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

In the title compound, C21H18O4, 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 6.60 (2)°. The meth-oxy groups on the benzene ring are essentially coplanar with the ring; the C-C-O-C torsion angles being 1.6 (2) and -177.1 (1)°. The hy-droxy group attached to the naphthalene ring is involved in an intra-molecular O-H⋯O hydrogen bond. The relative conformation of the two double bonds in the enone group is s-cisoid. In the crystal, weak C-H⋯O hydrogen bonds link the mol-ecules into chains propagating along [010].

Related literature

For the synthesis and biological properties of chalcone derivatives, see: Fuchigami et al. (2014 ▶); Kim et al. (2014 ▶); Mai et al. (2014 ▶); Smit & D′Na (2014 ▶). For details concerning benzochalcone derivatives, see: Juvale et al. (2013 ▶); Shin et al. (2013 ▶). For related structures, see: Ahn et al. (2013 ▶); Lim & Koh (2013 ▶).

Experimental

Crystal data

C21H18O4

M = 334.35

Monoclinic,

a = 14.1148 (9) Å

b = 14.7489 (9) Å

c = 15.5929 (10) Å

β = 92.804 (4)°

V = 3242.2 (4) Å3

Z = 8

Cu Kα radiation

μ = 0.77 mm−1

T = 147 K

0.19 × 0.12 × 0.08 mm

Data collection

Bruker Kappa APEX DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.669, T max = 0.753

8800 measured reflections

2755 independent reflections

2505 reflections with I > 2σ(I)

R int = 0.026

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.05

2755 reflections

232 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018704/su2770sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018704/su2770Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018704/su2770Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018704/su2770fig1.tif

The mol­ecular structure of the title mol­ecule, with atom labelling. The displacement ellipsoids are drawn at the 50% probability level

Click here for additional data file.

c . DOI: 10.1107/S1600536814018704/su2770fig2.tif

A partial view along the c axis of the crystal packing of the title compound. The C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1 for details; H atoms not involved in hydrogen bonding have been omitted for clarity).

CCDC reference: 1019819

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

C21H18O4	F(000) = 1408
Mr = 334.35	Dx = 1.370 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -C 2yc	Cell parameters from 4341 reflections
a = 14.1148 (9) Å	θ = 4.3–66.4°
b = 14.7489 (9) Å	µ = 0.77 mm−1
c = 15.5929 (10) Å	T = 147 K
β = 92.804 (4)°	Needle, orange
V = 3242.2 (4) Å3	0.19 × 0.12 × 0.08 mm
Z = 8

Bruker Kappa APEX DUO CCD diffractometer	2755 independent reflections
Radiation source: Bruker ImuS	2505 reflections with I > 2σ(I)
Multi-layer optics monochromator	Rint = 0.026
φ and ω scans	θmax = 66.5°, θmin = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→16
Tmin = 0.669, Tmax = 0.753	k = −17→17
8800 measured reflections	l = −13→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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.049P)2 + 1.958P] where P = (Fo2 + 2Fc2)/3
2755 reflections	(Δ/σ)max = 0.001
232 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.27 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	0.46036 (6)	0.17828 (6)	1.03233 (6)	0.0275 (2)
O2	0.19523 (6)	0.11183 (7)	0.85783 (7)	0.0345 (3)
O3	0.17234 (6)	−0.10692 (6)	0.63594 (6)	0.0266 (2)
O4	0.59612 (6)	0.24290 (6)	1.12130 (6)	0.0251 (2)
C1	0.51556 (9)	0.13224 (8)	0.98872 (8)	0.0210 (3)
C2	0.47622 (9)	0.07880 (8)	0.91593 (8)	0.0223 (3)
H2A	0.5173	0.0432	0.8832	0.027*
C3	0.38286 (9)	0.07983 (8)	0.89525 (8)	0.0213 (3)
H3A	0.3454	0.1177	0.9294	0.026*
C4	0.33198 (8)	0.03012 (8)	0.82693 (8)	0.0201 (3)
C5	0.23466 (9)	0.04712 (8)	0.80855 (8)	0.0226 (3)
C6	0.18419 (9)	0.00040 (9)	0.74439 (8)	0.0240 (3)
H6A	0.1190	0.0134	0.7324	0.029*
C7	0.22926 (9)	−0.06572 (9)	0.69744 (8)	0.0215 (3)
C8	0.32474 (9)	−0.08523 (9)	0.71418 (8)	0.0233 (3)
H8A	0.3557	−0.1302	0.6822	0.028*
C9	0.37358 (9)	−0.03735 (9)	0.77878 (8)	0.0222 (3)
H9A	0.4386	−0.0512	0.7908	0.027*
C10	0.09670 (11)	0.13031 (13)	0.84355 (13)	0.0516 (5)
H10A	0.0772	0.1763	0.8845	0.077*
H10B	0.0603	0.0746	0.8514	0.077*
H10C	0.0847	0.1528	0.7849	0.077*
C11	0.21279 (10)	−0.17857 (10)	0.58794 (9)	0.0339 (3)
H11A	0.1648	−0.2029	0.5466	0.051*
H11B	0.2349	−0.2269	0.6272	0.051*
H11C	0.2665	−0.1551	0.5571	0.051*
C12	0.61749 (8)	0.13277 (8)	1.01100 (8)	0.0193 (3)
C13	0.65294 (8)	0.18928 (8)	1.07709 (7)	0.0190 (3)
C14	0.75210 (8)	0.19224 (8)	1.10073 (7)	0.0193 (3)
C15	0.78867 (9)	0.25063 (8)	1.16617 (8)	0.0220 (3)
H15A	0.7470	0.2893	1.1952	0.026*
C16	0.88385 (9)	0.25175 (9)	1.18786 (8)	0.0251 (3)
H16A	0.9081	0.2916	1.2315	0.030*
C17	0.94584 (9)	0.19415 (9)	1.14567 (8)	0.0259 (3)
H17A	1.0117	0.1946	1.1616	0.031*
C18	0.91205 (9)	0.13741 (9)	1.08185 (8)	0.0246 (3)
H18A	0.9549	0.0991	1.0537	0.030*
C19	0.81422 (9)	0.13491 (8)	1.05720 (8)	0.0203 (3)
C20	0.77706 (9)	0.07710 (9)	0.99071 (8)	0.0228 (3)
H20A	0.8185	0.0382	0.9617	0.027*
C21	0.68288 (9)	0.07699 (8)	0.96827 (8)	0.0216 (3)
H21A	0.6599	0.0387	0.9229	0.026*
H4O	0.5337 (15)	0.2284 (14)	1.0965 (13)	0.059 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0193 (4)	0.0320 (5)	0.0312 (5)	0.0025 (4)	−0.0004 (4)	−0.0075 (4)
O2	0.0217 (5)	0.0350 (6)	0.0455 (6)	0.0096 (4)	−0.0106 (4)	−0.0179 (5)
O3	0.0286 (5)	0.0265 (5)	0.0242 (5)	−0.0033 (4)	−0.0046 (4)	−0.0038 (4)
O4	0.0202 (5)	0.0282 (5)	0.0267 (5)	0.0035 (4)	−0.0002 (4)	−0.0078 (4)
C1	0.0217 (6)	0.0192 (6)	0.0221 (6)	−0.0003 (5)	0.0010 (5)	0.0028 (5)
C2	0.0208 (6)	0.0227 (6)	0.0234 (6)	−0.0006 (5)	0.0006 (5)	−0.0010 (5)
C3	0.0229 (6)	0.0184 (6)	0.0224 (6)	−0.0006 (5)	−0.0001 (5)	0.0019 (5)
C4	0.0206 (6)	0.0188 (6)	0.0208 (6)	−0.0020 (5)	−0.0004 (5)	0.0037 (5)
C5	0.0228 (6)	0.0193 (6)	0.0254 (6)	0.0018 (5)	−0.0015 (5)	0.0003 (5)
C6	0.0207 (6)	0.0238 (7)	0.0270 (7)	0.0004 (5)	−0.0052 (5)	0.0009 (5)
C7	0.0251 (6)	0.0212 (6)	0.0179 (6)	−0.0055 (5)	−0.0019 (5)	0.0038 (5)
C8	0.0251 (6)	0.0234 (7)	0.0217 (6)	−0.0009 (5)	0.0046 (5)	0.0000 (5)
C9	0.0187 (6)	0.0255 (7)	0.0224 (6)	−0.0019 (5)	0.0012 (5)	0.0026 (5)
C10	0.0254 (8)	0.0575 (11)	0.0703 (12)	0.0182 (7)	−0.0136 (7)	−0.0335 (9)
C11	0.0387 (8)	0.0336 (8)	0.0291 (7)	−0.0041 (6)	−0.0006 (6)	−0.0114 (6)
C12	0.0201 (6)	0.0181 (6)	0.0197 (6)	−0.0007 (5)	−0.0004 (5)	0.0023 (5)
C13	0.0218 (6)	0.0168 (6)	0.0184 (6)	0.0011 (5)	0.0020 (5)	0.0020 (5)
C14	0.0209 (6)	0.0189 (6)	0.0178 (6)	−0.0012 (5)	−0.0009 (5)	0.0037 (5)
C15	0.0249 (6)	0.0215 (6)	0.0195 (6)	−0.0004 (5)	−0.0003 (5)	0.0008 (5)
C16	0.0266 (7)	0.0264 (7)	0.0218 (6)	−0.0045 (5)	−0.0051 (5)	0.0008 (5)
C17	0.0196 (6)	0.0320 (7)	0.0254 (6)	−0.0019 (5)	−0.0043 (5)	0.0039 (5)
C18	0.0204 (6)	0.0277 (7)	0.0255 (7)	0.0022 (5)	0.0000 (5)	0.0020 (5)
C19	0.0211 (6)	0.0207 (6)	0.0191 (6)	0.0001 (5)	−0.0004 (5)	0.0045 (5)
C20	0.0223 (6)	0.0224 (6)	0.0237 (6)	0.0030 (5)	0.0019 (5)	−0.0023 (5)
C21	0.0231 (6)	0.0204 (6)	0.0211 (6)	−0.0008 (5)	−0.0012 (5)	−0.0017 (5)

O1—C1	1.2580 (15)	C10—H10B	0.9800
O2—C5	1.3612 (16)	C10—H10C	0.9800
O2—C10	1.4239 (17)	C11—H11A	0.9800
O3—C7	1.3635 (15)	C11—H11B	0.9800
O3—C11	1.4299 (17)	C11—H11C	0.9800
O4—C13	1.3408 (15)	C12—C13	1.3987 (17)
O4—H4O	0.97 (2)	C12—C21	1.4258 (17)
C1—C12	1.4634 (17)	C13—C14	1.4306 (17)
C1—C2	1.4683 (18)	C14—C15	1.4133 (17)
C2—C3	1.3414 (18)	C14—C19	1.4152 (17)
C2—H2A	0.9500	C15—C16	1.3693 (18)
C3—C4	1.4537 (17)	C15—H15A	0.9500
C3—H3A	0.9500	C16—C17	1.4059 (19)
C4—C9	1.3936 (18)	C16—H16A	0.9500
C4—C5	1.4119 (17)	C17—C18	1.3680 (19)
C5—C6	1.3832 (18)	C17—H17A	0.9500
C6—C7	1.3919 (18)	C18—C19	1.4156 (17)
C6—H6A	0.9500	C18—H18A	0.9500
C7—C8	1.3902 (18)	C19—C20	1.4227 (18)
C8—C9	1.3858 (18)	C20—C21	1.3580 (17)
C8—H8A	0.9500	C20—H20A	0.9500
C9—H9A	0.9500	C21—H21A	0.9500
C10—H10A	0.9800
C5—O2—C10	117.97 (11)	O3—C11—H11A	109.5
C7—O3—C11	117.44 (10)	O3—C11—H11B	109.5
C13—O4—H4O	102.7 (12)	H11A—C11—H11B	109.5
O1—C1—C12	119.77 (11)	O3—C11—H11C	109.5
O1—C1—C2	119.13 (11)	H11A—C11—H11C	109.5
C12—C1—C2	121.11 (11)	H11B—C11—H11C	109.5
C3—C2—C1	120.65 (11)	C13—C12—C21	118.15 (11)
C3—C2—H2A	119.7	C13—C12—C1	119.35 (11)
C1—C2—H2A	119.7	C21—C12—C1	122.50 (11)
C2—C3—C4	127.94 (12)	O4—C13—C12	121.93 (11)
C2—C3—H3A	116.0	O4—C13—C14	116.85 (11)
C4—C3—H3A	116.0	C12—C13—C14	121.22 (11)
C9—C4—C5	116.67 (11)	C15—C14—C19	119.82 (11)
C9—C4—C3	123.29 (11)	C15—C14—C13	121.53 (11)
C5—C4—C3	120.00 (11)	C19—C14—C13	118.65 (11)
O2—C5—C6	123.18 (11)	C16—C15—C14	120.33 (12)
O2—C5—C4	115.50 (11)	C16—C15—H15A	119.8
C6—C5—C4	121.32 (12)	C14—C15—H15A	119.8
C5—C6—C7	119.80 (11)	C15—C16—C17	120.18 (12)
C5—C6—H6A	120.1	C15—C16—H16A	119.9
C7—C6—H6A	120.1	C17—C16—H16A	119.9
O3—C7—C8	124.91 (11)	C18—C17—C16	120.48 (12)
O3—C7—C6	114.42 (11)	C18—C17—H17A	119.8
C8—C7—C6	120.67 (11)	C16—C17—H17A	119.8
C9—C8—C7	118.31 (12)	C17—C18—C19	120.94 (12)
C9—C8—H8A	120.8	C17—C18—H18A	119.5
C7—C8—H8A	120.8	C19—C18—H18A	119.5
C8—C9—C4	123.21 (12)	C14—C19—C18	118.24 (11)
C8—C9—H9A	118.4	C14—C19—C20	119.51 (11)
C4—C9—H9A	118.4	C18—C19—C20	122.24 (11)
O2—C10—H10A	109.5	C21—C20—C19	120.66 (11)
O2—C10—H10B	109.5	C21—C20—H20A	119.7
H10A—C10—H10B	109.5	C19—C20—H20A	119.7
O2—C10—H10C	109.5	C20—C21—C12	121.79 (11)
H10A—C10—H10C	109.5	C20—C21—H21A	119.1
H10B—C10—H10C	109.5	C12—C21—H21A	119.1
O1—C1—C2—C3	0.91 (18)	C2—C1—C12—C21	−4.86 (18)
C12—C1—C2—C3	−179.00 (11)	C21—C12—C13—O4	−179.06 (10)
C1—C2—C3—C4	−178.69 (11)	C1—C12—C13—O4	0.41 (17)
C2—C3—C4—C9	9.1 (2)	C21—C12—C13—C14	0.81 (17)
C2—C3—C4—C5	−173.07 (12)	C1—C12—C13—C14	−179.73 (10)
C10—O2—C5—C6	1.6 (2)	O4—C13—C14—C15	−1.54 (17)
C10—O2—C5—C4	−178.52 (14)	C12—C13—C14—C15	178.59 (11)
C9—C4—C5—O2	178.52 (11)	O4—C13—C14—C19	178.34 (10)
C3—C4—C5—O2	0.59 (17)	C12—C13—C14—C19	−1.53 (17)
C9—C4—C5—C6	−1.56 (18)	C19—C14—C15—C16	−0.24 (18)
C3—C4—C5—C6	−179.48 (11)	C13—C14—C15—C16	179.64 (11)
O2—C5—C6—C7	−179.17 (12)	C14—C15—C16—C17	−0.57 (19)
C4—C5—C6—C7	0.91 (19)	C15—C16—C17—C18	0.90 (19)
C11—O3—C7—C8	3.18 (17)	C16—C17—C18—C19	−0.38 (19)
C11—O3—C7—C6	−177.12 (11)	C15—C14—C19—C18	0.74 (17)
C5—C6—C7—O3	−179.88 (11)	C13—C14—C19—C18	−179.15 (11)
C5—C6—C7—C8	−0.17 (19)	C15—C14—C19—C20	−179.25 (11)
O3—C7—C8—C9	179.82 (11)	C13—C14—C19—C20	0.86 (17)
C6—C7—C8—C9	0.13 (18)	C17—C18—C19—C14	−0.43 (18)
C7—C8—C9—C4	−0.87 (19)	C17—C18—C19—C20	179.56 (12)
C5—C4—C9—C8	1.56 (18)	C14—C19—C20—C21	0.52 (18)
C3—C4—C9—C8	179.41 (11)	C18—C19—C20—C21	−179.47 (12)
O1—C1—C12—C13	−4.21 (17)	C19—C20—C21—C12	−1.29 (19)
C2—C1—C12—C13	175.70 (11)	C13—C12—C21—C20	0.62 (18)
O1—C1—C12—C21	175.23 (11)	C1—C12—C21—C20	−178.83 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O1	0.97 (2)	1.59 (2)	2.499 (1)	155.1 (19)
C10—H10A···O1i	0.98	2.57	3.538 (2)	167
C11—H11B···O2ii	0.98	2.58	3.442 (2)	147

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4O⋯O1	0.97 (2)	1.59 (2)	2.499 (1)	155.1 (19)
C10—H10A⋯O1i	0.98	2.57	3.538 (2)	167
C11—H11B⋯O2ii	0.98	2.58	3.442 (2)	147

Symmetry codes: (i) ; (ii) .