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

In the title compound, C(21)H(24)O(3), the enone group adopts an s-cis conformation. The planes of the aromatic rings are inclined at an angle of 6.1 (1)°. The alk-oxy tail is not linear, with the maximum deviation from the least-squares plane being 0.375 (2) Å. Mol-ecules are connected into extended chains along the a axis through O-H⋯O(carbon-yl) hydrogen bonds and are inter-linked via C-H⋯O inter-actions to form a two-dimensional array parallel to the ab plane.

Related literature

For the biological properties of chalcone derivatives, see: Bhat et al. (2005 ▶); Xue et al. (2004 ▶); Zhao et al. (2005 ▶); Satyana­rayana et al. (2004 ▶); Won et al. (2005 ▶). For related structures, see: Razak et al. (2009 ▶); Razak et al. (2009a ▶,b ▶); Ngaini, Fadzillah et al. (2009 ▶); Ngaini, Rahman et al. (2009 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H24O3

M = 324.40

Orthorhombic,

a = 10.0237 (2) Å

b = 9.7695 (2) Å

c = 35.3220 (6) Å

V = 3458.96 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.25 × 0.12 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.980, T max = 0.995

25370 measured reflections

5659 independent reflections

3311 reflections with I > 2σ(I)

R int = 0.086

Refinement

R[F 2 > 2σ(F 2)] = 0.073

wR(F 2) = 0.139

S = 1.02

5659 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.25 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/S1600536809019436/tk2457sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809019436/tk2457Isup2.hkl

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

C21H24O3	F(000) = 1392
Mr = 324.40	Dx = 1.246 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2200 reflections
a = 10.0237 (2) Å	θ = 2.3–22.0°
b = 9.7695 (2) Å	µ = 0.08 mm−1
c = 35.3220 (6) Å	T = 100 K
V = 3458.96 (12) Å3	Block, colourless
Z = 8	0.25 × 0.12 × 0.07 mm

Bruker SMART APEXII CCD area-detector diffractometer	5659 independent reflections
Radiation source: sealed tube	3311 reflections with I > 2σ(I)
graphite	Rint = 0.086
φ and ω scans	θmax = 31.3°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −14→14
Tmin = 0.980, Tmax = 0.995	k = −14→14
25370 measured reflections	l = −51→50

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)] = 0.073	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.0389P)2 + 1.4637P] where P = (Fo2 + 2Fc2)/3
5659 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.25 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	0.45711 (14)	0.93154 (14)	0.31262 (3)	0.0203 (3)
O2	0.17214 (13)	0.81942 (14)	0.15690 (3)	0.0216 (3)
O3	0.47446 (13)	0.24927 (13)	0.00413 (4)	0.0207 (3)
C1	0.43756 (18)	0.74282 (19)	0.22313 (5)	0.0177 (4)
H1A	0.4783	0.6696	0.2109	0.021*
C2	0.47890 (19)	0.77884 (18)	0.25929 (5)	0.0183 (4)
H2A	0.5452	0.7286	0.2714	0.022*
C3	0.42085 (18)	0.89013 (19)	0.27736 (5)	0.0172 (4)
C4	0.32103 (19)	0.96503 (19)	0.25923 (5)	0.0198 (4)
H4A	0.2827	1.0402	0.2712	0.024*
C5	0.27945 (18)	0.92715 (19)	0.22348 (5)	0.0193 (4)
H5A	0.2127	0.9773	0.2116	0.023*
C6	0.33582 (18)	0.81466 (18)	0.20480 (5)	0.0163 (4)
C7	0.28184 (18)	0.77389 (19)	0.16745 (5)	0.0175 (4)
C8	0.35542 (18)	0.67861 (19)	0.14301 (5)	0.0177 (4)
H8A	0.4336	0.6379	0.1516	0.021*
C9	0.30968 (18)	0.65064 (19)	0.10828 (5)	0.0184 (4)
H9A	0.2357	0.7010	0.1007	0.022*
C10	0.35965 (18)	0.55225 (18)	0.08071 (5)	0.0169 (4)
C11	0.29114 (19)	0.5369 (2)	0.04661 (5)	0.0201 (4)
H11A	0.2197	0.5948	0.0415	0.024*
C12	0.32554 (19)	0.43872 (19)	0.02008 (5)	0.0201 (4)
H12A	0.2773	0.4303	−0.0023	0.024*
C13	0.43319 (18)	0.35286 (18)	0.02730 (5)	0.0176 (4)
C14	0.50604 (18)	0.3682 (2)	0.06095 (5)	0.0193 (4)
H14A	0.5795	0.3125	0.0655	0.023*
C15	0.46928 (18)	0.46577 (19)	0.08730 (5)	0.0180 (4)
H15A	0.5176	0.4743	0.1096	0.022*
C16	0.40164 (19)	0.2288 (2)	−0.03062 (5)	0.0207 (4)
H16A	0.4010	0.3125	−0.0454	0.025*
H16B	0.3101	0.2034	−0.0251	0.025*
C17	0.47013 (19)	0.11601 (19)	−0.05233 (5)	0.0211 (4)
H17A	0.4708	0.0334	−0.0371	0.025*
H17B	0.5620	0.1420	−0.0571	0.025*
C18	0.4013 (2)	0.0863 (2)	−0.08992 (5)	0.0229 (4)
H18A	0.3874	0.1717	−0.1033	0.027*
H18B	0.3145	0.0462	−0.0850	0.027*
C19	0.48161 (19)	−0.0107 (2)	−0.11501 (5)	0.0219 (4)
H19A	0.4997	−0.0939	−0.1009	0.026*
H19B	0.5667	0.0318	−0.1208	0.026*
C20	0.4129 (2)	−0.0490 (2)	−0.15221 (5)	0.0274 (5)
H20A	0.3798	0.0336	−0.1642	0.033*
H20B	0.4781	−0.0899	−0.1691	0.033*
C21	0.2977 (2)	−0.1482 (2)	−0.14688 (6)	0.0286 (5)
H21A	0.2614	−0.1722	−0.1711	0.043*
H21B	0.2297	−0.1057	−0.1317	0.043*
H21C	0.3291	−0.2292	−0.1344	0.043*
H1O1	0.529 (3)	0.886 (3)	0.3205 (7)	0.057 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0221 (7)	0.0227 (7)	0.0162 (6)	0.0010 (6)	−0.0029 (6)	−0.0022 (6)
O2	0.0217 (7)	0.0263 (7)	0.0169 (6)	0.0043 (6)	−0.0023 (5)	−0.0003 (6)
O3	0.0243 (7)	0.0219 (7)	0.0160 (6)	0.0026 (6)	−0.0010 (5)	−0.0046 (5)
C1	0.0195 (9)	0.0155 (9)	0.0182 (9)	−0.0003 (8)	0.0009 (8)	−0.0010 (7)
C2	0.0206 (10)	0.0158 (9)	0.0184 (9)	0.0010 (8)	−0.0036 (8)	0.0011 (7)
C3	0.0191 (9)	0.0193 (9)	0.0132 (8)	−0.0041 (7)	−0.0003 (7)	0.0001 (7)
C4	0.0196 (9)	0.0177 (9)	0.0221 (9)	0.0013 (8)	0.0019 (8)	−0.0025 (8)
C5	0.0192 (9)	0.0193 (9)	0.0194 (9)	0.0008 (8)	−0.0023 (7)	−0.0002 (8)
C6	0.0179 (9)	0.0163 (8)	0.0148 (8)	−0.0011 (7)	0.0003 (7)	0.0014 (7)
C7	0.0199 (9)	0.0173 (9)	0.0153 (9)	−0.0027 (8)	0.0010 (7)	0.0023 (7)
C8	0.0172 (9)	0.0183 (9)	0.0175 (9)	0.0012 (8)	0.0004 (7)	0.0023 (7)
C9	0.0179 (9)	0.0194 (9)	0.0178 (9)	−0.0005 (7)	0.0020 (7)	0.0020 (8)
C10	0.0189 (9)	0.0177 (9)	0.0141 (8)	−0.0026 (7)	0.0012 (7)	0.0015 (7)
C11	0.0201 (10)	0.0217 (10)	0.0184 (9)	0.0016 (8)	−0.0006 (8)	0.0025 (8)
C12	0.0228 (10)	0.0239 (10)	0.0135 (8)	−0.0005 (8)	−0.0026 (8)	−0.0007 (8)
C13	0.0211 (9)	0.0161 (9)	0.0155 (9)	−0.0023 (7)	0.0032 (7)	0.0018 (7)
C14	0.0167 (9)	0.0218 (9)	0.0195 (9)	0.0001 (8)	0.0001 (7)	0.0021 (8)
C15	0.0198 (9)	0.0214 (9)	0.0128 (8)	−0.0032 (8)	0.0001 (7)	0.0017 (7)
C16	0.0235 (10)	0.0228 (10)	0.0157 (9)	−0.0004 (8)	−0.0013 (8)	0.0010 (8)
C17	0.0238 (10)	0.0208 (9)	0.0188 (9)	0.0022 (8)	0.0017 (8)	−0.0009 (8)
C18	0.0270 (11)	0.0223 (10)	0.0194 (9)	0.0038 (8)	0.0010 (8)	−0.0017 (8)
C19	0.0253 (10)	0.0203 (9)	0.0201 (9)	−0.0005 (8)	0.0050 (8)	−0.0014 (8)
C20	0.0399 (13)	0.0245 (10)	0.0178 (10)	−0.0012 (10)	0.0031 (9)	−0.0018 (8)
C21	0.0344 (12)	0.0286 (11)	0.0228 (10)	0.0021 (10)	−0.0038 (9)	−0.0021 (9)

O1—C3	1.359 (2)	C12—C13	1.390 (3)
O1—H1O1	0.89 (3)	C12—H12A	0.9300
O2—C7	1.243 (2)	C13—C14	1.403 (2)
O3—C13	1.366 (2)	C14—C15	1.382 (3)
O3—C16	1.442 (2)	C14—H14A	0.9300
C1—C2	1.388 (2)	C15—H15A	0.9300
C1—C6	1.397 (2)	C16—C17	1.508 (3)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.389 (2)	C16—H16B	0.9700
C2—H2A	0.9300	C17—C18	1.524 (3)
C3—C4	1.395 (3)	C17—H17A	0.9700
C4—C5	1.380 (2)	C17—H17B	0.9700
C4—H4A	0.9300	C18—C19	1.526 (3)
C5—C6	1.401 (2)	C18—H18A	0.9700
C5—H5A	0.9300	C18—H18B	0.9700
C6—C7	1.481 (2)	C19—C20	1.530 (3)
C7—C8	1.468 (3)	C19—H19A	0.9700
C8—C9	1.338 (2)	C19—H19B	0.9700
C8—H8A	0.9300	C20—C21	1.519 (3)
C9—C10	1.457 (2)	C20—H20A	0.9700
C9—H9A	0.9300	C20—H20B	0.9700
C10—C11	1.394 (2)	C21—H21A	0.9600
C10—C15	1.405 (3)	C21—H21B	0.9600
C11—C12	1.385 (3)	C21—H21C	0.9600
C11—H11A	0.9300
C3—O1—H1O1	110.8 (17)	C15—C14—H14A	119.8
C13—O3—C16	117.35 (14)	C13—C14—H14A	119.8
C2—C1—C6	121.13 (17)	C14—C15—C10	120.75 (17)
C2—C1—H1A	119.4	C14—C15—H15A	119.6
C6—C1—H1A	119.4	C10—C15—H15A	119.6
C1—C2—C3	119.76 (17)	O3—C16—C17	107.68 (15)
C1—C2—H2A	120.1	O3—C16—H16A	110.2
C3—C2—H2A	120.1	C17—C16—H16A	110.2
O1—C3—C2	122.84 (16)	O3—C16—H16B	110.2
O1—C3—C4	117.15 (16)	C17—C16—H16B	110.2
C2—C3—C4	120.01 (16)	H16A—C16—H16B	108.5
C5—C4—C3	119.72 (17)	C16—C17—C18	112.12 (16)
C5—C4—H4A	120.1	C16—C17—H17A	109.2
C3—C4—H4A	120.1	C18—C17—H17A	109.2
C4—C5—C6	121.30 (17)	C16—C17—H17B	109.2
C4—C5—H5A	119.4	C18—C17—H17B	109.2
C6—C5—H5A	119.4	H17A—C17—H17B	107.9
C1—C6—C5	118.05 (16)	C17—C18—C19	112.69 (16)
C1—C6—C7	123.00 (16)	C17—C18—H18A	109.1
C5—C6—C7	118.90 (16)	C19—C18—H18A	109.1
O2—C7—C8	119.66 (16)	C17—C18—H18B	109.1
O2—C7—C6	119.61 (16)	C19—C18—H18B	109.1
C8—C7—C6	120.73 (16)	H18A—C18—H18B	107.8
C9—C8—C7	119.77 (17)	C18—C19—C20	114.40 (17)
C9—C8—H8A	120.1	C18—C19—H19A	108.7
C7—C8—H8A	120.1	C20—C19—H19A	108.7
C8—C9—C10	129.03 (18)	C18—C19—H19B	108.7
C8—C9—H9A	115.5	C20—C19—H19B	108.7
C10—C9—H9A	115.5	H19A—C19—H19B	107.6
C11—C10—C15	117.62 (17)	C21—C20—C19	113.07 (16)
C11—C10—C9	118.60 (17)	C21—C20—H20A	109.0
C15—C10—C9	123.68 (16)	C19—C20—H20A	109.0
C12—C11—C10	122.42 (18)	C21—C20—H20B	109.0
C12—C11—H11A	118.8	C19—C20—H20B	109.0
C10—C11—H11A	118.8	H20A—C20—H20B	107.8
C11—C12—C13	119.14 (17)	C20—C21—H21A	109.5
C11—C12—H12A	120.4	C20—C21—H21B	109.5
C13—C12—H12A	120.4	H21A—C21—H21B	109.5
O3—C13—C12	124.91 (16)	C20—C21—H21C	109.5
O3—C13—C14	115.42 (16)	H21A—C21—H21C	109.5
C12—C13—C14	119.66 (17)	H21B—C21—H21C	109.5
C15—C14—C13	120.37 (18)
C6—C1—C2—C3	−1.6 (3)	C8—C9—C10—C15	0.9 (3)
C1—C2—C3—O1	−179.56 (16)	C15—C10—C11—C12	1.6 (3)
C1—C2—C3—C4	0.2 (3)	C9—C10—C11—C12	−174.97 (17)
O1—C3—C4—C5	−179.55 (16)	C10—C11—C12—C13	−0.8 (3)
C2—C3—C4—C5	0.7 (3)	C16—O3—C13—C12	0.8 (3)
C3—C4—C5—C6	−0.2 (3)	C16—O3—C13—C14	179.42 (15)
C2—C1—C6—C5	2.0 (3)	C11—C12—C13—O3	177.71 (17)
C2—C1—C6—C7	−175.46 (17)	C11—C12—C13—C14	−0.9 (3)
C4—C5—C6—C1	−1.1 (3)	O3—C13—C14—C15	−177.06 (16)
C4—C5—C6—C7	176.46 (17)	C12—C13—C14—C15	1.7 (3)
C1—C6—C7—O2	162.42 (17)	C13—C14—C15—C10	−0.8 (3)
C5—C6—C7—O2	−15.0 (3)	C11—C10—C15—C14	−0.8 (3)
C1—C6—C7—C8	−16.6 (3)	C9—C10—C15—C14	175.58 (17)
C5—C6—C7—C8	165.93 (16)	C13—O3—C16—C17	176.52 (15)
O2—C7—C8—C9	5.7 (3)	O3—C16—C17—C18	−179.69 (15)
C6—C7—C8—C9	−175.26 (17)	C16—C17—C18—C19	170.71 (16)
C7—C8—C9—C10	−174.51 (17)	C17—C18—C19—C20	177.08 (17)
C8—C9—C10—C11	177.22 (19)	C18—C19—C20—C21	−73.4 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2i	0.89 (3)	1.77 (3)	2.6466 (19)	169 (2)
C1—H1A···O1ii	0.93	2.55	3.458 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O2i	0.89 (3)	1.77 (3)	2.6466 (19)	169 (2)
C1—H1A⋯O1ii	0.93	2.55	3.458 (2)	164

Symmetry codes: (i) ; (ii) .