(E)-1-(4-Meth­oxy­phen­yl)-3-(2,4,5-tri­meth­oxy­phen­yl)prop-2-en-1-one

Sunitha, V.M.; Naveen, S.; Dileep Kumar, A.; Ajay Kumar, K.; Lokanath, N.K.; Manivannan, V.; Manjunath, H.R.

doi:10.1107/S2414314616019350

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 12| December 2016| x161935

https://doi.org/10.1107/S2414314616019350

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access

(E)-1-(4-Methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one

V. M. Sunitha,^a,^b S. Naveen,^c A. Dileep Kumar,^d K. Ajay Kumar,^d N. K. Lokanath,^e ^* V. Manivannan ^b and H. R. Manjunath ^f ^*

^aDepartment of Physics, Shri Pillappa College of Engineering, Bengaluru 560 089, India, ^bDepartment of Physics, Prist University, Vallam, Tanjavur 513403, India, ^cInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^dDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, ^eDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, and ^fDepartment of Physics, Acharya Institute of Technology, Soldevanahalli, Bengaluru 560 107, India
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, manjunathhr@acharya.ac.in

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 30 November 2016; accepted 3 December 2016; online 13 December 2016)

In the title chalcone derivative, C₁₉H₂₀O₅, the dihedral angle between the planes of the benzene rings is 3.97 (8)°. In the monosubstituted ring, the methoxy C atom is almost coplanar with the ring [deviation = 0.016 (3) Å]. In the trisubstituted ring, the C atoms of the ortho, meta and para methoxy sustituents deviate by −0.030 (2), 1.127 (2) and −0.052 (2) Å, respectively. In the crystal, molecules are linked by weak C—H⋯O hydrogen bonds, forming C(9) chains propagating along [010].

Keywords: crystal structure; chalcone; weak C—H⋯O hydrogen bonds.

CCDC reference: 1520740

Structure description

As part of our ongoing work on chalcone derivatives (Naveen et al., 2016 ), we herein report the synthesis and crystal structure of the title compound.

The ORTEP of the molecule is shown in Fig. 1. The central part of the molecule is nearly planar: the dihedral angle between the benzene ring bridged by the olefinic double bond is 3.97 (8)°. The methoxy groups at C6, C4 and C16 are almost coplanar with the C1–C6 and C13–C18 benzene rings whereas the methoxy group at C3 lies outside the plane of the C1–C6 benzene ring, as indicated by the C7—O1—C3—C4 torsion angle of 78.1 (2)°. In the crystal, the molecules are linked via weak C—H⋯O hydrogen bonds (Table 1), forming chains propagating along [010] (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19C⋯O4ⁱ	0.96	2.48	3.293 (3)	143
Symmetry code: (i) x, y-1, z.

Figure 1
The molecular structure of the title compound, with displacement ellipsoids for non-H atoms drawn at the 50% probability level.

Figure 2
The packing of the molecules, viewed along the [100] direction. The dashed lines represent hydrogen bonds.

Synthesis and crystallization

A mixture of 2,4,5-trimethoxybenzaldehyde (5 mmol), 1-(4-methoxyphenyl)ethanone (5 mmol) and sodium hydroxide (5 mmol) in 95% ethyl alcohol (25 ml) was stirred at room temperature for 3 h. The progress of the reaction was monitored by TLC. After completion of the reaction, the mixture was poured into ice-cold water and kept in the refrigerator overnight. The solid that formed was filtered, and washed with cold hydrochloric acid (5%). Yellow prisms were obtained from methanol solution by slow solvent evaporation. Yield 91%, m.p. 104–105°C.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₂₀O₅
M_r	328.35
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	8.4043 (5), 8.5518 (5), 12.9352 (7)
α, β, γ (°)	75.400 (2), 88.427 (2), 68.014 (2)
V (Å³)	831.91 (8)
Z	2
Radiation type	Cu Kα
μ (mm⁻¹)	0.78
Crystal size (mm)	0.29 × 0.26 × 0.22

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.806, 0.847
No. of measured, independent and observed [I > 2σ(I)] reflections	7500, 2684, 2528
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.584

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.172, 1.07
No. of reflections	2684
No. of parameters	221
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.16
Computer programs: APEX2 and SAINT (Bruker, 2013), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1520740

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616019350/hb4102sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616019350/hb4102Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616019350/hb4102Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

(E)-1-(4-Methoxyphenyl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₉H₂₀O₅	Z = 2
M_r = 328.35	F(000) = 348
Triclinic, P1	D_x = 1.311 Mg m⁻³
Hall symbol: -P 1	Cu Kα radiation, λ = 1.54178 Å
a = 8.4043 (5) Å	Cell parameters from 2528 reflections
b = 8.5518 (5) Å	θ = 5.7–64.2°
c = 12.9352 (7) Å	µ = 0.78 mm⁻¹
α = 75.400 (2)°	T = 296 K
β = 88.427 (2)°	Prism, yellow
γ = 68.014 (2)°	0.29 × 0.26 × 0.22 mm
V = 831.91 (8) Å³

Data collection top

Bruker X8 Proteum diffractometer	2684 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2528 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.038
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.2°, θ_min = 5.7°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −9→9
T_min = 0.806, T_max = 0.847	l = −15→15
7500 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.172	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.1152P)² + 0.1101P] where P = (F_o² + 2F_c²)/3
2684 reflections	(Δ/σ)_max < 0.001
221 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > 2sigma(F²) is used only for calculating -R-factor-obs 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	−0.08544 (15)	0.66789 (16)	0.33941 (9)	0.0568 (4)
O2	−0.14008 (16)	1.00180 (16)	0.23295 (10)	0.0602 (4)
O3	0.30064 (17)	0.99036 (16)	0.47183 (10)	0.0619 (4)
O4	0.57780 (19)	0.52820 (17)	0.76489 (11)	0.0733 (5)
O5	0.7804 (2)	−0.26807 (16)	0.98697 (11)	0.0752 (5)
C1	0.23192 (19)	0.7438 (2)	0.48953 (12)	0.0424 (5)
C2	0.1357 (2)	0.6634 (2)	0.45203 (12)	0.0448 (5)
C3	0.0145 (2)	0.7502 (2)	0.36718 (12)	0.0458 (5)
C4	−0.0154 (2)	0.9247 (2)	0.31510 (12)	0.0463 (5)
C5	0.0797 (2)	1.0066 (2)	0.34882 (12)	0.0475 (5)
C6	0.20205 (19)	0.9174 (2)	0.43478 (12)	0.0441 (5)
C7	−0.0424 (3)	0.6121 (3)	0.24368 (16)	0.0684 (7)
C8	−0.1753 (2)	1.1788 (2)	0.17818 (14)	0.0592 (5)
C9	0.2730 (2)	1.1681 (2)	0.42455 (16)	0.0605 (6)
C10	0.3533 (2)	0.6570 (2)	0.58348 (12)	0.0461 (5)
C11	0.4058 (2)	0.4919 (2)	0.64046 (12)	0.0479 (5)
C12	0.5255 (2)	0.4286 (2)	0.73643 (13)	0.0486 (5)
C13	0.58235 (19)	0.2432 (2)	0.79999 (12)	0.0449 (5)
C14	0.7088 (2)	0.1848 (2)	0.88415 (13)	0.0527 (5)
C15	0.7692 (2)	0.0159 (2)	0.94495 (14)	0.0575 (6)
C16	0.7061 (2)	−0.1025 (2)	0.92435 (12)	0.0516 (5)
C17	0.5784 (2)	−0.0474 (2)	0.84262 (13)	0.0522 (6)
C18	0.5185 (2)	0.1237 (2)	0.78175 (13)	0.0496 (5)
C19	0.7183 (4)	−0.3948 (3)	0.9746 (2)	0.0885 (9)
H2	0.15480	0.54760	0.48580	0.0540*
H5	0.06150	1.12180	0.31380	0.0570*
H7A	−0.07100	0.71240	0.18330	0.1030*
H7B	−0.10590	0.54270	0.23520	0.1030*
H7C	0.07870	0.54360	0.24820	0.1030*
H8A	−0.20830	1.24950	0.22810	0.0890*
H8B	−0.26730	1.21820	0.12380	0.0890*
H8C	−0.07420	1.18830	0.14560	0.0890*
H9A	0.29970	1.18270	0.35100	0.0910*
H9B	0.34580	1.20220	0.46240	0.0910*
H9C	0.15480	1.23980	0.42830	0.0910*
H10	0.40020	0.72630	0.60660	0.0550*
H11	0.36660	0.41540	0.61960	0.0580*
H14	0.75260	0.26260	0.89890	0.0630*
H15	0.85320	−0.02000	1.00060	0.0690*
H17	0.53350	−0.12510	0.82900	0.0630*
H18	0.43300	0.16000	0.72700	0.0600*
H19A	0.60300	−0.36600	0.99660	0.1330*
H19B	0.79080	−0.50750	1.01810	0.1330*
H19C	0.71880	−0.39730	0.90080	0.1330*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0634 (8)	0.0655 (8)	0.0504 (7)	−0.0392 (6)	−0.0064 (5)	−0.0066 (5)
O2	0.0617 (8)	0.0535 (7)	0.0564 (7)	−0.0224 (6)	−0.0212 (5)	0.0045 (5)
O3	0.0686 (8)	0.0508 (7)	0.0689 (8)	−0.0324 (6)	−0.0183 (6)	−0.0028 (6)
O4	0.0887 (10)	0.0541 (8)	0.0762 (9)	−0.0311 (7)	−0.0355 (7)	−0.0048 (6)
O5	0.1034 (11)	0.0482 (7)	0.0655 (8)	−0.0280 (7)	−0.0345 (7)	0.0026 (6)
C1	0.0417 (8)	0.0441 (8)	0.0406 (8)	−0.0176 (6)	0.0007 (6)	−0.0074 (6)
C2	0.0485 (9)	0.0418 (8)	0.0424 (8)	−0.0196 (7)	−0.0011 (6)	−0.0036 (6)
C3	0.0480 (8)	0.0505 (9)	0.0422 (8)	−0.0253 (7)	−0.0006 (6)	−0.0073 (6)
C4	0.0445 (8)	0.0490 (9)	0.0412 (8)	−0.0174 (7)	−0.0035 (6)	−0.0046 (6)
C5	0.0514 (9)	0.0397 (8)	0.0469 (9)	−0.0175 (7)	−0.0014 (7)	−0.0028 (6)
C6	0.0435 (8)	0.0448 (8)	0.0468 (8)	−0.0204 (6)	0.0011 (6)	−0.0108 (6)
C7	0.0832 (13)	0.0698 (12)	0.0652 (11)	−0.0409 (10)	−0.0045 (9)	−0.0204 (9)
C8	0.0616 (10)	0.0489 (9)	0.0525 (9)	−0.0116 (8)	−0.0111 (7)	−0.0013 (7)
C9	0.0685 (11)	0.0506 (10)	0.0702 (11)	−0.0325 (8)	0.0001 (8)	−0.0135 (8)
C10	0.0446 (8)	0.0499 (9)	0.0450 (8)	−0.0205 (7)	−0.0018 (6)	−0.0101 (7)
C11	0.0505 (9)	0.0476 (9)	0.0448 (8)	−0.0185 (7)	−0.0068 (6)	−0.0096 (7)
C12	0.0488 (9)	0.0488 (9)	0.0484 (9)	−0.0188 (7)	−0.0055 (7)	−0.0119 (7)
C13	0.0418 (8)	0.0498 (9)	0.0413 (8)	−0.0155 (7)	−0.0029 (6)	−0.0109 (7)
C14	0.0577 (10)	0.0512 (9)	0.0508 (9)	−0.0228 (8)	−0.0114 (7)	−0.0114 (7)
C15	0.0632 (11)	0.0549 (10)	0.0501 (9)	−0.0203 (8)	−0.0210 (7)	−0.0069 (7)
C16	0.0601 (10)	0.0478 (9)	0.0421 (8)	−0.0181 (7)	−0.0066 (7)	−0.0062 (6)
C17	0.0568 (10)	0.0545 (10)	0.0492 (9)	−0.0272 (8)	−0.0053 (7)	−0.0101 (7)
C18	0.0471 (9)	0.0542 (9)	0.0458 (8)	−0.0202 (7)	−0.0094 (6)	−0.0071 (7)
C19	0.129 (2)	0.0526 (11)	0.0811 (14)	−0.0407 (12)	−0.0277 (13)	0.0008 (10)

Geometric parameters (Å, º) top

O1—C3	1.384 (2)	C16—C17	1.387 (2)
O1—C7	1.427 (2)	C17—C18	1.380 (2)
O2—C4	1.361 (2)	C2—H2	0.9300
O2—C8	1.420 (2)	C5—H5	0.9300
O3—C6	1.366 (2)	C7—H7A	0.9600
O3—C9	1.419 (2)	C7—H7B	0.9600
O4—C12	1.225 (2)	C7—H7C	0.9600
O5—C16	1.356 (2)	C8—H8A	0.9600
O5—C19	1.410 (3)	C8—H8B	0.9600
C1—C2	1.403 (2)	C8—H8C	0.9600
C1—C6	1.403 (2)	C9—H9A	0.9600
C1—C10	1.454 (2)	C9—H9B	0.9600
C2—C3	1.370 (2)	C9—H9C	0.9600
C3—C4	1.402 (2)	C10—H10	0.9300
C4—C5	1.383 (2)	C11—H11	0.9300
C5—C6	1.387 (2)	C14—H14	0.9300
C10—C11	1.326 (2)	C15—H15	0.9300
C11—C12	1.473 (2)	C17—H17	0.9300
C12—C13	1.488 (2)	C18—H18	0.9300
C13—C14	1.399 (2)	C19—H19A	0.9600
C13—C18	1.388 (2)	C19—H19B	0.9600
C14—C15	1.365 (2)	C19—H19C	0.9600
C15—C16	1.387 (2)

C3—O1—C7	114.51 (15)	O1—C7—H7A	109.00
C4—O2—C8	117.75 (14)	O1—C7—H7B	109.00
C6—O3—C9	119.38 (14)	O1—C7—H7C	109.00
C16—O5—C19	118.90 (17)	H7A—C7—H7B	110.00
C2—C1—C6	117.17 (14)	H7A—C7—H7C	109.00
C2—C1—C10	122.71 (15)	H7B—C7—H7C	109.00
C6—C1—C10	120.08 (15)	O2—C8—H8A	109.00
C1—C2—C3	122.07 (15)	O2—C8—H8B	109.00
O1—C3—C2	119.19 (14)	O2—C8—H8C	109.00
O1—C3—C4	120.94 (15)	H8A—C8—H8B	109.00
C2—C3—C4	119.69 (16)	H8A—C8—H8C	110.00
O2—C4—C3	115.81 (15)	H8B—C8—H8C	109.00
O2—C4—C5	124.56 (15)	O3—C9—H9A	110.00
C3—C4—C5	119.63 (15)	O3—C9—H9B	109.00
C4—C5—C6	120.15 (15)	O3—C9—H9C	110.00
O3—C6—C1	115.64 (14)	H9A—C9—H9B	109.00
O3—C6—C5	123.09 (15)	H9A—C9—H9C	109.00
C1—C6—C5	121.27 (15)	H9B—C9—H9C	109.00
C1—C10—C11	128.37 (16)	C1—C10—H10	116.00
C10—C11—C12	120.64 (15)	C11—C10—H10	116.00
O4—C12—C11	120.34 (15)	C10—C11—H11	120.00
O4—C12—C13	119.65 (15)	C12—C11—H11	120.00
C11—C12—C13	120.01 (15)	C13—C14—H14	119.00
C12—C13—C14	117.90 (15)	C15—C14—H14	119.00
C12—C13—C18	124.59 (15)	C14—C15—H15	120.00
C14—C13—C18	117.51 (15)	C16—C15—H15	120.00
C13—C14—C15	121.25 (16)	C16—C17—H17	120.00
C14—C15—C16	120.45 (16)	C18—C17—H17	120.00
O5—C16—C15	115.28 (15)	C13—C18—H18	119.00
O5—C16—C17	125.16 (16)	C17—C18—H18	119.00
C15—C16—C17	119.54 (15)	O5—C19—H19A	109.00
C16—C17—C18	119.41 (16)	O5—C19—H19B	109.00
C13—C18—C17	121.83 (16)	O5—C19—H19C	109.00
C1—C2—H2	119.00	H19A—C19—H19B	109.00
C3—C2—H2	119.00	H19A—C19—H19C	110.00
C4—C5—H5	120.00	H19B—C19—H19C	109.00
C6—C5—H5	120.00

C7—O1—C3—C2	−106.74 (18)	O2—C4—C5—C6	178.85 (16)
C7—O1—C3—C4	78.1 (2)	C3—C4—C5—C6	−1.0 (2)
C8—O2—C4—C3	179.72 (14)	C4—C5—C6—O3	179.76 (15)
C8—O2—C4—C5	−0.2 (2)	C4—C5—C6—C1	−0.2 (2)
C9—O3—C6—C1	−176.91 (15)	C1—C10—C11—C12	−177.62 (16)
C9—O3—C6—C5	3.1 (2)	C10—C11—C12—O4	0.1 (3)
C19—O5—C16—C15	177.11 (19)	C10—C11—C12—C13	179.59 (16)
C19—O5—C16—C17	−4.3 (3)	O4—C12—C13—C14	−6.7 (2)
C6—C1—C2—C3	−1.4 (2)	O4—C12—C13—C18	173.22 (17)
C10—C1—C2—C3	176.10 (16)	C11—C12—C13—C14	173.85 (15)
C2—C1—C6—O3	−178.56 (14)	C11—C12—C13—C18	−6.2 (3)
C2—C1—C6—C5	1.4 (2)	C12—C13—C14—C15	−179.02 (16)
C10—C1—C6—O3	3.8 (2)	C18—C13—C14—C15	1.1 (3)
C10—C1—C6—C5	−176.17 (15)	C12—C13—C18—C17	179.03 (16)
C2—C1—C10—C11	7.4 (3)	C14—C13—C18—C17	−1.1 (3)
C6—C1—C10—C11	−175.12 (17)	C13—C14—C15—C16	0.1 (3)
C1—C2—C3—O1	−174.99 (15)	C14—C15—C16—O5	177.44 (16)
C1—C2—C3—C4	0.2 (3)	C14—C15—C16—C17	−1.2 (3)
O1—C3—C4—O2	−3.7 (2)	O5—C16—C17—C18	−177.30 (16)
O1—C3—C4—C5	176.17 (15)	C15—C16—C17—C18	1.2 (3)
C2—C3—C4—O2	−178.85 (15)	C16—C17—C18—C13	−0.1 (3)
C2—C3—C4—C5	1.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19C···O4ⁱ	0.96	2.48	3.293 (3)	143

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors are grateful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility.

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