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

In the title compound, C(22)H(18)O(3), an intra-molecular O-H⋯O hydrogen bond stabilizes the mol-ecular structure, forming an S(6) ring motif. The central benzene ring forms a dihedral angle of 64.74 (5)° with the phenyl ring and a dihedral angle of 5.58 (5)° with the terminal benzene ring. In the crystal, mol-ecules are linked into columns along the a axis via inter-molecular C-H⋯O hydrogen bonds. C-H⋯π inter-actions involving the centroid of the hy-droxy-substituted benzene ring further stabilize the crystal structure.

Related literature

For the background to chalcones, see: Awad et al. (1960 ▶); Coudert et al. (1988 ▶); Insuasty et al. (1992 ▶, 1997 ▶); Kolos et al. (1996 ▶); Samshuddin et al. (2010 ▶); Fun et al. (2010 ▶); Sarojini et al. (2006 ▶); Shettigar et al. (2010 ▶); Sharma et al. (1997 ▶); Ravishankar et al. (2003 ▶, 2005 ▶); Butcher et al. (2006 ▶); Narayana et al. (2007 ▶); Sarojini et al. (2007 ▶); Jasinski et al. (2011 ▶). For bond-length data, see: Allen et al. (1987 ▶). For 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

C22H18O3

M = 330.36

Monoclinic,

a = 6.6343 (1) Å

b = 35.7706 (5) Å

c = 8.1537 (1) Å

β = 121.879 (1)°

V = 1643.12 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 100 K

0.46 × 0.41 × 0.28 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.960, T max = 0.976

23662 measured reflections

5994 independent reflections

5154 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.126

S = 1.04

5994 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.47 e Å−3

Δρmin = −0.21 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 datablocks global, I. DOI: 10.1107/S160053681101614X/sj5129sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681101614X/sj5129Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681101614X/sj5129Isup3.cml

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

C22H18O3	F(000) = 696
Mr = 330.36	Dx = 1.335 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9442 reflections
a = 6.6343 (1) Å	θ = 3.0–32.7°
b = 35.7706 (5) Å	µ = 0.09 mm−1
c = 8.1537 (1) Å	T = 100 K
β = 121.879 (1)°	Block, yellow
V = 1643.12 (4) Å3	0.46 × 0.41 × 0.28 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	5994 independent reflections
Radiation source: fine-focus sealed tube	5154 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 32.7°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→9
Tmin = 0.960, Tmax = 0.976	k = −54→54
23662 measured reflections	l = −12→12

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) = 0.126	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0608P)2 + 0.6186P] where P = (Fo2 + 2Fc2)/3
5994 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.47 e Å−3
0 restraints	Δρmin = −0.21 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	0.22678 (13)	−0.12255 (2)	0.64011 (11)	0.01788 (14)
O2	1.16788 (13)	0.04531 (2)	0.73546 (11)	0.01926 (15)
O3	1.37772 (13)	0.10727 (2)	0.82954 (12)	0.01960 (15)
H1	1.3290	0.0824	0.7790	0.029*
C1	0.1804 (2)	−0.21718 (3)	0.69912 (16)	0.0233 (2)
H1A	0.3438	−0.2209	0.7668	0.028*
C2	0.0347 (3)	−0.24325 (3)	0.71398 (18)	0.0297 (3)
H2A	0.1013	−0.2641	0.7926	0.036*
C3	−0.2084 (2)	−0.23818 (3)	0.61239 (18)	0.0283 (2)
H3A	−0.3055	−0.2557	0.6219	0.034*
C4	−0.3076 (2)	−0.20672 (3)	0.49557 (17)	0.0238 (2)
H4A	−0.4713	−0.2033	0.4264	0.029*
C5	−0.16259 (19)	−0.18037 (3)	0.48208 (15)	0.01870 (18)
H5A	−0.2296	−0.1593	0.4053	0.022*
C6	0.08311 (18)	−0.18549 (3)	0.58347 (14)	0.01668 (17)
C7	0.24046 (18)	−0.15803 (3)	0.56323 (14)	0.01653 (17)
H7A	0.4030	−0.1670	0.6331	0.020*
H7B	0.1891	−0.1553	0.4282	0.020*
C8	0.37550 (16)	−0.09508 (3)	0.64855 (13)	0.01453 (16)
C9	0.53008 (17)	−0.09903 (3)	0.58253 (14)	0.01643 (17)
H9A	0.5357	−0.1213	0.5262	0.020*
C10	0.67596 (17)	−0.06915 (3)	0.60209 (14)	0.01585 (17)
H10A	0.7794	−0.0719	0.5585	0.019*
C11	0.67167 (16)	−0.03522 (3)	0.68526 (13)	0.01424 (16)
C12	0.51140 (17)	−0.03170 (3)	0.74868 (14)	0.01541 (17)
H12A	0.5032	−0.0093	0.8028	0.018*
C13	0.36650 (17)	−0.06120 (3)	0.73120 (14)	0.01546 (17)
H13A	0.2626	−0.0586	0.7744	0.019*
C14	0.83060 (17)	−0.00553 (3)	0.70116 (13)	0.01512 (17)
H14A	0.9183	−0.0100	0.6443	0.018*
C15	0.86482 (17)	0.02778 (3)	0.78915 (14)	0.01564 (17)
H15A	0.7793	0.0338	0.8463	0.019*
C16	1.03580 (16)	0.05459 (3)	0.79541 (13)	0.01431 (16)
C17	1.05437 (16)	0.09259 (3)	0.87343 (13)	0.01351 (16)
C18	0.90277 (17)	0.10566 (3)	0.93231 (14)	0.01700 (17)
H18A	0.7872	0.0898	0.9246	0.020*
C19	0.92093 (19)	0.14160 (3)	1.00144 (15)	0.02028 (19)
H19A	0.8178	0.1497	1.0388	0.024*
C20	1.09498 (19)	0.16556 (3)	1.01480 (15)	0.01988 (19)
H20A	1.1082	0.1897	1.0618	0.024*
C21	1.24825 (18)	0.15361 (3)	0.95848 (14)	0.01802 (18)
H21A	1.3642	0.1697	0.9682	0.022*
C22	1.22862 (16)	0.11736 (3)	0.88693 (13)	0.01474 (17)

	U11	U22	U33	U12	U13	U23
O1	0.0210 (3)	0.0121 (3)	0.0250 (4)	−0.0031 (2)	0.0152 (3)	−0.0037 (3)
O2	0.0199 (3)	0.0171 (3)	0.0267 (4)	−0.0001 (3)	0.0163 (3)	−0.0017 (3)
O3	0.0174 (3)	0.0188 (3)	0.0277 (4)	−0.0011 (3)	0.0154 (3)	−0.0008 (3)
C1	0.0310 (5)	0.0153 (4)	0.0192 (5)	0.0003 (4)	0.0103 (4)	0.0007 (3)
C2	0.0488 (7)	0.0159 (5)	0.0248 (5)	−0.0033 (5)	0.0197 (5)	0.0015 (4)
C3	0.0467 (7)	0.0181 (5)	0.0315 (6)	−0.0120 (5)	0.0284 (5)	−0.0067 (4)
C4	0.0291 (5)	0.0209 (5)	0.0293 (5)	−0.0068 (4)	0.0207 (5)	−0.0066 (4)
C5	0.0239 (5)	0.0151 (4)	0.0212 (4)	−0.0005 (3)	0.0148 (4)	−0.0015 (3)
C6	0.0233 (4)	0.0123 (4)	0.0156 (4)	−0.0013 (3)	0.0110 (3)	−0.0024 (3)
C7	0.0195 (4)	0.0131 (4)	0.0177 (4)	0.0000 (3)	0.0103 (3)	−0.0017 (3)
C8	0.0145 (4)	0.0131 (4)	0.0155 (4)	−0.0004 (3)	0.0076 (3)	−0.0002 (3)
C9	0.0179 (4)	0.0145 (4)	0.0181 (4)	−0.0010 (3)	0.0104 (3)	−0.0028 (3)
C10	0.0167 (4)	0.0157 (4)	0.0165 (4)	−0.0002 (3)	0.0098 (3)	−0.0009 (3)
C11	0.0145 (4)	0.0133 (4)	0.0140 (4)	0.0004 (3)	0.0069 (3)	0.0009 (3)
C12	0.0168 (4)	0.0121 (4)	0.0171 (4)	0.0007 (3)	0.0089 (3)	0.0001 (3)
C13	0.0167 (4)	0.0139 (4)	0.0179 (4)	0.0010 (3)	0.0105 (3)	−0.0001 (3)
C14	0.0147 (4)	0.0146 (4)	0.0153 (4)	0.0006 (3)	0.0074 (3)	0.0018 (3)
C15	0.0163 (4)	0.0153 (4)	0.0169 (4)	−0.0005 (3)	0.0098 (3)	0.0005 (3)
C16	0.0140 (4)	0.0141 (4)	0.0146 (4)	0.0005 (3)	0.0074 (3)	0.0010 (3)
C17	0.0129 (4)	0.0134 (4)	0.0146 (4)	0.0005 (3)	0.0075 (3)	0.0003 (3)
C18	0.0166 (4)	0.0177 (4)	0.0193 (4)	0.0002 (3)	0.0113 (3)	−0.0008 (3)
C19	0.0217 (5)	0.0207 (5)	0.0215 (5)	0.0022 (4)	0.0136 (4)	−0.0025 (3)
C20	0.0237 (5)	0.0169 (4)	0.0169 (4)	0.0007 (3)	0.0093 (4)	−0.0022 (3)
C21	0.0184 (4)	0.0157 (4)	0.0178 (4)	−0.0034 (3)	0.0080 (3)	−0.0017 (3)
C22	0.0130 (4)	0.0162 (4)	0.0146 (4)	0.0004 (3)	0.0070 (3)	0.0011 (3)

O1—C8	1.3683 (11)	C10—C11	1.3978 (13)
O1—C7	1.4395 (12)	C10—H10A	0.9300
O2—C16	1.2528 (11)	C11—C12	1.4123 (13)
O3—C22	1.3477 (11)	C11—C14	1.4535 (13)
O3—H1	0.9618	C12—C13	1.3833 (13)
C1—C2	1.3942 (17)	C12—H12A	0.9300
C1—C6	1.3956 (14)	C13—H13A	0.9300
C1—H1A	0.9300	C14—C15	1.3467 (13)
C2—C3	1.382 (2)	C14—H14A	0.9300
C2—H2A	0.9300	C15—C16	1.4656 (13)
C3—C4	1.3946 (17)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.4780 (13)
C4—C5	1.3924 (14)	C17—C18	1.4038 (13)
C4—H4A	0.9300	C17—C22	1.4139 (13)
C5—C6	1.3966 (15)	C18—C19	1.3833 (14)
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.5044 (14)	C19—C20	1.3952 (15)
C7—H7A	0.9700	C19—H19A	0.9300
C7—H7B	0.9700	C20—C21	1.3860 (15)
C8—C9	1.3945 (13)	C20—H20A	0.9300
C8—C13	1.4031 (13)	C21—C22	1.3996 (14)
C9—C10	1.3933 (13)	C21—H21A	0.9300
C9—H9A	0.9300
C8—O1—C7	116.46 (7)	C10—C11—C14	118.56 (8)
C22—O3—H1	104.7	C12—C11—C14	123.57 (8)
C2—C1—C6	120.49 (11)	C13—C12—C11	120.71 (9)
C2—C1—H1A	119.8	C13—C12—H12A	119.6
C6—C1—H1A	119.8	C11—C12—H12A	119.6
C3—C2—C1	120.24 (11)	C12—C13—C8	120.33 (9)
C3—C2—H2A	119.9	C12—C13—H13A	119.8
C1—C2—H2A	119.9	C8—C13—H13A	119.8
C2—C3—C4	119.74 (11)	C15—C14—C11	127.18 (9)
C2—C3—H3A	120.1	C15—C14—H14A	116.4
C4—C3—H3A	120.1	C11—C14—H14A	116.4
C5—C4—C3	120.24 (11)	C14—C15—C16	120.47 (9)
C5—C4—H4A	119.9	C14—C15—H15A	119.8
C3—C4—H4A	119.9	C16—C15—H15A	119.8
C4—C5—C6	120.25 (10)	O2—C16—C15	120.07 (9)
C4—C5—H5A	119.9	O2—C16—C17	119.68 (8)
C6—C5—H5A	119.9	C15—C16—C17	120.26 (8)
C1—C6—C5	119.03 (10)	C18—C17—C22	117.95 (9)
C1—C6—C7	120.27 (9)	C18—C17—C16	122.79 (8)
C5—C6—C7	120.66 (9)	C22—C17—C16	119.25 (8)
O1—C7—C6	108.71 (8)	C19—C18—C17	121.67 (9)
O1—C7—H7A	109.9	C19—C18—H18A	119.2
C6—C7—H7A	109.9	C17—C18—H18A	119.2
O1—C7—H7B	109.9	C18—C19—C20	119.54 (9)
C6—C7—H7B	109.9	C18—C19—H19A	120.2
H7A—C7—H7B	108.3	C20—C19—H19A	120.2
O1—C8—C9	124.44 (8)	C21—C20—C19	120.43 (9)
O1—C8—C13	115.60 (8)	C21—C20—H20A	119.8
C9—C8—C13	119.96 (9)	C19—C20—H20A	119.8
C10—C9—C8	119.09 (9)	C20—C21—C22	120.05 (9)
C10—C9—H9A	120.5	C20—C21—H21A	120.0
C8—C9—H9A	120.5	C22—C21—H21A	120.0
C9—C10—C11	122.04 (9)	O3—C22—C21	117.97 (9)
C9—C10—H10A	119.0	O3—C22—C17	121.68 (9)
C11—C10—H10A	119.0	C21—C22—C17	120.35 (9)
C10—C11—C12	117.87 (8)
C6—C1—C2—C3	0.73 (17)	C9—C8—C13—C12	−0.39 (14)
C1—C2—C3—C4	−0.38 (17)	C10—C11—C14—C15	−174.62 (9)
C2—C3—C4—C5	−0.40 (17)	C12—C11—C14—C15	5.66 (15)
C3—C4—C5—C6	0.83 (16)	C11—C14—C15—C16	178.92 (9)
C2—C1—C6—C5	−0.30 (15)	C14—C15—C16—O2	−6.92 (14)
C2—C1—C6—C7	−178.15 (10)	C14—C15—C16—C17	173.44 (9)
C4—C5—C6—C1	−0.47 (15)	O2—C16—C17—C18	176.07 (9)
C4—C5—C6—C7	177.37 (9)	C15—C16—C17—C18	−4.29 (14)
C8—O1—C7—C6	174.51 (8)	O2—C16—C17—C22	−2.76 (13)
C1—C6—C7—O1	−117.15 (10)	C15—C16—C17—C22	176.88 (8)
C5—C6—C7—O1	65.04 (11)	C22—C17—C18—C19	0.09 (14)
C7—O1—C8—C9	2.20 (13)	C16—C17—C18—C19	−178.75 (9)
C7—O1—C8—C13	−177.49 (8)	C17—C18—C19—C20	−0.48 (15)
O1—C8—C9—C10	−178.92 (9)	C18—C19—C20—C21	0.32 (16)
C13—C8—C9—C10	0.75 (14)	C19—C20—C21—C22	0.24 (15)
C8—C9—C10—C11	−0.25 (15)	C20—C21—C22—O3	178.42 (9)
C9—C10—C11—C12	−0.60 (14)	C20—C21—C22—C17	−0.64 (14)
C9—C10—C11—C14	179.67 (9)	C18—C17—C22—O3	−178.55 (9)
C10—C11—C12—C13	0.97 (14)	C16—C17—C22—O3	0.33 (14)
C14—C11—C12—C13	−179.32 (9)	C18—C17—C22—C21	0.47 (14)
C11—C12—C13—C8	−0.49 (14)	C16—C17—C22—C21	179.36 (8)
O1—C8—C13—C12	179.31 (8)

Cg is the centroid of the C17–C22 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
O3—H1···O2	0.96	1.62	2.5121 (11)	152
C5—H5A···O3i	0.93	2.47	3.3912 (13)	170
C18—H18A···O3ii	0.93	2.48	3.1235 (16)	127
C7—H7B···Cg1i	0.97	2.75	3.6633 (11)	158

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H1⋯O2	0.96	1.62	2.5121 (11)	152
C5—H5A⋯O3i	0.93	2.47	3.3912 (13)	170
C18—H18A⋯O3ii	0.93	2.48	3.1235 (16)	127
C7—H7B⋯Cg1i	0.97	2.75	3.6633 (11)	158

Symmetry codes: (i) ; (ii) .