Crystal structure of (E)-3-(3,4-di-meth-oxy-phen-yl)-1-(1-hy-droxy-naphthalen-2-yl)prop-2-en-1-one.

The mol-ecular structure of the title compound, C21H18O4, consists of a 3,4-di-meth-oxy-phenyl ring and a naphthalene ring system linked via a prop-2-en-1-one spacer. The mol-ecule is almost planar, with a dihedral angle between the benzene ring and the naphthalene ring system of 2.68 (12)°. There is an intra-molecular O-H⋯O hydrogen bond involving the adjacent hy-droxy and carbonyl groups. The mol-ecule has an E conformation about the C=C bond and the carbonyl group is syn with respect to the C=C bond. In the crystal, mol-ecules are linked by bifurcated C-H⋯(O,O) hydrogen bonds, enclosing an R 2 (1)(6) ring motif, and by a further C-H⋯O hydrogen bond, forming undulating sheets extending in b- and c-axis directions. There are π-π inter-actions between the sheets, involving inversion-related naphthalene and benzene rings [inter-centroid distance = 3.7452 (17) Å], forming a three-dimensional structure.

Related literature

For the biological activity of chalcone derivatives, see: Sashidhara et al. (2011 ▸); Go et al. (2005 ▸); Mukherjee et al. (2001 ▸); Liu et al. (2003 ▸); Sivakumar et al. (2007 ▸); Viana et al. (2003 ▸); Ducki et al. (1998 ▸); Rahman et al. (2007 ▸). For a related structure, see: Ahn et al. (2013 ▸). For the synthesis, see: Ezhilarasi et al. (2014 ▸); Sathya et al. (2014 ▸).

Experimental

Crystal data

C21H18O4

M = 334.35

Monoclinic,

a = 9.8784 (10) Å

b = 15.4108 (15) Å

c = 11.2288 (11) Å

β = 92.674 (2)°

V = 1707.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004 ▸) T min = 0.973, T max = 0.982

34671 measured reflections

3568 independent reflections

1992 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.247

S = 1.08

3568 reflections

230 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2004 ▸); cell refinement: APEX2 and SAINT (Bruker, 2004 ▸); data reduction: SAINT and XPREP (Bruker, 2004 ▸); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: SHELXL2014 and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, Global. DOI: 10.1107/S2056989015008087/su5109sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015008087/su5109Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015008087/su5109Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015008087/su5109fig1.tif

The mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

Click here for additional data file.

c . DOI: 10.1107/S2056989015008087/su5109fig2.tif

A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1 for details).

CCDC reference: 1051679

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H18O4	F(000) = 704
Mr = 334.35	Dx = 1.301 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.8784 (10) Å	Cell parameters from 3582 reflections
b = 15.4108 (15) Å	θ = 2.3–26.6°
c = 11.2288 (11) Å	µ = 0.09 mm−1
β = 92.674 (2)°	T = 293 K
V = 1707.5 (3) Å3	Block, redish
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker Kappa APEXII CCD diffractometer	3568 independent reflections
Radiation source: fine-focus sealed tube	1992 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
ω and φ scan	θmax = 26.6°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −12→12
Tmin = 0.973, Tmax = 0.982	k = −19→19
34671 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.068	H-atom parameters constrained
wR(F2) = 0.247	w = 1/[σ2(Fo2) + (0.125P)2 + 0.6413P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3568 reflections	Δρmax = 0.29 e Å−3
230 parameters	Δρmin = −0.29 e Å−3
0 restraints	Extinction correction: SHELXL2014 (Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.212 (16)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

	x	y	z	Uiso*/Ueq
O1	−0.0402 (2)	0.54423 (14)	0.26187 (18)	0.0626 (6)
O2	0.1324 (2)	0.65677 (13)	0.22420 (16)	0.0568 (6)
H2A	0.0852	0.6136	0.2119	0.085*
O3	−0.5102 (2)	0.41489 (16)	0.74635 (18)	0.0691 (7)
O4	−0.6337 (2)	0.28908 (15)	0.63862 (19)	0.0664 (7)
C1	0.1882 (3)	0.76195 (17)	0.3705 (2)	0.0468 (7)
C2	0.2833 (3)	0.8011 (2)	0.2974 (3)	0.0589 (8)
H2	0.2972	0.7784	0.2222	0.071*
C3	0.3548 (3)	0.8720 (2)	0.3366 (3)	0.0702 (10)
H3	0.4157	0.8983	0.2872	0.084*
C4	0.3372 (4)	0.9050 (2)	0.4501 (4)	0.0757 (10)
H4	0.3872	0.9530	0.4762	0.091*
C5	0.2474 (3)	0.8680 (2)	0.5235 (3)	0.0667 (9)
H5	0.2372	0.8907	0.5993	0.080*
C6	0.1701 (3)	0.79568 (19)	0.4855 (3)	0.0533 (8)
C7	0.0772 (3)	0.7555 (2)	0.5598 (3)	0.0599 (8)
H7	0.0658	0.7770	0.6361	0.072*
C8	0.0047 (3)	0.68597 (19)	0.5208 (3)	0.0552 (8)
H8	−0.0557	0.6606	0.5715	0.066*
C9	0.0170 (3)	0.65037 (17)	0.4059 (2)	0.0439 (7)
C10	0.1113 (3)	0.68788 (17)	0.3329 (2)	0.0445 (7)
C11	−0.0608 (3)	0.57509 (17)	0.3629 (2)	0.0479 (7)
C12	−0.1620 (3)	0.53573 (18)	0.4362 (3)	0.0505 (7)
H12	−0.1748	0.5582	0.5118	0.061*
C13	−0.2369 (3)	0.46840 (19)	0.3981 (3)	0.0514 (7)
H13	−0.2211	0.4483	0.3219	0.062*
C14	−0.3399 (3)	0.42287 (18)	0.4610 (2)	0.0484 (7)
C15	−0.3725 (3)	0.44398 (18)	0.5770 (2)	0.0482 (7)
H15	−0.3268	0.4891	0.6165	0.058*
C16	−0.4709 (3)	0.39945 (19)	0.6339 (2)	0.0494 (7)
C17	−0.5390 (3)	0.33076 (19)	0.5753 (3)	0.0502 (7)
C18	−0.5085 (3)	0.30938 (19)	0.4609 (3)	0.0549 (8)
H18	−0.5543	0.2644	0.4213	0.066*
C19	−0.4089 (3)	0.35528 (19)	0.4049 (3)	0.0565 (8)
H19	−0.3881	0.3402	0.3277	0.068*
C20	−0.4327 (4)	0.4750 (3)	0.8165 (3)	0.0800 (11)
H20A	−0.4646	0.4758	0.8960	0.120*
H20B	−0.4418	0.5318	0.7820	0.120*
H20C	−0.3391	0.4580	0.8191	0.120*
C21	−0.6958 (4)	0.2140 (2)	0.5876 (3)	0.0770 (10)
H21A	−0.7562	0.1892	0.6429	0.116*
H21B	−0.6273	0.1723	0.5700	0.116*
H21C	−0.7459	0.2295	0.5155	0.116*

	U11	U22	U33	U12	U13	U23
O1	0.0739 (15)	0.0598 (13)	0.0553 (13)	−0.0084 (11)	0.0161 (10)	−0.0062 (10)
O2	0.0683 (14)	0.0591 (13)	0.0440 (11)	−0.0023 (10)	0.0119 (10)	0.0030 (9)
O3	0.0801 (15)	0.0796 (16)	0.0486 (13)	−0.0189 (12)	0.0110 (11)	−0.0048 (10)
O4	0.0678 (14)	0.0696 (15)	0.0620 (13)	−0.0185 (11)	0.0060 (11)	0.0058 (11)
C1	0.0443 (15)	0.0449 (15)	0.0511 (16)	0.0067 (12)	−0.0003 (12)	0.0070 (12)
C2	0.0584 (19)	0.0583 (18)	0.0597 (18)	−0.0032 (15)	0.0013 (15)	0.0102 (14)
C3	0.064 (2)	0.065 (2)	0.081 (2)	−0.0109 (17)	0.0006 (18)	0.0163 (18)
C4	0.067 (2)	0.058 (2)	0.101 (3)	−0.0055 (17)	−0.016 (2)	−0.0005 (19)
C5	0.065 (2)	0.058 (2)	0.076 (2)	0.0049 (16)	−0.0085 (17)	−0.0108 (16)
C6	0.0528 (17)	0.0486 (16)	0.0580 (17)	0.0084 (13)	−0.0023 (14)	−0.0008 (13)
C7	0.0643 (19)	0.065 (2)	0.0507 (17)	0.0067 (16)	0.0061 (14)	−0.0116 (15)
C8	0.0566 (18)	0.0566 (18)	0.0536 (17)	0.0026 (14)	0.0134 (14)	0.0002 (14)
C9	0.0465 (15)	0.0433 (15)	0.0424 (14)	0.0090 (11)	0.0068 (12)	0.0019 (11)
C10	0.0476 (16)	0.0442 (15)	0.0417 (15)	0.0094 (12)	0.0031 (12)	0.0041 (11)
C11	0.0500 (16)	0.0440 (15)	0.0499 (16)	0.0081 (12)	0.0056 (12)	0.0051 (12)
C12	0.0536 (17)	0.0500 (16)	0.0485 (16)	0.0039 (13)	0.0094 (13)	0.0060 (12)
C13	0.0510 (17)	0.0515 (17)	0.0519 (16)	0.0057 (13)	0.0053 (13)	0.0049 (13)
C14	0.0455 (15)	0.0469 (16)	0.0529 (17)	0.0042 (12)	0.0027 (12)	0.0064 (12)
C15	0.0475 (16)	0.0463 (15)	0.0506 (16)	0.0017 (12)	0.0001 (12)	0.0034 (12)
C16	0.0506 (16)	0.0539 (17)	0.0435 (15)	0.0011 (13)	−0.0004 (12)	0.0036 (12)
C17	0.0481 (16)	0.0517 (16)	0.0507 (17)	0.0012 (13)	0.0007 (13)	0.0094 (13)
C18	0.0562 (18)	0.0526 (17)	0.0554 (18)	−0.0042 (14)	−0.0023 (14)	−0.0007 (13)
C19	0.0605 (18)	0.0581 (18)	0.0512 (17)	0.0002 (14)	0.0064 (14)	−0.0053 (14)
C20	0.093 (3)	0.092 (3)	0.056 (2)	−0.018 (2)	0.0084 (18)	−0.0162 (18)
C21	0.069 (2)	0.073 (2)	0.089 (3)	−0.0219 (18)	0.0025 (19)	0.0060 (19)

O1—C11	1.255 (3)	C9—C10	1.395 (4)
O2—C10	1.336 (3)	C9—C11	1.462 (4)
O2—H2A	0.8200	C11—C12	1.457 (4)
O3—C16	1.359 (3)	C12—C13	1.333 (4)
O3—C20	1.417 (4)	C12—H12	0.9300
O4—C17	1.361 (3)	C13—C14	1.446 (4)
O4—C21	1.418 (4)	C13—H13	0.9300
C1—C6	1.411 (4)	C14—C19	1.381 (4)
C1—C2	1.411 (4)	C14—C15	1.395 (4)
C1—C10	1.425 (4)	C15—C16	1.372 (4)
C2—C3	1.363 (5)	C15—H15	0.9300
C2—H2	0.9300	C16—C17	1.402 (4)
C3—C4	1.391 (5)	C17—C18	1.374 (4)
C3—H3	0.9300	C18—C19	1.385 (4)
C4—C5	1.365 (5)	C18—H18	0.9300
C4—H4	0.9300	C19—H19	0.9300
C5—C6	1.406 (4)	C20—H20A	0.9600
C5—H5	0.9300	C20—H20B	0.9600
C6—C7	1.412 (4)	C20—H20C	0.9600
C7—C8	1.350 (4)	C21—H21A	0.9600
C7—H7	0.9300	C21—H21B	0.9600
C8—C9	1.412 (4)	C21—H21C	0.9600
C8—H8	0.9300
C10—O2—H2A	109.5	C13—C12—C11	121.8 (3)
C16—O3—C20	117.4 (2)	C13—C12—H12	119.1
C17—O4—C21	118.0 (2)	C11—C12—H12	119.1
C6—C1—C2	119.4 (3)	C12—C13—C14	127.8 (3)
C6—C1—C10	118.6 (2)	C12—C13—H13	116.1
C2—C1—C10	122.0 (3)	C14—C13—H13	116.1
C3—C2—C1	120.2 (3)	C19—C14—C15	118.1 (3)
C3—C2—H2	119.9	C19—C14—C13	119.2 (3)
C1—C2—H2	119.9	C15—C14—C13	122.8 (3)
C2—C3—C4	120.3 (3)	C16—C15—C14	121.2 (3)
C2—C3—H3	119.9	C16—C15—H15	119.4
C4—C3—H3	119.9	C14—C15—H15	119.4
C5—C4—C3	120.9 (3)	O3—C16—C15	125.8 (3)
C5—C4—H4	119.6	O3—C16—C17	114.6 (2)
C3—C4—H4	119.6	C15—C16—C17	119.6 (3)
C4—C5—C6	120.5 (3)	O4—C17—C18	124.1 (3)
C4—C5—H5	119.8	O4—C17—C16	116.0 (3)
C6—C5—H5	119.8	C18—C17—C16	119.9 (3)
C5—C6—C1	118.7 (3)	C17—C18—C19	119.6 (3)
C5—C6—C7	121.8 (3)	C17—C18—H18	120.2
C1—C6—C7	119.5 (3)	C19—C18—H18	120.2
C8—C7—C6	120.4 (3)	C14—C19—C18	121.6 (3)
C8—C7—H7	119.8	C14—C19—H19	119.2
C6—C7—H7	119.8	C18—C19—H19	119.2
C7—C8—C9	122.5 (3)	O3—C20—H20A	109.5
C7—C8—H8	118.7	O3—C20—H20B	109.5
C9—C8—H8	118.7	H20A—C20—H20B	109.5
C10—C9—C8	117.7 (3)	O3—C20—H20C	109.5
C10—C9—C11	119.3 (2)	H20A—C20—H20C	109.5
C8—C9—C11	122.9 (2)	H20B—C20—H20C	109.5
O2—C10—C9	121.7 (2)	O4—C21—H21A	109.5
O2—C10—C1	117.0 (2)	O4—C21—H21B	109.5
C9—C10—C1	121.3 (2)	H21A—C21—H21B	109.5
O1—C11—C12	119.8 (3)	O4—C21—H21C	109.5
O1—C11—C9	119.6 (2)	H21A—C21—H21C	109.5
C12—C11—C9	120.5 (2)	H21B—C21—H21C	109.5
C6—C1—C2—C3	−1.4 (4)	C8—C9—C11—O1	−176.6 (3)
C10—C1—C2—C3	179.9 (3)	C10—C9—C11—C12	−178.7 (2)
C1—C2—C3—C4	1.6 (5)	C8—C9—C11—C12	3.4 (4)
C2—C3—C4—C5	−0.7 (5)	O1—C11—C12—C13	−1.7 (4)
C3—C4—C5—C6	−0.4 (5)	C9—C11—C12—C13	178.3 (2)
C4—C5—C6—C1	0.5 (4)	C11—C12—C13—C14	179.7 (3)
C4—C5—C6—C7	179.5 (3)	C12—C13—C14—C19	178.6 (3)
C2—C1—C6—C5	0.4 (4)	C12—C13—C14—C15	−1.7 (5)
C10—C1—C6—C5	179.1 (3)	C19—C14—C15—C16	−0.4 (4)
C2—C1—C6—C7	−178.6 (3)	C13—C14—C15—C16	179.9 (2)
C10—C1—C6—C7	0.1 (4)	C20—O3—C16—C15	−8.0 (4)
C5—C6—C7—C8	−179.8 (3)	C20—O3—C16—C17	171.3 (3)
C1—C6—C7—C8	−0.9 (5)	C14—C15—C16—O3	−180.0 (3)
C6—C7—C8—C9	−0.2 (5)	C14—C15—C16—C17	0.8 (4)
C7—C8—C9—C10	2.0 (4)	C21—O4—C17—C18	6.1 (4)
C7—C8—C9—C11	179.9 (3)	C21—O4—C17—C16	−174.0 (3)
C8—C9—C10—O2	178.1 (2)	O3—C16—C17—O4	−0.3 (4)
C11—C9—C10—O2	0.0 (4)	C15—C16—C17—O4	179.0 (2)
C8—C9—C10—C1	−2.7 (4)	O3—C16—C17—C18	179.6 (3)
C11—C9—C10—C1	179.2 (2)	C15—C16—C17—C18	−1.0 (4)
C6—C1—C10—O2	−179.0 (2)	O4—C17—C18—C19	−179.1 (3)
C2—C1—C10—O2	−0.3 (4)	C16—C17—C18—C19	0.9 (4)
C6—C1—C10—C9	1.8 (4)	C15—C14—C19—C18	0.3 (4)
C2—C1—C10—C9	−179.6 (2)	C13—C14—C19—C18	180.0 (3)
C10—C9—C11—O1	1.3 (4)	C17—C18—C19—C14	−0.6 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1	0.82	1.75	2.482 (3)	148
C7—H7···O3i	0.93	2.57	3.368 (4)	144
C7—H7···O4i	0.93	2.59	3.445 (4)	152
C18—H18···O2ii	0.93	2.43	3.333 (4)	165

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2AO1	0.82	1.75	2.482(3)	148
C7H7O3i	0.93	2.57	3.368(4)	144
C7H7O4i	0.93	2.59	3.445(4)	152
C18H18O2ii	0.93	2.43	3.333(4)	165

Symmetry codes: (i) ; (ii) .