Crystal structure of (2E)-1-(4-hy­droxy-3-meth­oxy­phen­yl)-3-(4-hy­droxy­phen­yl)prop-2-en-1-one

Sathya, S.; Reuben Jonathan, D.; Prathebha, K.; Jovita, J.; Usha, G.

doi:10.1107/S1600536814021953

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1158-o1159

doi:10.1107/S1600536814021953

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Crystal structure of (2E)-1-(4-hydroxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one

S. Sathya,^a D. Reuben Jonathan,^b K. Prathebha,^a J. Jovita ^a and G. Usha ^a ^*

^aPG and Research Department of Physics, Queen Mary's College, Chennai-4, Tamilnadu, India, and ^bDepartment of Chemistry, Madras Christian College, Chennai-59, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by A. J. Lough, University of Toronto, Canada (Received 11 July 2014; accepted 6 October 2014; online 15 October 2014)

In the title moleclue, C₁₆H₁₄O₄, the dihedral angle between the benzene rings is 16.1 (3)°. The methoxy group is essentially coplanar with the benzene ring to which it is attached, with a C—O—C C torsion angle of 5.5 (9)°. In the crystal, molecules are linked by O—H⋯O and bifurcated O—H⋯(O,O) hydrogen bonds, forming a three-dimensional network. The structure was refined as a two-component inversion twin.

Keywords: crystal structure; prop-2-en-1-one; chalcones; biological activity; hydrogen bonding.

CCDC reference: 1011152

1. Related literature

For the biological activity of chalcones, see: Prasad et al. (2008 ); Won et al. (2005 ); Yu et al. (1982 ); Ram et al. (2000 ); Khatib et al. (2005 ); Papo & Shai (2003 ). For related structures, see: Jasinski et al. (2011 ); Sathya et al. (2014 ). For the synthesis, see: Sidharthan et al. (2012 ); Chitra et al. (2013 ); Jasmine Francis et al. (2014 ).

2. Experimental

2.1. Crystal data

C₁₆H₁₄O₄
M_r = 270.27
Orthorhombic, P n a 2₁
a = 7.686 (16) Å
b = 28.346 (7) Å
c = 6.297 (12) Å
V = 1371.9 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.35 × 0.30 × 0.25 mm

2.2. Data collection

Bruker Kappa APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.968, T_max = 0.977
6436 measured reflections
2996 independent reflections
1928 reflections with I > 2σ(I)
R_int = 0.055
Standard reflections: ?

2.3. Refinement

R[F² > 2σ(F²)] = 0.077
wR(F²) = 0.244
S = 1.07
2996 reflections
186 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.30 e Å⁻³
Absolute structure: refined as an inversion twin (1113 Friedel pairs)
Absolute structure parameter: −2 (4)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O3ⁱ	0.82	2.59	3.060 (6)	118
O2—H2A⋯O4ⁱ	0.82	2.02	2.833 (7)	172
O3—H3A⋯O1ⁱⁱ	0.82	1.87	2.618 (7)	151
Symmetry codes: (i) $[-x-{\script{1\over 2}}, y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+1]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Supporting information

CCDC reference: 1011152

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814021953/lh5720sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814021953/lh5720Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814021953/lh5720Isup3.cml

checkCIF report

Comment top

Chalcones constitute an important group of natural products due to their unforeseen pharmacological potential. Chemically, they consist of open chain flavanoids in which the two aromatic rings are joined by a three carbon alpha, beta unsaturated carbonyl system. The presence of a reactive alpha, beta unsaturated keto group in chalcones is mainly responsible for their antimicrobial activity (Prasad et al., 2008). In recent years a variety of chalcones have been reviewed for their cytotoxic, anticancer chemopreventive and mutagenic as well as antiviral, insecticidal and enzyme inhibitory properties (Won et al., 2005; Yu et al., 1982). A number of chalcones having hydroxy, alkoxy groups in different position have been reported to possess vasodilatory (Ram et al., 2000), antimitotic (Khatib et al., 2005), antimalarial activities (Papo et al., 2003). The enormous research potentials of these group of compounds motivated us to synthesize the title compound.

The molecular structure of the title compound is shown in Fig. 1. The bond lengths are comparable to literature values (Sathya et al., 2014; Jasinski et al., 2011). The C10—C9—C8 and C8—C7—C4 angles are slightly distorted compared to the values expected in terms of hybridization principles and this may be due to intra- and intermolecular steric interactions. In the crystal, molecules are linked by O—H···O and bifurcated O—H···(O,O) hydrogen bonds forming a three-dimensional network (Fig. 2 and Table 1).

Related literature top

For the biological activity of chalcones, see: Prasad et al. (2008); Won et al. (2005); Yu et al. (1982); Ram et al. (2000); Khatib et al. (2005); Papo & Shai (2003). For related structures, see: Jasinski et al. (2011); Sathya et al. (2014). For the synthesis, see: Sidharthan et al. (2012); Chitra et al. (2013); Jasmin Francis et al. (2014).

Experimental top

This acid catalyzed Claisen–Schmidt reaction and the procedure (Sidharthan et al., 2012, Chitra et al., 2013, Jasmine Francis et al.,2014) adopted in the synthesis of the typical chalcone diol namely (2E)-1-(4-hydroxy-3- methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one is represented herein. Dry HCl gas was passed through a well cooled and stirred solution of 4-hydroxy-methoxyacetophenone (0.03 mol) and 4-hydroxybenzaldehyde (0.03 mol) in 125 mL of dry ethanol taken in a 250 mL round-bottomed flask for about one hour. Wine red coloured solution was formed to which ice cold water was added. The yellow coloured crystals of (2E)-1-(4-hydroxy-3-methoxyphenyl)-3- (4-hydroxyphenyl)prop-2-en-1-one which got separated was washed with double distilled water and re-crystallized from hot ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

Fig. 2. Part of the crystal structure with dashed lines indicating hydrogen bonds.

(2E)-1-(4-Hydroxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₆H₁₄O₄	D_x = 1.309 Mg m⁻³
M_r = 270.27	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pna2₁	Cell parameters from 2996 reflections
a = 7.686 (16) Å	θ = 1.4–28.6°
b = 28.346 (7) Å	µ = 0.09 mm⁻¹
c = 6.297 (12) Å	T = 293 K
V = 1371.9 (5) Å³	Block, yellow
Z = 4	0.35 × 0.30 × 0.25 mm
F(000) = 568

Data collection top

Bruker Kappa APEXII diffractometer	1928 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
ω and ϕ scans	θ_max = 28.6°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −10→7
T_min = 0.968, T_max = 0.977	k = −38→19
6436 measured reflections	l = −8→8
2996 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.077	w = 1/[σ²(F_o²) + (0.1225P)² + 0.7988P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.244	(Δ/σ)_max = 0.001
S = 1.07	Δρ_max = 0.33 e Å⁻³
2996 reflections	Δρ_min = −0.30 e Å⁻³
186 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: −2 (4)

Crystal data top

C₁₆H₁₄O₄	V = 1371.9 (5) Å³
M_r = 270.27	Z = 4
Orthorhombic, Pna2₁	Mo Kα radiation
a = 7.686 (16) Å	µ = 0.09 mm⁻¹
b = 28.346 (7) Å	T = 293 K
c = 6.297 (12) Å	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker Kappa APEXII diffractometer	2996 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1928 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.977	R_int = 0.055
6436 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.077	H-atom parameters constrained
wR(F²) = 0.244	Δρ_max = 0.33 e Å⁻³
S = 1.07	Δρ_min = −0.30 e Å⁻³
2996 reflections	Absolute structure: Refined as an inversion twin.
186 parameters	Absolute structure parameter: −2 (4)
1 restraint

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. Refined as a two-component inversion twin (1113 Friedel pairs).

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

	x	y	z	U_iso*/U_eq
O1	−0.3786 (6)	0.30979 (16)	−0.5710 (8)	0.0619 (14)
O2	−0.1472 (7)	0.59683 (14)	−0.4180 (10)	0.0668 (14)
H2A	−0.1936	0.6120	−0.5132	0.100*
O3	−0.0576 (6)	0.16926 (13)	0.0881 (8)	0.0509 (11)
H3A	−0.0369	0.1764	0.2118	0.076*
O4	−0.2259 (7)	0.15243 (14)	−0.2582 (7)	0.0554 (12)
C1	−0.1999 (8)	0.5514 (2)	−0.4288 (11)	0.0489 (14)
C2	−0.1264 (9)	0.5197 (2)	−0.2908 (11)	0.0532 (16)
H2	−0.0474	0.5303	−0.1897	0.064*
C3	−0.1667 (9)	0.4730 (2)	−0.2989 (11)	0.0543 (17)
H3	−0.1154	0.4522	−0.2031	0.065*
C4	−0.2855 (8)	0.4557 (2)	−0.4510 (11)	0.0477 (15)
C5	−0.3587 (9)	0.4886 (2)	−0.5881 (12)	0.0547 (17)
H5	−0.4368	0.4782	−0.6908	0.066*
C6	−0.3199 (9)	0.5359 (2)	−0.5777 (11)	0.0552 (17)
H6	−0.3734	0.5572	−0.6692	0.066*
C7	−0.3207 (8)	0.4055 (2)	−0.4780 (12)	0.0526 (17)
H7	−0.3885	0.3972	−0.5946	0.063*
C8	−0.2672 (8)	0.3700 (2)	−0.3556 (11)	0.0497 (16)
H8	−0.2055	0.3772	−0.2328	0.060*
C9	−0.3000 (8)	0.3208 (2)	−0.4035 (11)	0.0478 (14)
C10	−0.2331 (7)	0.2830 (2)	−0.2685 (11)	0.0400 (13)
C11	−0.1520 (8)	0.2909 (2)	−0.0730 (10)	0.0458 (15)
H11	−0.1373	0.3216	−0.0243	0.055*
C12	−0.0934 (8)	0.2536 (2)	0.0485 (11)	0.0470 (15)
H12	−0.0376	0.2595	0.1768	0.056*
C13	−0.1165 (8)	0.2079 (2)	−0.0180 (10)	0.0430 (14)
C14	−0.2036 (8)	0.1996 (2)	−0.2123 (9)	0.0406 (13)
C15	−0.2577 (8)	0.2362 (2)	−0.3315 (9)	0.0424 (14)
H15	−0.3132	0.2302	−0.4599	0.051*
C16	−0.3006 (10)	0.1410 (2)	−0.4595 (11)	0.0587 (18)
H16A	−0.3047	0.1073	−0.4757	0.088*
H16B	−0.2310	0.1543	−0.5708	0.088*
H16C	−0.4165	0.1535	−0.4673	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.064 (3)	0.060 (3)	0.062 (3)	−0.001 (2)	−0.022 (3)	0.010 (2)
O2	0.082 (4)	0.045 (3)	0.072 (3)	0.005 (2)	−0.019 (3)	−0.001 (3)
O3	0.061 (3)	0.046 (2)	0.045 (2)	−0.0050 (19)	−0.012 (2)	0.007 (2)
O4	0.077 (3)	0.040 (2)	0.049 (3)	−0.007 (2)	−0.010 (2)	0.001 (2)
C1	0.049 (3)	0.049 (3)	0.049 (3)	0.009 (3)	−0.001 (3)	0.000 (3)
C2	0.053 (4)	0.055 (4)	0.051 (4)	0.007 (3)	−0.013 (3)	0.002 (3)
C3	0.056 (4)	0.055 (4)	0.051 (4)	0.011 (3)	−0.014 (4)	0.006 (3)
C4	0.038 (3)	0.049 (3)	0.057 (4)	0.004 (2)	−0.002 (3)	0.009 (3)
C5	0.051 (4)	0.056 (4)	0.057 (4)	0.001 (3)	−0.019 (3)	0.008 (3)
C6	0.053 (4)	0.052 (4)	0.060 (4)	0.007 (3)	−0.009 (4)	0.015 (3)
C7	0.042 (4)	0.054 (4)	0.061 (4)	−0.001 (3)	−0.006 (3)	0.008 (3)
C8	0.046 (3)	0.049 (4)	0.054 (4)	−0.002 (3)	−0.005 (3)	0.007 (3)
C9	0.041 (3)	0.048 (4)	0.054 (4)	0.001 (2)	0.002 (3)	0.006 (3)
C10	0.025 (3)	0.049 (3)	0.046 (3)	−0.003 (2)	−0.001 (2)	0.001 (3)
C11	0.042 (3)	0.042 (3)	0.053 (4)	0.001 (2)	−0.004 (3)	−0.003 (3)
C12	0.043 (3)	0.052 (4)	0.046 (4)	−0.006 (2)	0.002 (3)	0.000 (3)
C13	0.038 (3)	0.050 (3)	0.041 (3)	−0.003 (2)	−0.001 (3)	0.004 (3)
C14	0.038 (3)	0.043 (3)	0.041 (3)	−0.005 (2)	0.002 (3)	0.003 (2)
C15	0.033 (3)	0.053 (4)	0.042 (3)	−0.002 (2)	−0.001 (2)	0.002 (2)
C16	0.064 (4)	0.059 (4)	0.053 (4)	−0.012 (3)	−0.008 (4)	−0.004 (3)

Geometric parameters (Å, º) top

O1—C9	1.256 (8)	C7—C8	1.331 (9)
O2—C1	1.351 (7)	C7—H7	0.9300
O2—H2A	0.8200	C8—C9	1.449 (9)
O3—C13	1.361 (7)	C8—H8	0.9300
O3—H3A	0.8200	C9—C10	1.462 (8)
O4—C14	1.378 (7)	C10—C15	1.396 (8)
O4—C16	1.429 (8)	C10—C11	1.398 (9)
C1—C2	1.372 (9)	C11—C12	1.381 (9)
C1—C6	1.387 (9)	C11—H11	0.9300
C2—C3	1.360 (9)	C12—C13	1.371 (8)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.412 (9)	C13—C14	1.414 (8)
C3—H3	0.9300	C14—C15	1.348 (8)
C4—C5	1.390 (9)	C15—H15	0.9300
C4—C7	1.459 (8)	C16—H16A	0.9600
C5—C6	1.375 (9)	C16—H16B	0.9600
C5—H5	0.9300	C16—H16C	0.9600
C6—H6	0.9300

C1—O2—H2A	109.5	O1—C9—C8	119.9 (6)
C13—O3—H3A	109.5	O1—C9—C10	118.4 (5)
C14—O4—C16	117.2 (5)	C8—C9—C10	121.6 (6)
O2—C1—C2	118.0 (6)	C15—C10—C11	117.5 (5)
O2—C1—C6	122.4 (6)	C15—C10—C9	118.9 (6)
C2—C1—C6	119.6 (6)	C11—C10—C9	123.5 (5)
C3—C2—C1	121.3 (6)	C12—C11—C10	120.8 (5)
C3—C2—H2	119.3	C12—C11—H11	119.6
C1—C2—H2	119.3	C10—C11—H11	119.6
C2—C3—C4	120.7 (6)	C13—C12—C11	120.7 (6)
C2—C3—H3	119.6	C13—C12—H12	119.6
C4—C3—H3	119.6	C11—C12—H12	119.6
C5—C4—C3	116.7 (6)	O3—C13—C12	124.5 (6)
C5—C4—C7	120.5 (6)	O3—C13—C14	116.6 (5)
C3—C4—C7	122.6 (5)	C12—C13—C14	118.9 (5)
C6—C5—C4	122.5 (6)	C15—C14—O4	126.3 (6)
C6—C5—H5	118.7	C15—C14—C13	119.9 (5)
C4—C5—H5	118.7	O4—C14—C13	113.8 (5)
C5—C6—C1	119.0 (6)	C14—C15—C10	122.1 (6)
C5—C6—H6	120.5	C14—C15—H15	118.9
C1—C6—H6	120.5	C10—C15—H15	118.9
C8—C7—C4	127.7 (7)	O4—C16—H16A	109.5
C8—C7—H7	116.1	O4—C16—H16B	109.5
C4—C7—H7	116.1	H16A—C16—H16B	109.5
C7—C8—C9	123.5 (7)	O4—C16—H16C	109.5
C7—C8—H8	118.2	H16A—C16—H16C	109.5
C9—C8—H8	118.2	H16B—C16—H16C	109.5

O2—C1—C2—C3	−176.8 (6)	O1—C9—C10—C11	−176.4 (6)
C6—C1—C2—C3	1.0 (10)	C8—C9—C10—C11	7.9 (9)
C1—C2—C3—C4	0.3 (10)	C15—C10—C11—C12	2.2 (8)
C2—C3—C4—C5	−0.6 (10)	C9—C10—C11—C12	179.2 (6)
C2—C3—C4—C7	174.4 (7)	C10—C11—C12—C13	−1.3 (9)
C3—C4—C5—C6	−0.4 (10)	C11—C12—C13—O3	177.6 (6)
C7—C4—C5—C6	−175.5 (7)	C11—C12—C13—C14	−0.8 (8)
C4—C5—C6—C1	1.7 (10)	C16—O4—C14—C15	5.5 (9)
O2—C1—C6—C5	175.8 (7)	C16—O4—C14—C13	−175.3 (5)
C2—C1—C6—C5	−2.0 (10)	O3—C13—C14—C15	−176.6 (5)
C5—C4—C7—C8	−176.8 (6)	C12—C13—C14—C15	1.9 (8)
C3—C4—C7—C8	8.5 (11)	O3—C13—C14—O4	4.1 (7)
C4—C7—C8—C9	−175.9 (6)	C12—C13—C14—O4	−177.3 (5)
C7—C8—C9—O1	2.0 (10)	O4—C14—C15—C10	178.2 (5)
C7—C8—C9—C10	177.6 (6)	C13—C14—C15—C10	−1.0 (9)
O1—C9—C10—C15	0.5 (9)	C11—C10—C15—C14	−1.1 (8)
C8—C9—C10—C15	−175.2 (5)	C9—C10—C15—C14	−178.2 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	2.59	3.060 (6)	118
O2—H2A···O4ⁱ	0.82	2.02	2.833 (7)	172
O3—H3A···O1ⁱⁱ	0.82	1.87	2.618 (7)	151

Symmetry codes: (i) −x−1/2, y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O3ⁱ	0.82	2.59	3.060 (6)	118.0
O2—H2A···O4ⁱ	0.82	2.02	2.833 (7)	172.0
O3—H3A···O1ⁱⁱ	0.82	1.87	2.618 (7)	150.6

Symmetry codes: (i) −x−1/2, y+1/2, z−1/2; (ii) x+1/2, −y+1/2, z+1.

Acknowledgements

The authors thank Professor D. Velmurugan, Centre for Advanced Study in Crystallography and Biophysics, University of Madras, for providing data collection and computer facilities.

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1158-o1159

doi:10.1107/S1600536814021953

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

Crystal structure of (2E)-1-(4-hy­dr­oxy-3-meth­­oxy­phen­yl)-3-(4-hy­dr­oxy­phen­yl)prop-2-en-1-one

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

Acknowledgements

References

organic compounds

Crystal structure of (2E)-1-(4-hydroxy-3-methoxyphenyl)-3-(4-hydroxyphenyl)prop-2-en-1-one