Crystal structure of (E)-4-ethyl-2-(4-meth­oxy­benzyl­idene)-3,4-di­hydro­naphthalen-1(2H)-one

Akhazzane, M.; Al Houari, G.; El Yazidi, M.; Saadi, M.; El Ammari, L.

doi:10.1107/S205698901501004X

organic compounds

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Volume 71| Part 6| June 2015| Page o432

doi:10.1107/S205698901501004X

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Crystal structure of (E)-4-ethyl-2-(4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-one

Mohamed Akhazzane,^a Ghali Al Houari,^a Mohamed El Yazidi,^a ^* Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: elyazidimohamed@hotmail.com

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 22 May 2015; accepted 23 May 2015; online 30 May 2015)

In the title compound, C₂₀H₂₀O₂, the exocyclic C=C double bond has an E conformation. The ethyl substituent on the cyclohexanone ring is in an axial orientation. The cyclohexanone ring adopts a screw-boat conformation, with the methylene C atom and the C atom bearing the 4-methoxybenzylidene group displaced from the other atoms by 0.812 (1) and 0.334 (1) Å, respectively. The dihedral angle between the planes of the benzene rings is 42.20 (8)°. In the crystal, no directional interactions beyond van der Waals contacts are observed.

Keywords: crystal structure; benzylidene; naphthalenone; dipolar 1,3-cycloaddition reactions.

CCDC reference: 1402624

1. Related literature

For general background to dipolar 1,3-cycloaddition reactions, see: Bennani et al. (2007 ); Kerbal et al. (1988 ); Al Houari et al. (2008 ). For a related structure, see: Akhazzane et al. (2010 ).

2. Experimental

2.1. Crystal data

C₂₀H₂₀O₂
M_r = 292.36
Monoclinic, P 2₁ /c
a = 12.0411 (13) Å
b = 8.9698 (9) Å
c = 15.5832 (18) Å
β = 110.721 (3)°
V = 1574.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.38 × 0.16 × 0.12 mm

2.2. Data collection

Bruker X8 APEX CCD diffractometer
25378 measured reflections
4068 independent reflections
2552 reflections with I > 2σ(I)
R_int = 0.046

2.3. Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.129
S = 1.01
4068 reflections
200 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015 ); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1402624

Crystal structure: contains datablock I. DOI: 10.1107/S205698901501004X/hb7434sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S205698901501004X/hb7434Isup2.hkl

Supporting information file. DOI: 10.1107/S205698901501004X/hb7434Isup3.cml

checkCIF report

Comment top

Knowledge of the configuration and conformation of the title compound is necessary to understand its behaviour in dipolar-1,3 cycloaddition reactions (Bennani et al., 2007; Al Houari et al., 2008). To confirm the (E) conformation of the exocyclic C=C double bond, an X-ray crystal structure determination has been carried out. The present work is a continuation of the investigation of the dihydronaphthalene derivatives published recently by Akhazzane et al., 2010.

The molecule of the title compound is formed by two fused rings linked to an ethyl group and to a 4-methoxybenzylidene moities as shown in Fig.1. The cyclohexanone ring adopts a screw-boat conformation as indicated by the total puckering amplitude QT = 0.477 (2) Å and spherical polar angle θ = 115.9 (2)° with ϕ = 35.6 (2)°. The benzene rings form a dihedral angle of 42.20 (8)°.

Related literature top

For general background to dipolar 1,3-cycloaddition reactions, see: Bennani et al. (2007); Kerbal et al. (1988); Al Houari et al. (2008). For a related structure, see: Akhazzane et al. (2010).

Experimental top

The synthesis of the title compound was achieved using the method reported by Kerbal et al., 1988. By a condensation of para anisaldehyde with 4-ethyl-3,4-dihydronaphthalen- 1(2H)-one in an alkaline medium in ethanol. The resulting residue was recrystallized from ethanol solution by slow evaporation to afford the title compound as colourless needles.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

Fig. 1. : Plot of the molecule of the title compound with displacement ellipsoids drawn at the 50% probability level.

(E)-4-Ethyl-2-(4-methoxybenzylidene)-3,4-dihydronaphthalen-1(2H)-\ one top

Crystal data top

C₂₀H₂₀O₂	D_x = 1.234 Mg m⁻³
M_r = 292.36	Melting point: 383 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.0411 (13) Å	Cell parameters from 4068 reflections
b = 8.9698 (9) Å	θ = 2.7–28.7°
c = 15.5832 (18) Å	µ = 0.08 mm⁻¹
β = 110.721 (3)°	T = 296 K
V = 1574.2 (3) Å³	Needles, colourless
Z = 4	0.38 × 0.16 × 0.12 mm
F(000) = 624

Data collection top

Bruker X8 APEX CCD diffractometer	2552 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.046
Graphite monochromator	θ_max = 28.7°, θ_min = 2.7°
ϕ and ω scans	h = −14→16
25378 measured reflections	k = −12→12
4068 independent reflections	l = −20→21

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0546P)² + 0.2497P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.129	(Δ/σ)_max < 0.001
S = 1.01	Δρ_max = 0.16 e Å⁻³
4068 reflections	Δρ_min = −0.15 e Å⁻³
200 parameters	Extinction correction: SHELXL2013 (Sheldrick, 2015), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0088 (16)

Crystal data top

C₂₀H₂₀O₂	V = 1574.2 (3) Å³
M_r = 292.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 12.0411 (13) Å	µ = 0.08 mm⁻¹
b = 8.9698 (9) Å	T = 296 K
c = 15.5832 (18) Å	0.38 × 0.16 × 0.12 mm
β = 110.721 (3)°

Data collection top

Bruker X8 APEX CCD diffractometer	2552 reflections with I > 2σ(I)
25378 measured reflections	R_int = 0.046
4068 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
4068 reflections	Δρ_min = −0.15 e Å⁻³
200 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	0.64653 (13)	0.60708 (16)	0.83826 (9)	0.0452 (3)
C2	0.52292 (13)	0.64122 (14)	0.83030 (9)	0.0415 (3)
C3	0.49026 (15)	0.62928 (17)	0.90761 (10)	0.0520 (4)
H3	0.5468	0.6017	0.9636	0.062*
C4	0.37607 (17)	0.65769 (19)	0.90212 (11)	0.0614 (4)
H4	0.3552	0.6486	0.9539	0.074*
C5	0.29205 (16)	0.6999 (2)	0.81910 (12)	0.0621 (4)
H5	0.2144	0.7191	0.8150	0.075*
C6	0.32321 (14)	0.71366 (17)	0.74230 (10)	0.0514 (4)
H6	0.2662	0.7429	0.6870	0.062*
C7	0.43793 (12)	0.68471 (14)	0.74609 (9)	0.0405 (3)
C8	0.47260 (12)	0.69755 (15)	0.66233 (9)	0.0415 (3)
H8	0.4205	0.7717	0.6213	0.050*
C9	0.60029 (13)	0.75335 (16)	0.68939 (10)	0.0466 (4)
H9A	0.6231	0.7542	0.6356	0.056*
H9B	0.6047	0.8549	0.7118	0.056*
C10	0.68618 (12)	0.65723 (15)	0.76252 (9)	0.0432 (3)
C11	0.79269 (12)	0.60980 (17)	0.76459 (10)	0.0485 (4)
H11	0.8315	0.5479	0.8140	0.058*
C12	0.85911 (12)	0.63703 (16)	0.70394 (10)	0.0464 (3)
C13	0.84423 (13)	0.75855 (17)	0.64532 (11)	0.0521 (4)
H13	0.7884	0.8310	0.6440	0.063*
C14	0.91024 (13)	0.77445 (17)	0.58897 (11)	0.0530 (4)
H14	0.8978	0.8561	0.5499	0.064*
C15	0.99443 (13)	0.66918 (18)	0.59086 (11)	0.0525 (4)
C16	1.01364 (15)	0.5491 (2)	0.65050 (12)	0.0643 (5)
H16	1.0715	0.4788	0.6531	0.077*
C17	0.94721 (14)	0.53437 (19)	0.70550 (12)	0.0602 (4)
H17	0.9612	0.4534	0.7452	0.072*
C18	0.45730 (13)	0.55031 (17)	0.60935 (10)	0.0509 (4)
H18A	0.4894	0.5627	0.5608	0.061*
H18B	0.5042	0.4744	0.6508	0.061*
C19	0.33144 (15)	0.4944 (2)	0.56723 (12)	0.0692 (5)
H19A	0.3303	0.4052	0.5329	0.104*
H19C	0.2833	0.5692	0.5271	0.104*
H19B	0.3006	0.4732	0.6149	0.104*
O2	1.06414 (11)	0.67254 (15)	0.53835 (9)	0.0708 (4)
C20	1.05297 (19)	0.7950 (2)	0.47844 (14)	0.0811 (6)
H20A	1.1071	0.7828	0.4462	0.122*
H20B	1.0711	0.8857	0.5134	0.122*
H20C	0.9731	0.7995	0.4352	0.122*
O1	0.71294 (10)	0.54013 (13)	0.90568 (7)	0.0630 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0520 (8)	0.0409 (7)	0.0352 (7)	−0.0027 (6)	0.0061 (6)	0.0005 (6)
C2	0.0554 (8)	0.0349 (7)	0.0328 (7)	−0.0029 (6)	0.0138 (6)	−0.0014 (5)
C3	0.0705 (11)	0.0487 (8)	0.0354 (7)	−0.0050 (7)	0.0167 (7)	−0.0013 (6)
C4	0.0812 (12)	0.0662 (11)	0.0471 (9)	−0.0006 (9)	0.0356 (9)	−0.0030 (8)
C5	0.0641 (10)	0.0721 (11)	0.0578 (10)	0.0081 (8)	0.0311 (9)	−0.0022 (9)
C6	0.0540 (9)	0.0578 (9)	0.0428 (8)	0.0075 (7)	0.0179 (7)	0.0000 (7)
C7	0.0511 (8)	0.0347 (7)	0.0354 (7)	0.0002 (6)	0.0150 (6)	−0.0028 (6)
C8	0.0475 (8)	0.0427 (7)	0.0324 (7)	0.0081 (6)	0.0119 (6)	0.0052 (6)
C9	0.0515 (8)	0.0464 (8)	0.0421 (8)	0.0026 (6)	0.0170 (7)	0.0080 (6)
C10	0.0461 (8)	0.0407 (7)	0.0377 (7)	−0.0043 (6)	0.0086 (6)	−0.0005 (6)
C11	0.0450 (8)	0.0477 (8)	0.0435 (8)	−0.0032 (6)	0.0043 (6)	0.0020 (6)
C12	0.0367 (7)	0.0495 (8)	0.0461 (8)	−0.0051 (6)	0.0060 (6)	−0.0018 (7)
C13	0.0423 (8)	0.0444 (8)	0.0663 (10)	−0.0017 (6)	0.0151 (7)	0.0018 (7)
C14	0.0443 (8)	0.0502 (9)	0.0592 (9)	−0.0053 (7)	0.0119 (7)	0.0068 (7)
C15	0.0413 (8)	0.0611 (9)	0.0507 (9)	−0.0044 (7)	0.0110 (7)	−0.0033 (7)
C16	0.0520 (10)	0.0674 (11)	0.0740 (11)	0.0157 (8)	0.0227 (9)	0.0117 (9)
C17	0.0490 (9)	0.0637 (10)	0.0617 (10)	0.0096 (7)	0.0120 (8)	0.0167 (8)
C18	0.0550 (9)	0.0558 (9)	0.0396 (8)	0.0073 (7)	0.0138 (7)	−0.0057 (7)
C19	0.0635 (11)	0.0683 (11)	0.0614 (10)	0.0017 (9)	0.0042 (9)	−0.0173 (9)
O2	0.0642 (7)	0.0829 (9)	0.0717 (8)	0.0064 (6)	0.0320 (6)	0.0094 (7)
C20	0.0813 (14)	0.0945 (15)	0.0748 (13)	−0.0010 (11)	0.0367 (11)	0.0165 (11)
O1	0.0627 (7)	0.0745 (8)	0.0423 (6)	0.0079 (6)	0.0068 (5)	0.0166 (5)

Geometric parameters (Å, º) top

C1—O1	1.2285 (16)	C11—H11	0.9300
C1—C2	1.481 (2)	C12—C13	1.392 (2)
C1—C10	1.491 (2)	C12—C17	1.398 (2)
C2—C3	1.3975 (19)	C13—C14	1.385 (2)
C2—C7	1.4040 (19)	C13—H13	0.9300
C3—C4	1.371 (2)	C14—C15	1.378 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.384 (2)	C15—O2	1.3644 (19)
C4—H4	0.9300	C15—C16	1.387 (2)
C5—C6	1.381 (2)	C16—C17	1.370 (2)
C5—H5	0.9300	C16—H16	0.9300
C6—C7	1.386 (2)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.508 (2)
C7—C8	1.5089 (18)	C18—H18A	0.9700
C8—C9	1.528 (2)	C18—H18B	0.9700
C8—C18	1.5337 (19)	C19—H19A	0.9600
C8—H8	0.9800	C19—H19C	0.9600
C9—C10	1.5092 (19)	C19—H19B	0.9600
C9—H9A	0.9700	O2—C20	1.417 (2)
C9—H9B	0.9700	C20—H20A	0.9600
C10—C11	1.341 (2)	C20—H20B	0.9600
C11—C12	1.459 (2)	C20—H20C	0.9600

O1—C1—C2	120.23 (13)	C12—C11—H11	114.0
O1—C1—C10	122.05 (14)	C13—C12—C17	116.60 (14)
C2—C1—C10	117.72 (12)	C13—C12—C11	125.69 (14)
C3—C2—C7	119.51 (14)	C17—C12—C11	117.70 (14)
C3—C2—C1	119.53 (13)	C14—C13—C12	121.82 (15)
C7—C2—C1	120.95 (12)	C14—C13—H13	119.1
C4—C3—C2	120.93 (14)	C12—C13—H13	119.1
C4—C3—H3	119.5	C15—C14—C13	119.92 (15)
C2—C3—H3	119.5	C15—C14—H14	120.0
C3—C4—C5	119.65 (15)	C13—C14—H14	120.0
C3—C4—H4	120.2	O2—C15—C14	125.17 (15)
C5—C4—H4	120.2	O2—C15—C16	115.27 (15)
C6—C5—C4	120.12 (16)	C14—C15—C16	119.56 (15)
C6—C5—H5	119.9	C17—C16—C15	119.89 (15)
C4—C5—H5	119.9	C17—C16—H16	120.1
C5—C6—C7	121.25 (15)	C15—C16—H16	120.1
C5—C6—H6	119.4	C16—C17—C12	122.17 (15)
C7—C6—H6	119.4	C16—C17—H17	118.9
C6—C7—C2	118.54 (13)	C12—C17—H17	118.9
C6—C7—C8	121.70 (12)	C19—C18—C8	115.56 (13)
C2—C7—C8	119.76 (13)	C19—C18—H18A	108.4
C7—C8—C9	110.23 (11)	C8—C18—H18A	108.4
C7—C8—C18	112.49 (12)	C19—C18—H18B	108.4
C9—C8—C18	110.38 (11)	C8—C18—H18B	108.4
C7—C8—H8	107.9	H18A—C18—H18B	107.5
C9—C8—H8	107.9	C18—C19—H19A	109.5
C18—C8—H8	107.9	C18—C19—H19C	109.5
C10—C9—C8	112.04 (11)	H19A—C19—H19C	109.5
C10—C9—H9A	109.2	C18—C19—H19B	109.5
C8—C9—H9A	109.2	H19A—C19—H19B	109.5
C10—C9—H9B	109.2	H19C—C19—H19B	109.5
C8—C9—H9B	109.2	C15—O2—C20	118.51 (14)
H9A—C9—H9B	107.9	O2—C20—H20A	109.5
C11—C10—C1	117.18 (13)	O2—C20—H20B	109.5
C11—C10—C9	126.41 (13)	H20A—C20—H20B	109.5
C1—C10—C9	116.38 (12)	O2—C20—H20C	109.5
C10—C11—C12	132.10 (14)	H20A—C20—H20C	109.5
C10—C11—H11	114.0	H20B—C20—H20C	109.5

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀O₂
M_r	292.36
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	12.0411 (13), 8.9698 (9), 15.5832 (18)
β (°)	110.721 (3)
V (Å³)	1574.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.38 × 0.16 × 0.12

Data collection
Diffractometer	Bruker X8 APEX CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	25378, 4068, 2552
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.676

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.129, 1.01
No. of reflections	4068
No. of parameters	200
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS2013 (Sheldrick, 2008), SHELXL2013 (Sheldrick, 2015), ORTEPIII (Burnett & Johnson, 1996) and ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

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