(E)-3-(3,5-Dimeth-oxy-phen-yl)-1-(1-hy-droxy-naphthalen-2-yl)prop-2-en-1-one.

In the title mol-ecule, C21H18O4, the C=C bond of the central enone group adopts a trans conformation. The dihedral angle formed by the naphthalene ring system and the benzene ring is 2.97 (11)°. The hy-droxy group 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 [001].

Related literature

For the synthesis and biological properties of chalcone derivatives, see: Sharma et al. (2012 ▶); Singh et al. (2012 ▶); Bandgar et al. (2010 ▶); Hans et al. (2010 ▶); Hwang et al. (2011 ▶). For related structures, see: Fadzillah et al. (2012 ▶); Jasinski et al. (2011 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H18O4

M = 334.35

Orthorhombic,

a = 30.179 (3) Å

b = 3.9127 (3) Å

c = 13.7363 (12) Å

V = 1622.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.24 × 0.22 × 0.17 mm

Data collection

Bruker SMART CCD diffractometer

11095 measured reflections

3479 independent reflections

1828 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.102

S = 0.94

3479 reflections

229 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.23 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/S1600536812046715/lh5555sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812046715/lh5555Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812046715/lh5555Isup3.cml

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

C21H18O4	F(000) = 704
Mr = 334.35	Dx = 1.369 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 2578 reflections
a = 30.179 (3) Å	θ = 2.7–27.8°
b = 3.9127 (3) Å	µ = 0.09 mm−1
c = 13.7363 (12) Å	T = 200 K
V = 1622.0 (2) Å3	Block, orange
Z = 4	0.24 × 0.22 × 0.17 mm

Bruker SMART CCD diffractometer	1828 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.064
Graphite monochromator	θmax = 28.3°, θmin = 1.4°
φ and ω scans	h = −32→40
11095 measured reflections	k = −5→5
3479 independent reflections	l = −16→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.102	H-atom parameters constrained
S = 0.94	w = 1/[σ2(Fo2) + (0.0276P)2] where P = (Fo2 + 2Fc2)/3
3479 reflections	(Δ/σ)max < 0.001
229 parameters	Δρmax = 0.22 e Å−3
1 restraint	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
C1	0.35700 (10)	0.8619 (7)	0.4892 (2)	0.0348 (7)
O1	0.36736 (7)	0.9296 (6)	0.57454 (14)	0.0485 (6)
C2	0.38738 (10)	0.9586 (8)	0.4096 (2)	0.0362 (8)
H2	0.3791	0.9009	0.3449	0.043*
C3	0.42532 (10)	1.1203 (7)	0.4228 (2)	0.0352 (7)
H3	0.4326	1.1809	0.4878	0.042*
C4	0.45715 (10)	1.2153 (7)	0.3474 (2)	0.0312 (7)
C5	0.49588 (10)	1.3745 (7)	0.3726 (2)	0.0340 (7)
H5	0.5011	1.4326	0.4388	0.041*
C6	0.52799 (10)	1.4530 (7)	0.3019 (2)	0.0335 (8)
O2	0.56629 (7)	1.5970 (6)	0.33591 (14)	0.0424 (6)
C7	0.59853 (11)	1.7037 (8)	0.2650 (2)	0.0420 (9)
H7A	0.6101	1.5029	0.2307	0.063*
H7B	0.6229	1.8220	0.2979	0.063*
H7C	0.5846	1.8587	0.2182	0.063*
C8	0.52006 (10)	1.3789 (7)	0.2050 (2)	0.0334 (7)
H8	0.5414	1.4332	0.1565	0.040*
C9	0.48010 (10)	1.2229 (7)	0.1799 (2)	0.0322 (7)
O3	0.47555 (7)	1.1594 (5)	0.08193 (15)	0.0416 (5)
C10	0.43530 (10)	1.0023 (8)	0.0509 (2)	0.0428 (8)
H10A	0.4337	0.7696	0.0771	0.064*
H10B	0.4345	0.9936	−0.0204	0.064*
H10C	0.4100	1.1357	0.0746	0.064*
C11	0.44877 (10)	1.1405 (7)	0.2483 (2)	0.0343 (8)
H11	0.4218	1.0346	0.2293	0.041*
C12	0.31508 (10)	0.6927 (7)	0.4670 (2)	0.0290 (7)
C13	0.28636 (10)	0.6041 (8)	0.5424 (2)	0.0319 (7)
O4	0.29656 (7)	0.6743 (6)	0.63545 (14)	0.0437 (6)
H4	0.3204	0.7843	0.6375	0.066*
C14	0.24525 (10)	0.4418 (7)	0.5241 (2)	0.0311 (7)
C15	0.21607 (10)	0.3500 (8)	0.6006 (2)	0.0377 (8)
H15	0.2241	0.3941	0.6663	0.045*
C16	0.17643 (10)	0.1979 (8)	0.5797 (2)	0.0408 (8)
H16	0.1568	0.1392	0.6311	0.049*
C17	0.16454 (10)	0.1281 (8)	0.4837 (2)	0.0398 (8)
H17	0.1368	0.0242	0.4702	0.048*
C18	0.19236 (11)	0.2075 (8)	0.4093 (2)	0.0366 (8)
H18	0.1841	0.1533	0.3444	0.044*
C19	0.23315 (10)	0.3683 (7)	0.4268 (2)	0.0293 (7)
C20	0.26243 (10)	0.4564 (7)	0.3506 (2)	0.0360 (8)
H20	0.2545	0.4061	0.2852	0.043*
C21	0.30156 (10)	0.6117 (8)	0.3696 (2)	0.0351 (8)
H21	0.3206	0.6686	0.3170	0.042*

	U11	U22	U33	U12	U13	U23
C1	0.0311 (19)	0.0388 (19)	0.0344 (19)	−0.0019 (15)	−0.0011 (14)	0.0023 (16)
O1	0.0434 (15)	0.0720 (17)	0.0302 (13)	−0.0130 (12)	−0.0004 (10)	−0.0007 (12)
C2	0.0288 (19)	0.049 (2)	0.0312 (18)	−0.0061 (15)	0.0035 (13)	−0.0010 (15)
C3	0.035 (2)	0.0414 (19)	0.0297 (16)	−0.0024 (16)	−0.0001 (15)	0.0006 (16)
C4	0.0289 (18)	0.0324 (18)	0.0324 (18)	0.0014 (14)	−0.0023 (14)	0.0011 (14)
C5	0.0316 (19)	0.0379 (19)	0.0324 (17)	−0.0025 (15)	0.0020 (14)	0.0014 (15)
C6	0.0286 (19)	0.0322 (18)	0.0396 (19)	−0.0001 (14)	−0.0033 (14)	0.0036 (15)
O2	0.0314 (13)	0.0531 (14)	0.0428 (14)	−0.0114 (11)	−0.0010 (11)	0.0022 (11)
C7	0.031 (2)	0.043 (2)	0.052 (2)	−0.0077 (16)	0.0043 (16)	0.0082 (17)
C8	0.0286 (19)	0.0368 (18)	0.0348 (18)	−0.0012 (14)	0.0022 (14)	0.0004 (15)
C9	0.0363 (19)	0.0325 (17)	0.0279 (18)	0.0032 (14)	−0.0055 (14)	0.0035 (14)
O3	0.0376 (14)	0.0555 (15)	0.0316 (12)	−0.0060 (11)	−0.0007 (10)	−0.0017 (11)
C10	0.042 (2)	0.049 (2)	0.0380 (19)	−0.0040 (17)	−0.0094 (15)	−0.0001 (15)
C11	0.0290 (19)	0.040 (2)	0.0342 (18)	−0.0053 (15)	0.0003 (14)	0.0021 (15)
C12	0.0258 (18)	0.0345 (18)	0.0266 (16)	−0.0016 (14)	−0.0005 (13)	0.0018 (14)
C13	0.0304 (19)	0.0373 (18)	0.0281 (17)	−0.0001 (14)	0.0012 (14)	−0.0002 (15)
O4	0.0414 (16)	0.0659 (16)	0.0237 (12)	−0.0129 (12)	−0.0014 (10)	−0.0015 (11)
C14	0.0303 (19)	0.0304 (16)	0.0326 (18)	0.0000 (14)	0.0012 (13)	0.0024 (14)
C15	0.036 (2)	0.045 (2)	0.0329 (19)	−0.0040 (15)	0.0036 (14)	0.0042 (15)
C16	0.035 (2)	0.045 (2)	0.042 (2)	−0.0020 (16)	0.0060 (16)	0.0032 (17)
C17	0.029 (2)	0.0414 (19)	0.049 (2)	−0.0073 (15)	0.0001 (16)	−0.0013 (17)
C18	0.034 (2)	0.038 (2)	0.0383 (19)	−0.0013 (15)	−0.0026 (14)	0.0020 (15)
C19	0.0282 (18)	0.0269 (16)	0.0329 (16)	−0.0012 (13)	0.0003 (14)	0.0009 (14)
C20	0.035 (2)	0.0434 (19)	0.0293 (17)	−0.0006 (15)	−0.0047 (14)	−0.0002 (15)
C21	0.0327 (19)	0.045 (2)	0.0279 (17)	−0.0018 (15)	0.0016 (14)	0.0014 (15)

C1—O1	1.242 (3)	C10—H10B	0.9800
C1—C12	1.460 (4)	C10—H10C	0.9800
C1—C2	1.476 (4)	C11—H11	0.9500
C2—C3	1.321 (4)	C12—C13	1.395 (4)
C2—H2	0.9500	C12—C21	1.433 (4)
C3—C4	1.460 (4)	C13—O4	1.343 (3)
C3—H3	0.9500	C13—C14	1.416 (4)
C4—C5	1.369 (4)	O4—H4	0.8400
C4—C11	1.416 (4)	C14—C19	1.414 (4)
C5—C6	1.406 (4)	C14—C15	1.418 (4)
C5—H5	0.9500	C15—C16	1.367 (4)
C6—O2	1.368 (3)	C15—H15	0.9500
C6—C8	1.384 (4)	C16—C17	1.394 (4)
O2—C7	1.438 (3)	C16—H16	0.9500
C7—H7A	0.9800	C17—C18	1.359 (4)
C7—H7B	0.9800	C17—H17	0.9500
C7—H7C	0.9800	C18—C19	1.403 (4)
C8—C9	1.395 (4)	C18—H18	0.9500
C8—H8	0.9500	C19—C20	1.413 (4)
C9—C11	1.371 (4)	C20—C21	1.354 (4)
C9—O3	1.375 (3)	C20—H20	0.9500
O3—C10	1.427 (3)	C21—H21	0.9500
C10—H10A	0.9800
O1—C1—C12	120.8 (3)	H10A—C10—H10C	109.5
O1—C1—C2	119.2 (3)	H10B—C10—H10C	109.5
C12—C1—C2	120.0 (3)	C9—C11—C4	119.2 (3)
C3—C2—C1	124.1 (3)	C9—C11—H11	120.4
C3—C2—H2	118.0	C4—C11—H11	120.4
C1—C2—H2	118.0	C13—C12—C21	117.5 (3)
C2—C3—C4	126.5 (3)	C13—C12—C1	119.7 (3)
C2—C3—H3	116.7	C21—C12—C1	122.8 (3)
C4—C3—H3	116.7	O4—C13—C12	120.9 (3)
C5—C4—C11	119.3 (3)	O4—C13—C14	117.5 (2)
C5—C4—C3	119.9 (3)	C12—C13—C14	121.6 (3)
C11—C4—C3	120.8 (3)	C13—O4—H4	109.5
C4—C5—C6	120.9 (3)	C19—C14—C13	119.0 (3)
C4—C5—H5	119.6	C19—C14—C15	119.2 (3)
C6—C5—H5	119.6	C13—C14—C15	121.7 (3)
O2—C6—C8	124.1 (3)	C16—C15—C14	119.9 (3)
O2—C6—C5	115.9 (3)	C16—C15—H15	120.0
C8—C6—C5	120.0 (3)	C14—C15—H15	120.0
C6—O2—C7	117.4 (2)	C15—C16—C17	120.6 (3)
O2—C7—H7A	109.5	C15—C16—H16	119.7
O2—C7—H7B	109.5	C17—C16—H16	119.7
H7A—C7—H7B	109.5	C18—C17—C16	120.5 (3)
O2—C7—H7C	109.5	C18—C17—H17	119.7
H7A—C7—H7C	109.5	C16—C17—H17	119.7
H7B—C7—H7C	109.5	C17—C18—C19	121.0 (3)
C6—C8—C9	118.6 (3)	C17—C18—H18	119.5
C6—C8—H8	120.7	C19—C18—H18	119.5
C9—C8—H8	120.7	C18—C19—C20	122.0 (3)
C11—C9—O3	124.0 (3)	C18—C19—C14	118.7 (3)
C11—C9—C8	122.0 (3)	C20—C19—C14	119.3 (3)
O3—C9—C8	114.0 (3)	C21—C20—C19	120.8 (3)
C9—O3—C10	117.1 (2)	C21—C20—H20	119.6
O3—C10—H10A	109.5	C19—C20—H20	119.6
O3—C10—H10B	109.5	C20—C21—C12	121.9 (3)
H10A—C10—H10B	109.5	C20—C21—H21	119.1
O3—C10—H10C	109.5	C12—C21—H21	119.1
O1—C1—C2—C3	−1.1 (5)	C21—C12—C13—O4	−179.4 (3)
C12—C1—C2—C3	178.1 (3)	C1—C12—C13—O4	0.5 (4)
C1—C2—C3—C4	178.4 (3)	C21—C12—C13—C14	−0.3 (4)
C2—C3—C4—C5	−178.1 (3)	C1—C12—C13—C14	179.6 (3)
C2—C3—C4—C11	1.0 (5)	O4—C13—C14—C19	179.1 (3)
C11—C4—C5—C6	−2.3 (5)	C12—C13—C14—C19	0.0 (4)
C3—C4—C5—C6	176.8 (3)	O4—C13—C14—C15	−1.2 (4)
C4—C5—C6—O2	−177.0 (3)	C12—C13—C14—C15	179.7 (3)
C4—C5—C6—C8	2.0 (4)	C19—C14—C15—C16	−1.2 (5)
C8—C6—O2—C7	5.5 (4)	C13—C14—C15—C16	179.1 (3)
C5—C6—O2—C7	−175.6 (3)	C14—C15—C16—C17	0.8 (5)
O2—C6—C8—C9	178.2 (3)	C15—C16—C17—C18	0.6 (5)
C5—C6—C8—C9	−0.7 (4)	C16—C17—C18—C19	−1.5 (5)
C6—C8—C9—C11	−0.3 (4)	C17—C18—C19—C20	−179.3 (3)
C6—C8—C9—O3	−179.8 (3)	C17—C18—C19—C14	1.0 (4)
C11—C9—O3—C10	0.9 (4)	C13—C14—C19—C18	180.0 (3)
C8—C9—O3—C10	−179.6 (2)	C15—C14—C19—C18	0.3 (4)
O3—C9—C11—C4	179.4 (3)	C13—C14—C19—C20	0.4 (4)
C8—C9—C11—C4	−0.1 (4)	C15—C14—C19—C20	−179.3 (3)
C5—C4—C11—C9	1.3 (5)	C18—C19—C20—C21	179.9 (3)
C3—C4—C11—C9	−177.8 (3)	C14—C19—C20—C21	−0.4 (4)
O1—C1—C12—C13	−0.4 (4)	C19—C20—C21—C12	0.1 (4)
C2—C1—C12—C13	−179.6 (3)	C13—C12—C21—C20	0.3 (4)
O1—C1—C12—C21	179.5 (3)	C1—C12—C21—C20	−179.6 (3)
C2—C1—C12—C21	0.3 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O1	0.84	1.75	2.503 (3)	147
C7—H7C···O1i	0.98	2.59	3.157 (4)	117
C10—H10B···O2i	0.98	2.54	3.344 (4)	139

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4⋯O1	0.84	1.75	2.503 (3)	147
C7—H7C⋯O1i	0.98	2.59	3.157 (4)	117
C10—H10B⋯O2i	0.98	2.54	3.344 (4)	139

Symmetry code: (i) .