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

In the title compound, C(21)H(24)O(3), the enone moiety adopts an s-cis conformation and the dihedral angle between the benzene rings is 12.89 (6)°. The hex-yloxy tail adopts an extended conformation. In the crystal, inversion dimers are linked by pairs of O-H⋯O hydrogen bonds and pairs of C-H⋯O inter-actions, forming two R(2) (2)(7) and one R(2) (2)(10) loops. The dimers are then arranged into sheets lying parallel to (201) and weak C-H⋯π inter-actions consolidate the packing.

Related literature

For a related structure and background to the biological properties of chalcones, see: Ngaini et al. (2011 ▶). For related structures, see: Razak et al. (2009 ▶); Ngaini et al. (2010 ▶). 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) ▶.

Experimental

Crystal data

C21H24O3

M = 324.40

Triclinic,

a = 7.485 (2) Å

b = 10.834 (3) Å

c = 11.673 (3) Å

α = 73.858 (5)°

β = 77.961 (6)°

γ = 76.941 (6)°

V = 874.9 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.47 × 0.14 × 0.12 mm

Data collection

Bruker APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.963, T max = 0.991

17565 measured reflections

4576 independent reflections

3781 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.133

S = 1.02

4576 reflections

222 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.23 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/S1600536812038007/hb6948sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812038007/hb6948Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812038007/hb6948Isup3.cml

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

C21H24O3	Z = 2
Mr = 324.40	F(000) = 348
Triclinic, P1	Dx = 1.231 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.485 (2) Å	Cell parameters from 6758 reflections
b = 10.834 (3) Å	θ = 2.4–31.7°
c = 11.673 (3) Å	µ = 0.08 mm−1
α = 73.858 (5)°	T = 100 K
β = 77.961 (6)°	Block, yellow
γ = 76.941 (6)°	0.47 × 0.14 × 0.12 mm
V = 874.9 (4) Å3

Bruker APEX DUO CCD diffractometer	4576 independent reflections
Radiation source: fine-focus sealed tube	3781 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.026
φ and ω scans	θmax = 29.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
Tmin = 0.963, Tmax = 0.991	k = −14→14
17565 measured reflections	l = −15→15

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + (0.077P)2 + 0.2082P] where P = (Fo2 + 2Fc2)/3
4576 reflections	(Δ/σ)max < 0.001
222 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.23 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	0.10199 (12)	0.82681 (7)	0.77465 (7)	0.02537 (19)
O2	0.05000 (12)	1.13926 (7)	1.00412 (7)	0.02580 (19)
O3	0.26974 (11)	0.74559 (8)	0.24879 (7)	0.02478 (19)
C1	0.23994 (15)	1.29725 (10)	0.70042 (10)	0.0229 (2)
H1A	0.2848	1.2773	0.6260	0.027*
C2	0.24424 (16)	1.41983 (11)	0.71304 (11)	0.0261 (2)
H2A	0.2922	1.4812	0.6477	0.031*
C3	0.17661 (16)	1.45074 (10)	0.82374 (11)	0.0256 (2)
H3A	0.1763	1.5338	0.8318	0.031*
C4	0.10963 (15)	1.35851 (10)	0.92229 (10)	0.0232 (2)
H4A	0.0655	1.3794	0.9964	0.028*
C5	0.10858 (14)	1.23422 (10)	0.91002 (10)	0.0198 (2)
C6	0.16962 (14)	1.20282 (10)	0.79729 (10)	0.0194 (2)
C7	0.15502 (14)	1.07449 (10)	0.78689 (10)	0.0205 (2)
H7A	0.1211	1.0145	0.8581	0.025*
C8	0.18600 (15)	1.03496 (10)	0.68408 (10)	0.0226 (2)
H8A	0.2266	1.0912	0.6119	0.027*
C9	0.15789 (14)	0.90539 (10)	0.68181 (10)	0.0201 (2)
C10	0.19366 (14)	0.86986 (10)	0.56431 (10)	0.0199 (2)
C11	0.14263 (15)	0.75378 (10)	0.56113 (10)	0.0223 (2)
H11A	0.0896	0.7018	0.6320	0.027*
C12	0.17005 (15)	0.71606 (11)	0.45458 (10)	0.0239 (2)
H12A	0.1349	0.6392	0.4541	0.029*
C13	0.25034 (14)	0.79245 (10)	0.34708 (10)	0.0213 (2)
C14	0.30205 (15)	0.90824 (11)	0.34783 (10)	0.0235 (2)
H14A	0.3550	0.9600	0.2767	0.028*
C15	0.27332 (15)	0.94525 (10)	0.45625 (10)	0.0232 (2)
H15A	0.3082	1.0222	0.4567	0.028*
C16	0.35636 (15)	0.81399 (11)	0.13354 (10)	0.0226 (2)
H16A	0.4699	0.8376	0.1415	0.027*
H16B	0.2734	0.8929	0.1006	0.027*
C17	0.39770 (15)	0.72005 (10)	0.05308 (10)	0.0225 (2)
H17A	0.2820	0.6985	0.0464	0.027*
H17B	0.4742	0.6400	0.0907	0.027*
C18	0.49635 (15)	0.77343 (11)	−0.07282 (10)	0.0227 (2)
H18A	0.6055	0.8039	−0.0667	0.027*
H18B	0.4144	0.8473	−0.1147	0.027*
C19	0.55427 (16)	0.66941 (11)	−0.14528 (10)	0.0243 (2)
H19A	0.6362	0.5961	−0.1027	0.029*
H19B	0.4446	0.6381	−0.1491	0.029*
C20	0.65178 (16)	0.71628 (12)	−0.27296 (10)	0.0275 (2)
H20A	0.7597	0.7501	−0.2699	0.033*
H20B	0.5685	0.7871	−0.3171	0.033*
C21	0.7131 (2)	0.60782 (14)	−0.34014 (12)	0.0375 (3)
H21A	0.7817	0.6400	−0.4180	0.056*
H21B	0.6058	0.5795	−0.3500	0.056*
H21C	0.7904	0.5356	−0.2947	0.056*
H1O2	0.001 (3)	1.1676 (18)	1.0758 (18)	0.058 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0357 (4)	0.0204 (4)	0.0196 (4)	−0.0082 (3)	−0.0005 (3)	−0.0046 (3)
O2	0.0370 (4)	0.0201 (4)	0.0197 (4)	−0.0094 (3)	0.0018 (3)	−0.0052 (3)
O3	0.0294 (4)	0.0283 (4)	0.0181 (4)	−0.0101 (3)	0.0017 (3)	−0.0081 (3)
C1	0.0254 (5)	0.0209 (5)	0.0214 (5)	−0.0045 (4)	−0.0036 (4)	−0.0033 (4)
C2	0.0300 (5)	0.0200 (5)	0.0266 (6)	−0.0080 (4)	−0.0036 (4)	−0.0009 (4)
C3	0.0291 (5)	0.0180 (5)	0.0315 (6)	−0.0062 (4)	−0.0065 (4)	−0.0058 (4)
C4	0.0258 (5)	0.0209 (5)	0.0252 (6)	−0.0040 (4)	−0.0051 (4)	−0.0084 (4)
C5	0.0207 (5)	0.0183 (5)	0.0203 (5)	−0.0048 (4)	−0.0036 (4)	−0.0032 (4)
C6	0.0200 (4)	0.0173 (4)	0.0211 (5)	−0.0030 (4)	−0.0041 (4)	−0.0043 (4)
C7	0.0226 (5)	0.0164 (4)	0.0220 (5)	−0.0038 (4)	−0.0032 (4)	−0.0038 (4)
C8	0.0285 (5)	0.0184 (5)	0.0205 (5)	−0.0052 (4)	−0.0037 (4)	−0.0035 (4)
C9	0.0214 (5)	0.0184 (5)	0.0198 (5)	−0.0023 (4)	−0.0028 (4)	−0.0048 (4)
C10	0.0214 (5)	0.0179 (5)	0.0197 (5)	−0.0018 (4)	−0.0027 (4)	−0.0051 (4)
C11	0.0267 (5)	0.0193 (5)	0.0193 (5)	−0.0054 (4)	−0.0006 (4)	−0.0035 (4)
C12	0.0274 (5)	0.0218 (5)	0.0239 (6)	−0.0078 (4)	−0.0007 (4)	−0.0074 (4)
C13	0.0209 (5)	0.0234 (5)	0.0197 (5)	−0.0022 (4)	−0.0028 (4)	−0.0073 (4)
C14	0.0279 (5)	0.0222 (5)	0.0194 (5)	−0.0076 (4)	0.0000 (4)	−0.0036 (4)
C15	0.0276 (5)	0.0201 (5)	0.0220 (5)	−0.0073 (4)	−0.0013 (4)	−0.0051 (4)
C16	0.0236 (5)	0.0263 (5)	0.0168 (5)	−0.0056 (4)	−0.0002 (4)	−0.0047 (4)
C17	0.0227 (5)	0.0238 (5)	0.0205 (5)	−0.0028 (4)	−0.0022 (4)	−0.0064 (4)
C18	0.0241 (5)	0.0233 (5)	0.0198 (5)	−0.0029 (4)	−0.0039 (4)	−0.0044 (4)
C19	0.0287 (5)	0.0251 (5)	0.0192 (5)	−0.0080 (4)	−0.0010 (4)	−0.0052 (4)
C20	0.0303 (6)	0.0317 (6)	0.0202 (5)	−0.0099 (5)	−0.0004 (4)	−0.0049 (4)
C21	0.0431 (7)	0.0501 (8)	0.0255 (6)	−0.0195 (6)	0.0053 (5)	−0.0180 (6)

O1—C9	1.2382 (13)	C12—C13	1.3976 (15)
O2—C5	1.3534 (13)	C12—H12A	0.9300
O2—H1O2	0.94 (2)	C13—C14	1.3967 (15)
O3—C13	1.3477 (13)	C14—C15	1.3922 (15)
O3—C16	1.4416 (13)	C14—H14A	0.9300
C1—C2	1.3844 (15)	C15—H15A	0.9300
C1—C6	1.3978 (15)	C16—C17	1.5106 (15)
C1—H1A	0.9300	C16—H16A	0.9700
C2—C3	1.3891 (17)	C16—H16B	0.9700
C2—H2A	0.9300	C17—C18	1.5189 (16)
C3—C4	1.3856 (16)	C17—H17A	0.9700
C3—H3A	0.9300	C17—H17B	0.9700
C4—C5	1.3951 (14)	C18—C19	1.5263 (15)
C4—H4A	0.9300	C18—H18A	0.9700
C5—C6	1.4086 (15)	C18—H18B	0.9700
C6—C7	1.4587 (14)	C19—C20	1.5181 (16)
C7—C8	1.3424 (15)	C19—H19A	0.9700
C7—H7A	0.9300	C19—H19B	0.9700
C8—C9	1.4738 (14)	C20—C21	1.5247 (17)
C8—H8A	0.9300	C20—H20A	0.9700
C9—C10	1.4815 (15)	C20—H20B	0.9700
C10—C15	1.3953 (15)	C21—H21A	0.9600
C10—C11	1.4064 (14)	C21—H21B	0.9600
C11—C12	1.3763 (15)	C21—H21C	0.9600
C11—H11A	0.9300
C5—O2—H1O2	113.6 (11)	C15—C14—H14A	120.4
C13—O3—C16	119.91 (8)	C13—C14—H14A	120.4
C2—C1—C6	121.38 (11)	C14—C15—C10	121.74 (10)
C2—C1—H1A	119.3	C14—C15—H15A	119.1
C6—C1—H1A	119.3	C10—C15—H15A	119.1
C1—C2—C3	119.72 (10)	O3—C16—C17	105.61 (9)
C1—C2—H2A	120.1	O3—C16—H16A	110.6
C3—C2—H2A	120.1	C17—C16—H16A	110.6
C4—C3—C2	120.39 (10)	O3—C16—H16B	110.6
C4—C3—H3A	119.8	C17—C16—H16B	110.6
C2—C3—H3A	119.8	H16A—C16—H16B	108.7
C3—C4—C5	119.82 (10)	C16—C17—C18	113.53 (9)
C3—C4—H4A	120.1	C16—C17—H17A	108.9
C5—C4—H4A	120.1	C18—C17—H17A	108.9
O2—C5—C4	122.26 (10)	C16—C17—H17B	108.9
O2—C5—C6	117.18 (9)	C18—C17—H17B	108.9
C4—C5—C6	120.56 (10)	H17A—C17—H17B	107.7
C1—C6—C5	118.05 (9)	C17—C18—C19	111.28 (9)
C1—C6—C7	123.26 (10)	C17—C18—H18A	109.4
C5—C6—C7	118.68 (9)	C19—C18—H18A	109.4
C8—C7—C6	126.09 (10)	C17—C18—H18B	109.4
C8—C7—H7A	117.0	C19—C18—H18B	109.4
C6—C7—H7A	117.0	H18A—C18—H18B	108.0
C7—C8—C9	122.19 (10)	C20—C19—C18	114.28 (9)
C7—C8—H8A	118.9	C20—C19—H19A	108.7
C9—C8—H8A	118.9	C18—C19—H19A	108.7
O1—C9—C8	121.95 (10)	C20—C19—H19B	108.7
O1—C9—C10	119.27 (9)	C18—C19—H19B	108.7
C8—C9—C10	118.76 (9)	H19A—C19—H19B	107.6
C15—C10—C11	117.94 (10)	C19—C20—C21	112.35 (10)
C15—C10—C9	123.98 (9)	C19—C20—H20A	109.1
C11—C10—C9	118.07 (9)	C21—C20—H20A	109.1
C12—C11—C10	120.94 (10)	C19—C20—H20B	109.1
C12—C11—H11A	119.5	C21—C20—H20B	109.1
C10—C11—H11A	119.5	H20A—C20—H20B	107.9
C11—C12—C13	120.47 (10)	C20—C21—H21A	109.5
C11—C12—H12A	119.8	C20—C21—H21B	109.5
C13—C12—H12A	119.8	H21A—C21—H21B	109.5
O3—C13—C14	125.30 (10)	C20—C21—H21C	109.5
O3—C13—C12	115.01 (9)	H21A—C21—H21C	109.5
C14—C13—C12	119.69 (10)	H21B—C21—H21C	109.5
C15—C14—C13	119.22 (10)
C6—C1—C2—C3	−0.37 (17)	C8—C9—C10—C11	−171.57 (9)
C1—C2—C3—C4	1.75 (17)	C15—C10—C11—C12	−0.18 (16)
C2—C3—C4—C5	−0.56 (16)	C9—C10—C11—C12	179.21 (9)
C3—C4—C5—O2	177.95 (9)	C10—C11—C12—C13	0.31 (17)
C3—C4—C5—C6	−2.02 (16)	C16—O3—C13—C14	2.51 (16)
C2—C1—C6—C5	−2.13 (16)	C16—O3—C13—C12	−178.00 (9)
C2—C1—C6—C7	177.29 (10)	C11—C12—C13—O3	−179.89 (9)
O2—C5—C6—C1	−176.65 (9)	C11—C12—C13—C14	−0.37 (16)
C4—C5—C6—C1	3.32 (15)	O3—C13—C14—C15	179.78 (10)
O2—C5—C6—C7	3.90 (14)	C12—C13—C14—C15	0.31 (16)
C4—C5—C6—C7	−176.13 (9)	C13—C14—C15—C10	−0.19 (17)
C1—C6—C7—C8	−7.76 (17)	C11—C10—C15—C14	0.12 (16)
C5—C6—C7—C8	171.66 (10)	C9—C10—C15—C14	−179.23 (10)
C6—C7—C8—C9	−176.61 (9)	C13—O3—C16—C17	166.42 (9)
C7—C8—C9—O1	0.88 (17)	O3—C16—C17—C18	−178.07 (8)
C7—C8—C9—C10	179.45 (10)	C16—C17—C18—C19	173.51 (9)
O1—C9—C10—C15	−173.62 (10)	C17—C18—C19—C20	179.26 (9)
C8—C9—C10—C15	7.77 (15)	C18—C19—C20—C21	177.93 (10)
O1—C9—C10—C11	7.04 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O1i	0.94 (2)	1.78 (2)	2.6862 (15)	163.3 (19)
C7—H7A···O2i	0.93	2.37	3.2526 (18)	158
C16—H16A···Cg1ii	0.97	2.91	3.6117 (16)	130

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O1i	0.94 (2)	1.78 (2)	2.6862 (15)	163.3 (19)
C7—H7A⋯O2i	0.93	2.37	3.2526 (18)	158
C16—H16A⋯Cg1ii	0.97	2.91	3.6117 (16)	130

Symmetry codes: (i) ; (ii) .