	C17—H17B	0.97
C1—C6	1.400 (3)	C18—C19	1.522 (3)
C1—H1	0.93	C18—H18A	0.97
C2—C3	1.395 (3)	C18—H18B	0.97
C2—H2	0.93	C19—C20	1.522 (3)
C3—C4	1.392 (3)	C19—H19A	0.97
C4—C5	1.385 (3)	C19—H19B	0.97
C4—H4	0.93	C20—C21	1.522 (3)
C5—C6	1.399 (3)	C20—H20A	0.97
C5—H5	0.93	C20—H20B	0.97
C6—C7	1.479 (3)	C21—C22	1.518 (3)
C7—C8	1.477 (3)	C21—H21A	0.97
C8—C9	1.340 (3)	C21—H21B	0.97
C8—H8	0.93	C22—C23	1.518 (3)
C9—C10	1.461 (3)	C22—H22A	0.97
C9—H9	0.93	C22—H22B	0.97
C10—C15	1.396 (3)	C23—C24	1.513 (3)
C10—C11	1.403 (3)	C23—H23A	0.97
C11—C12	1.376 (3)	C23—H23B	0.97
C11—H11	0.93	C24—C25	1.526 (3)
C12—C13	1.397 (3)	C24—H24A	0.97
C12—H12	0.93	C24—H24B	0.97
C13—C14	1.384 (3)	C25—H25A	0.96
C14—C15	1.393 (3)	C25—H25B	0.96
C14—H14	0.93	C25—H25C	0.96
C15—H15	0.93
C3—O1—H1O1	115.1 (18)	C16—C17—H17A	109.2
C13—O3—C16	117.84 (15)	C18—C17—H17A	109.2
C2—C1—C6	121.44 (19)	C16—C17—H17B	109.2
C2—C1—H1	119.3	C18—C17—H17B	109.2
C6—C1—H1	119.3	H17A—C17—H17B	107.9
C1—C2—C3	119.77 (19)	C17—C18—C19	113.01 (17)
C1—C2—H2	120.1	C17—C18—H18A	109.0
C3—C2—H2	120.1	C19—C18—H18A	109.0
O1—C3—C4	122.77 (18)	C17—C18—H18B	109.0
O1—C3—C2	117.63 (18)	C19—C18—H18B	109.0
C4—C3—C2	119.60 (18)	H18A—C18—H18B	107.8
C5—C4—C3	120.12 (19)	C18—C19—C20	113.81 (17)
C5—C4—H4	119.9	C18—C19—H19A	108.8
C3—C4—H4	119.9	C20—C19—H19A	108.8
C4—C5—C6	121.03 (19)	C18—C19—H19B	108.8
C4—C5—H5	119.5	C20—C19—H19B	108.8
C6—C5—H5	119.5	H19A—C19—H19B	107.7
C5—C6—C1	117.92 (18)	C21—C20—C19	113.30 (17)
C5—C6—C7	122.43 (18)	C21—C20—H20A	108.9
C1—C6—C7	119.38 (17)	C19—C20—H20A	108.9
O2—C7—C8	119.34 (17)	C21—C20—H20B	108.9
O2—C7—C6	120.14 (18)	C19—C20—H20B	108.9
C8—C7—C6	120.48 (17)	H20A—C20—H20B	107.7
C9—C8—C7	120.40 (18)	C22—C21—C20	113.74 (17)
C9—C8—H8	119.8	C22—C21—H21A	108.8
C7—C8—H8	119.8	C20—C21—H21A	108.8
C8—C9—C10	128.13 (19)	C22—C21—H21B	108.8
C8—C9—H9	115.9	C20—C21—H21B	108.8
C10—C9—H9	115.9	H21A—C21—H21B	107.7
C15—C10—C11	117.26 (18)	C23—C22—C21	114.78 (17)
C15—C10—C9	119.05 (18)	C23—C22—H22A	108.6
C11—C10—C9	123.63 (18)	C21—C22—H22A	108.6
C12—C11—C10	121.05 (18)	C23—C22—H22B	108.6
C12—C11—H11	119.5	C21—C22—H22B	108.6
C10—C11—H11	119.5	H22A—C22—H22B	107.5
C11—C12—C13	120.53 (19)	C24—C23—C22	113.59 (18)
C11—C12—H12	119.7	C24—C23—H23A	108.8
C13—C12—H12	119.7	C22—C23—H23A	108.8
O3—C13—C14	124.86 (17)	C24—C23—H23B	108.8
O3—C13—C12	115.28 (17)	C22—C23—H23B	108.8
C14—C13—C12	119.86 (18)	H23A—C23—H23B	107.7
C13—C14—C15	118.92 (18)	C23—C24—C25	112.84 (19)
C13—C14—H14	120.5	C23—C24—H24A	109.0
C15—C14—H14	120.5	C25—C24—H24A	109.0
C14—C15—C10	122.36 (19)	C23—C24—H24B	109.0
C14—C15—H15	118.8	C25—C24—H24B	109.0
C10—C15—H15	118.8	H24A—C24—H24B	107.8
O3—C16—C17	107.35 (15)	C24—C25—H25A	109.5
O3—C16—H16A	110.2	C24—C25—H25B	109.5
C17—C16—H16A	110.2	H25A—C25—H25B	109.5
O3—C16—H16B	110.2	C24—C25—H25C	109.5
C17—C16—H16B	110.2	H25A—C25—H25C	109.5
H16A—C16—H16B	108.5	H25B—C25—H25C	109.5
C16—C17—C18	111.91 (17)
C6—C1—C2—C3	0.5 (3)	C9—C10—C11—C12	−177.86 (19)
C1—C2—C3—O1	176.56 (18)	C10—C11—C12—C13	−0.6 (3)
C1—C2—C3—C4	−3.1 (3)	C16—O3—C13—C14	−1.2 (3)
O1—C3—C4—C5	−176.75 (18)	C16—O3—C13—C12	179.30 (17)
C2—C3—C4—C5	2.9 (3)	C11—C12—C13—O3	−179.39 (17)
C3—C4—C5—C6	−0.1 (3)	C11—C12—C13—C14	1.1 (3)
C4—C5—C6—C1	−2.5 (3)	O3—C13—C14—C15	−179.93 (18)
C4—C5—C6—C7	171.60 (18)	C12—C13—C14—C15	−0.5 (3)
C2—C1—C6—C5	2.3 (3)	C13—C14—C15—C10	−0.7 (3)
C2—C1—C6—C7	−171.99 (18)	C11—C10—C15—C14	1.2 (3)
C5—C6—C7—O2	−160.79 (19)	C9—C10—C15—C14	178.62 (19)
C1—C6—C7—O2	13.2 (3)	C13—O3—C16—C17	175.86 (16)
C5—C6—C7—C8	17.0 (3)	O3—C16—C17—C18	178.90 (16)
C1—C6—C7—C8	−168.94 (18)	C16—C17—C18—C19	177.92 (17)
O2—C7—C8—C9	5.4 (3)	C17—C18—C19—C20	175.44 (17)
C6—C7—C8—C9	−172.41 (18)	C18—C19—C20—C21	−178.11 (18)
C7—C8—C9—C10	177.52 (18)	C19—C20—C21—C22	175.79 (18)
C8—C9—C10—C15	−179.9 (2)	C20—C21—C22—C23	177.99 (18)
C8—C9—C10—C11	−2.7 (3)	C21—C22—C23—C24	−176.90 (19)
C15—C10—C11—C12	−0.6 (3)	C22—C23—C24—C25	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.95 (3)	1.71 (3)	2.655 (2)	177 (3)
C5—H5···O1ii	0.93	2.48	3.340 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.95 (3)	1.71 (3)	2.655 (2)	177 (3)
C5—H5⋯O1ii	0.93	2.48	3.340 (2)	155

Symmetry codes: (i) ; (ii) .