(E)-3-[4-(Hex-yloxy)phen-yl]-1-(2-hydroxy-phen-yl)prop-2-en-1-one.

In the title compound, C(21)H(24)O(3), the conformation of the enone group is s-cis. The benzene rings are inclined at an angle of 7.9 (1)°. The alk-oxy tail is planar, with a maximum deviation from the least-squares plane of 0.009 (2) Å, and adopts a trans conformation throughout. An intra-molecular O-H⋯O inter-action between the keto and hydr-oxy groups forms S(6) ring motifs. In the crystal, mol-ecules are arranged in a head-to-tail manner down the a axis and are subsequently stacked along the b axis, forming mol-ecular sheets parallel to the ab plane. The crystal structure is further stabilized by weak C-H⋯π inter-actions and short C⋯O [3.376 (2) Å] contacts.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Zhao et al. (2005 ▶); Lee et al. (2006 ▶). For related structures, see: Razak, Fun, Ngaini, Rahman & Hussain (2009 ▶); Razak, Fun, Ngaini, Fadzillah & Hussain (2009a ▶,b ▶); Ngaini, Fadzillah et al. (2009 ▶); Ngaini, Rahman et al. (2009 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H24O3

M = 324.40

Monoclinic,

a = 19.6443 (5) Å

b = 7.1966 (2) Å

c = 12.6520 (3) Å

β = 106.438 (2)°

V = 1715.53 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.47 × 0.12 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.962, T max = 0.997

20873 measured reflections

5025 independent reflections

2783 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.070

wR(F 2) = 0.190

S = 1.05

5025 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.29 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/S1600536809017577/sj2623sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017577/sj2623Isup2.hkl

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

C21H24O3	F(000) = 696
Mr = 324.40	Dx = 1.256 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3217 reflections
a = 19.6443 (5) Å	θ = 3.0–30.0°
b = 7.1966 (2) Å	µ = 0.08 mm−1
c = 12.6520 (3) Å	T = 100 K
β = 106.438 (2)°	Needle, yellow
V = 1715.53 (8) Å3	0.47 × 0.12 × 0.04 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5025 independent reflections
Radiation source: sealed tube	2783 reflections with I > 2σ(I)
graphite	Rint = 0.057
φ and ω scans	θmax = 30.1°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −27→27
Tmin = 0.962, Tmax = 0.997	k = −9→10
20873 measured reflections	l = −17→17

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)] = 0.070	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.190	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0907P)2] where P = (Fo2 + 2Fc2)/3
5025 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.53 e Å−3
0 restraints	Δρmin = −0.29 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	0.31582 (7)	0.61343 (19)	−0.09249 (11)	0.0210 (3)
O2	0.20488 (6)	0.60487 (18)	−0.03200 (11)	0.0203 (3)
O3	−0.06969 (6)	0.61140 (17)	0.36275 (11)	0.0168 (3)
C1	0.35907 (9)	0.6404 (2)	0.20871 (16)	0.0159 (4)
H1A	0.3371	0.6462	0.2648	0.019*
C2	0.43212 (9)	0.6445 (3)	0.23554 (17)	0.0202 (4)
H2A	0.4590	0.6512	0.3089	0.024*
C3	0.46535 (9)	0.6386 (3)	0.15149 (16)	0.0194 (4)
H3A	0.5146	0.6415	0.1691	0.023*
C4	0.42582 (9)	0.6283 (3)	0.04267 (16)	0.0175 (4)
H4A	0.4485	0.6249	−0.0126	0.021*
C5	0.35182 (9)	0.6230 (2)	0.01518 (15)	0.0149 (4)
C6	0.31698 (9)	0.6276 (2)	0.09933 (15)	0.0137 (4)
C7	0.23827 (9)	0.6181 (2)	0.06736 (15)	0.0138 (4)
C8	0.19935 (9)	0.6221 (2)	0.15096 (16)	0.0146 (4)
H8A	0.2236	0.6250	0.2256	0.018*
C9	0.12783 (9)	0.6216 (2)	0.11734 (16)	0.0153 (4)
H9A	0.1076	0.6215	0.0414	0.018*
C10	0.07792 (8)	0.6213 (2)	0.18274 (15)	0.0130 (4)
C11	0.00511 (9)	0.6329 (2)	0.12710 (16)	0.0154 (4)
H11A	−0.0091	0.6438	0.0507	0.018*
C12	−0.04606 (9)	0.6284 (3)	0.18360 (16)	0.0160 (4)
H12A	−0.0940	0.6344	0.1454	0.019*
C13	−0.02488 (9)	0.6148 (2)	0.29733 (16)	0.0135 (4)
C14	0.04731 (9)	0.6028 (2)	0.35469 (16)	0.0156 (4)
H14A	0.0612	0.5925	0.4311	0.019*
C15	0.09760 (9)	0.6064 (2)	0.29794 (16)	0.0154 (4)
H15A	0.1454	0.5988	0.3366	0.019*
C16	−0.14479 (8)	0.6211 (3)	0.31008 (15)	0.0153 (4)
H16A	−0.1602	0.5148	0.2621	0.018*
H16B	−0.1565	0.7335	0.2664	0.018*
C17	−0.18025 (9)	0.6212 (3)	0.40186 (15)	0.0151 (4)
H17A	−0.1631	0.7269	0.4496	0.018*
H17B	−0.1667	0.5094	0.4455	0.018*
C18	−0.26094 (9)	0.6306 (3)	0.36018 (15)	0.0149 (4)
H18A	−0.2785	0.5255	0.3122	0.018*
H18B	−0.2750	0.7434	0.3176	0.018*
C19	−0.29383 (9)	0.6284 (3)	0.45638 (15)	0.0144 (4)
H19A	−0.2785	0.5166	0.4994	0.017*
H19B	−0.2759	0.7341	0.5037	0.017*
C20	−0.37459 (9)	0.6351 (3)	0.42130 (16)	0.0162 (4)
H20A	−0.3931	0.5290	0.3747	0.019*
H20B	−0.3904	0.7469	0.3786	0.019*
C21	−0.40379 (9)	0.6331 (3)	0.52132 (17)	0.0219 (5)
H21A	−0.4547	0.6385	0.4969	0.033*
H21B	−0.3859	0.7386	0.5672	0.033*
H21C	−0.3892	0.5210	0.5626	0.033*
H1O1	0.2698 (14)	0.605 (3)	−0.094 (2)	0.059 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0199 (7)	0.0333 (9)	0.0108 (7)	−0.0030 (6)	0.0060 (6)	0.0011 (6)
O2	0.0166 (6)	0.0309 (8)	0.0131 (7)	0.0007 (6)	0.0035 (6)	0.0021 (6)
O3	0.0115 (6)	0.0264 (8)	0.0139 (7)	0.0003 (5)	0.0060 (5)	−0.0003 (6)
C1	0.0167 (8)	0.0195 (10)	0.0137 (10)	0.0012 (8)	0.0078 (7)	0.0006 (8)
C2	0.0174 (9)	0.0295 (12)	0.0132 (10)	−0.0017 (8)	0.0035 (8)	0.0002 (9)
C3	0.0142 (8)	0.0238 (11)	0.0213 (11)	−0.0006 (8)	0.0068 (8)	0.0018 (9)
C4	0.0179 (8)	0.0193 (10)	0.0198 (11)	0.0006 (8)	0.0125 (8)	0.0021 (9)
C5	0.0203 (9)	0.0132 (10)	0.0127 (10)	−0.0009 (7)	0.0071 (8)	0.0018 (8)
C6	0.0149 (8)	0.0130 (10)	0.0146 (10)	0.0012 (7)	0.0068 (7)	0.0004 (8)
C7	0.0154 (8)	0.0125 (9)	0.0147 (10)	0.0010 (7)	0.0061 (7)	0.0016 (8)
C8	0.0149 (8)	0.0162 (10)	0.0135 (10)	0.0005 (7)	0.0055 (7)	0.0018 (8)
C9	0.0164 (8)	0.0146 (10)	0.0157 (10)	0.0012 (7)	0.0061 (7)	0.0005 (8)
C10	0.0122 (8)	0.0126 (9)	0.0149 (10)	−0.0001 (7)	0.0049 (7)	−0.0004 (8)
C11	0.0162 (8)	0.0180 (10)	0.0119 (10)	0.0012 (7)	0.0041 (7)	0.0008 (8)
C12	0.0120 (8)	0.0196 (10)	0.0168 (10)	0.0023 (7)	0.0046 (7)	0.0017 (9)
C13	0.0135 (8)	0.0132 (9)	0.0152 (10)	0.0000 (7)	0.0062 (7)	−0.0021 (8)
C14	0.0152 (8)	0.0202 (11)	0.0111 (10)	−0.0004 (7)	0.0031 (7)	0.0007 (8)
C15	0.0115 (8)	0.0173 (10)	0.0170 (10)	−0.0010 (7)	0.0033 (7)	−0.0027 (8)
C16	0.0102 (7)	0.0197 (10)	0.0156 (10)	0.0000 (7)	0.0030 (7)	−0.0002 (8)
C17	0.0145 (8)	0.0177 (10)	0.0142 (10)	0.0016 (7)	0.0061 (7)	0.0004 (8)
C18	0.0148 (8)	0.0167 (10)	0.0153 (10)	−0.0005 (7)	0.0076 (7)	−0.0008 (8)
C19	0.0148 (8)	0.0158 (10)	0.0138 (10)	0.0000 (7)	0.0060 (7)	0.0003 (8)
C20	0.0150 (8)	0.0172 (10)	0.0175 (10)	−0.0002 (7)	0.0065 (7)	0.0011 (8)
C21	0.0176 (9)	0.0283 (12)	0.0231 (12)	0.0018 (8)	0.0112 (8)	0.0040 (10)

O1—C5	1.347 (2)	C12—C13	1.384 (3)
O1—H1O1	0.90 (3)	C12—H12A	0.9300
O2—C7	1.246 (2)	C13—C14	1.401 (2)
O3—C13	1.369 (2)	C14—C15	1.376 (2)
O3—C16	1.438 (2)	C14—H14A	0.9300
C1—C2	1.378 (2)	C15—H15A	0.9300
C1—C6	1.400 (3)	C16—C17	1.514 (2)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.397 (3)	C16—H16B	0.9700
C2—H2A	0.9300	C17—C18	1.524 (2)
C3—C4	1.378 (3)	C17—H17A	0.9700
C3—H3A	0.9300	C17—H17B	0.9700
C4—C5	1.396 (2)	C18—C19	1.531 (2)
C4—H4A	0.9300	C18—H18A	0.9700
C5—C6	1.420 (2)	C18—H18B	0.9700
C6—C7	1.485 (2)	C19—C20	1.522 (2)
C7—C8	1.470 (2)	C19—H19A	0.9700
C8—C9	1.348 (2)	C19—H19B	0.9700
C8—H8A	0.9300	C20—C21	1.530 (3)
C9—C10	1.451 (2)	C20—H20A	0.9700
C9—H9A	0.9300	C20—H20B	0.9700
C10—C15	1.402 (3)	C21—H21A	0.9600
C10—C11	1.406 (2)	C21—H21B	0.9600
C11—C12	1.389 (2)	C21—H21C	0.9600
C11—H11A	0.9300
C5—O1—H1O1	105.5 (18)	C15—C14—H14A	120.0
C13—O3—C16	118.03 (14)	C13—C14—H14A	120.0
C2—C1—C6	121.83 (17)	C14—C15—C10	121.08 (16)
C2—C1—H1A	119.1	C14—C15—H15A	119.5
C6—C1—H1A	119.1	C10—C15—H15A	119.5
C1—C2—C3	119.35 (19)	O3—C16—C17	106.20 (15)
C1—C2—H2A	120.3	O3—C16—H16A	110.5
C3—C2—H2A	120.3	C17—C16—H16A	110.5
C4—C3—C2	120.63 (17)	O3—C16—H16B	110.5
C4—C3—H3A	119.7	C17—C16—H16B	110.5
C2—C3—H3A	119.7	H16A—C16—H16B	108.7
C3—C4—C5	120.20 (17)	C16—C17—C18	113.20 (15)
C3—C4—H4A	119.9	C16—C17—H17A	108.9
C5—C4—H4A	119.9	C18—C17—H17A	108.9
O1—C5—C4	117.70 (16)	C16—C17—H17B	108.9
O1—C5—C6	122.21 (16)	C18—C17—H17B	108.9
C4—C5—C6	120.09 (17)	H17A—C17—H17B	107.8
C1—C6—C5	117.89 (15)	C17—C18—C19	110.86 (15)
C1—C6—C7	123.40 (16)	C17—C18—H18A	109.5
C5—C6—C7	118.71 (17)	C19—C18—H18A	109.5
O2—C7—C8	119.66 (16)	C17—C18—H18B	109.5
O2—C7—C6	119.24 (15)	C19—C18—H18B	109.5
C8—C7—C6	121.09 (17)	H18A—C18—H18B	108.1
C9—C8—C7	118.73 (18)	C20—C19—C18	114.03 (15)
C9—C8—H8A	120.6	C20—C19—H19A	108.7
C7—C8—H8A	120.6	C18—C19—H19A	108.7
C8—C9—C10	129.22 (19)	C20—C19—H19B	108.7
C8—C9—H9A	115.4	C18—C19—H19B	108.7
C10—C9—H9A	115.4	H19A—C19—H19B	107.6
C15—C10—C11	117.84 (15)	C19—C20—C21	111.23 (16)
C15—C10—C9	124.12 (16)	C19—C20—H20A	109.4
C11—C10—C9	118.03 (17)	C21—C20—H20A	109.4
C12—C11—C10	121.51 (17)	C19—C20—H20B	109.4
C12—C11—H11A	119.2	C21—C20—H20B	109.4
C10—C11—H11A	119.2	H20A—C20—H20B	108.0
C13—C12—C11	119.23 (16)	C20—C21—H21A	109.5
C13—C12—H12A	120.4	C20—C21—H21B	109.5
C11—C12—H12A	120.4	H21A—C21—H21B	109.5
O3—C13—C12	125.07 (15)	C20—C21—H21C	109.5
O3—C13—C14	114.56 (16)	H21A—C21—H21C	109.5
C12—C13—C14	120.37 (16)	H21B—C21—H21C	109.5
C15—C14—C13	119.97 (17)
C6—C1—C2—C3	0.9 (3)	C8—C9—C10—C11	175.97 (18)
C1—C2—C3—C4	−0.1 (3)	C15—C10—C11—C12	−0.5 (3)
C2—C3—C4—C5	−0.2 (3)	C9—C10—C11—C12	178.26 (17)
C3—C4—C5—O1	179.86 (18)	C10—C11—C12—C13	0.9 (3)
C3—C4—C5—C6	−0.2 (3)	C16—O3—C13—C12	0.5 (2)
C2—C1—C6—C5	−1.3 (3)	C16—O3—C13—C14	−179.34 (15)
C2—C1—C6—C7	178.43 (16)	C11—C12—C13—O3	179.13 (17)
O1—C5—C6—C1	−179.10 (17)	C11—C12—C13—C14	−1.0 (3)
C4—C5—C6—C1	1.0 (3)	O3—C13—C14—C15	−179.48 (16)
O1—C5—C6—C7	1.1 (3)	C12—C13—C14—C15	0.6 (3)
C4—C5—C6—C7	−178.82 (16)	C13—C14—C15—C10	−0.2 (3)
C1—C6—C7—O2	−179.21 (18)	C11—C10—C15—C14	0.1 (3)
C5—C6—C7—O2	0.6 (3)	C9—C10—C15—C14	−178.55 (17)
C1—C6—C7—C8	0.2 (3)	C13—O3—C16—C17	−178.12 (14)
C5—C6—C7—C8	179.95 (16)	O3—C16—C17—C18	−179.87 (14)
O2—C7—C8—C9	−3.6 (3)	C16—C17—C18—C19	179.43 (15)
C6—C7—C8—C9	177.02 (16)	C17—C18—C19—C20	−179.30 (15)
C7—C8—C9—C10	178.62 (18)	C18—C19—C20—C21	−179.83 (15)
C8—C9—C10—C15	−5.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.90 (3)	1.68 (3)	2.507 (2)	152 (2)
C20—H20A···Cg1i	0.97	2.84	3.657 (2)	142
C20—H20B···Cg1ii	0.97	2.78	3.637 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2	0.90 (3)	1.68 (3)	2.507 (2)	152 (2)
C20—H20A⋯Cg1i	0.97	2.84	3.657 (2)	142
C20—H20B⋯Cg1ii	0.97	2.78	3.637 (2)	147

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