(E)-1-(1-Hy-droxy-naphthalen-2-yl)-3-(2,4,5-trimeth-oxy-phen-yl)prop-2-en-1-one.

In the title mol-ecule, C22H20O5, the C=C bond of the central enone group adopts an E conformation. The dihedral angle formed by the benzene ring and the naphthalene ring system is 12.6 (4)°. The hy-droxy group attached to the naphthalene ring is involved in an intra-molecular O-H⋯O hydrogen bond. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into chains along [010]. In addition, π-π stacking inter-actions are present, with centroid-centroid distances of 3.6648 (15) and 3.8661 (15) Å between the benzene and two naphthalene rings.

Related literature

For the synthesis and biological properties of chalcone deriv­atives, see: Shenvi et al. (2013 ▶); Hsieh et al. (2012 ▶); Sharma et al. (2012 ▶); Sashidhara et al. (2011 ▶); Aponte et al. (2010 ▶); Hans et al. (2010 ▶) Jo et al. (2012 ▶). For related structures, see: Park et al. (2013 ▶); Fadzillah et al. (2012 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C22H20O5

M = 364.38

Monoclinic,

a = 9.7919 (12) Å

b = 13.7559 (18) Å

c = 13.2761 (17) Å

β = 96.165 (3)°

V = 1777.9 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 200 K

0.36 × 0.26 × 0.22 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.966, T max = 0.979

12937 measured reflections

4420 independent reflections

2550 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.053

wR(F 2) = 0.187

S = 1.10

4420 reflections

248 parameters

H-atom parameters constrained

Δρmax = 0.31 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006843/aa2085sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006843/aa2085Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006843/aa2085Isup3.cml

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

C22H20O5	F(000) = 768
Mr = 364.38	Dx = 1.361 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3912 reflections
a = 9.7919 (12) Å	θ = 2.5–28.2°
b = 13.7559 (18) Å	µ = 0.10 mm−1
c = 13.2761 (17) Å	T = 200 K
β = 96.165 (3)°	Block, red
V = 1777.9 (4) Å3	0.36 × 0.26 × 0.22 mm
Z = 4

Bruker SMART CCD diffractometer	4420 independent reflections
Radiation source: fine-focus sealed tube	2550 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.032
φ and ω scans	θmax = 28.3°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −13→12
Tmin = 0.966, Tmax = 0.979	k = −17→18
12937 measured reflections	l = −12→17

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.187	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0702P)2 + 1.1296P] where P = (Fo2 + 2Fc2)/3
4420 reflections	(Δ/σ)max < 0.001
248 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.40 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
C1	0.3412 (2)	0.91056 (17)	0.00657 (18)	0.0317 (5)
O1	0.22475 (17)	0.94630 (13)	−0.02165 (13)	0.0404 (4)
C2	0.4142 (3)	0.93980 (17)	0.10242 (18)	0.0345 (5)
H2	0.5043	0.9158	0.1210	0.041*
C3	0.3569 (2)	1.00024 (17)	0.16584 (18)	0.0338 (5)
H3	0.2662	1.0212	0.1439	0.041*
C4	0.4152 (2)	1.03710 (17)	0.26228 (18)	0.0320 (5)
C5	0.3361 (2)	1.09604 (17)	0.32022 (18)	0.0336 (5)
O2	0.20245 (17)	1.11129 (14)	0.27987 (14)	0.0450 (5)
C6	0.1146 (3)	1.1618 (2)	0.3405 (2)	0.0518 (7)
H6A	0.1132	1.1282	0.4054	0.078*
H6B	0.0214	1.1639	0.3052	0.078*
H6C	0.1485	1.2283	0.3525	0.078*
C7	0.3909 (2)	1.13575 (18)	0.41125 (19)	0.0356 (6)
H7	0.3356	1.1760	0.4486	0.043*
C8	0.5259 (2)	1.11725 (18)	0.44823 (18)	0.0346 (5)
O3	0.59060 (18)	1.15449 (14)	0.53450 (14)	0.0454 (5)
C9	0.5169 (3)	1.2224 (2)	0.5899 (2)	0.0528 (8)
H9A	0.4829	1.2757	0.5451	0.079*
H9B	0.5782	1.2485	0.6467	0.079*
H9C	0.4391	1.1895	0.6159	0.079*
C10	0.6075 (2)	1.05692 (17)	0.39235 (19)	0.0341 (5)
O4	0.74055 (18)	1.04546 (13)	0.43608 (13)	0.0437 (5)
C11	0.8242 (3)	0.9805 (2)	0.3870 (2)	0.0468 (7)
H11A	0.7824	0.9157	0.3840	0.070*
H11B	0.9156	0.9773	0.4250	0.070*
H11C	0.8323	1.0037	0.3181	0.070*
C12	0.5528 (2)	1.01849 (17)	0.30251 (18)	0.0336 (5)
H12	0.6084	0.9780	0.2657	0.040*
C13	0.3995 (2)	0.83943 (16)	−0.05961 (17)	0.0286 (5)
C14	0.3299 (2)	0.81550 (16)	−0.15212 (17)	0.0293 (5)
O5	0.20698 (16)	0.85556 (12)	−0.18480 (13)	0.0366 (4)
H5	0.1858	0.8966	−0.1422	0.055*
C15	0.3832 (2)	0.74664 (17)	−0.21887 (17)	0.0306 (5)
C16	0.3122 (3)	0.72114 (18)	−0.31235 (19)	0.0373 (6)
H16	0.2270	0.7516	−0.3340	0.045*
C17	0.3644 (3)	0.65246 (19)	−0.3731 (2)	0.0435 (6)
H17	0.3151	0.6351	−0.4361	0.052*
C18	0.4906 (3)	0.6082 (2)	−0.3416 (2)	0.0441 (6)
H18	0.5263	0.5606	−0.3835	0.053*
C19	0.5629 (3)	0.63260 (19)	−0.2518 (2)	0.0418 (6)
H19	0.6491	0.6025	−0.2325	0.050*
C20	0.5116 (2)	0.70218 (17)	−0.18647 (18)	0.0331 (5)
C21	0.5822 (3)	0.72680 (19)	−0.0915 (2)	0.0389 (6)
H21	0.6679	0.6969	−0.0702	0.047*
C22	0.5289 (2)	0.79279 (18)	−0.03049 (18)	0.0361 (6)
H22	0.5783	0.8084	0.0329	0.043*

	U11	U22	U33	U12	U13	U23
C1	0.0357 (13)	0.0287 (12)	0.0309 (12)	−0.0018 (10)	0.0048 (10)	0.0028 (9)
O1	0.0385 (10)	0.0434 (10)	0.0383 (10)	0.0090 (8)	−0.0004 (8)	−0.0037 (8)
C2	0.0345 (13)	0.0341 (13)	0.0343 (13)	−0.0023 (10)	0.0006 (10)	−0.0004 (10)
C3	0.0358 (12)	0.0315 (12)	0.0336 (13)	−0.0068 (10)	0.0009 (10)	0.0007 (10)
C4	0.0352 (12)	0.0284 (12)	0.0326 (12)	−0.0061 (9)	0.0044 (10)	0.0005 (9)
C5	0.0302 (12)	0.0354 (13)	0.0349 (13)	−0.0018 (10)	0.0022 (10)	−0.0005 (10)
O2	0.0339 (9)	0.0566 (12)	0.0439 (11)	0.0061 (8)	0.0016 (8)	−0.0103 (9)
C6	0.0406 (15)	0.067 (2)	0.0478 (16)	0.0113 (14)	0.0061 (13)	−0.0046 (15)
C7	0.0331 (12)	0.0386 (13)	0.0360 (13)	0.0004 (10)	0.0081 (10)	−0.0055 (10)
C8	0.0353 (13)	0.0353 (13)	0.0332 (13)	−0.0057 (10)	0.0033 (10)	−0.0069 (10)
O3	0.0399 (10)	0.0559 (12)	0.0397 (10)	−0.0011 (9)	0.0007 (8)	−0.0197 (9)
C9	0.0534 (17)	0.0592 (18)	0.0459 (16)	−0.0023 (14)	0.0053 (13)	−0.0252 (14)
C10	0.0292 (12)	0.0365 (13)	0.0361 (13)	−0.0016 (10)	0.0011 (10)	−0.0015 (10)
O4	0.0367 (10)	0.0513 (11)	0.0419 (10)	0.0065 (8)	−0.0013 (8)	−0.0126 (8)
C11	0.0413 (14)	0.0516 (17)	0.0468 (16)	0.0090 (13)	0.0008 (12)	−0.0044 (13)
C12	0.0351 (12)	0.0319 (12)	0.0339 (13)	−0.0026 (10)	0.0049 (10)	−0.0021 (10)
C13	0.0261 (11)	0.0303 (11)	0.0289 (12)	−0.0017 (9)	0.0006 (9)	0.0032 (9)
C14	0.0266 (11)	0.0270 (11)	0.0337 (12)	−0.0021 (9)	0.0008 (9)	0.0041 (9)
O5	0.0327 (9)	0.0403 (10)	0.0361 (9)	0.0061 (7)	0.0004 (7)	−0.0037 (7)
C15	0.0304 (12)	0.0290 (12)	0.0326 (12)	−0.0027 (9)	0.0036 (9)	0.0005 (9)
C16	0.0351 (13)	0.0382 (14)	0.0376 (14)	−0.0025 (10)	−0.0001 (10)	−0.0033 (11)
C17	0.0514 (16)	0.0403 (15)	0.0387 (14)	−0.0050 (12)	0.0043 (12)	−0.0099 (11)
C18	0.0446 (15)	0.0415 (15)	0.0467 (16)	0.0035 (12)	0.0083 (12)	−0.0089 (12)
C19	0.0380 (14)	0.0378 (14)	0.0499 (16)	0.0058 (11)	0.0061 (12)	−0.0014 (12)
C20	0.0326 (12)	0.0306 (12)	0.0363 (13)	−0.0013 (10)	0.0047 (10)	0.0019 (10)
C21	0.0309 (12)	0.0419 (14)	0.0432 (14)	0.0042 (11)	0.0000 (11)	0.0009 (11)
C22	0.0341 (13)	0.0394 (14)	0.0340 (13)	−0.0008 (10)	−0.0004 (10)	0.0005 (10)

C1—O1	1.262 (3)	O4—C11	1.417 (3)
C1—C2	1.448 (3)	C11—H11A	0.9800
C1—C13	1.470 (3)	C11—H11B	0.9800
C2—C3	1.347 (3)	C11—H11C	0.9800
C2—H2	0.9500	C12—H12	0.9500
C3—C4	1.437 (3)	C13—C14	1.379 (3)
C3—H3	0.9500	C13—C22	1.436 (3)
C4—C5	1.406 (3)	C14—O5	1.352 (3)
C4—C12	1.418 (3)	C14—C15	1.433 (3)
C5—O2	1.376 (3)	O5—H5	0.8400
C5—C7	1.381 (3)	C15—C16	1.401 (3)
O2—C6	1.421 (3)	C15—C20	1.422 (3)
C6—H6A	0.9800	C16—C17	1.376 (4)
C6—H6B	0.9800	C16—H16	0.9500
C6—H6C	0.9800	C17—C18	1.400 (4)
C7—C8	1.383 (3)	C17—H17	0.9500
C7—H7	0.9500	C18—C19	1.362 (4)
C8—O3	1.349 (3)	C18—H18	0.9500
C8—C10	1.416 (3)	C19—C20	1.419 (3)
O3—C9	1.432 (3)	C19—H19	0.9500
C9—H9A	0.9800	C20—C21	1.412 (3)
C9—H9B	0.9800	C21—C22	1.358 (3)
C9—H9C	0.9800	C21—H21	0.9500
C10—C12	1.361 (3)	C22—H22	0.9500
C10—O4	1.378 (3)
O1—C1—C2	119.8 (2)	O4—C11—H11B	109.5
O1—C1—C13	118.6 (2)	H11A—C11—H11B	109.5
C2—C1—C13	121.6 (2)	O4—C11—H11C	109.5
C3—C2—C1	121.5 (2)	H11A—C11—H11C	109.5
C3—C2—H2	119.3	H11B—C11—H11C	109.5
C1—C2—H2	119.3	C10—C12—C4	121.9 (2)
C2—C3—C4	128.5 (2)	C10—C12—H12	119.1
C2—C3—H3	115.8	C4—C12—H12	119.1
C4—C3—H3	115.8	C14—C13—C22	118.1 (2)
C5—C4—C12	117.1 (2)	C14—C13—C1	120.3 (2)
C5—C4—C3	120.1 (2)	C22—C13—C1	121.6 (2)
C12—C4—C3	122.8 (2)	O5—C14—C13	121.7 (2)
O2—C5—C7	123.0 (2)	O5—C14—C15	116.21 (19)
O2—C5—C4	115.6 (2)	C13—C14—C15	122.0 (2)
C7—C5—C4	121.4 (2)	C14—O5—H5	109.5
C5—O2—C6	117.6 (2)	C16—C15—C20	119.9 (2)
O2—C6—H6A	109.5	C16—C15—C14	122.3 (2)
O2—C6—H6B	109.5	C20—C15—C14	117.8 (2)
H6A—C6—H6B	109.5	C17—C16—C15	120.7 (2)
O2—C6—H6C	109.5	C17—C16—H16	119.6
H6A—C6—H6C	109.5	C15—C16—H16	119.6
H6B—C6—H6C	109.5	C16—C17—C18	119.7 (2)
C5—C7—C8	120.3 (2)	C16—C17—H17	120.1
C5—C7—H7	119.9	C18—C17—H17	120.1
C8—C7—H7	119.9	C19—C18—C17	120.9 (2)
O3—C8—C7	125.1 (2)	C19—C18—H18	119.6
O3—C8—C10	115.3 (2)	C17—C18—H18	119.6
C7—C8—C10	119.6 (2)	C18—C19—C20	121.1 (2)
C8—O3—C9	117.9 (2)	C18—C19—H19	119.4
O3—C9—H9A	109.5	C20—C19—H19	119.4
O3—C9—H9B	109.5	C21—C20—C19	122.4 (2)
H9A—C9—H9B	109.5	C21—C20—C15	119.9 (2)
O3—C9—H9C	109.5	C19—C20—C15	117.7 (2)
H9A—C9—H9C	109.5	C22—C21—C20	120.7 (2)
H9B—C9—H9C	109.5	C22—C21—H21	119.7
C12—C10—O4	126.2 (2)	C20—C21—H21	119.7
C12—C10—C8	119.7 (2)	C21—C22—C13	121.5 (2)
O4—C10—C8	114.1 (2)	C21—C22—H22	119.2
C10—O4—C11	116.46 (19)	C13—C22—H22	119.2
O4—C11—H11A	109.5
O1—C1—C2—C3	4.1 (4)	C2—C1—C13—C14	−177.7 (2)
C13—C1—C2—C3	−175.7 (2)	O1—C1—C13—C22	−177.4 (2)
C1—C2—C3—C4	−179.1 (2)	C2—C1—C13—C22	2.5 (3)
C2—C3—C4—C5	−176.7 (2)	C22—C13—C14—O5	179.5 (2)
C2—C3—C4—C12	4.6 (4)	C1—C13—C14—O5	−0.3 (3)
C12—C4—C5—O2	−178.9 (2)	C22—C13—C14—C15	−0.3 (3)
C3—C4—C5—O2	2.3 (3)	C1—C13—C14—C15	179.9 (2)
C12—C4—C5—C7	1.4 (3)	O5—C14—C15—C16	−0.6 (3)
C3—C4—C5—C7	−177.4 (2)	C13—C14—C15—C16	179.2 (2)
C7—C5—O2—C6	−6.7 (4)	O5—C14—C15—C20	−179.3 (2)
C4—C5—O2—C6	173.6 (2)	C13—C14—C15—C20	0.5 (3)
O2—C5—C7—C8	179.6 (2)	C20—C15—C16—C17	0.8 (4)
C4—C5—C7—C8	−0.7 (4)	C14—C15—C16—C17	−177.9 (2)
C5—C7—C8—O3	178.0 (2)	C15—C16—C17—C18	−0.6 (4)
C5—C7—C8—C10	−0.3 (4)	C16—C17—C18—C19	−0.3 (4)
C7—C8—O3—C9	−3.4 (4)	C17—C18—C19—C20	1.1 (4)
C10—C8—O3—C9	174.9 (2)	C18—C19—C20—C21	178.1 (3)
O3—C8—C10—C12	−177.8 (2)	C18—C19—C20—C15	−1.0 (4)
C7—C8—C10—C12	0.6 (4)	C16—C15—C20—C21	−179.0 (2)
O3—C8—C10—O4	0.5 (3)	C14—C15—C20—C21	−0.3 (3)
C7—C8—C10—O4	178.9 (2)	C16—C15—C20—C19	0.0 (3)
C12—C10—O4—C11	−6.0 (4)	C14—C15—C20—C19	178.8 (2)
C8—C10—O4—C11	175.8 (2)	C19—C20—C21—C22	−179.1 (2)
O4—C10—C12—C4	−178.0 (2)	C15—C20—C21—C22	−0.1 (4)
C8—C10—C12—C4	0.1 (4)	C20—C21—C22—C13	0.2 (4)
C5—C4—C12—C10	−1.1 (3)	C14—C13—C22—C21	−0.1 (4)
C3—C4—C12—C10	177.6 (2)	C1—C13—C22—C21	179.7 (2)
O1—C1—C13—C14	2.4 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O1	0.84	1.74	2.490 (2)	147
C21—H21···O3i	0.95	2.43	3.362 (3)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O1	0.84	1.74	2.490 (2)	147
C21—H21⋯O3i	0.95	2.43	3.362 (3)	166

Symmetry code: (i) .