(E)-1-(1,3-Benzodioxol-5-yl)-3-[4-(di­methyl­amino)­phen­yl]prop-2-en-1-one

Kumara, K.; Naveen, S.; Dileep Kumar, A.; Ajay Kumar, K.; Lokanath, N.K.; Warad, I.

doi:10.1107/S2414314616020290

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 1| January 2017| x162029

https://doi.org/10.1107/S2414314616020290

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(E)-1-(1,3-Benzodioxol-5-yl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one

Karthik Kumara,^a S. Naveen,^b A. Dileep Kumar,^c K. Ajay Kumar,^c N. K. Lokanath ^a ^* and Ismail Warad ^d ^*

^aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru 570 006, India, ^cDepartment of Chemistry, Yuvaraja's College, University of Mysore, Mysuru 570 005, India, and ^dDepartment of Chemistry, Science College, An-Najah National University, PO Box 7, Nablus, West Bank, Palestinian Territories
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in, khalil.i@najah.edu

Edited by O. Blacque, University of Zürich, Switzerland (Received 19 December 2016; accepted 21 December 2016; online 6 January 2017)

In the title compound, C₁₈H₁₇NO₃, the olefinic double bond adopts an E conformation. The molecule is nearly planar as indicated by the dihedral angle of 3.11 (6)° between the benzodioxole and benzene rings. The carbonyl group lies in the plane of the olefinic double bond and the benzodioxole ring. The trans conformation of the C=C double bond in the central enone group is confirmed by the C=C—C—C torsion angle of −177.82 (14)°.

Keywords: crystal structure; bis-chalcone; E conformation.

CCDC reference: 1523974

Structure description

Chalcones constitute the central core for the construction of a wide range of bioactive compounds (Ajay Kumar et al., 2010 ). Chalcones and their derivatives demonstrate a wide range of biological activities, such as antioxidant, antifungal, antibacterial, cardioprotective. In view of the broad spectrum of applications associated with chalcones and as a part of our ongoing work on such molecules (Tejkiran et al., 2016 ; Naveen et al., 2016a ), we report herein on the synthesis and crystal structure of the title compound.

The molecule (Fig. 1) is nearly planar, with a dihedral angle of 3.11 (6)° between the benzodioxole and benzene rings that are bridged by the olefinic double bond. This value is less than that reported for the dihedral angle between the aromatic rings [19.13 (15)°] in the related chalcone derivative (E)-3-(2,3-dichlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (Naveen et al., 2016b ). The trans conformation about the C7=C8 double bond in the central enone group is confirmed by the C7=C8—C9—C10 torsion angle of −177.82 (14)°. The carbonyl group at C9 lies in the plane of the olefinic double bond and the benzodioxole ring, as indicated by the O3—C9—C8—C7 and O3—C9—C10—C16 torsion angles of 2.0 (2)° and 3.7 (2)°, respectively. No classical hydrogen bonds are found in the structure.

Figure 1
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

Synthesis and crystallization

A mixture of 4-(dimethylamino)benzaldehyde (5 mmol), 1-(benzo[d][1,3]dioxol-5-yl)ethanone (5 mmol) and sodium hydroxide (5 mmol) in ethyl alcohol (25 ml) was stirred at room temperature for 3 h. The progress of the reaction was monitored by TLC. After the completion of the reaction, the mixture was poured into ice-cold water and kept in the refrigerator for 18 h. The solid formed was filtered, and washed with cold hydrochloric acid (5%). Single crystals suitable for X-ray diffraction studies were obtained from methyl alcohol and a few drops of acetonitrile by slow evaporation of the solvents (yield 88%, m.p. 93–94°C).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 1.

Table 1
Experimental details

Crystal data
Chemical formula	C₁₈H₁₇NO₃
M_r	295.33
Crystal system, space group	Monoclinic, P2₁/a
Temperature (K)	293
a, b, c (Å)	11.915 (10), 10.8405 (10), 12.184 (11)
β (°)	101.922 (8)
V (Å³)	1539.8 (19)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.29 × 0.27 × 0.24

Data collection
Diffractometer	Rigaku Saturn724+ CCD
Absorption correction	Multi-scan (NUMABS; Rigaku, 1999 )
T_min, T_max	0.975, 0.979
No. of measured, independent and observed [I > 2σ(I)] reflections	7186, 3479, 2629
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.146, 1.04
No. of reflections	3479
No. of parameters	201
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.15
Computer programs: CrystalClear SM-Expert (Rigaku, 2011 ), SHELXS97 and SHELXL97 (Sheldrick, 208 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1523974

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616020290/zq4014sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616020290/zq4014Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616020290/zq4014Isup3.cml

checkCIF report

Computing details top

Data collection: CrystalClear SM-Expert (Rigaku, 2011); cell refinement: CrystalClear SM-Expert (Rigaku, 2011); data reduction: CrystalClear SM-Expert (Rigaku, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2015); 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-[4-(dimethylamino)phenyl]prop-2-en-1-one top

Crystal data top

C₁₈H₁₇NO₃	F(000) = 624
M_r = 295.33	D_x = 1.274 Mg m⁻³
Monoclinic, P2₁/a	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yab	Cell parameters from 2629 reflections
a = 11.915 (10) Å	θ = 3.3–27.5°
b = 10.8405 (10) Å	µ = 0.09 mm⁻¹
c = 12.184 (11) Å	T = 293 K
β = 101.922 (8)°	Rectangle, brown
V = 1539.8 (19) Å³	0.29 × 0.27 × 0.24 mm
Z = 4

Data collection top

Rigaku Saturn724+ CCD diffractometer	3479 independent reflections
Radiation source: fine-focus sealed tube	2629 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
profile data from ω–scans	h = −13→15
Absorption correction: multi-scan (NUMABS; Rigaku, 1999)	k = −14→11
T_min = 0.975, T_max = 0.979	l = −15→14
7186 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0758P)² + 0.1951P] where P = (F_o² + 2F_c²)/3
3479 reflections	(Δ/σ)_max < 0.001
201 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.15 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
O3	0.37832 (9)	0.20251 (12)	−0.19163 (9)	0.0595 (4)
O4	0.51384 (9)	0.08096 (12)	0.22013 (9)	0.0590 (4)
O5	0.70923 (10)	0.11039 (14)	0.26761 (9)	0.0721 (5)
N1	0.65091 (13)	0.44829 (15)	−0.73998 (12)	0.0652 (5)
C1	0.61229 (13)	0.40498 (13)	−0.64936 (12)	0.0479 (4)
C2	0.68837 (13)	0.37874 (15)	−0.54635 (13)	0.0535 (5)
C3	0.64905 (13)	0.33658 (15)	−0.45519 (12)	0.0505 (5)
C4	0.53234 (12)	0.31754 (13)	−0.45929 (11)	0.0436 (4)
C5	0.45761 (12)	0.34319 (14)	−0.56122 (12)	0.0487 (4)
C6	0.49551 (13)	0.38484 (14)	−0.65357 (12)	0.0501 (4)
C7	0.48650 (13)	0.27767 (13)	−0.36412 (12)	0.0464 (4)
C8	0.54391 (13)	0.25066 (14)	−0.26054 (12)	0.0480 (4)
C9	0.48377 (12)	0.21340 (13)	−0.17243 (12)	0.0445 (4)
C10	0.55141 (12)	0.18863 (13)	−0.05724 (11)	0.0428 (4)
C11	0.66948 (13)	0.20478 (17)	−0.02721 (13)	0.0570 (5)
C12	0.73073 (14)	0.1804 (2)	0.08137 (14)	0.0676 (6)
C13	0.66965 (13)	0.13966 (15)	0.15751 (12)	0.0528 (5)
C14	0.61240 (15)	0.07070 (16)	0.30885 (13)	0.0581 (5)
C15	0.55270 (12)	0.12316 (12)	0.12871 (11)	0.0435 (4)
C16	0.49093 (11)	0.14651 (13)	0.02312 (11)	0.0427 (4)
C23	0.57384 (18)	0.46946 (17)	−0.84656 (14)	0.0659 (6)
C24	0.7710 (2)	0.4674 (3)	−0.7342 (2)	0.0959 (10)
H2	0.76670	0.39040	−0.54050	0.0640*
H3	0.70140	0.32020	−0.38890	0.0610*
H5	0.37930	0.33160	−0.56660	0.0580*
H6	0.44280	0.39990	−0.71990	0.0600*
H7	0.40710	0.26980	−0.37650	0.0560*
H8	0.62360	0.25560	−0.24410	0.0580*
H11	0.70880	0.23260	−0.08090	0.0680*
H12	0.80970	0.19150	0.10090	0.0810*
H14A	0.60300	0.12160	0.37180	0.0700*
H14B	0.62250	−0.01420	0.33410	0.0700*
H16	0.41190	0.13500	0.00510	0.0510*
H23A	0.54370	0.39200	−0.87780	0.0990*
H23B	0.61470	0.50890	−0.89700	0.0990*
H23C	0.51190	0.52150	−0.83570	0.0990*
H24A	0.79840	0.53100	−0.68050	0.1440*
H24B	0.78310	0.49180	−0.80660	0.1440*
H24C	0.81180	0.39220	−0.71160	0.1440*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0409 (6)	0.0826 (8)	0.0527 (6)	−0.0020 (5)	0.0045 (5)	0.0061 (5)
O4	0.0485 (6)	0.0820 (8)	0.0468 (6)	−0.0035 (5)	0.0107 (5)	0.0075 (5)
O5	0.0517 (7)	0.1137 (11)	0.0457 (6)	−0.0125 (7)	−0.0020 (5)	0.0123 (6)
N1	0.0612 (9)	0.0786 (10)	0.0588 (8)	−0.0033 (7)	0.0197 (7)	0.0107 (7)
C1	0.0506 (8)	0.0465 (7)	0.0479 (8)	−0.0007 (6)	0.0133 (6)	−0.0004 (6)
C2	0.0375 (7)	0.0663 (9)	0.0561 (9)	−0.0027 (7)	0.0086 (6)	−0.0024 (7)
C3	0.0411 (7)	0.0617 (9)	0.0462 (8)	0.0008 (7)	0.0030 (6)	−0.0015 (6)
C4	0.0408 (7)	0.0475 (7)	0.0417 (7)	0.0010 (6)	0.0066 (5)	−0.0026 (5)
C5	0.0389 (7)	0.0569 (8)	0.0486 (8)	−0.0012 (6)	0.0049 (6)	0.0015 (6)
C6	0.0459 (8)	0.0570 (8)	0.0444 (7)	0.0005 (6)	0.0025 (6)	0.0032 (6)
C7	0.0421 (7)	0.0507 (8)	0.0459 (7)	−0.0004 (6)	0.0077 (6)	−0.0023 (6)
C8	0.0440 (7)	0.0542 (8)	0.0455 (7)	0.0025 (6)	0.0086 (6)	−0.0004 (6)
C9	0.0428 (7)	0.0461 (7)	0.0437 (7)	0.0006 (6)	0.0067 (6)	−0.0038 (6)
C10	0.0400 (7)	0.0438 (7)	0.0437 (7)	0.0003 (6)	0.0067 (6)	−0.0047 (5)
C11	0.0431 (8)	0.0799 (11)	0.0485 (8)	−0.0087 (7)	0.0106 (6)	0.0042 (7)
C12	0.0395 (8)	0.1049 (14)	0.0553 (9)	−0.0146 (8)	0.0024 (7)	0.0091 (9)
C13	0.0432 (8)	0.0673 (9)	0.0442 (8)	−0.0049 (7)	0.0002 (6)	0.0005 (7)
C14	0.0597 (10)	0.0676 (10)	0.0443 (8)	−0.0061 (8)	0.0045 (7)	0.0022 (7)
C15	0.0439 (7)	0.0445 (7)	0.0430 (7)	−0.0008 (6)	0.0113 (6)	−0.0034 (5)
C16	0.0362 (7)	0.0460 (7)	0.0454 (7)	0.0014 (5)	0.0070 (5)	−0.0046 (6)
C23	0.0866 (13)	0.0609 (10)	0.0524 (9)	0.0040 (9)	0.0192 (9)	0.0070 (7)
C24	0.0721 (14)	0.132 (2)	0.0898 (15)	−0.0227 (13)	0.0314 (12)	0.0242 (14)

Geometric parameters (Å, º) top

O3—C9	1.235 (2)	C12—C13	1.365 (3)
O4—C14	1.427 (2)	C13—C15	1.377 (2)
O4—C15	1.370 (2)	C15—C16	1.367 (2)
O5—C13	1.364 (2)	C2—H2	0.9300
O5—C14	1.417 (3)	C3—H3	0.9300
N1—C1	1.364 (2)	C5—H5	0.9300
N1—C23	1.446 (3)	C6—H6	0.9300
N1—C24	1.433 (3)	C7—H7	0.9300
C1—C2	1.417 (2)	C8—H8	0.9300
C1—C6	1.399 (3)	C11—H11	0.9300
C2—C3	1.370 (2)	C12—H12	0.9300
C3—C4	1.397 (2)	C14—H14A	0.9700
C4—C5	1.398 (2)	C14—H14B	0.9700
C4—C7	1.446 (2)	C16—H16	0.9300
C5—C6	1.373 (2)	C23—H23A	0.9600
C7—C8	1.338 (2)	C23—H23B	0.9600
C8—C9	1.465 (2)	C23—H23C	0.9600
C9—C10	1.491 (2)	C24—H24A	0.9600
C10—C11	1.390 (2)	C24—H24B	0.9600
C10—C16	1.406 (2)	C24—H24C	0.9600
C11—C12	1.398 (3)

C14—O4—C15	106.17 (12)	C3—C2—H2	119.00
C13—O5—C14	106.13 (12)	C2—C3—H3	119.00
C1—N1—C23	121.59 (15)	C4—C3—H3	119.00
C1—N1—C24	120.68 (16)	C4—C5—H5	119.00
C23—N1—C24	117.63 (16)	C6—C5—H5	119.00
N1—C1—C2	121.66 (15)	C1—C6—H6	120.00
N1—C1—C6	121.55 (14)	C5—C6—H6	120.00
C2—C1—C6	116.78 (13)	C4—C7—H7	116.00
C1—C2—C3	121.45 (14)	C8—C7—H7	116.00
C2—C3—C4	121.67 (14)	C7—C8—H8	119.00
C3—C4—C5	116.68 (13)	C9—C8—H8	119.00
C3—C4—C7	123.62 (13)	C10—C11—H11	119.00
C5—C4—C7	119.66 (13)	C12—C11—H11	119.00
C4—C5—C6	122.45 (14)	C11—C12—H12	121.00
C1—C6—C5	120.96 (14)	C13—C12—H12	121.00
C4—C7—C8	128.14 (15)	O4—C14—H14A	110.00
C7—C8—C9	121.29 (14)	O4—C14—H14B	110.00
O3—C9—C8	121.32 (13)	O5—C14—H14A	110.00
O3—C9—C10	119.46 (13)	O5—C14—H14B	110.00
C8—C9—C10	119.22 (13)	H14A—C14—H14B	108.00
C9—C10—C11	123.09 (13)	C10—C16—H16	121.00
C9—C10—C16	117.30 (13)	C15—C16—H16	121.00
C11—C10—C16	119.61 (13)	N1—C23—H23A	109.00
C10—C11—C12	121.85 (15)	N1—C23—H23B	110.00
C11—C12—C13	117.19 (15)	N1—C23—H23C	109.00
O5—C13—C12	128.23 (15)	H23A—C23—H23B	109.00
O5—C13—C15	110.28 (13)	H23A—C23—H23C	109.00
C12—C13—C15	121.50 (14)	H23B—C23—H23C	109.00
O4—C14—O5	108.10 (12)	N1—C24—H24A	109.00
O4—C15—C13	109.30 (12)	N1—C24—H24B	109.00
O4—C15—C16	128.32 (13)	N1—C24—H24C	109.00
C13—C15—C16	122.38 (13)	H24A—C24—H24B	110.00
C10—C16—C15	117.48 (13)	H24A—C24—H24C	109.00
C1—C2—H2	119.00	H24B—C24—H24C	110.00

C15—O4—C14—O5	1.21 (17)	C4—C5—C6—C1	−0.7 (2)
C14—O4—C15—C13	−0.31 (16)	C4—C7—C8—C9	178.89 (14)
C14—O4—C15—C16	179.25 (14)	C7—C8—C9—O3	2.0 (2)
C14—O5—C13—C12	−178.77 (18)	C7—C8—C9—C10	−177.82 (14)
C14—O5—C13—C15	1.48 (18)	O3—C9—C10—C11	−176.62 (15)
C13—O5—C14—O4	−1.65 (18)	O3—C9—C10—C16	3.7 (2)
C23—N1—C1—C2	177.02 (15)	C8—C9—C10—C11	3.2 (2)
C24—N1—C1—C2	0.8 (3)	C8—C9—C10—C16	−176.56 (13)
C23—N1—C1—C6	−3.3 (2)	C9—C10—C11—C12	−179.77 (16)
C24—N1—C1—C6	−179.52 (19)	C16—C10—C11—C12	−0.1 (3)
N1—C1—C2—C3	179.25 (15)	C9—C10—C16—C15	179.72 (13)
C6—C1—C2—C3	−0.5 (2)	C11—C10—C16—C15	0.0 (2)
N1—C1—C6—C5	−178.90 (15)	C10—C11—C12—C13	0.0 (3)
C2—C1—C6—C5	0.8 (2)	C11—C12—C13—O5	−179.69 (17)
C1—C2—C3—C4	−0.1 (3)	C11—C12—C13—C15	0.0 (3)
C2—C3—C4—C5	0.2 (2)	O5—C13—C15—O4	−0.75 (18)
C2—C3—C4—C7	−177.57 (15)	O5—C13—C15—C16	179.66 (14)
C3—C4—C5—C6	0.1 (2)	C12—C13—C15—O4	179.48 (16)
C7—C4—C5—C6	178.02 (14)	C12—C13—C15—C16	−0.1 (2)
C3—C4—C7—C8	−1.3 (2)	O4—C15—C16—C10	−179.42 (14)
C5—C4—C7—C8	−179.10 (15)	C13—C15—C16—C10	0.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···O3	0.93	2.46	2.804 (3)	102

Acknowledgements

The authors are grateful to the National Facility, Department of Studies in Physics, University of Mysore, India, for providing the single-crystal X-ray diffractometer facility.

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