(2E)-2-(3,4-Di­meth­oxy­benzyl­idene)-3,4-di­hydro­naphthalen-1(2H)-one

Shirmila, D.A.; Jonathan, D.R.; Priya, M.K.; Hemalatha, J.; Usha, G.

doi:10.1107/S2414314621003096

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 6| Part 3| March 2021| x210309

https://doi.org/10.1107/S2414314621003096

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(2E)-2-(3,4-Dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one

D. Angeline Shirmila,^a D. Reuben Jonathan,^b M. Krishna Priya,^a J. Hemalatha ^a and G. Usha ^a ^*

^aPG and Research Department of Physics, Queen Mary's College, Affiliated to University of Madras, Chennai-4, Tamil Nadu, India, and ^bDepartment of Chemistry, Madras Christian College, Affiliated to University of Madras, Chennai-59, Tamil Nadu, India
^*Correspondence e-mail: guqmc@yahoo.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 19 March 2021; accepted 24 March 2021; online 26 March 2021)

In the title chalcone derivative, C₁₉H₁₈O₃, the cyclohexanone ring adopts a distorted half-chair conformation and the dihedral angle between the aromatic rings is 52.20 (15)°. In the crystal, weak C—H⋯O hydrogen bonds link the molecules into C(12) [001] chains.

Keywords: crystal structure; chalcone derivative.

CCDC reference: 1968703

Structure description

Chalcone derivatives exhibit various biological activities (Tajuddeen et al., 2018 ) and those that crystallize in non-centrosymmetric space groups are candidates for non-linear optical materials (Shettigar et al., 2006 ). As part of our studies in this area, we now describe the synthesis and structure of the title compound, C₁₉H₁₈O₃, (I), (Fig. 1).

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at 30% probability level. Hydrogen atoms are shown as arbitrary spheres.

The geometrical data for (I) are similar to those in related structures (Biruntha et al., 2018 ; Baydere et al., 2019 ). The C5–C10 cyclohexanone ring adopts a distorted half-chair conformation with C9 and C10 deviating from C5–C8 (r.m.s. deviation = 0.086 Å) by −0.381 (3) and 0.285 (4) Å, respectively. The dihedral angle between the C1–C6 and C12–C17 aromatic rings is 52.20 (15)° and the C atoms of both methoxy groups lie close to the C12–C17 plane [deviations = 0.057 (4) for C18 and 0.148 (6) Å for C19].

In the crystal, weak C2—H2⋯O3 hydrogen bonds link the molecules into C(12) zigzag chains propagating in the [001] direction with adjacent molecules related by a 2₁ screw axis (Table 1, Fig. 2). The chains pack without any identifiable directional interactions between them beyond van der Waals contacts.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	0.93	2.52	3.385 (4)	155
Symmetry code: (i) $[-x+{\script{3\over 2}}, -y+1, z+{\script{1\over 2}}]$ .

Figure 2
Packing of the molecules along the c axis with C—H⋯O interactions running in a zigzag head-to-tail fashion, viewed along the a axis. The hydrogen bonds are shown as dashed lines. Hydrogen atoms not involved in hydrogen bonds are omitted for clarity.

Synthesis and crystallization

The title compound was prepared by a Claisen–Schmidt condensation (Dong et al., 2008 ): equimolar quantities of 3,4-dimethoxy benzaldehyde (2.51 g, 0.015 mol) and α-tetralone (2.0 ml, 0.015 mol) were dissolved in ethanol in a 250 ml conical flask and stirred for 15 min. Freshly prepared 10% NaOH solution was added to the mixture and stirred again for 1 h. This mixture was kept at room temperature for 24 h and then poured into ice-cold water. A yellow precipitate formed, which was washed with distilled water to remove any traces of NaOH. The filtered, dried crude product was recrystallized three times from acetone solution. After four days, yellow blocks of (I) were harvested (yield 78%; m.p. 110°C).

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O₃
M_r	294.33
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	7.9229 (15), 9.4474 (19), 20.875 (4)
V (Å³)	1562.5 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.15 × 0.15

Data collection
Diffractometer	Bruker Kappa APEX3 CMOS
Absorption correction	Multi-scan (SADABS; Bruker 2016 )
T_min, T_max	0.985, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	34283, 3886, 3101
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.180, 1.04
No. of reflections	3886
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.23
Absolute structure	Flack x determined using 1195 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	0.5 (3)
Computer programs: APEX3 and SAINT (Bruker, 2016), SHELXT2014/4 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and ORTEP-3 for Windows (Farrugia, 2012 ).

Structural data

CCDC reference: 1968703

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003096/hb4379sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621003096/hb4379Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621003096/hb4379Isup3.cml

checkCIF report

Computing details top

Data collection: APEX3 (Bruker, 2016); cell refinement: SAINT (Bruker, 2016); data reduction: SAINT (Bruker, 2016); program(s) used to solve structure: SHELXT2014/4 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL2018/3 (Sheldrick, 2015b).

(2E)-2-(3,4-Dimethoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one top

Crystal data top

C₁₉H₁₈O₃	D_x = 1.251 Mg m⁻³
M_r = 294.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 9801 reflections
a = 7.9229 (15) Å	θ = 2.9–28.2°
b = 9.4474 (19) Å	µ = 0.08 mm⁻¹
c = 20.875 (4) Å	T = 296 K
V = 1562.5 (5) Å³	Block, yellow
Z = 4	0.20 × 0.15 × 0.15 mm
F(000) = 624

Data collection top

Bruker Kappa APEX3 CMOS diffractometer	3101 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.043
ω and φ scan	θ_max = 28.3°, θ_min = 3.4°
Absorption correction: multi-scan (SADABS; Bruker 2016)	h = −10→10
T_min = 0.985, T_max = 0.987	k = −12→12
34283 measured reflections	l = −22→27
3886 independent reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.1074P)² + 0.3866P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.057	(Δ/σ)_max < 0.001
wR(F²) = 0.180	Δρ_max = 0.24 e Å⁻³
S = 1.04	Δρ_min = −0.23 e Å⁻³
3886 reflections	Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
200 parameters	Extinction coefficient: 0.35 (3)
0 restraints	Absolute structure: Flack x determined using 1195 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.5 (3)

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Hydrogen atoms were fixed geometrically and treated as riding atoms, with C—H = 0.93–0.97 Å and U_iso(H)= 1.2U_eq(C) or 1.5U_eq(C-methyl).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O2	0.6008 (3)	0.1479 (3)	0.28091 (12)	0.0624 (7)
O3	0.8450 (3)	−0.0282 (3)	0.26479 (12)	0.0649 (7)
O1	0.9071 (4)	0.4782 (3)	0.59032 (11)	0.0649 (7)
C13	0.7334 (4)	0.2526 (3)	0.37495 (14)	0.0458 (6)
H13	0.644379	0.315256	0.381066	0.055*
C14	0.7278 (4)	0.1574 (3)	0.32452 (14)	0.0464 (7)
C16	0.9976 (4)	0.0639 (3)	0.35657 (16)	0.0519 (7)
H16	1.087221	0.001746	0.350367	0.062*
C15	0.8614 (4)	0.0615 (3)	0.31555 (14)	0.0479 (7)
C8	0.8296 (4)	0.4838 (3)	0.48040 (13)	0.0441 (6)
C17	1.0009 (4)	0.1591 (3)	0.40715 (15)	0.0503 (7)
H17	1.092160	0.158070	0.435149	0.060*
C6	0.8282 (4)	0.7030 (3)	0.55210 (13)	0.0446 (6)
C12	0.8722 (4)	0.2556 (3)	0.41712 (14)	0.0449 (6)
C5	0.8007 (4)	0.7892 (3)	0.49871 (15)	0.0475 (7)
C11	0.8832 (4)	0.3505 (3)	0.47233 (14)	0.0471 (7)
H11	0.936499	0.311604	0.507916	0.057*
C7	0.8610 (4)	0.5492 (3)	0.54443 (13)	0.0467 (7)
C10	0.8113 (5)	0.7267 (3)	0.43275 (15)	0.0533 (7)
H10A	0.927775	0.728510	0.418478	0.064*
H10B	0.745607	0.784317	0.403441	0.064*
C9	0.7464 (4)	0.5751 (3)	0.43063 (15)	0.0510 (7)
H9A	0.625376	0.575024	0.437596	0.061*
H9B	0.767737	0.535552	0.388515	0.061*
C1	0.8256 (4)	0.7620 (4)	0.61349 (16)	0.0545 (8)
H1	0.844547	0.704442	0.648899	0.065*
C4	0.7687 (4)	0.9330 (4)	0.50842 (18)	0.0566 (8)
H4	0.748799	0.991456	0.473385	0.068*
C2	0.7953 (5)	0.9042 (4)	0.62230 (18)	0.0616 (9)
H2	0.794300	0.942688	0.663314	0.074*
C3	0.7665 (5)	0.9893 (4)	0.5695 (2)	0.0636 (9)
H3	0.745332	1.085375	0.575098	0.076*
C18	0.4641 (5)	0.2440 (5)	0.2858 (2)	0.0755 (12)
H18A	0.384295	0.225412	0.252249	0.113*
H18B	0.410051	0.232675	0.326635	0.113*
H18C	0.505437	0.339161	0.281840	0.113*
C19	0.9838 (8)	−0.1150 (5)	0.2497 (3)	0.0900 (15)
H19A	0.956607	−0.172841	0.213369	0.135*
H19B	1.079682	−0.056856	0.239872	0.135*
H19C	1.009656	−0.174440	0.285713	0.135*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0552 (13)	0.0737 (15)	0.0584 (13)	0.0130 (12)	−0.0132 (11)	−0.0127 (12)
O3	0.0695 (15)	0.0658 (14)	0.0595 (13)	0.0162 (13)	−0.0077 (12)	−0.0208 (11)
O1	0.0899 (18)	0.0574 (13)	0.0472 (12)	0.0076 (13)	−0.0097 (12)	0.0031 (10)
C13	0.0449 (14)	0.0442 (13)	0.0484 (15)	0.0035 (12)	0.0014 (11)	0.0008 (12)
C14	0.0465 (15)	0.0472 (15)	0.0454 (14)	0.0009 (12)	−0.0005 (12)	0.0013 (12)
C16	0.0543 (17)	0.0452 (15)	0.0563 (17)	0.0087 (13)	−0.0016 (14)	0.0000 (13)
C15	0.0529 (16)	0.0449 (14)	0.0459 (14)	0.0044 (13)	0.0002 (13)	−0.0013 (11)
C8	0.0437 (14)	0.0459 (14)	0.0426 (13)	−0.0015 (11)	0.0025 (11)	−0.0006 (11)
C17	0.0541 (16)	0.0430 (14)	0.0539 (16)	0.0053 (13)	−0.0081 (14)	0.0004 (13)
C6	0.0434 (14)	0.0482 (14)	0.0423 (14)	−0.0036 (12)	0.0044 (11)	−0.0030 (11)
C12	0.0480 (14)	0.0404 (13)	0.0464 (14)	−0.0012 (12)	0.0010 (12)	0.0017 (11)
C5	0.0449 (14)	0.0449 (14)	0.0526 (16)	−0.0019 (12)	0.0001 (13)	0.0000 (12)
C11	0.0514 (15)	0.0444 (14)	0.0455 (14)	0.0000 (13)	−0.0021 (12)	0.0013 (11)
C7	0.0485 (15)	0.0494 (15)	0.0422 (14)	0.0006 (13)	0.0013 (12)	0.0038 (11)
C10	0.0654 (19)	0.0499 (15)	0.0447 (15)	0.0008 (15)	0.0005 (14)	0.0048 (12)
C9	0.0573 (17)	0.0487 (15)	0.0468 (15)	0.0033 (14)	−0.0040 (14)	−0.0023 (13)
C1	0.0555 (17)	0.0594 (18)	0.0485 (16)	−0.0067 (15)	0.0053 (14)	−0.0046 (14)
C4	0.0534 (16)	0.0466 (15)	0.070 (2)	0.0028 (14)	−0.0008 (15)	0.0021 (15)
C2	0.060 (2)	0.063 (2)	0.062 (2)	−0.0014 (16)	0.0079 (16)	−0.0173 (16)
C3	0.0573 (18)	0.0519 (17)	0.082 (2)	0.0048 (15)	0.0002 (18)	−0.0172 (17)
C18	0.059 (2)	0.094 (3)	0.074 (2)	0.026 (2)	−0.0121 (18)	−0.008 (2)
C19	0.093 (3)	0.095 (3)	0.082 (3)	0.033 (3)	−0.007 (2)	−0.036 (2)

Geometric parameters (Å, º) top

O2—C14	1.360 (4)	C5—C4	1.397 (4)
O2—C18	1.417 (4)	C5—C10	1.500 (4)
O3—C15	1.363 (4)	C11—H11	0.9300
O3—C19	1.407 (5)	C10—C9	1.523 (4)
O1—C7	1.225 (4)	C10—H10A	0.9700
C13—C14	1.385 (4)	C10—H10B	0.9700
C13—C12	1.409 (4)	C9—H9A	0.9700
C13—H13	0.9300	C9—H9B	0.9700
C14—C15	1.406 (4)	C1—C2	1.377 (5)
C16—C15	1.378 (5)	C1—H1	0.9300
C16—C17	1.388 (4)	C4—C3	1.381 (5)
C16—H16	0.9300	C4—H4	0.9300
C8—C11	1.340 (4)	C2—C3	1.384 (6)
C8—C7	1.493 (4)	C2—H2	0.9300
C8—C9	1.502 (4)	C3—H3	0.9300
C17—C12	1.383 (4)	C18—H18A	0.9600
C17—H17	0.9300	C18—H18B	0.9600
C6—C5	1.397 (4)	C18—H18C	0.9600
C6—C1	1.398 (4)	C19—H19A	0.9600
C6—C7	1.485 (4)	C19—H19B	0.9600
C12—C11	1.463 (4)	C19—H19C	0.9600

C14—O2—C18	118.3 (3)	C5—C10—H10A	109.2
C15—O3—C19	117.5 (3)	C9—C10—H10A	109.2
C14—C13—C12	120.9 (3)	C5—C10—H10B	109.2
C14—C13—H13	119.6	C9—C10—H10B	109.2
C12—C13—H13	119.6	H10A—C10—H10B	107.9
O2—C14—C13	125.1 (3)	C8—C9—C10	111.8 (3)
O2—C14—C15	115.2 (3)	C8—C9—H9A	109.2
C13—C14—C15	119.7 (3)	C10—C9—H9A	109.2
C15—C16—C17	119.9 (3)	C8—C9—H9B	109.2
C15—C16—H16	120.1	C10—C9—H9B	109.2
C17—C16—H16	120.1	H9A—C9—H9B	107.9
O3—C15—C16	124.6 (3)	C2—C1—C6	121.0 (3)
O3—C15—C14	115.6 (3)	C2—C1—H1	119.5
C16—C15—C14	119.8 (3)	C6—C1—H1	119.5
C11—C8—C7	116.6 (3)	C3—C4—C5	120.7 (3)
C11—C8—C9	126.3 (3)	C3—C4—H4	119.6
C7—C8—C9	117.0 (3)	C5—C4—H4	119.6
C12—C17—C16	121.9 (3)	C1—C2—C3	119.3 (3)
C12—C17—H17	119.1	C1—C2—H2	120.4
C16—C17—H17	119.1	C3—C2—H2	120.4
C5—C6—C1	119.8 (3)	C4—C3—C2	120.6 (3)
C5—C6—C7	120.8 (2)	C4—C3—H3	119.7
C1—C6—C7	119.5 (3)	C2—C3—H3	119.7
C17—C12—C13	117.9 (3)	O2—C18—H18A	109.5
C17—C12—C11	118.6 (3)	O2—C18—H18B	109.5
C13—C12—C11	123.5 (3)	H18A—C18—H18B	109.5
C4—C5—C6	118.6 (3)	O2—C18—H18C	109.5
C4—C5—C10	121.7 (3)	H18A—C18—H18C	109.5
C6—C5—C10	119.6 (3)	H18B—C18—H18C	109.5
C8—C11—C12	131.0 (3)	O3—C19—H19A	109.5
C8—C11—H11	114.5	O3—C19—H19B	109.5
C12—C11—H11	114.5	H19A—C19—H19B	109.5
O1—C7—C6	120.2 (3)	O3—C19—H19C	109.5
O1—C7—C8	121.5 (3)	H19A—C19—H19C	109.5
C6—C7—C8	118.2 (2)	H19B—C19—H19C	109.5
C5—C10—C9	112.2 (3)

C18—O2—C14—C13	1.5 (5)	C17—C12—C11—C8	147.4 (3)
C18—O2—C14—C15	−178.2 (3)	C13—C12—C11—C8	−35.7 (5)
C12—C13—C14—O2	−179.0 (3)	C5—C6—C7—O1	170.2 (3)
C12—C13—C14—C15	0.7 (4)	C1—C6—C7—O1	−9.5 (5)
C19—O3—C15—C16	−6.3 (5)	C5—C6—C7—C8	−12.2 (4)
C19—O3—C15—C14	173.1 (4)	C1—C6—C7—C8	168.1 (3)
C17—C16—C15—O3	−179.5 (3)	C11—C8—C7—O1	−11.9 (5)
C17—C16—C15—C14	1.1 (5)	C9—C8—C7—O1	170.1 (3)
O2—C14—C15—O3	−0.4 (4)	C11—C8—C7—C6	170.6 (3)
C13—C14—C15—O3	179.9 (3)	C9—C8—C7—C6	−7.4 (4)
O2—C14—C15—C16	179.0 (3)	C4—C5—C10—C9	−146.9 (3)
C13—C14—C15—C16	−0.7 (5)	C6—C5—C10—C9	35.0 (4)
C15—C16—C17—C12	−1.6 (5)	C11—C8—C9—C10	−138.6 (3)
C16—C17—C12—C13	1.6 (5)	C7—C8—C9—C10	39.2 (4)
C16—C17—C12—C11	178.7 (3)	C5—C10—C9—C8	−52.3 (4)
C14—C13—C12—C17	−1.1 (4)	C5—C6—C1—C2	0.4 (5)
C14—C13—C12—C11	−178.1 (3)	C7—C6—C1—C2	−179.9 (3)
C1—C6—C5—C4	−0.9 (5)	C6—C5—C4—C3	0.8 (5)
C7—C6—C5—C4	179.4 (3)	C10—C5—C4—C3	−177.3 (3)
C1—C6—C5—C10	177.3 (3)	C6—C1—C2—C3	0.3 (6)
C7—C6—C5—C10	−2.4 (4)	C5—C4—C3—C2	−0.2 (5)
C7—C8—C11—C12	179.4 (3)	C1—C2—C3—C4	−0.4 (6)
C9—C8—C11—C12	−2.8 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	0.93	2.52	3.385 (4)	155

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

Acknowledgements

The authors thank the Central Instrumentation Facility (DST– FIST), Queen Mary's College (A), Chennai-4 for the research and computing facility and the SAIF, IIT, Madras, for the single-crystal X-ray diffraction data collection facility.

References

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