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

In the title compound, C(21)H(24)O(3), inter-molecular O-H⋯O and C-H⋯O inter-actions form bifurcated acceptor bonds, generating R(2) (1)(6) ring motifs. These ring motifs link the mol-ecules into extended chains along [010]. The crystal structure is further stabilized by C-H⋯π inter-actions.

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 et al. (2009 ▶, 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 ▶). For bond-length data, see: Allen et al. (1987) ▶.

Experimental

Crystal data

C21H24O3

M = 324.40

Monoclinic,

a = 10.2807 (2) Å

b = 16.6322 (2) Å

c = 11.4736 (2) Å

β = 113.439 (1)°

V = 1799.99 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.53 × 0.46 × 0.09 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.960, T max = 0.993

35735 measured reflections

5839 independent reflections

4743 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.135

S = 1.03

5839 reflections

219 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.20 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/S1600536810052086/fj2369sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810052086/fj2369Isup2.hkl

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

C21H24O3	F(000) = 696
Mr = 324.40	Dx = 1.197 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9960 reflections
a = 10.2807 (2) Å	θ = 2.3–31.1°
b = 16.6322 (2) Å	µ = 0.08 mm−1
c = 11.4736 (2) Å	T = 100 K
β = 113.439 (1)°	Plate, yellow
V = 1799.99 (5) Å3	0.53 × 0.46 × 0.09 mm
Z = 4

Bruker APEXII CCD area-detector diffractometer	5839 independent reflections
Radiation source: sealed tube	4743 reflections with I > 2σ(I)
graphite	Rint = 0.034
π and ω scans	θmax = 31.3°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −15→14
Tmin = 0.960, Tmax = 0.993	k = −24→24
35735 measured reflections	l = −16→16

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.135	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0702P)2 + 0.4086P] where P = (Fo2 + 2Fc2)/3
5839 reflections	(Δ/σ)max = 0.001
219 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.20 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	0.15448 (9)	0.50631 (5)	0.96314 (7)	0.02611 (17)
O2	−0.08883 (8)	0.02224 (4)	0.78756 (7)	0.02446 (16)
H2	−0.1115	0.0146	0.7095	0.037*
O3	0.37607 (9)	0.61122 (5)	1.53438 (7)	0.02772 (18)
C1	0.03955 (11)	0.20205 (6)	0.97710 (9)	0.0226 (2)
H1A	0.0805	0.2163	1.0645	0.027*
C2	0.00156 (11)	0.12297 (6)	0.94356 (9)	0.0231 (2)
H2A	0.0155	0.0836	1.0074	0.028*
C3	−0.05759 (10)	0.10104 (6)	0.81509 (9)	0.02014 (19)
C4	−0.08238 (10)	0.15987 (6)	0.72177 (9)	0.02078 (19)
H4A	−0.1251	0.1457	0.6344	0.025*
C5	−0.04439 (11)	0.23904 (6)	0.75716 (9)	0.02089 (19)
H5A	−0.0618	0.2787	0.6931	0.025*
C6	0.01911 (10)	0.26189 (6)	0.88518 (9)	0.01983 (18)
C7	0.06282 (10)	0.34531 (6)	0.91739 (9)	0.02114 (19)
H7A	0.0432	0.3814	0.8483	0.025*
C8	0.12779 (10)	0.37647 (6)	1.03444 (9)	0.02112 (19)
H8A	0.1482	0.3426	1.1062	0.025*
C9	0.16801 (10)	0.46172 (6)	1.05398 (9)	0.01995 (18)
C10	0.22628 (10)	0.49587 (6)	1.18407 (9)	0.01980 (19)
C11	0.24298 (10)	0.45194 (6)	1.29304 (9)	0.02125 (19)
H11A	0.2192	0.3964	1.2853	0.025*
C12	0.29373 (11)	0.48771 (6)	1.41261 (10)	0.0228 (2)
H12A	0.3043	0.4570	1.4856	0.027*
C13	0.32897 (11)	0.56930 (6)	1.42408 (10)	0.0227 (2)
C14	0.31631 (11)	0.61369 (6)	1.31623 (10)	0.0256 (2)
H14A	0.3432	0.6687	1.3244	0.031*
C15	0.26496 (11)	0.57768 (6)	1.19849 (10)	0.0239 (2)
H15A	0.2555	0.6085	1.1258	0.029*
C16	0.38894 (11)	0.57030 (7)	1.64912 (10)	0.0251 (2)
H16A	0.4594	0.5263	1.6688	0.030*
H16B	0.2966	0.5472	1.6399	0.030*
C17	0.43689 (12)	0.63306 (7)	1.75310 (10)	0.0281 (2)
H17A	0.3622	0.6745	1.7340	0.034*
H17B	0.5234	0.6597	1.7539	0.034*
C18	0.46809 (12)	0.59804 (7)	1.88375 (10)	0.0269 (2)
H18A	0.5392	0.5546	1.9007	0.032*
H18B	0.3803	0.5737	1.8838	0.032*
C19	0.52330 (13)	0.65975 (7)	1.99042 (11)	0.0298 (2)
H19A	0.4449	0.6959	1.9856	0.036*
H19B	0.5975	0.6928	1.9792	0.036*
C20	0.58473 (13)	0.61976 (7)	2.12078 (11)	0.0321 (2)
H20A	0.5103	0.5862	2.1308	0.038*
H20B	0.6628	0.5836	2.1247	0.038*
C21	0.64050 (18)	0.67832 (10)	2.23034 (13)	0.0502 (4)
H21A	0.6852	0.6485	2.3102	0.075*
H21B	0.5619	0.7105	2.2330	0.075*
H21C	0.7105	0.7139	2.2189	0.075*

	U11	U22	U33	U12	U13	U23
O1	0.0332 (4)	0.0223 (3)	0.0210 (4)	0.0006 (3)	0.0089 (3)	0.0028 (3)
O2	0.0315 (4)	0.0194 (3)	0.0214 (4)	−0.0027 (3)	0.0093 (3)	−0.0019 (3)
O3	0.0343 (4)	0.0242 (4)	0.0233 (4)	−0.0042 (3)	0.0100 (3)	−0.0070 (3)
C1	0.0279 (5)	0.0224 (4)	0.0164 (4)	−0.0004 (4)	0.0076 (4)	−0.0011 (3)
C2	0.0293 (5)	0.0217 (4)	0.0179 (4)	0.0000 (4)	0.0091 (4)	0.0016 (3)
C3	0.0213 (4)	0.0196 (4)	0.0199 (4)	−0.0004 (3)	0.0086 (4)	−0.0015 (3)
C4	0.0230 (4)	0.0220 (4)	0.0167 (4)	0.0003 (4)	0.0073 (4)	−0.0018 (3)
C5	0.0243 (4)	0.0214 (4)	0.0164 (4)	0.0012 (4)	0.0075 (4)	0.0011 (3)
C6	0.0220 (4)	0.0200 (4)	0.0177 (4)	0.0002 (3)	0.0081 (3)	−0.0011 (3)
C7	0.0225 (4)	0.0205 (4)	0.0202 (4)	0.0008 (3)	0.0083 (4)	0.0004 (3)
C8	0.0233 (4)	0.0191 (4)	0.0201 (4)	0.0002 (3)	0.0076 (4)	0.0002 (3)
C9	0.0185 (4)	0.0201 (4)	0.0201 (4)	0.0016 (3)	0.0064 (3)	−0.0002 (3)
C10	0.0179 (4)	0.0193 (4)	0.0205 (4)	0.0007 (3)	0.0058 (3)	−0.0008 (3)
C11	0.0214 (4)	0.0202 (4)	0.0213 (5)	−0.0028 (3)	0.0077 (4)	−0.0016 (3)
C12	0.0229 (4)	0.0239 (5)	0.0207 (5)	−0.0029 (4)	0.0078 (4)	−0.0017 (4)
C13	0.0209 (4)	0.0231 (5)	0.0226 (5)	−0.0015 (4)	0.0071 (4)	−0.0049 (4)
C14	0.0283 (5)	0.0183 (4)	0.0274 (5)	−0.0006 (4)	0.0082 (4)	−0.0025 (4)
C15	0.0265 (5)	0.0197 (4)	0.0234 (5)	0.0011 (4)	0.0076 (4)	0.0015 (4)
C16	0.0247 (5)	0.0269 (5)	0.0234 (5)	−0.0025 (4)	0.0093 (4)	−0.0054 (4)
C17	0.0294 (5)	0.0276 (5)	0.0256 (5)	−0.0027 (4)	0.0091 (4)	−0.0088 (4)
C18	0.0260 (5)	0.0267 (5)	0.0257 (5)	−0.0008 (4)	0.0077 (4)	−0.0071 (4)
C19	0.0310 (5)	0.0274 (5)	0.0271 (5)	0.0000 (4)	0.0074 (4)	−0.0078 (4)
C20	0.0324 (6)	0.0314 (6)	0.0295 (6)	0.0017 (5)	0.0093 (5)	−0.0061 (4)
C21	0.0633 (10)	0.0464 (8)	0.0306 (7)	−0.0042 (7)	0.0078 (6)	−0.0100 (6)

O1—C9	1.2410 (12)	C12—C13	1.3971 (14)
O2—C3	1.3563 (12)	C12—H12A	0.9500
O2—H2	0.8400	C13—C14	1.4018 (15)
O3—C13	1.3545 (12)	C14—C15	1.3766 (15)
O3—C16	1.4406 (13)	C14—H14A	0.9500
C1—C2	1.3824 (14)	C15—H15A	0.9500
C1—C6	1.4039 (14)	C16—C17	1.5127 (14)
C1—H1A	0.9500	C16—H16A	0.9900
C2—C3	1.4009 (14)	C16—H16B	0.9900
C2—H2A	0.9500	C17—C18	1.5187 (16)
C3—C4	1.3971 (13)	C17—H17A	0.9900
C4—C5	1.3874 (14)	C17—H17B	0.9900
C4—H4A	0.9500	C18—C19	1.5235 (15)
C5—C6	1.4019 (13)	C18—H18A	0.9900
C5—H5A	0.9500	C18—H18B	0.9900
C6—C7	1.4598 (14)	C19—C20	1.5253 (17)
C7—C8	1.3435 (14)	C19—H19A	0.9900
C7—H7A	0.9500	C19—H19B	0.9900
C8—C9	1.4690 (13)	C20—C21	1.5113 (18)
C8—H8A	0.9500	C20—H20A	0.9900
C9—C10	1.4826 (14)	C20—H20B	0.9900
C10—C11	1.3985 (14)	C21—H21A	0.9800
C10—C15	1.4088 (14)	C21—H21B	0.9800
C11—C12	1.3925 (14)	C21—H21C	0.9800
C11—H11A	0.9500
C3—O2—H2	109.5	C15—C14—H14A	119.9
C13—O3—C16	118.65 (8)	C13—C14—H14A	119.9
C2—C1—C6	121.61 (9)	C14—C15—C10	121.04 (10)
C2—C1—H1A	119.2	C14—C15—H15A	119.5
C6—C1—H1A	119.2	C10—C15—H15A	119.5
C1—C2—C3	119.80 (9)	O3—C16—C17	106.11 (9)
C1—C2—H2A	120.1	O3—C16—H16A	110.5
C3—C2—H2A	120.1	C17—C16—H16A	110.5
O2—C3—C4	122.97 (9)	O3—C16—H16B	110.5
O2—C3—C2	117.40 (9)	C17—C16—H16B	110.5
C4—C3—C2	119.64 (9)	H16A—C16—H16B	108.7
C5—C4—C3	119.74 (9)	C16—C17—C18	112.85 (9)
C5—C4—H4A	120.1	C16—C17—H17A	109.0
C3—C4—H4A	120.1	C18—C17—H17A	109.0
C4—C5—C6	121.57 (9)	C16—C17—H17B	109.0
C4—C5—H5A	119.2	C18—C17—H17B	109.0
C6—C5—H5A	119.2	H17A—C17—H17B	107.8
C5—C6—C1	117.59 (9)	C17—C18—C19	113.55 (9)
C5—C6—C7	119.41 (9)	C17—C18—H18A	108.9
C1—C6—C7	122.99 (9)	C19—C18—H18A	108.9
C8—C7—C6	126.90 (9)	C17—C18—H18B	108.9
C8—C7—H7A	116.6	C19—C18—H18B	108.9
C6—C7—H7A	116.6	H18A—C18—H18B	107.7
C7—C8—C9	121.52 (9)	C18—C19—C20	111.76 (10)
C7—C8—H8A	119.2	C18—C19—H19A	109.3
C9—C8—H8A	119.2	C20—C19—H19A	109.3
O1—C9—C8	121.19 (9)	C18—C19—H19B	109.3
O1—C9—C10	118.82 (9)	C20—C19—H19B	109.3
C8—C9—C10	119.99 (9)	H19A—C19—H19B	107.9
C11—C10—C15	118.10 (9)	C21—C20—C19	114.00 (11)
C11—C10—C9	123.83 (9)	C21—C20—H20A	108.8
C15—C10—C9	118.06 (9)	C19—C20—H20A	108.8
C12—C11—C10	121.48 (9)	C21—C20—H20B	108.8
C12—C11—H11A	119.3	C19—C20—H20B	108.8
C10—C11—H11A	119.3	H20A—C20—H20B	107.6
C11—C12—C13	119.29 (10)	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	124.81 (10)	C20—C21—H21C	109.5
O3—C13—C14	115.26 (9)	H21A—C21—H21C	109.5
C12—C13—C14	119.93 (9)	H21B—C21—H21C	109.5
C15—C14—C13	120.12 (10)
C6—C1—C2—C3	0.63 (16)	C8—C9—C10—C15	179.28 (9)
C1—C2—C3—O2	177.98 (9)	C15—C10—C11—C12	1.21 (15)
C1—C2—C3—C4	−2.28 (15)	C9—C10—C11—C12	−177.74 (9)
O2—C3—C4—C5	−178.39 (9)	C10—C11—C12—C13	−0.09 (15)
C2—C3—C4—C5	1.89 (15)	C16—O3—C13—C12	−1.30 (15)
C3—C4—C5—C6	0.16 (15)	C16—O3—C13—C14	178.63 (9)
C4—C5—C6—C1	−1.76 (15)	C11—C12—C13—O3	178.38 (9)
C4—C5—C6—C7	177.29 (9)	C11—C12—C13—C14	−1.55 (15)
C2—C1—C6—C5	1.36 (15)	O3—C13—C14—C15	−177.87 (9)
C2—C1—C6—C7	−177.65 (10)	C12—C13—C14—C15	2.07 (16)
C5—C6—C7—C8	−178.26 (10)	C13—C14—C15—C10	−0.93 (16)
C1—C6—C7—C8	0.73 (16)	C11—C10—C15—C14	−0.70 (15)
C6—C7—C8—C9	179.19 (9)	C9—C10—C15—C14	178.32 (9)
C7—C8—C9—O1	−6.32 (15)	C13—O3—C16—C17	−177.53 (9)
C7—C8—C9—C10	173.83 (9)	O3—C16—C17—C18	−175.01 (9)
O1—C9—C10—C11	178.37 (9)	C16—C17—C18—C19	177.23 (9)
C8—C9—C10—C11	−1.77 (14)	C17—C18—C19—C20	−166.95 (10)
O1—C9—C10—C15	−0.58 (14)	C18—C19—C20—C21	−179.71 (11)

Cg2 is the centroid of C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1i	0.84	1.86	2.694 (1)	175
C4—H4A···O1i	0.95	2.54	3.213 (1)	128
C16—H16A···Cg2ii	0.99	2.77	3.666 (1)	151

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1i	0.84	1.86	2.694 (1)	175
C4—H4A⋯O1i	0.95	2.54	3.213 (1)	128
C16—H16A⋯Cg2ii	0.99	2.77	3.666 (1)	151

Symmetry codes: (i) ; (ii) .