(2E)-3-(3-Benzyl-oxyphen-yl)-1-(2-hydroxy-5-methyl-phen-yl)prop-2-en-1-one.

In the mol-ecule of the title compound, C(23)H(20)O(3), an intra-molecular O-H⋯O hydrogen bond generates an S(6) ring. The central benzene ring makes dihedral angles of 80.17 (8) and 16.99 (7)°, respectively, with the benz-yloxy and hy-droxy-methyl phenyl rings. In the crystal, mol-ecules are linked via inter-molecular C-H⋯O hydrogen bonds to form dimers. The dimers are connected by C-H⋯O hydrogen bonds and C-H⋯π inter-actions to form columns down the b axis.

Related literature

For general background and applications of chalcones, see: Awad et al. (1960 ▶); Coudert et al. (1988 ▶); Insuasty et al. (1992 ▶, 1997 ▶); Kolos et al. (1996 ▶); Sarojini et al. (2006 ▶); Shettigar et al. (2010 ▶); Samshuddin et al. (2010 ▶); Fun et al. (2010 ▶). For related structures, see: Butcher et al. (2006 ▶); Ravishankar et al. (2003 ▶, 2005 ▶); Narayana et al. (2007 ▶); Sarojini, Narayana et al. (2007 ▶); Sarojini, Yathirajan et al. (2007 ▶); Sharma et al. (1997 ▶); Jasinski et al. (2011 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C23H20O3

M = 344.39

Triclinic,

a = 8.7308 (5) Å

b = 9.5721 (5) Å

c = 11.5286 (6) Å

α = 106.547 (1)°

β = 94.572 (1)°

γ = 101.671 (1)°

V = 894.74 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.08 mm−1

T = 296 K

0.42 × 0.37 × 0.28 mm

Data collection

Bruker SMART APEXII DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.966, T max = 0.977

18270 measured reflections

5238 independent reflections

3853 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.163

S = 1.03

5238 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 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 datablocks global, I. DOI: 10.1107/S1600536811016977/ci5187sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016977/ci5187Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016977/ci5187Isup3.cml

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

C23H20O3	Z = 2
Mr = 344.39	F(000) = 364
Triclinic, P1	Dx = 1.278 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.7308 (5) Å	Cell parameters from 5803 reflections
b = 9.5721 (5) Å	θ = 2.8–30.0°
c = 11.5286 (6) Å	µ = 0.08 mm−1
α = 106.547 (1)°	T = 296 K
β = 94.572 (1)°	Block, orange
γ = 101.671 (1)°	0.42 × 0.37 × 0.28 mm
V = 894.74 (8) Å3

Bruker SMART APEXII DUO CCD area-detector diffractometer	5238 independent reflections
Radiation source: fine-focus sealed tube	3853 reflections with I > 2σ(I)
graphite	Rint = 0.020
φ and ω scans	θmax = 30.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −12→12
Tmin = 0.966, Tmax = 0.977	k = −13→13
18270 measured reflections	l = −15→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0847P)2 + 0.1176P] where P = (Fo2 + 2Fc2)/3
5238 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.16772 (13)	0.30000 (11)	−0.13861 (10)	0.0679 (3)
O2	0.43323 (13)	−0.41373 (11)	0.37191 (11)	0.0644 (3)
O3	0.37319 (15)	−0.32210 (11)	0.19276 (10)	0.0681 (3)
C1	0.66751 (15)	−0.03177 (14)	0.42278 (11)	0.0459 (3)
H1A	0.6795	0.0439	0.3861	0.055*
C2	0.76064 (15)	−0.00671 (14)	0.53313 (11)	0.0485 (3)
C3	0.73915 (17)	−0.12245 (17)	0.58579 (13)	0.0552 (3)
H3A	0.8003	−0.1083	0.6599	0.066*
C4	0.63119 (17)	−0.25623 (16)	0.53216 (13)	0.0561 (3)
H4A	0.6195	−0.3308	0.5700	0.067*
C5	0.53927 (15)	−0.28026 (14)	0.42114 (12)	0.0475 (3)
C6	0.55590 (14)	−0.16674 (13)	0.36425 (10)	0.0428 (2)
C7	0.45402 (16)	−0.19356 (14)	0.24783 (11)	0.0475 (3)
C8	0.44225 (16)	−0.07006 (14)	0.19893 (11)	0.0484 (3)
H8A	0.5083	0.0245	0.2364	0.058*
C9	0.33780 (17)	−0.09225 (15)	0.10131 (12)	0.0526 (3)
H9A	0.2805	−0.1906	0.0646	0.063*
C10	0.30100 (16)	0.01655 (14)	0.04420 (11)	0.0490 (3)
C11	0.1932 (2)	−0.03475 (16)	−0.06343 (15)	0.0703 (5)
H11A	0.1479	−0.1369	−0.0963	0.084*
C12	0.1525 (2)	0.06119 (17)	−0.12187 (15)	0.0732 (5)
H12A	0.0811	0.0237	−0.1939	0.088*
C13	0.21741 (16)	0.21433 (14)	−0.07401 (12)	0.0511 (3)
C14	0.32657 (17)	0.26857 (15)	0.03205 (12)	0.0536 (3)
H14A	0.3720	0.3708	0.0644	0.064*
C15	0.36739 (17)	0.16958 (15)	0.08932 (12)	0.0537 (3)
H15A	0.4413	0.2066	0.1600	0.064*
C16	0.24447 (19)	0.45417 (15)	−0.10512 (15)	0.0644 (4)
H16A	0.3565	0.4657	−0.1101	0.077*
H16B	0.2321	0.5047	−0.0218	0.077*
C17	0.17020 (16)	0.52033 (13)	−0.19193 (13)	0.0526 (3)
C18	0.01997 (18)	0.54490 (19)	−0.18521 (17)	0.0677 (4)
H18A	−0.0364	0.5200	−0.1259	0.081*
C19	−0.04746 (19)	0.60627 (19)	−0.26593 (18)	0.0711 (4)
H19A	−0.1485	0.6225	−0.2604	0.085*
C20	0.0337 (2)	0.64284 (18)	−0.35342 (15)	0.0685 (4)
H20A	−0.0119	0.6837	−0.4077	0.082*
C21	0.1825 (2)	0.6194 (2)	−0.36131 (15)	0.0724 (4)
H21A	0.2380	0.6446	−0.4209	0.087*
C22	0.25088 (19)	0.55839 (17)	−0.28101 (14)	0.0615 (4)
H22A	0.3521	0.5429	−0.2871	0.074*
C23	0.87881 (19)	0.13954 (18)	0.59510 (15)	0.0658 (4)
H23A	0.8420	0.2194	0.5759	0.099*
H23B	0.9787	0.1346	0.5670	0.099*
H23C	0.8911	0.1579	0.6820	0.099*
H1O2	0.392 (3)	−0.406 (3)	0.298 (2)	0.110 (8)*

	U11	U22	U33	U12	U13	U23
O1	0.0792 (7)	0.0450 (5)	0.0711 (7)	0.0010 (5)	−0.0301 (5)	0.0254 (5)
O2	0.0715 (6)	0.0486 (5)	0.0734 (7)	0.0049 (4)	−0.0062 (5)	0.0304 (5)
O3	0.0917 (8)	0.0466 (5)	0.0566 (6)	0.0033 (5)	−0.0159 (5)	0.0173 (4)
C1	0.0530 (6)	0.0458 (6)	0.0430 (6)	0.0145 (5)	0.0042 (5)	0.0188 (5)
C2	0.0505 (6)	0.0519 (6)	0.0451 (6)	0.0164 (5)	0.0027 (5)	0.0162 (5)
C3	0.0606 (7)	0.0635 (8)	0.0473 (6)	0.0225 (6)	−0.0012 (5)	0.0232 (6)
C4	0.0668 (8)	0.0557 (7)	0.0561 (7)	0.0199 (6)	0.0032 (6)	0.0310 (6)
C5	0.0523 (6)	0.0452 (6)	0.0514 (6)	0.0162 (5)	0.0064 (5)	0.0217 (5)
C6	0.0498 (6)	0.0437 (6)	0.0397 (5)	0.0165 (5)	0.0050 (4)	0.0168 (4)
C7	0.0571 (7)	0.0454 (6)	0.0417 (6)	0.0137 (5)	0.0029 (5)	0.0162 (5)
C8	0.0589 (7)	0.0453 (6)	0.0431 (6)	0.0135 (5)	0.0012 (5)	0.0177 (5)
C9	0.0681 (8)	0.0453 (6)	0.0431 (6)	0.0117 (5)	−0.0031 (5)	0.0156 (5)
C10	0.0585 (7)	0.0458 (6)	0.0415 (6)	0.0108 (5)	−0.0038 (5)	0.0157 (5)
C11	0.0894 (11)	0.0432 (7)	0.0645 (9)	−0.0001 (7)	−0.0308 (8)	0.0175 (6)
C12	0.0889 (11)	0.0487 (7)	0.0666 (9)	−0.0018 (7)	−0.0384 (8)	0.0198 (7)
C13	0.0563 (7)	0.0444 (6)	0.0507 (7)	0.0082 (5)	−0.0092 (5)	0.0190 (5)
C14	0.0607 (7)	0.0423 (6)	0.0500 (7)	0.0045 (5)	−0.0112 (5)	0.0128 (5)
C15	0.0617 (7)	0.0495 (6)	0.0436 (6)	0.0075 (5)	−0.0129 (5)	0.0139 (5)
C16	0.0729 (9)	0.0446 (7)	0.0673 (9)	0.0019 (6)	−0.0206 (7)	0.0211 (6)
C17	0.0583 (7)	0.0372 (5)	0.0567 (7)	0.0047 (5)	−0.0095 (6)	0.0153 (5)
C18	0.0572 (8)	0.0691 (9)	0.0813 (10)	0.0046 (7)	0.0034 (7)	0.0390 (8)
C19	0.0524 (7)	0.0668 (9)	0.0942 (12)	0.0110 (7)	−0.0089 (7)	0.0323 (9)
C20	0.0812 (10)	0.0570 (8)	0.0655 (9)	0.0160 (7)	−0.0137 (8)	0.0229 (7)
C21	0.0939 (12)	0.0728 (10)	0.0581 (9)	0.0244 (9)	0.0113 (8)	0.0287 (8)
C22	0.0650 (8)	0.0560 (8)	0.0647 (8)	0.0207 (6)	0.0057 (7)	0.0172 (7)
C23	0.0657 (9)	0.0635 (8)	0.0607 (8)	0.0067 (7)	−0.0080 (7)	0.0178 (7)

O1—C13	1.3622 (14)	C11—H11A	0.93
O1—C16	1.4178 (16)	C12—C13	1.3884 (18)
O2—C5	1.3551 (16)	C12—H12A	0.93
O2—H1O2	0.93 (3)	C13—C14	1.3876 (17)
O3—C7	1.2439 (16)	C14—C15	1.3843 (18)
C1—C2	1.3854 (17)	C14—H14A	0.93
C1—C6	1.4011 (17)	C15—H15A	0.93
C1—H1A	0.93	C16—C17	1.4990 (19)
C2—C3	1.3958 (19)	C16—H16A	0.97
C2—C23	1.504 (2)	C16—H16B	0.97
C3—C4	1.371 (2)	C17—C22	1.381 (2)
C3—H3A	0.93	C17—C18	1.383 (2)
C4—C5	1.3889 (18)	C18—C19	1.386 (2)
C4—H4A	0.93	C18—H18A	0.93
C5—C6	1.4104 (16)	C19—C20	1.363 (3)
C6—C7	1.4764 (16)	C19—H19A	0.93
C7—C8	1.4647 (17)	C20—C21	1.368 (3)
C8—C9	1.3286 (17)	C20—H20A	0.93
C8—H8A	0.93	C21—C22	1.384 (2)
C9—C10	1.4538 (17)	C21—H21A	0.93
C9—H9A	0.93	C22—H22A	0.93
C10—C15	1.3880 (18)	C23—H23A	0.96
C10—C11	1.3950 (18)	C23—H23B	0.96
C11—C12	1.3674 (19)	C23—H23C	0.96
C13—O1—C16	118.66 (10)	O1—C13—C12	115.52 (11)
C5—O2—H1O2	102.3 (15)	C14—C13—C12	119.36 (12)
C2—C1—C6	122.54 (11)	C15—C14—C13	119.56 (12)
C2—C1—H1A	118.7	C15—C14—H14A	120.2
C6—C1—H1A	118.7	C13—C14—H14A	120.2
C1—C2—C3	117.23 (12)	C14—C15—C10	121.81 (11)
C1—C2—C23	121.74 (12)	C14—C15—H15A	119.1
C3—C2—C23	121.03 (12)	C10—C15—H15A	119.1
C4—C3—C2	122.34 (12)	O1—C16—C17	107.69 (11)
C4—C3—H3A	118.8	O1—C16—H16A	110.2
C2—C3—H3A	118.8	C17—C16—H16A	110.2
C3—C4—C5	119.85 (12)	O1—C16—H16B	110.2
C3—C4—H4A	120.1	C17—C16—H16B	110.2
C5—C4—H4A	120.1	H16A—C16—H16B	108.5
O2—C5—C4	117.85 (11)	C22—C17—C18	118.30 (13)
O2—C5—C6	122.05 (11)	C22—C17—C16	120.52 (14)
C4—C5—C6	120.09 (12)	C18—C17—C16	121.18 (14)
C1—C6—C5	117.95 (11)	C17—C18—C19	120.67 (15)
C1—C6—C7	122.97 (10)	C17—C18—H18A	119.7
C5—C6—C7	119.07 (11)	C19—C18—H18A	119.7
O3—C7—C8	119.66 (11)	C20—C19—C18	120.23 (15)
O3—C7—C6	119.36 (11)	C20—C19—H19A	119.9
C8—C7—C6	120.94 (11)	C18—C19—H19A	119.9
C9—C8—C7	120.42 (12)	C19—C20—C21	119.87 (14)
C9—C8—H8A	119.8	C19—C20—H20A	120.1
C7—C8—H8A	119.8	C21—C20—H20A	120.1
C8—C9—C10	128.73 (12)	C20—C21—C22	120.30 (16)
C8—C9—H9A	115.6	C20—C21—H21A	119.8
C10—C9—H9A	115.6	C22—C21—H21A	119.8
C15—C10—C11	117.27 (12)	C17—C22—C21	120.62 (15)
C15—C10—C9	124.19 (11)	C17—C22—H22A	119.7
C11—C10—C9	118.54 (12)	C21—C22—H22A	119.7
C12—C11—C10	121.74 (13)	C2—C23—H23A	109.5
C12—C11—H11A	119.1	C2—C23—H23B	109.5
C10—C11—H11A	119.1	H23A—C23—H23B	109.5
C11—C12—C13	120.24 (12)	C2—C23—H23C	109.5
C11—C12—H12A	119.9	H23A—C23—H23C	109.5
C13—C12—H12A	119.9	H23B—C23—H23C	109.5
O1—C13—C14	125.12 (11)
C6—C1—C2—C3	−0.22 (19)	C9—C10—C11—C12	179.73 (17)
C6—C1—C2—C23	−179.44 (13)	C10—C11—C12—C13	−0.6 (3)
C1—C2—C3—C4	0.0 (2)	C16—O1—C13—C14	7.7 (2)
C23—C2—C3—C4	179.26 (14)	C16—O1—C13—C12	−171.44 (16)
C2—C3—C4—C5	0.4 (2)	C11—C12—C13—O1	−179.34 (17)
C3—C4—C5—O2	−179.51 (12)	C11—C12—C13—C14	1.5 (3)
C3—C4—C5—C6	−0.6 (2)	O1—C13—C14—C15	−179.99 (14)
C2—C1—C6—C5	0.00 (18)	C12—C13—C14—C15	−0.9 (2)
C2—C1—C6—C7	178.84 (11)	C13—C14—C15—C10	−0.6 (2)
O2—C5—C6—C1	179.27 (11)	C11—C10—C15—C14	1.4 (2)
C4—C5—C6—C1	0.41 (19)	C9—C10—C15—C14	−179.16 (13)
O2—C5—C6—C7	0.39 (19)	C13—O1—C16—C17	178.62 (13)
C4—C5—C6—C7	−178.47 (11)	O1—C16—C17—C22	−107.22 (16)
C1—C6—C7—O3	170.34 (13)	O1—C16—C17—C18	72.78 (18)
C5—C6—C7—O3	−10.84 (19)	C22—C17—C18—C19	0.0 (2)
C1—C6—C7—C8	−12.05 (19)	C16—C17—C18—C19	179.95 (14)
C5—C6—C7—C8	166.77 (11)	C17—C18—C19—C20	0.2 (3)
O3—C7—C8—C9	4.9 (2)	C18—C19—C20—C21	−0.2 (3)
C6—C7—C8—C9	−172.75 (12)	C19—C20—C21—C22	0.1 (3)
C7—C8—C9—C10	175.62 (13)	C18—C17—C22—C21	0.0 (2)
C8—C9—C10—C15	−3.7 (2)	C16—C17—C22—C21	179.96 (14)
C8—C9—C10—C11	175.79 (16)	C20—C21—C22—C17	0.0 (2)
C15—C10—C11—C12	−0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H1O2···O3	0.93 (2)	1.65 (3)	2.521 (2)	155 (3)
C16—H16B···O3i	0.97	2.60	3.445 (2)	146
C22—H22A···O2ii	0.93	2.56	3.435 (2)	158
C11—H11A···Cg1iii	0.93	2.80	3.660 (2)	153

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H1O2⋯O3	0.93 (2)	1.65 (3)	2.521 (2)	155 (3)
C16—H16B⋯O3i	0.97	2.60	3.445 (2)	146
C22—H22A⋯O2ii	0.93	2.56	3.435 (2)	158
C11—H11A⋯Cg1iii	0.93	2.80	3.660 (2)	153

Symmetry codes: (i) ; (ii) ; (iii) .