(E)-3-(4-Hexyl-oxyphen-yl)-1-(3-hydroxy-phen-yl)prop-2-en-one.

In the title compound, C(21)H(24)O(3), the enone unit is in the s-cis configuration. The dihedral angle between the benzene rings is 2.18 (4)°. In the crystal, mol-ecules are linked by pairs of O-H⋯O inter-molecular hydrogen bonds, forming inversion dimers. The crystal structure is also consolidated by C-H⋯π inter-actions.

Related literature

For general background to the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Won et al. (2005 ▶); Yayli et al. (2006 ▶). For related structures, see: Ng, Razak et al. (2006 ▶); Ng, Patil et al. (2006 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller uded in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H24O3

M = 324.40

Monoclinic,

a = 8.5918 (2) Å

b = 17.1320 (3) Å

c = 12.4192 (2) Å

β = 109.083 (1)°

V = 1727.58 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.52 × 0.43 × 0.37 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.959, T max = 0.970

32772 measured reflections

7567 independent reflections

5739 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.131

S = 1.04

7567 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.48 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/S1600536809010617/fj2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809010617/fj2200Isup2.hkl

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

C21H24O3	F(000) = 696
Mr = 324.40	Dx = 1.247 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9979 reflections
a = 8.5918 (2) Å	θ = 2.8–39.2°
b = 17.1320 (3) Å	µ = 0.08 mm−1
c = 12.4192 (2) Å	T = 100 K
β = 109.083 (1)°	Block, colourless
V = 1727.58 (6) Å3	0.52 × 0.43 × 0.37 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	7567 independent reflections
Radiation source: sealed tube	5739 reflections with I > 2σ(I)
graphite	Rint = 0.026
φ and ω scans	θmax = 35.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→13
Tmin = 0.959, Tmax = 0.970	k = −22→27
32772 measured reflections	l = −18→20

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0658P)2 + 0.3447P] where P = (Fo2 + 2Fc2)/3
7567 reflections	(Δ/σ)max = 0.001
222 parameters	Δρmax = 0.48 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	−0.67033 (8)	−0.16211 (4)	−0.11538 (5)	0.02019 (13)
O2	−0.24091 (8)	0.00815 (4)	0.14823 (5)	0.01889 (12)
O3	0.57829 (7)	0.01121 (4)	0.74453 (5)	0.01808 (12)
C1	−0.43937 (9)	−0.11205 (4)	0.03753 (6)	0.01426 (13)
H1A	−0.4490	−0.0636	0.0023	0.017*
C2	−0.54671 (10)	−0.17174 (5)	−0.01437 (6)	0.01515 (14)
C3	−0.53013 (10)	−0.24523 (5)	0.03709 (7)	0.01738 (15)
H3A	−0.6009	−0.2856	0.0020	0.021*
C4	−0.40736 (10)	−0.25769 (5)	0.14089 (7)	0.01789 (15)
H4A	−0.3966	−0.3066	0.1751	0.021*
C5	−0.30007 (10)	−0.19778 (5)	0.19442 (7)	0.01605 (14)
H5A	−0.2183	−0.2066	0.2639	0.019*
C6	−0.31644 (9)	−0.12429 (4)	0.14274 (6)	0.01352 (13)
C7	−0.20986 (9)	−0.05615 (5)	0.19509 (6)	0.01364 (13)
C8	−0.06986 (10)	−0.06665 (5)	0.30060 (6)	0.01473 (13)
H8A	−0.0520	−0.1146	0.3376	0.018*
C9	0.03228 (10)	−0.00634 (5)	0.34327 (6)	0.01478 (14)
H9A	0.0084	0.0398	0.3016	0.018*
C10	0.17496 (9)	−0.00406 (5)	0.44610 (6)	0.01412 (13)
C11	0.22794 (10)	−0.06753 (5)	0.52147 (7)	0.01577 (14)
H11A	0.1714	−0.1147	0.5049	0.019*
C12	0.36209 (10)	−0.06102 (5)	0.61936 (7)	0.01651 (14)
H12A	0.3952	−0.1036	0.6679	0.020*
C13	0.44893 (9)	0.00985 (5)	0.64597 (6)	0.01485 (14)
C14	0.39946 (10)	0.07342 (5)	0.57204 (7)	0.01645 (14)
H14A	0.4560	0.1205	0.5886	0.020*
C15	0.26459 (10)	0.06536 (5)	0.47334 (7)	0.01590 (14)
H15A	0.2331	0.1076	0.4239	0.019*
C16	0.66971 (10)	0.08312 (5)	0.77343 (7)	0.01598 (14)
H16A	0.5981	0.1248	0.7818	0.019*
H16B	0.7137	0.0975	0.7135	0.019*
C17	0.80851 (10)	0.07101 (5)	0.88414 (7)	0.01625 (14)
H17A	0.8812	0.0303	0.8742	0.019*
H17B	0.7636	0.0540	0.9425	0.019*
C18	0.90687 (10)	0.14613 (5)	0.92278 (7)	0.01651 (14)
H18A	0.9536	0.1620	0.8649	0.020*
H18B	0.8326	0.1871	0.9295	0.020*
C19	1.04510 (10)	0.13787 (5)	1.03599 (7)	0.01726 (14)
H19A	1.1188	0.0966	1.0296	0.021*
H19B	0.9984	0.1227	1.0942	0.021*
C20	1.14369 (11)	0.21270 (5)	1.07309 (8)	0.02270 (17)
H20A	1.1893	0.2283	1.0145	0.027*
H20B	1.0704	0.2538	1.0806	0.027*
C21	1.28308 (13)	0.20366 (7)	1.18553 (9)	0.0326 (2)
H21A	1.3478	0.2505	1.2015	0.049*
H21B	1.3514	0.1604	1.1805	0.049*
H21C	1.2379	0.1943	1.2456	0.049*
H101	−0.6888 (18)	−0.1130 (9)	−0.1279 (12)	0.042 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0200 (3)	0.0164 (3)	0.0173 (3)	0.0002 (2)	−0.0033 (2)	−0.0017 (2)
O2	0.0204 (3)	0.0150 (3)	0.0177 (3)	−0.0006 (2)	0.0015 (2)	0.0025 (2)
O3	0.0152 (3)	0.0188 (3)	0.0162 (3)	−0.0034 (2)	−0.0005 (2)	−0.0007 (2)
C1	0.0138 (3)	0.0135 (3)	0.0142 (3)	0.0008 (2)	0.0029 (3)	0.0001 (2)
C2	0.0138 (3)	0.0162 (3)	0.0137 (3)	0.0009 (3)	0.0020 (2)	−0.0016 (2)
C3	0.0171 (3)	0.0145 (3)	0.0187 (3)	−0.0014 (3)	0.0033 (3)	−0.0015 (3)
C4	0.0192 (4)	0.0138 (3)	0.0190 (3)	0.0003 (3)	0.0038 (3)	0.0017 (3)
C5	0.0165 (3)	0.0155 (3)	0.0144 (3)	0.0008 (3)	0.0026 (3)	0.0010 (3)
C6	0.0125 (3)	0.0143 (3)	0.0131 (3)	0.0005 (2)	0.0034 (2)	−0.0006 (2)
C7	0.0129 (3)	0.0151 (3)	0.0127 (3)	0.0001 (2)	0.0037 (2)	−0.0003 (2)
C8	0.0134 (3)	0.0156 (3)	0.0137 (3)	0.0003 (2)	0.0025 (2)	0.0006 (2)
C9	0.0136 (3)	0.0161 (3)	0.0139 (3)	0.0004 (3)	0.0036 (2)	−0.0008 (2)
C10	0.0128 (3)	0.0156 (3)	0.0136 (3)	−0.0009 (2)	0.0039 (2)	−0.0013 (2)
C11	0.0146 (3)	0.0153 (3)	0.0164 (3)	−0.0019 (3)	0.0037 (3)	−0.0007 (3)
C12	0.0155 (3)	0.0164 (3)	0.0161 (3)	−0.0008 (3)	0.0030 (3)	0.0009 (3)
C13	0.0123 (3)	0.0179 (3)	0.0136 (3)	−0.0004 (3)	0.0032 (2)	−0.0014 (2)
C14	0.0157 (3)	0.0156 (3)	0.0168 (3)	−0.0025 (3)	0.0035 (3)	−0.0013 (3)
C15	0.0160 (3)	0.0148 (3)	0.0156 (3)	−0.0006 (3)	0.0033 (3)	0.0004 (3)
C16	0.0135 (3)	0.0175 (3)	0.0160 (3)	−0.0021 (3)	0.0035 (3)	−0.0019 (3)
C17	0.0133 (3)	0.0190 (3)	0.0150 (3)	−0.0011 (3)	0.0025 (3)	−0.0004 (3)
C18	0.0143 (3)	0.0172 (3)	0.0161 (3)	−0.0003 (3)	0.0023 (3)	−0.0003 (3)
C19	0.0152 (3)	0.0190 (4)	0.0153 (3)	−0.0007 (3)	0.0020 (3)	−0.0003 (3)
C20	0.0204 (4)	0.0199 (4)	0.0235 (4)	−0.0004 (3)	0.0012 (3)	−0.0051 (3)
C21	0.0271 (5)	0.0418 (6)	0.0223 (4)	−0.0072 (4)	−0.0010 (4)	−0.0104 (4)

O1—C2	1.3631 (9)	C12—C13	1.4067 (11)
O1—H101	0.861 (16)	C12—H12A	0.9300
O2—C7	1.2336 (9)	C13—C14	1.3980 (11)
O3—C13	1.3581 (9)	C14—C15	1.3912 (11)
O3—C16	1.4419 (10)	C14—H14A	0.9300
C1—C2	1.3867 (11)	C15—H15A	0.9300
C1—C6	1.4016 (11)	C16—C17	1.5111 (11)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.3980 (11)	C16—H16B	0.9700
C3—C4	1.3895 (11)	C17—C18	1.5282 (11)
C3—H3A	0.9300	C17—H17A	0.9700
C4—C5	1.3944 (11)	C17—H17B	0.9700
C4—H4A	0.9300	C18—C19	1.5217 (11)
C5—C6	1.3993 (11)	C18—H18A	0.9700
C5—H5A	0.9300	C18—H18B	0.9700
C6—C7	1.4949 (11)	C19—C20	1.5225 (12)
C7—C8	1.4717 (11)	C19—H19A	0.9700
C8—C9	1.3470 (11)	C19—H19B	0.9700
C8—H8A	0.9300	C20—C21	1.5214 (13)
C9—C10	1.4531 (11)	C20—H20A	0.9700
C9—H9A	0.9300	C20—H20B	0.9700
C10—C15	1.3971 (11)	C21—H21A	0.9600
C10—C11	1.4096 (11)	C21—H21B	0.9600
C11—C12	1.3794 (11)	C21—H21C	0.9600
C11—H11A	0.9300
C2—O1—H101	109.0 (10)	C15—C14—H14A	120.4
C13—O3—C16	117.24 (6)	C13—C14—H14A	120.4
C2—C1—C6	120.45 (7)	C14—C15—C10	122.15 (7)
C2—C1—H1A	119.8	C14—C15—H15A	118.9
C6—C1—H1A	119.8	C10—C15—H15A	118.9
O1—C2—C1	122.56 (7)	O3—C16—C17	108.23 (6)
O1—C2—C3	117.51 (7)	O3—C16—H16A	110.1
C1—C2—C3	119.92 (7)	C17—C16—H16A	110.1
C4—C3—C2	119.70 (7)	O3—C16—H16B	110.1
C4—C3—H3A	120.1	C17—C16—H16B	110.1
C2—C3—H3A	120.1	H16A—C16—H16B	108.4
C3—C4—C5	120.81 (7)	C16—C17—C18	111.16 (7)
C3—C4—H4A	119.6	C16—C17—H17A	109.4
C5—C4—H4A	119.6	C18—C17—H17A	109.4
C4—C5—C6	119.47 (7)	C16—C17—H17B	109.4
C4—C5—H5A	120.3	C18—C17—H17B	109.4
C6—C5—H5A	120.3	H17A—C17—H17B	108.0
C5—C6—C1	119.63 (7)	C19—C18—C17	113.34 (7)
C5—C6—C7	123.22 (7)	C19—C18—H18A	108.9
C1—C6—C7	117.14 (7)	C17—C18—H18A	108.9
O2—C7—C8	121.13 (7)	C19—C18—H18B	108.9
O2—C7—C6	119.01 (7)	C17—C18—H18B	108.9
C8—C7—C6	119.86 (7)	H18A—C18—H18B	107.7
C9—C8—C7	119.62 (7)	C18—C19—C20	112.97 (7)
C9—C8—H8A	120.2	C18—C19—H19A	109.0
C7—C8—H8A	120.2	C20—C19—H19A	109.0
C8—C9—C10	128.33 (7)	C18—C19—H19B	109.0
C8—C9—H9A	115.8	C20—C19—H19B	109.0
C10—C9—H9A	115.8	H19A—C19—H19B	107.8
C15—C10—C11	117.59 (7)	C21—C20—C19	112.66 (8)
C15—C10—C9	118.39 (7)	C21—C20—H20A	109.1
C11—C10—C9	124.01 (7)	C19—C20—H20A	109.1
C12—C11—C10	121.22 (7)	C21—C20—H20B	109.1
C12—C11—H11A	119.4	C19—C20—H20B	109.1
C10—C11—H11A	119.4	H20A—C20—H20B	107.8
C11—C12—C13	120.19 (7)	C20—C21—H21A	109.5
C11—C12—H12A	119.9	C20—C21—H21B	109.5
C13—C12—H12A	119.9	H21A—C21—H21B	109.5
O3—C13—C14	124.19 (7)	C20—C21—H21C	109.5
O3—C13—C12	116.20 (7)	H21A—C21—H21C	109.5
C14—C13—C12	119.61 (7)	H21B—C21—H21C	109.5
C15—C14—C13	119.22 (7)
C6—C1—C2—O1	178.55 (7)	C8—C9—C10—C11	−1.52 (13)
C6—C1—C2—C3	−1.49 (11)	C15—C10—C11—C12	0.84 (11)
O1—C2—C3—C4	−179.16 (7)	C9—C10—C11—C12	−178.31 (7)
C1—C2—C3—C4	0.88 (12)	C10—C11—C12—C13	0.14 (12)
C2—C3—C4—C5	−0.11 (12)	C16—O3—C13—C14	−0.26 (11)
C3—C4—C5—C6	−0.05 (12)	C16—O3—C13—C12	179.73 (7)
C4—C5—C6—C1	−0.54 (11)	C11—C12—C13—O3	179.37 (7)
C4—C5—C6—C7	178.46 (7)	C11—C12—C13—C14	−0.64 (12)
C2—C1—C6—C5	1.32 (11)	O3—C13—C14—C15	−179.87 (7)
C2—C1—C6—C7	−177.75 (7)	C12—C13—C14—C15	0.13 (12)
C5—C6—C7—O2	−174.30 (7)	C13—C14—C15—C10	0.89 (12)
C1—C6—C7—O2	4.73 (10)	C11—C10—C15—C14	−1.37 (11)
C5—C6—C7—C8	6.05 (11)	C9—C10—C15—C14	177.83 (7)
C1—C6—C7—C8	−174.92 (7)	C13—O3—C16—C17	−178.97 (6)
O2—C7—C8—C9	−4.05 (11)	O3—C16—C17—C18	−177.65 (6)
C6—C7—C8—C9	175.59 (7)	C16—C17—C18—C19	178.18 (6)
C7—C8—C9—C10	179.11 (7)	C17—C18—C19—C20	179.31 (7)
C8—C9—C10—C15	179.34 (8)	C18—C19—C20—C21	−179.22 (8)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···O2i	0.86 (2)	1.89 (2)	2.739 (1)	171 (2)
C16—H16A···Cg1ii	0.97	2.72	3.572 (1)	146
C20—H20A···Cg1iii	0.97	2.82	3.642 (1)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H101⋯O2i	0.86 (2)	1.89 (2)	2.739 (1)	171 (2)
C16—H16A⋯Cg1ii	0.97	2.72	3.572 (1)	146
C20—H20A⋯Cg1iii	0.97	2.82	3.642 (1)	143

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of C1–C6 ring.