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

Vasanthi, R.; Reuben Jonathan, D.; Elizhlarasi, K.S.; Revathi, B.K.; Usha, G.

doi:10.1107/S1600536814023368

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1202-o1203

doi:10.1107/S1600536814023368

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

R. Vasanthi,^a D. Reuben Jonathan,^b K. S. Elizhlarasi,^a B. K. Revathi ^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 G. Smith, Queensland University of Technology, Australia (Received 26 September 2014; accepted 23 October 2014; online 29 October 2014)

In the title compound, C₁₇H₁₆O₄, the dihedral angle between the benzene rings is 21.22 (1)° and the mean plane of the prop-2-en-1-one group makes dihedral angles of 10.60 (1) and 11.28 (1)°, respectively, with those of the hydroxyphenyl and ethoxyphenyl rings. The ethoxy substituent forms a dihedral angle of 88.79 (2)° with the the prop-2-en-1-one group, which is found to be slightly twisted. In the crystal, phenolic O—H⋯O hydrogen bonds to the carbonyl O atom form a two-dimensional supramolecular network structure lying parallel to (010).

Keywords: crystal structure; prop-2-en-1-one; hydrogen bonding,.

CCDC reference: 1030607

1. Related literature

For the biological activity of chalcone derivatives, see: Nowakowska (2007 ); Ram et al. (2000 ); Khatib et al. (2005 ); Papo & Shai (2003 ). For related structures, see: Jasinski et al. (2011 ); Sathya et al. (2014 ); Joothamongkhon et al. (2010 ); Horkaew et al. (2010 ). For the synthesis, see: Sidharthan et al. (2012 ); Chitra et al. (2013 ); Sathya et al. (2014).

2. Experimental

2.1. Crystal data

C₁₇H₁₆O₄
M_r = 284.30
Orthorhombic, P b c a
a = 16.3670 (4) Å
b = 10.5512 (3) Å
c = 16.6153 (4) Å
V = 2869.32 (13) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 293 K
0.22 × 0.21 × 0.19 mm

2.2. Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2004 ) T_min = 0.970, T_max = 0.985
14416 measured reflections
3592 independent reflections
2619 reflections with I > 2σ(I)
R_int = 0.028

2.3. Refinement

R[F² > 2σ(F²)] = 0.058
wR(F²) = 0.215
S = 0.72
3592 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 0.74 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.82	2.25	2.958 (2)	145
O3—H3A⋯O4ⁱⁱ	0.82	1.95	2.766 (2)	171
Symmetry codes: (i) $[x, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ .

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 1030607

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536814023368/zs2316sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023368/zs2316Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023368/zs2316Isup3.cml

checkCIF report

Comment top

Chalcones belonging to the flavonoid family constitute an important group of natural products due to their unforseen pharmacological potential. Chemically they consist of open-chain flavonoids in which the two aromatic rings are joined by a three-carbon α,β-unsaturated carbonyl system. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using the compounds or chalcone-rich plant extracts as drugs or food preservatives. Chalcones have been reported to possess many exciting activities which include anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, anti-tumor and anticancer (Nowakowska, 2007). A number of chalcones having hydroxy or alkoxy groups in different position have been observed to possess vasodilatory (Ram et al., 2000), antimitotic (Khatib et al., 2005) and antimalarial activities (Papo & Shai, 2003). The crystal structures of closely related chalcones, viz., (E)-3-(4-ethoxyphenyl)-1-(2-hydroxyphenyl)prop-2-en-one (Horkaew et al., 2010) (Z)-3-(anthracen-9-yl)-1-(2-ethoxyphenyl)prop-2-en-one (Joothamongkhon et al., 2010) have been reported. The enormous research potentials of this group of compounds prompted us to synthesize an analogous compound, the chalcone derivative C₁₇H₁₆O₄ and we report the crystal structure in this communication.

In the title compound, the C—C bond lengths of the hydroxyphenyl and ethoxyphenyl rings are in the range of 1.376 (3)–1.398 (3)Å and 1.366 (3)–1.408 (3) Å, respectively, and are in good agreement with similar reported values [1.374 (3)–1.389 (3) Å and 1.369 (3)–1.401 (3) Å] (Sathya et al., 2014). The C—O bond lengths 1.354 (2)–1.450 (3)Å and 1.237 (2)Å, respectively, indicate the single and double bond characters and are comparable with literature values. The bond angles C9—C10—C11 [118.40 (15)°], C5—C7—C9 [127.10 (19)°] are comparable with those in similar reported structure (Sathya et al., 2014; Jasinski et al., 2011). The prop-2-en-1-one group is twisted slightly with O4—C10—C11—C12 and C7—C9—C10—O4 torsion angles of -10.8 (3) and -14.2 (3)°, respectively, and are comparable with those in similar reported structures (Sathya et al., 2014; Jasinski et al., 2011). The torsion angle C1—O2—C17—C1 [76.2 (3)°] indicates that the ethoxy group is in a +synclinal (+sc) orientation with respect to the benzene ring. The dihedral angle between the benzene rings is 21.22 (1)°. The prop-2-en-one group makes dihedral angles of 10.60 (1) and 11.28 (1)° with the hydroxyphenyl and ethoxyphenyl rings, respectively. The ethoxy substituent forms a dihedral angle of 88.79 (2)° with the prop-2-en-one group. The molecular conformation is stabilized by interamolecular O1—H···O2 and C7—H···O4 interactions (Table 1).

In the crystal packing (Fig. 2), the molecule are linked through hydroxyl O1—H···O4ⁱ and O3—H···O4ⁱⁱ hydrogen bonds to the carbonyl O-atom acceptor (Table 1). Atom O4 acts as a tricentre being involved also in the previously mentioned intramolecular interaction with C7—H7. The overall structure is a two-dimensional supramolecular network lying parallel to (010).

Related literature top

For the biological activity of chalcone derivatives, see: Nowakowska (2007); Ram et al. (2000); Khatib et al. (2005); Papo & Shai (2003). For related structures, see: Jasinski et al. (2011); Sathya et al. (2014); Joothamongkhon et al. (2010); Horkaew et al. (2010). For the synthesis, see: Sidharthan et al. (2012); Chitra et al. (2013); Sathya et al. (2014).

Experimental top

This is the acid catalyzed Claisen-Schmidt reaction and the procedure (Sidharthan et al., 2012; Chitra et al., 2013; Sathya et al., 2014) adopted in the synthesis of the typical chalcone diol is represented here. Dry HCl gas was passed for one hour through a well cooled and stirred solution of 4-hydroxyacetophenone (0.05 mol) and 4-hydroxy-3-ethoxybenzaldehyde (0.05 mol) in 120 mL of absolute alcohol in a 250 mL round-bottomed flask. A wine red coloured solution was formed. On addition of a sufficient quantity of ice cold water, a yellow precipitate of (2E)-3-(4-hydroxy-3-ethoxyphenyl)-1-(4-hydroxyphenyl)prop-2-en -1-one was formed, which was filtered, then washed with double distilled water and finally allowed to dry. The dried product was re-crystallized from hot ethanol: yield 80%.

Computing details top

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: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

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

Fig. 2. The packing of the molecules in the unit cell. Non-associative H-atoms are omitted and dashed lines indicate hydrogen bonds.

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

Crystal data top

C₁₇H₁₆O₄	F(000) = 1200
M_r = 284.30	D_x = 1.316 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3592 reflections
a = 16.3670 (4) Å	θ = 2.5–28.4°
b = 10.5512 (3) Å	µ = 0.09 mm⁻¹
c = 16.6153 (4) Å	T = 293 K
V = 2869.32 (13) Å³	Block, colourless
Z = 8	0.22 × 0.21 × 0.19 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3592 independent reflections
Radiation source: fine-focus sealed tube	2619 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω and ϕ scan	θ_max = 28.4°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −21→21
T_min = 0.970, T_max = 0.985	k = −11→14
14416 measured reflections	l = −21→22

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)] = 0.058	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.215	H-atom parameters constrained
S = 0.72	w = 1/[σ²(F_o²) + (0.189P)² + 2.3286P] where P = (F_o² + 2F_c²)/3
3592 reflections	(Δ/σ)_max < 0.001
190 parameters	Δρ_max = 0.74 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₁₇H₁₆O₄	V = 2869.32 (13) Å³
M_r = 284.30	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 16.3670 (4) Å	µ = 0.09 mm⁻¹
b = 10.5512 (3) Å	T = 293 K
c = 16.6153 (4) Å	0.22 × 0.21 × 0.19 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	3592 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2004)	2619 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.985	R_int = 0.028
14416 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.058	0 restraints
wR(F²) = 0.215	H-atom parameters constrained
S = 0.72	Δρ_max = 0.74 e Å⁻³
3592 reflections	Δρ_min = −0.43 e Å⁻³
190 parameters

Special details top

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.

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 > 2sigma(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
C8	0.4080 (2)	1.4090 (4)	0.5257 (2)	0.0948 (11)
H8A	0.4638	1.3812	0.5246	0.142*
H8B	0.4060	1.4969	0.5404	0.142*
H8C	0.3841	1.3980	0.4734	0.142*
C1	0.22651 (13)	1.3374 (2)	0.52630 (13)	0.0481 (5)
C2	0.14997 (13)	1.39834 (19)	0.52749 (12)	0.0459 (5)
C3	0.09113 (13)	1.3644 (2)	0.47328 (13)	0.0519 (5)
H3	0.0402	1.4036	0.4748	0.062*
C4	0.10695 (12)	1.2720 (2)	0.41605 (12)	0.0464 (5)
H4	0.0662	1.2491	0.3798	0.056*
C5	0.18244 (11)	1.21328 (18)	0.41214 (11)	0.0405 (4)
C6	0.24215 (12)	1.2466 (2)	0.46881 (13)	0.0491 (5)
H6	0.2929	1.2069	0.4676	0.059*
C7	0.19783 (11)	1.11972 (18)	0.34958 (11)	0.0405 (4)
H7	0.1538	1.0987	0.3169	0.049*
C9	0.26765 (11)	1.0613 (2)	0.33418 (12)	0.0424 (4)
H9	0.3122	1.0779	0.3673	0.051*
C10	0.27837 (10)	0.97178 (17)	0.26748 (11)	0.0353 (4)
C11	0.36197 (10)	0.93496 (16)	0.24468 (10)	0.0331 (4)
C12	0.37395 (11)	0.83378 (18)	0.19164 (12)	0.0404 (4)
H12	0.3289	0.7928	0.1695	0.048*
C13	0.45150 (11)	0.79391 (19)	0.17169 (12)	0.0439 (5)
H13	0.4586	0.7265	0.1363	0.053*
C14	0.51931 (10)	0.85457 (17)	0.20461 (11)	0.0369 (4)
C15	0.50858 (11)	0.95616 (18)	0.25631 (12)	0.0388 (4)
H15	0.5537	0.9978	0.2777	0.047*
C16	0.43087 (11)	0.99521 (17)	0.27588 (11)	0.0383 (4)
H16	0.4241	1.0634	0.3107	0.046*
C17	0.36220 (17)	1.3339 (3)	0.58491 (17)	0.0685 (7)
H17A	0.3649	1.2449	0.5706	0.082*
H17B	0.3866	1.3443	0.6377	0.082*
O1	0.13388 (11)	1.48915 (16)	0.58349 (10)	0.0614 (5)
H1	0.1742	1.4996	0.6120	0.092*
O2	0.27758 (11)	1.3744 (2)	0.58724 (11)	0.0693 (5)
O3	0.59416 (8)	0.81036 (15)	0.18410 (10)	0.0521 (4)
H3A	0.6294	0.8522	0.2071	0.078*
O4	0.21879 (8)	0.92718 (14)	0.23142 (9)	0.0459 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C8	0.073 (2)	0.102 (3)	0.109 (3)	−0.0156 (18)	0.0008 (18)	−0.020 (2)
C1	0.0428 (10)	0.0523 (11)	0.0490 (11)	0.0000 (8)	0.0078 (8)	−0.0092 (8)
C2	0.0484 (11)	0.0444 (9)	0.0447 (10)	0.0038 (8)	0.0164 (8)	0.0003 (8)
C3	0.0447 (11)	0.0565 (12)	0.0546 (12)	0.0179 (9)	0.0094 (9)	0.0036 (9)
C4	0.0383 (10)	0.0543 (11)	0.0468 (11)	0.0080 (8)	0.0016 (8)	0.0021 (9)
C5	0.0352 (9)	0.0435 (9)	0.0430 (10)	0.0025 (7)	0.0056 (7)	0.0001 (7)
C6	0.0351 (9)	0.0587 (12)	0.0536 (12)	0.0053 (8)	0.0009 (8)	−0.0135 (9)
C7	0.0327 (8)	0.0458 (9)	0.0429 (10)	0.0003 (7)	−0.0004 (7)	−0.0022 (7)
C9	0.0291 (8)	0.0559 (11)	0.0423 (10)	0.0000 (7)	−0.0010 (7)	−0.0087 (8)
C10	0.0264 (8)	0.0425 (9)	0.0370 (9)	−0.0010 (6)	0.0000 (6)	0.0016 (7)
C11	0.0265 (8)	0.0395 (8)	0.0334 (8)	−0.0017 (6)	−0.0007 (6)	−0.0007 (6)
C12	0.0300 (8)	0.0465 (10)	0.0447 (10)	−0.0037 (7)	−0.0052 (7)	−0.0093 (7)
C13	0.0347 (9)	0.0460 (9)	0.0510 (11)	0.0021 (7)	−0.0030 (7)	−0.0160 (8)
C14	0.0266 (8)	0.0411 (8)	0.0428 (9)	0.0009 (6)	0.0008 (6)	0.0003 (7)
C15	0.0262 (8)	0.0459 (9)	0.0444 (10)	−0.0062 (7)	−0.0030 (7)	−0.0063 (7)
C16	0.0302 (9)	0.0414 (9)	0.0433 (10)	−0.0036 (7)	0.0007 (7)	−0.0081 (7)
C17	0.0640 (16)	0.0714 (16)	0.0699 (16)	0.0077 (12)	−0.0186 (12)	−0.0210 (13)
O1	0.0625 (10)	0.0616 (9)	0.0600 (10)	0.0136 (8)	0.0132 (8)	−0.0155 (7)
O2	0.0556 (10)	0.0857 (12)	0.0666 (11)	0.0044 (9)	−0.0012 (8)	−0.0341 (10)
O3	0.0292 (7)	0.0553 (8)	0.0719 (10)	0.0039 (6)	0.0018 (6)	−0.0147 (7)
O4	0.0266 (6)	0.0603 (9)	0.0508 (8)	−0.0045 (6)	−0.0024 (5)	−0.0078 (6)

Geometric parameters (Å, º) top

C8—C17	1.469 (5)	C9—H9	0.9300
C8—H8A	0.9600	C10—O4	1.237 (2)
C8—H8B	0.9600	C10—C11	1.472 (2)
C8—H8C	0.9600	C11—C16	1.394 (2)
C1—O2	1.370 (3)	C11—C12	1.398 (2)
C1—C6	1.377 (3)	C12—C13	1.378 (3)
C1—C2	1.408 (3)	C12—H12	0.9300
C2—O1	1.361 (2)	C13—C14	1.393 (3)
C2—C3	1.366 (3)	C13—H13	0.9300
C3—C4	1.387 (3)	C14—O3	1.354 (2)
C3—H3	0.9300	C14—C15	1.385 (3)
C4—C5	1.384 (3)	C15—C16	1.376 (3)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.402 (3)	C16—H16	0.9300
C5—C7	1.455 (3)	C17—O2	1.450 (3)
C6—H6	0.9300	C17—H17A	0.9700
C7—C9	1.323 (3)	C17—H17B	0.9700
C7—H7	0.9300	O1—H1	0.8200
C9—C10	1.467 (3)	O3—H3A	0.8200

C17—C8—H8A	109.5	O4—C10—C9	121.10 (16)
C17—C8—H8B	109.5	O4—C10—C11	120.50 (16)
H8A—C8—H8B	109.5	C9—C10—C11	118.40 (15)
C17—C8—H8C	109.5	C16—C11—C12	117.97 (16)
H8A—C8—H8C	109.5	C16—C11—C10	122.39 (16)
H8B—C8—H8C	109.5	C12—C11—C10	119.61 (15)
O2—C1—C6	126.71 (19)	C13—C12—C11	120.93 (16)
O2—C1—C2	113.72 (18)	C13—C12—H12	119.5
C6—C1—C2	119.5 (2)	C11—C12—H12	119.5
O1—C2—C3	119.90 (19)	C12—C13—C14	119.96 (17)
O1—C2—C1	120.2 (2)	C12—C13—H13	120.0
C3—C2—C1	119.88 (18)	C14—C13—H13	120.0
C2—C3—C4	120.31 (19)	O3—C14—C15	122.50 (16)
C2—C3—H3	119.8	O3—C14—C13	117.62 (17)
C4—C3—H3	119.8	C15—C14—C13	119.88 (16)
C5—C4—C3	120.91 (19)	C16—C15—C14	119.71 (16)
C5—C4—H4	119.5	C16—C15—H15	120.1
C3—C4—H4	119.5	C14—C15—H15	120.1
C4—C5—C6	118.62 (18)	C15—C16—C11	121.54 (16)
C4—C5—C7	119.44 (18)	C15—C16—H16	119.2
C6—C5—C7	121.93 (17)	C11—C16—H16	119.2
C1—C6—C5	120.71 (19)	O2—C17—C8	110.3 (3)
C1—C6—H6	119.6	O2—C17—H17A	109.6
C5—C6—H6	119.6	C8—C17—H17A	109.6
C9—C7—C5	127.10 (18)	O2—C17—H17B	109.6
C9—C7—H7	116.4	C8—C17—H17B	109.6
C5—C7—H7	116.4	H17A—C17—H17B	108.1
C7—C9—C10	123.31 (17)	C2—O1—H1	109.5
C7—C9—H9	118.3	C1—O2—C17	118.63 (17)
C10—C9—H9	118.3	C14—O3—H3A	109.5

O2—C1—C2—O1	2.9 (3)	O4—C10—C11—C16	171.05 (18)
C6—C1—C2—O1	−179.4 (2)	C9—C10—C11—C16	−9.5 (3)
O2—C1—C2—C3	−175.8 (2)	O4—C10—C11—C12	−10.8 (3)
C6—C1—C2—C3	1.9 (3)	C9—C10—C11—C12	168.66 (18)
O1—C2—C3—C4	−179.95 (19)	C16—C11—C12—C13	0.8 (3)
C1—C2—C3—C4	−1.3 (3)	C10—C11—C12—C13	−177.40 (18)
C2—C3—C4—C5	−0.6 (3)	C11—C12—C13—C14	0.1 (3)
C3—C4—C5—C6	1.8 (3)	C12—C13—C14—O3	178.93 (19)
C3—C4—C5—C7	−177.92 (19)	C12—C13—C14—C15	−1.1 (3)
O2—C1—C6—C5	176.6 (2)	O3—C14—C15—C16	−178.90 (18)
C2—C1—C6—C5	−0.7 (3)	C13—C14—C15—C16	1.1 (3)
C4—C5—C6—C1	−1.1 (3)	C14—C15—C16—C11	−0.1 (3)
C7—C5—C6—C1	178.6 (2)	C12—C11—C16—C15	−0.8 (3)
C4—C5—C7—C9	175.3 (2)	C10—C11—C16—C15	177.37 (18)
C6—C5—C7—C9	−4.5 (3)	C6—C1—O2—C17	12.3 (4)
C5—C7—C9—C10	−177.43 (18)	C2—C1—O2—C17	−170.2 (2)
C7—C9—C10—O4	−14.2 (3)	C8—C17—O2—C1	76.2 (3)
C7—C9—C10—C11	166.32 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	2.25	2.958 (2)	145
O3—H3A···O4ⁱⁱ	0.82	1.95	2.766 (2)	171
C7—H7···O4	0.93	2.53	2.846 (2)	100

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) x+1/2, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.82	2.25	2.958 (2)	145
O3—H3A···O4ⁱⁱ	0.82	1.95	2.766 (2)	171
C7—H7···O4	0.93	2.53	2.846 (2)	100.

Symmetry codes: (i) x, −y+5/2, z+1/2; (ii) x+1/2, y, −z+1/2.

Acknowledgements

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

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Volume 70| Part 11| November 2014| Pages o1202-o1203

doi:10.1107/S1600536814023368

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

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