(E)-1-(1,3-Benzodioxol-5-yl)-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/S2414314616020265

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x162026

https://doi.org/10.1107/S2414314616020265

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(E)-1-(1,3-Benzodioxol-5-yl)-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 513 403, 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: naveen@ioe.uni-mysore.ac.in, manjunathhr@acharya.ac.in

Edited by C. Rizzoli, Universita degli Studi di Parma, Italy (Received 13 December 2016; accepted 21 December 2016; online 6 January 2017)

The molecule of the title compound C₁₉H₁₈O₆, adopts an E conformation about the C=C double bond and the C—C=C—C torsion angle is −179.30 (16)°. The molecule is nearly planar, as indicated by the dihedral angle of 6.99 (6)° between the benzene ring and the benzodioxalane ring. In the crystal, molecules are linked via weak C—H⋯O hydrogen bonds, forming zigzag chains propagating along the b axis.

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

CCDC reference: 1523870

Structure description

Chalcones form the central core for the construction of a variety of bioactive compounds. The usual method for the synthesis of chalcones involves the condensation of an aromatic aldehyde and an aromatic ketone in the presence of aqueous alkaline bases (Naveen et al., 2016 ). Chalcones and their derivatives demonstrate a wide range of biological activities such as anti-diabetic, antineoplastic, antihypertensive, anti-inflammatory, antimalarial, antioxidant and antifungal activities (Mahapatra et al., 2015 ). The α,β-unsaturated carbonyl system of chalcones made them useful building blocks in organic synthesis. They have been efficiently employed as precursors in the syntheses of biologically potent benzothiazepines (Manjunath et al., 2014 ). In view of diversified applications of chalcones and as a part of our ongoing work on such molecules (Tejkiran et al., 2016 ), we report herein the synthesis and crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. The molecule is nearly planar with a dihedral angle of 6.99 (6)° between the benzene and benzodioxalane rings that are bridged by the olefinic double bond. This value is less than the value of 19.13 (15)° between the aromatic rings in the related chalcone derivative (E)-3-(2,3-dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (Naveen et al., 2016). The trans conformation of the C7=C8 double bond in the central enone group is confirmed by the value of the C1—C7=C8—C9 torsion angle −179.30 (16)°. The methoxy groups at C3, C4 and C6 are nearly coplanar with the C1–C6 benzene ring. In the crystal, the molecules are linked via weak C—H⋯O hydrogen bonds (Table 1), forming zigzag chains parallel to the b axis (Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13B⋯O4ⁱ	0.97	2.54	3.464 (2)	159
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

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

Figure 2
Partial packing diagram of the title compound, showing the formation of a molecular chain parallel to the b axis via C—H⋯O hydrogen bonds (dotted lines).

Synthesis and crystallization

A mixture of 2,4,5-trimethoxybenzaldehyde (5 mmol), 1-(benzo[d][1,3]dioxol-5-yl)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 rectangular crystals were obtained by slow evaporation of a solution in methanol (yield 89%, m.p. 399–401 K).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O₆
M_r	342.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	10.9127 (2), 13.4406 (3), 11.1011 (2)
β (°)	106.287 (1)
V (Å³)	1562.89 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.91
Crystal size (mm)	0.29 × 0.26 × 0.24

Data collection
Diffractometer	Bruker X8 Proteum
Absorption correction	Multi-scan (SADABS; Bruker, 2011 )
T_min, T_max	0.779, 0.812
No. of measured, independent and observed [I > 2σ(I)] reflections	12593, 2568, 2283
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.586

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.145, 1.09
No. of reflections	2568
No. of parameters	229
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.30
Computer programs: APEX2 and SAINT (Bruker, 2011), SHELXS97 and SHELXL97 (Sheldrick, 2008 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1523870

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616020265/rz4009sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616020265/rz4009Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616020265/rz4009Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2011); cell refinement: SAINT (Bruker, 2011); data reduction: SAINT (Bruker, 2011); 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-(1,3-Benzodioxol-5-yl)-3-(2,4,5-trimethoxyphenyl)prop-2-en-1-one top

Crystal data top

C₁₉H₁₈O₆	F(000) = 720
M_r = 342.33	D_x = 1.455 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 2568 reflections
a = 10.9127 (2) Å	θ = 5.3–64.5°
b = 13.4406 (3) Å	µ = 0.91 mm⁻¹
c = 11.1011 (2) Å	T = 296 K
β = 106.287 (1)°	Block, yellow
V = 1562.89 (5) Å³	0.29 × 0.26 × 0.24 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	2568 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2283 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.054
Detector resolution: 18.4 pixels mm^-1	θ_max = 64.5°, θ_min = 5.3°
φ and ω scans	h = −11→12
Absorption correction: multi-scan (SADABS; Bruker, 2011)	k = −15→15
T_min = 0.779, T_max = 0.812	l = −12→12
12593 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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.145	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.1062P)² + 0.0554P] where P = (F_o² + 2F_c²)/3
2568 reflections	(Δ/σ)_max = 0.001
229 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.30 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	0.91113 (10)	1.12891 (8)	1.26097 (10)	0.0195 (3)
O2	1.03766 (10)	1.20902 (8)	1.12453 (10)	0.0211 (3)
O3	0.78978 (11)	1.03030 (9)	0.75876 (10)	0.0253 (4)
O4	0.48629 (11)	0.80424 (9)	0.74724 (10)	0.0256 (4)
O5	0.11332 (10)	0.58892 (9)	0.77554 (10)	0.0225 (3)
O6	0.11852 (11)	0.57683 (9)	0.98559 (11)	0.0239 (4)
C1	0.75134 (14)	1.00721 (11)	0.95591 (15)	0.0168 (5)
C2	0.77990 (14)	1.03224 (11)	1.08453 (14)	0.0166 (5)
C3	0.87534 (14)	1.09951 (12)	1.13825 (14)	0.0170 (5)
C4	0.94560 (14)	1.14401 (11)	1.06326 (15)	0.0173 (5)
C5	0.91856 (15)	1.12160 (11)	0.93735 (15)	0.0186 (5)
C6	0.82250 (15)	1.05351 (12)	0.88408 (14)	0.0179 (5)
C7	0.65492 (15)	0.93450 (11)	0.89609 (15)	0.0179 (5)
C8	0.57013 (15)	0.88508 (11)	0.94087 (15)	0.0184 (5)
C9	0.48403 (14)	0.81406 (12)	0.85739 (15)	0.0185 (5)
C10	0.39080 (14)	0.75351 (11)	0.90211 (14)	0.0167 (4)
C11	0.29852 (14)	0.70065 (11)	0.80904 (14)	0.0180 (5)
C12	0.21113 (14)	0.64612 (11)	0.84800 (15)	0.0174 (5)
C13	0.04917 (16)	0.54733 (12)	0.86066 (15)	0.0218 (5)
C14	0.21371 (15)	0.63905 (11)	0.97324 (15)	0.0178 (5)
C15	0.30402 (15)	0.68775 (12)	1.06610 (15)	0.0198 (5)
C16	0.39221 (15)	0.74662 (12)	1.02786 (15)	0.0183 (5)
C17	0.84472 (16)	1.08758 (13)	1.34227 (15)	0.0234 (5)
C18	1.11336 (15)	1.25347 (13)	1.05277 (15)	0.0227 (5)
C19	0.87351 (16)	1.06180 (12)	0.68832 (15)	0.0226 (5)
H2	0.73360	1.00290	1.13380	0.0200*
H5	0.96430	1.15180	0.88820	0.0220*
H7	0.65140	0.91980	0.81330	0.0220*
H8	0.56590	0.89550	1.02240	0.0220*
H11	0.29740	0.70290	0.72500	0.0210*
H13A	−0.03790	0.57170	0.84070	0.0260*
H13B	0.04680	0.47540	0.85400	0.0260*
H15	0.30640	0.68190	1.15020	0.0240*
H16	0.45330	0.78200	1.08790	0.0220*
H17A	0.75530	1.10180	1.31010	0.0350*
H17B	0.87660	1.11610	1.42440	0.0350*
H17C	0.85740	1.01680	1.34720	0.0350*
H18A	1.15250	1.20220	1.01600	0.0340*
H18B	1.17840	1.29410	1.10660	0.0340*
H18C	1.06000	1.29390	0.98760	0.0340*
H19A	0.87440	1.13320	0.68500	0.0340*
H19B	0.84450	1.03560	0.60470	0.0340*
H19C	0.95820	1.03790	0.72780	0.0340*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0220 (6)	0.0216 (6)	0.0148 (6)	−0.0055 (4)	0.0049 (5)	−0.0011 (4)
O2	0.0203 (6)	0.0225 (6)	0.0193 (6)	−0.0070 (4)	0.0035 (5)	−0.0002 (4)
O3	0.0311 (7)	0.0300 (7)	0.0164 (6)	−0.0111 (5)	0.0094 (5)	−0.0039 (5)
O4	0.0303 (7)	0.0282 (7)	0.0202 (6)	−0.0094 (5)	0.0104 (5)	−0.0053 (5)
O5	0.0215 (6)	0.0247 (6)	0.0206 (6)	−0.0080 (5)	0.0047 (5)	−0.0030 (5)
O6	0.0209 (6)	0.0287 (7)	0.0230 (7)	−0.0076 (5)	0.0077 (5)	0.0005 (5)
C1	0.0151 (8)	0.0146 (8)	0.0198 (8)	0.0023 (6)	0.0033 (6)	0.0010 (6)
C2	0.0159 (8)	0.0152 (8)	0.0194 (8)	0.0004 (6)	0.0061 (6)	0.0013 (6)
C3	0.0166 (8)	0.0177 (8)	0.0162 (8)	0.0020 (6)	0.0037 (6)	0.0009 (6)
C4	0.0151 (8)	0.0145 (8)	0.0211 (9)	0.0020 (6)	0.0032 (6)	0.0016 (6)
C5	0.0178 (8)	0.0178 (8)	0.0216 (9)	0.0014 (6)	0.0080 (6)	0.0038 (6)
C6	0.0189 (8)	0.0187 (8)	0.0158 (8)	0.0024 (6)	0.0044 (7)	−0.0006 (6)
C7	0.0183 (8)	0.0166 (8)	0.0184 (8)	0.0045 (6)	0.0043 (6)	0.0003 (6)
C8	0.0187 (8)	0.0171 (8)	0.0190 (8)	0.0019 (6)	0.0046 (7)	−0.0004 (6)
C9	0.0190 (8)	0.0164 (8)	0.0205 (9)	0.0043 (6)	0.0063 (7)	0.0011 (6)
C10	0.0165 (8)	0.0131 (7)	0.0202 (8)	0.0033 (6)	0.0046 (6)	0.0002 (6)
C11	0.0206 (8)	0.0167 (8)	0.0167 (8)	0.0022 (6)	0.0054 (7)	0.0000 (6)
C12	0.0159 (7)	0.0141 (8)	0.0214 (9)	0.0016 (6)	0.0039 (6)	−0.0020 (6)
C13	0.0205 (8)	0.0237 (9)	0.0226 (9)	−0.0055 (7)	0.0082 (7)	−0.0034 (7)
C14	0.0164 (8)	0.0153 (8)	0.0228 (9)	0.0031 (6)	0.0073 (6)	0.0018 (6)
C15	0.0205 (8)	0.0212 (9)	0.0178 (8)	0.0021 (6)	0.0054 (7)	0.0013 (6)
C16	0.0168 (8)	0.0158 (8)	0.0206 (9)	0.0025 (6)	0.0025 (6)	−0.0009 (6)
C17	0.0271 (9)	0.0264 (9)	0.0177 (9)	−0.0070 (7)	0.0079 (7)	−0.0006 (6)
C18	0.0196 (9)	0.0225 (9)	0.0266 (9)	−0.0038 (7)	0.0076 (7)	0.0011 (7)
C19	0.0281 (9)	0.0234 (9)	0.0187 (9)	−0.0001 (7)	0.0107 (7)	0.0005 (6)

Geometric parameters (Å, º) top

O1—C3	1.3661 (18)	C11—C12	1.366 (2)
O1—C17	1.420 (2)	C12—C14	1.386 (2)
O2—C4	1.3609 (19)	C14—C15	1.376 (2)
O2—C18	1.429 (2)	C15—C16	1.401 (2)
O3—C6	1.3717 (18)	C2—H2	0.9300
O3—C19	1.424 (2)	C5—H5	0.9300
O4—C9	1.2370 (19)	C7—H7	0.9300
O5—C12	1.3769 (19)	C8—H8	0.9300
O5—C13	1.438 (2)	C11—H11	0.9300
O6—C13	1.437 (2)	C13—H13A	0.9700
O6—C14	1.370 (2)	C13—H13B	0.9700
C1—C2	1.414 (2)	C15—H15	0.9300
C1—C6	1.405 (2)	C16—H16	0.9300
C1—C7	1.453 (2)	C17—H17A	0.9600
C2—C3	1.382 (2)	C17—H17B	0.9600
C3—C4	1.413 (2)	C17—H17C	0.9600
C4—C5	1.379 (2)	C18—H18A	0.9600
C5—C6	1.392 (2)	C18—H18B	0.9600
C7—C8	1.343 (2)	C18—H18C	0.9600
C8—C9	1.471 (2)	C19—H19A	0.9600
C9—C10	1.492 (2)	C19—H19B	0.9600
C10—C11	1.415 (2)	C19—H19C	0.9600
C10—C16	1.395 (2)

C3—O1—C17	117.82 (12)	C1—C2—H2	119.00
C4—O2—C18	116.80 (12)	C3—C2—H2	119.00
C6—O3—C19	117.70 (13)	C4—C5—H5	120.00
C12—O5—C13	105.89 (12)	C6—C5—H5	120.00
C13—O6—C14	106.30 (12)	C1—C7—H7	115.00
C2—C1—C6	117.87 (14)	C8—C7—H7	115.00
C2—C1—C7	123.22 (14)	C7—C8—H8	121.00
C6—C1—C7	118.90 (14)	C9—C8—H8	121.00
C1—C2—C3	121.16 (14)	C10—C11—H11	121.00
O1—C3—C2	126.14 (14)	C12—C11—H11	121.00
O1—C3—C4	114.49 (14)	O5—C13—H13A	110.00
C2—C3—C4	119.38 (14)	O5—C13—H13B	110.00
O2—C4—C3	115.07 (14)	O6—C13—H13A	110.00
O2—C4—C5	124.41 (14)	O6—C13—H13B	110.00
C3—C4—C5	120.51 (14)	H13A—C13—H13B	108.00
C4—C5—C6	119.73 (15)	C14—C15—H15	122.00
O3—C6—C1	116.54 (14)	C16—C15—H15	122.00
O3—C6—C5	122.08 (14)	C10—C16—H16	119.00
C1—C6—C5	121.35 (14)	C15—C16—H16	119.00
C1—C7—C8	130.50 (15)	O1—C17—H17A	109.00
C7—C8—C9	118.20 (14)	O1—C17—H17B	110.00
O4—C9—C8	120.37 (15)	O1—C17—H17C	109.00
O4—C9—C10	118.37 (14)	H17A—C17—H17B	110.00
C8—C9—C10	121.25 (14)	H17A—C17—H17C	109.00
C9—C10—C11	116.28 (13)	H17B—C17—H17C	109.00
C9—C10—C16	123.50 (14)	O2—C18—H18A	109.00
C11—C10—C16	120.21 (14)	O2—C18—H18B	109.00
C10—C11—C12	117.09 (14)	O2—C18—H18C	109.00
O5—C12—C11	127.62 (14)	H18A—C18—H18B	109.00
O5—C12—C14	110.01 (13)	H18A—C18—H18C	110.00
C11—C12—C14	122.34 (15)	H18B—C18—H18C	109.00
O5—C13—O6	107.78 (13)	O3—C19—H19A	109.00
O6—C14—C12	109.85 (14)	O3—C19—H19B	109.00
O6—C14—C15	128.27 (15)	O3—C19—H19C	109.00
C12—C14—C15	121.86 (15)	H19A—C19—H19B	109.00
C14—C15—C16	116.77 (15)	H19A—C19—H19C	109.00
C10—C16—C15	121.68 (15)	H19B—C19—H19C	109.00

C17—O1—C3—C2	−0.3 (2)	C2—C3—C4—C5	0.7 (2)
C17—O1—C3—C4	179.87 (13)	O2—C4—C5—C6	179.72 (14)
C18—O2—C4—C3	178.25 (13)	C3—C4—C5—C6	−0.9 (2)
C18—O2—C4—C5	−2.4 (2)	C4—C5—C6—O3	178.47 (15)
C19—O3—C6—C1	−169.19 (14)	C4—C5—C6—C1	0.4 (2)
C19—O3—C6—C5	12.7 (2)	C1—C7—C8—C9	−179.30 (16)
C13—O5—C12—C11	−179.87 (15)	C7—C8—C9—O4	−3.4 (2)
C13—O5—C12—C14	2.25 (17)	C7—C8—C9—C10	177.58 (15)
C12—O5—C13—O6	−3.93 (16)	O4—C9—C10—C11	−9.5 (2)
C14—O6—C13—O5	4.16 (16)	O4—C9—C10—C16	169.88 (15)
C13—O6—C14—C12	−2.82 (17)	C8—C9—C10—C11	169.58 (14)
C13—O6—C14—C15	178.86 (16)	C8—C9—C10—C16	−11.1 (2)
C6—C1—C2—C3	−0.5 (2)	C9—C10—C11—C12	−178.97 (14)
C7—C1—C2—C3	177.87 (15)	C16—C10—C11—C12	1.7 (2)
C2—C1—C6—O3	−177.88 (14)	C9—C10—C16—C15	−179.06 (15)
C2—C1—C6—C5	0.3 (2)	C11—C10—C16—C15	0.2 (2)
C7—C1—C6—O3	3.7 (2)	C10—C11—C12—O5	−179.86 (14)
C7—C1—C6—C5	−178.14 (15)	C10—C11—C12—C14	−2.2 (2)
C2—C1—C7—C8	6.3 (3)	O5—C12—C14—O6	0.37 (18)
C6—C1—C7—C8	−175.42 (17)	O5—C12—C14—C15	178.81 (14)
C1—C2—C3—O1	−179.85 (14)	C11—C12—C14—O6	−177.65 (14)
C1—C2—C3—C4	0.0 (2)	C11—C12—C14—C15	0.8 (2)
O1—C3—C4—O2	0.0 (2)	O6—C14—C15—C16	179.32 (15)
O1—C3—C4—C5	−179.42 (14)	C12—C14—C15—C16	1.2 (2)
C2—C3—C4—O2	−179.86 (14)	C14—C15—C16—C10	−1.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···O4ⁱ	0.97	2.54	3.464 (2)	159

Symmetry code: (i) −x+1/2, y−1/2, −z+3/2.

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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