Crystal structure of (E)-3-(2,4-di­meth­oxy­phen­yl)-1-(1-hy­droxy­naphthalen-2-yl)prop-2-en-1-one

Koh, D.

doi:10.1107/S1600536814018704

organic compounds

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ISSN: 2056-9890

Volume 70| Part 9| September 2014| Pages o1034-o1035

doi:10.1107/S1600536814018704

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Crystal structure of (E)-3-(2,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one

Dongsoo Koh ^a ^*

^aDepartment of Applied Chemistry, Dongduk Women's University, Seoul 136-714, Republic of Korea
^*Correspondence e-mail: dskoh@dongduk.ac.kr

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 7 August 2014; accepted 18 August 2014; online 23 August 2014)

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 methoxy 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 hydroxy group attached to the naphthalene ring is involved in an intramolecular 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 molecules into chains propagating along [010].

Keywords: crystal structure; chalcone; enone; benzochalcone; naphthalene.

CCDC reference: 1019819

1. 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 ).

2. Experimental

2.1. Crystal data

C₂₁H₁₈O₄
M_r = 334.35
Monoclinic, C 2/c
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

2.2. 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

2.3. Refinement

R[F² > 2σ(F²)] = 0.036
wR(F²) = 0.095
S = 1.05
2755 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.27 e Å⁻³

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) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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).

Supporting information

CCDC reference: 1019819

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814018704/su2770sup1.cif

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

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

checkCIF report

Synthesis and crystallization top

To a solution of 2,4-dimethoxybenzaldehyde (830 mg, 5 mmol) in 50 ml of ethanol was added 1-hydroxy-2-acetonaphthone (930 mg, 1 mmol) and the temperature was adjusted to around 275–276 K in an ice-bath. To the cooled reaction mixture 5 ml of 50% aqueous KOH solution was added, and the reaction mixture was stirred at room temperature for 24 h. This mixture was poured into iced water (100 ml) and was acidified (pH = 3) with 6 N HCl solution to give a precipitate. Filtration and washing with water afforded the crude solid of the title compound (520 mg, 31%). Recrystallization of the solid from ethanol gave single crystals crystals which were suitable for X-ray diffraction (M.p. 434–435 K).

Refinement details top

The OH H atom was located in a difference Fourier map and freely refined. The C-bound H atoms were placed in calculated positions and refined as riding atoms: C–H = 0.95 - 0.98 Å with U_iso(H) = 1.5U_eq(C-methyl) and = 1.2U_eq(C) for other H atoms.

Related literature top

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).

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title molecule, with atom labelling. The displacement ellipsoids are drawn at the 50% probability level
	Fig. 2. 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).

(E)-3-(2,4-Dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one top

Crystal data top

C₂₁H₁₈O₄	F(000) = 1408
M_r = 334.35	D_x = 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

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2755 independent reflections
Radiation source: Bruker ImuS	2505 reflections with I > 2σ(I)
Multi-layer optics monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 66.5°, θ_min = 4.3°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −16→16
T_min = 0.669, T_max = 0.753	k = −17→17
8800 measured reflections	l = −13→18

Refinement top

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(F_o²) + (0.049P)² + 1.958P] where P = (F_o² + 2F_c²)/3
2755 reflections	(Δ/σ)_max = 0.001
232 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.27 e Å⁻³

Crystal data top

C₂₁H₁₈O₄	V = 3242.2 (4) Å³
M_r = 334.35	Z = 8
Monoclinic, C2/c	Cu Kα radiation
a = 14.1148 (9) Å	µ = 0.77 mm⁻¹
b = 14.7489 (9) Å	T = 147 K
c = 15.5929 (10) Å	0.19 × 0.12 × 0.08 mm
β = 92.804 (4)°

Data collection top

Bruker Kappa APEX DUO CCD diffractometer	2755 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2007)	2505 reflections with I > 2σ(I)
T_min = 0.669, T_max = 0.753	R_int = 0.026
8800 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.036	0 restraints
wR(F²) = 0.095	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.15 e Å⁻³
2755 reflections	Δρ_min = −0.27 e Å⁻³
232 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, −y+1/2, −z+2; (ii) −x+1/2, y−1/2, −z+3/2.

Hydrogen-bond geometry (Å, º) top

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) −x+1/2, −y+1/2, −z+2; (ii) −x+1/2, y−1/2, −z+3/2.

References

Ahn, S., Lee, H.-J., Lim, Y. & Koh, D. (2013). Acta Cryst. E69, o666. CSD CrossRef IUCr Journals Google Scholar
Bruker (2007). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Fuchigami, T., Yamashita, Y., Haratake, M., Ono, M. & Yoshida, S. (2014). Bioorg. Med. Chem. 22, 2622–2628. Web of Science CrossRef CAS PubMed Google Scholar
Juvale, K., Stefan, K. & Wiese, M. (2013). Eur. J. Med. Chem. 67, 115–126. Web of Science CrossRef CAS PubMed Google Scholar
Kim, S.-J., Kim, C. G., Yun, S.-R., Kim, J.-K. & Jun, J.-G. (2014). Bioorg. Med. Chem. Lett. 24, 181–185. Web of Science CrossRef CAS PubMed Google Scholar
Lim, Y. & Koh, D. (2013). Acta Cryst. E69, o514. CSD CrossRef IUCr Journals Google Scholar
Mai, C. W., Yaebhoobi, M., Abd-Rhaman, N., Kang, Y. B. & Pichchika, M. R. (2014). Eur. J. Med. Chem. 77, 378–387. Web of Science CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shin, S. Y., Yoon, H., Hwang, D., Ahn, S., Kim, D.-W., Koh, D., Lee, Y. H. & Lim, Y. (2013). Bioorg. Med. Chem. 21, 7018–7024. Web of Science CrossRef CAS PubMed Google Scholar
Smit, F. J. & D'Na, D. D. (2014). Bioorg. Med. Chem. 22, 1128–1138. Web of Science CrossRef CAS PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 9| September 2014| Pages o1034-o1035

doi:10.1107/S1600536814018704

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Crystal structure of (E)-3-(2,4-di­meth­­oxy­phen­yl)-1-(1-hy­dr­oxy­naphthalen-2-yl)prop-2-en-1-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

References

organic compounds

Crystal structure of (E)-3-(2,4-dimethoxyphenyl)-1-(1-hydroxynaphthalen-2-yl)prop-2-en-1-one