(2E)-1-(2-Hydroxy­phen­yl)-3-(4-methoxy­phen­yl)prop-2-en-1-one

Geometric parameters of the title compound, C₁₆H₁₄O₃, a chalcone derivative, are in the usual ranges. The C=C double bond is trans configured. The mol­ecule is essentially planar (r.m.s. deviation for all non-H atoms = 0.066 Å). The mol­ecular conformation is stabilized by an O—H...O hydrogen bond.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.091
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           28.24
           From the CIF: _reflns_number_total               1624
           Count of symmetry unique reflns         1643
           Completeness (_total/calc)             98.84%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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S1. Comment

Chalcones are a class of naturally occurring compounds with wide spectrum of biological activities. Chalcones can be easily obtained from the aldol condensation of aromatic aldehydes and aromatic ketones. This class of compounds presents interesting biological properties such as cytotoxicity (Pandey et al., 2005) and antiherpes activity and antitumour activity (Conti, 2006) and may be useful for the chemotherapy of leishmaniasis among others (Lawrence et al., 2001). Chalcone derivatives are also used as antibiotics (Nielsen et al., 2005) and as anti malerials (Domínguez et al., 2005). A natural medicine genus Angelica is known to contain large number of naturally occurring chalcones (Sarker & Nahar, 2004). Chalcone derivatives are recognized for NLO properties and have good crystallization ability (Goto et al., 1991; Indira et al., 2002; Sarojini et al., 2006). Structures of few related chalcones viz., (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxy-3-methoxyphenyl)prop-2-en-1-one (Yathirajan, Mayekar, Narayana et al., 2007), (2E)-1-(2,4-dichlorophenyl)-3-(2-hydroxyphenyl)prop-2-en-1-one (Yathirajan, Mayekar, Sarojini et al., 2007), 3-[4-(methylsulfanyl)phenyl]-1-(4-nitrophenyl)prop-2-en-1-one (Harrison et al., 2006), 2E)-1-(3-hydroxyphenyl)-3-(4-methylphenyl)prop-2-en-1-one (Butcher et al., 2007), (2E)-3-(biphenyl-4-yl)-1-(4-methoxyphenyl)prop-2-en-1-one (Fischer et al., 2007). In continuation of our studies on chalcones, a new chalcone is synthesized and its crystal structure is reported.

Geometric parameters of the title compound are in the usual ranges. The C—C double bond is trans configured. The molecule is essentially planar [r.m.s. deviation for all non-H atoms 0.066 Å]. The molecular conformation is stabilized by a O—H···O hydrogen bond.

Related literature

For related literature, see: Butcher et al. (2007); Conti (2006); Domínguez et al. (2005); Fischer et al. (2007); Goto et al. (1991); Harrison et al. (2006); Indira et al. (2002); Lawrence et al. (2001); Nielsen et al. (2005); Pandey et al. (2005); Sarker & Nahar (2004); Sarojini et al. (2006); Yathirajan, Mayekar, Narayana et al. (2007); Yathirajan, Mayekar, Sarojini et al. (2007).

S2. Experimental

To a solution of 2-hydroxyacetophenone (1.36 g, 0.01 mol) and 4-methoxybenzaldehyde (1.36 g, 0.01 mol) in 25 ml e thanol, 50% KOH (2.5 ml) was added at 273 K. The mixture was stirred overnight at room temperature and then poured onto ice water. The pH of this mixture was adjusted to 3–4 with 2 M HCl aqueous solution. A yellow precipitate was collected by filtration and purified by recrystallization in ethanol. The single crystals were grown from acetone by slow evaporation method [m.p.: 343–348 K]. Analysis for C₁₆H₁₄O₃: Found (Calculated): C 75.63 (75.57), H 5.57% (5.55%).

S3. Refinement

All H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 U_eq(C) or U(H) = 1.5 U_eq(C_methyl)] using a riding model with C—H = 0.95 Å or 0.98 Å for C_aromatic—H and C_methyl—H, respectively. The methyl group was allowed to rotate but not to tip. The hydroxyl H atom was freely refined.

Computing details

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures

	Fig. 1. Perspective view of the title compound with the atom numbering; displacement ellipsoids are at the 50% probability level.
	Fig. 2. The formation of the title compound.

(2E)-1-(2-Hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one

Crystal data

C16H14O3	F(000) = 536
Mr = 254.27	Dx = 1.329 Mg m^−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 15446 reflections
a = 25.4158 (15) Å	θ = 2.4–28.5°
b = 3.9662 (3) Å	µ = 0.09 mm^−1
c = 12.6046 (10) Å	T = 173 K
V = 1270.60 (16) Å^3	Block, yellow
Z = 4	0.41 × 0.37 × 0.36 mm

Data collection

Stoe IPDSII two-circle diffractometer	1503 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.079
Graphite monochromator	θmax = 28.2°, θmin = 2.3°
ω scans	h = −33→30
15514 measured reflections	k = −5→5
1624 independent reflections	l = −16→16

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.036	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0683P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.07	(Δ/σ)max < 0.001
1624 reflections	Δρmax = 0.17 e Å^−3
178 parameters	Δρmin = −0.17 e Å^−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.039 (7)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1	0.70169 (5)	0.6375 (4)	0.06637 (10)	0.0467 (3)
O2	0.79198 (6)	0.8269 (4)	0.00672 (10)	0.0481 (3)
H2O	0.7584 (14)	0.728 (7)	0.007 (3)	0.072 (8)*
O3	0.45867 (5)	0.2359 (3)	0.50165 (10)	0.0446 (3)
C1	0.70874 (7)	0.7522 (4)	0.15759 (14)	0.0370 (3)
C2	0.66887 (7)	0.7011 (4)	0.24036 (13)	0.0391 (4)
H2	0.6747	0.7888	0.3095	0.047*
C3	0.62427 (6)	0.5316 (4)	0.21939 (14)	0.0382 (4)
H3	0.6203	0.4512	0.1489	0.046*
C11	0.75813 (6)	0.9345 (4)	0.18289 (12)	0.0356 (3)
C12	0.79809 (7)	0.9589 (5)	0.10509 (13)	0.0386 (4)
C13	0.84559 (7)	1.1199 (5)	0.12829 (15)	0.0441 (4)
H13	0.8724	1.1336	0.0759	0.053*
C14	0.85365 (8)	1.2593 (4)	0.22747 (16)	0.0443 (4)
H14	0.8861	1.3679	0.2428	0.053*
C15	0.81458 (8)	1.2424 (5)	0.30568 (15)	0.0419 (4)
H15	0.8203	1.3404	0.3735	0.050*
C16	0.76767 (7)	1.0818 (5)	0.28309 (13)	0.0383 (4)
H16	0.7412	1.0702	0.3362	0.046*
C21	0.58134 (6)	0.4570 (4)	0.29245 (12)	0.0366 (3)
C22	0.53658 (7)	0.2907 (4)	0.25529 (13)	0.0396 (4)
H22	0.5349	0.2281	0.1826	0.048*
C23	0.49439 (7)	0.2138 (4)	0.32126 (14)	0.0391 (4)
H23	0.4641	0.1036	0.2938	0.047*
C24	0.49723 (7)	0.3013 (4)	0.42859 (13)	0.0370 (3)
C25	0.54173 (7)	0.4687 (5)	0.46771 (14)	0.0404 (4)
H25	0.5434	0.5307	0.5404	0.048*
C26	0.58315 (7)	0.5436 (4)	0.40097 (14)	0.0390 (4)
H26	0.6133	0.6550	0.4285	0.047*
C27	0.41243 (7)	0.0677 (5)	0.46422 (16)	0.0443 (4)
H27A	0.3965	0.1995	0.4068	0.066*
H27B	0.3872	0.0449	0.5226	0.066*
H27C	0.4219	−0.1565	0.4377	0.066*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0402 (6)	0.0677 (9)	0.0323 (5)	−0.0018 (6)	0.0003 (5)	−0.0049 (6)
O2	0.0422 (7)	0.0725 (8)	0.0294 (6)	−0.0016 (6)	0.0050 (5)	0.0000 (6)
O3	0.0356 (6)	0.0602 (8)	0.0381 (6)	−0.0025 (5)	0.0047 (5)	0.0017 (6)
C1	0.0348 (8)	0.0457 (8)	0.0305 (7)	0.0029 (6)	−0.0015 (6)	0.0016 (6)
C2	0.0342 (8)	0.0490 (9)	0.0341 (8)	0.0016 (6)	0.0005 (6)	0.0009 (7)
C3	0.0371 (8)	0.0445 (8)	0.0332 (7)	0.0016 (6)	0.0002 (6)	0.0001 (6)
C11	0.0326 (8)	0.0441 (8)	0.0300 (7)	0.0029 (6)	0.0006 (6)	0.0041 (6)
C12	0.0379 (8)	0.0479 (9)	0.0299 (7)	0.0029 (7)	0.0012 (6)	0.0053 (6)
C13	0.0376 (8)	0.0551 (10)	0.0396 (9)	−0.0004 (8)	0.0062 (7)	0.0082 (8)
C14	0.0371 (9)	0.0486 (9)	0.0473 (10)	−0.0032 (6)	−0.0028 (7)	0.0035 (7)
C15	0.0397 (8)	0.0475 (8)	0.0386 (8)	0.0010 (7)	−0.0032 (7)	−0.0008 (7)
C16	0.0376 (8)	0.0444 (8)	0.0329 (7)	0.0027 (6)	0.0007 (6)	0.0015 (6)
C21	0.0329 (7)	0.0426 (8)	0.0341 (8)	0.0014 (6)	−0.0012 (6)	0.0014 (6)
C22	0.0393 (8)	0.0475 (8)	0.0320 (7)	−0.0010 (7)	−0.0011 (6)	−0.0015 (7)
C23	0.0355 (8)	0.0458 (8)	0.0360 (8)	−0.0015 (6)	−0.0006 (7)	−0.0007 (7)
C24	0.0326 (8)	0.0436 (7)	0.0348 (8)	0.0026 (6)	0.0006 (6)	0.0027 (6)
C25	0.0350 (8)	0.0531 (9)	0.0329 (7)	0.0021 (7)	−0.0009 (6)	−0.0014 (7)
C26	0.0336 (8)	0.0477 (8)	0.0356 (7)	−0.0017 (6)	−0.0029 (6)	−0.0014 (7)
C27	0.0350 (8)	0.0500 (9)	0.0479 (9)	−0.0027 (7)	0.0048 (7)	0.0024 (8)

Geometric parameters (Å, º)

O1—C1	1.249 (2)	C14—H14	0.9500
O2—C12	1.355 (2)	C15—C16	1.381 (3)
O2—H2O	0.94 (3)	C15—H15	0.9500
O3—C24	1.370 (2)	C16—H16	0.9500
O3—C27	1.431 (2)	C21—C22	1.396 (2)
C1—C2	1.468 (2)	C21—C26	1.411 (2)
C1—C11	1.483 (2)	C22—C23	1.391 (2)
C2—C3	1.344 (2)	C22—H22	0.9500
C2—H2	0.9500	C23—C24	1.398 (2)
C3—C21	1.458 (2)	C23—H23	0.9500
C3—H3	0.9500	C24—C25	1.401 (2)
C11—C16	1.413 (2)	C25—C26	1.380 (2)
C11—C12	1.415 (2)	C25—H25	0.9500
C12—C13	1.397 (3)	C26—H26	0.9500
C13—C14	1.382 (3)	C27—H27A	0.9800
C13—H13	0.9500	C27—H27B	0.9800
C14—C15	1.401 (3)	C27—H27C	0.9800
C12—O2—H2O	105.4 (19)	C15—C16—H16	119.2
C24—O3—C27	117.02 (14)	C11—C16—H16	119.2
O1—C1—C2	120.31 (16)	C22—C21—C26	117.82 (15)
O1—C1—C11	119.78 (16)	C22—C21—C3	119.59 (14)
C2—C1—C11	119.90 (15)	C26—C21—C3	122.59 (15)
C3—C2—C1	120.75 (15)	C23—C22—C21	122.09 (15)
C3—C2—H2	119.6	C23—C22—H22	119.0
C1—C2—H2	119.6	C21—C22—H22	119.0
C2—C3—C21	127.47 (16)	C22—C23—C24	118.96 (16)
C2—C3—H3	116.3	C22—C23—H23	120.5
C21—C3—H3	116.3	C24—C23—H23	120.5
C16—C11—C12	117.90 (15)	O3—C24—C23	124.50 (15)
C16—C11—C1	122.63 (15)	O3—C24—C25	115.52 (14)
C12—C11—C1	119.46 (15)	C23—C24—C25	119.98 (16)
O2—C12—C13	117.86 (16)	C26—C25—C24	120.22 (15)
O2—C12—C11	121.71 (16)	C26—C25—H25	119.9
C13—C12—C11	120.44 (16)	C24—C25—H25	119.9
C14—C13—C12	120.02 (17)	C25—C26—C21	120.91 (16)
C14—C13—H13	120.0	C25—C26—H26	119.5
C12—C13—H13	120.0	C21—C26—H26	119.5
C13—C14—C15	120.82 (17)	O3—C27—H27A	109.5
C13—C14—H14	119.6	O3—C27—H27B	109.5
C15—C14—H14	119.6	H27A—C27—H27B	109.5
C16—C15—C14	119.26 (16)	O3—C27—H27C	109.5
C16—C15—H15	120.4	H27A—C27—H27C	109.5
C14—C15—H15	120.4	H27B—C27—H27C	109.5
C15—C16—C11	121.55 (16)
O1—C1—C2—C3	−0.2 (3)	C12—C11—C16—C15	−0.6 (2)
C11—C1—C2—C3	−178.87 (16)	C1—C11—C16—C15	178.22 (17)
C1—C2—C3—C21	179.38 (15)	C2—C3—C21—C22	176.94 (18)
O1—C1—C11—C16	177.43 (16)	C2—C3—C21—C26	−3.7 (3)
C2—C1—C11—C16	−3.9 (2)	C26—C21—C22—C23	0.8 (3)
O1—C1—C11—C12	−3.7 (3)	C3—C21—C22—C23	−179.84 (15)
C2—C1—C11—C12	174.95 (14)	C21—C22—C23—C24	−1.0 (3)
C16—C11—C12—O2	−179.46 (15)	C27—O3—C24—C23	−0.3 (2)
C1—C11—C12—O2	1.7 (2)	C27—O3—C24—C25	179.49 (15)
C16—C11—C12—C13	0.9 (2)	C22—C23—C24—O3	−179.20 (15)
C1—C11—C12—C13	−177.94 (15)	C22—C23—C24—C25	1.0 (3)
O2—C12—C13—C14	179.82 (17)	O3—C24—C25—C26	179.33 (15)
C11—C12—C13—C14	−0.6 (3)	C23—C24—C25—C26	−0.9 (3)
C12—C13—C14—C15	−0.2 (3)	C24—C25—C26—C21	0.7 (3)
C13—C14—C15—C16	0.5 (3)	C22—C21—C26—C25	−0.6 (3)
C14—C15—C16—C11	−0.1 (3)	C3—C21—C26—C25	−179.97 (15)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O1	0.94 (3)	1.66 (3)	2.529 (2)	151 (3)