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

In the title moleclue, C16H14O4, the dihedral angle between the benzene rings is 16.1 (3)°. The meth-oxy 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, mol-ecules 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.

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 ▶).

Experimental

Crystal data

C16H14O4

M = 270.27

Orthorhombic,

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

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: ?

Refinement

R[F 2 > 2σ(F 2)] = 0.077

wR(F 2) = 0.244

S = 1.07

2996 reflections

186 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.30 e Å−3

Absolute structure: refined as an inversion twin (1113 Friedel pairs)

Absolute structure parameter: −2 (4)

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 ▶).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814021953/lh5720sup1.cif

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

Click here for additional data file.

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

Click here for additional data file.

. DOI: 10.1107/S1600536814021953/lh5720fig1.tif

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

Click here for additional data file.

. DOI: 10.1107/S1600536814021953/lh5720fig2.tif

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

CCDC reference: 1011152

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

C16H14O4	Dx = 1.309 Mg m−3
Mr = 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

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

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(Fo2) + (0.1225P)2 + 0.7988P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.244	(Δ/σ)max = 0.001
S = 1.07	Δρmax = 0.33 e Å−3
2996 reflections	Δρmin = −0.30 e Å−3
186 parameters	Absolute structure: Refined as an inversion twin.
1 restraint	Absolute structure parameter: −2 (4)

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).

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
O2H2AO3i	0.82	2.59	3.060(6)	118
O2H2AO4i	0.82	2.02	2.833(7)	172
O3H3AO1ii	0.82	1.87	2.618(7)	151

Symmetry codes: (i) ; (ii) .