2-(4-Meth­oxy­benzyl­idene)-4,4-dimethyl-3,4-dihydro­naphthalen-1(2H)-one

Akhazzane, M.; Zouihri, H.; Daran, J.-C.; Kerbal, A.; Al Houari, G.

doi:10.1107/S1600536810044387

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3067

https://doi.org/10.1107/S1600536810044387

Open

access

2-(4-Methoxybenzylidene)-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one

Mohamed Akhazzane,^a Hafid Zouihri,^b Jean-Claude Daran,^c Abdelali Kerbal ^a and Ghali Al Houari ^a ^*

^aLaboratoire de Chimie Organique, Faculté des Sciences Dhar el Mahraz, Université Sidi Mohammed Ben Abdellah, Fès, Morocco, ^bLaboratoire de Diffraction des Rayons X, Division UATRS, Centre National pour la Recherche Scientifique et Technique, Rabat, Morocco, and ^cLaboratoire de Chimie de Coordination, 205 Route de Narbonne, 31077 Toulouse Cedex, France
^*Correspondence e-mail: ghali68@yahoo.fr

(Received 15 October 2010; accepted 29 October 2010; online 6 November 2010)

The title compound C₂₀H₂₀O₂, has the exocyclic C=C double bond in an E configuration. The two benzene rings form a dihedral angle of 72.92 (6)°.

Related literature

For general background to dipolar-1,3 cycloaddition reactions, see: Kerbal et al. (1988 ), Bennani et al. (2007 ); Al Houari et al. (2008 ). For a related structure, see: Al Houari et al. (2005 ).

Experimental

Crystal data

C₂₀H₂₀O₂
M_r = 292.36
Monoclinic, P 2₁ /n
a = 11.8587 (3) Å
b = 8.7536 (2) Å
c = 14.9392 (4) Å
β = 96.527 (1)°
V = 1540.73 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 190 K
0.19 × 0.15 × 0.13 mm

Data collection

Bruker APEXII CCD detector diffractometer
15082 measured reflections
3159 independent reflections
2709 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.08
3159 reflections
202 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810044387/ds2066sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810044387/ds2066Isup2.hkl

checkCIF report

Comment top

Knowledge of the configuration and conformation of the title compound, (1), 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 configuration of the exocyclic C=C double bond, an X-ray crystal structure determination has been carried out.

In the title compound, C₂₀H₂₀O₂, the two benzene rings form a dihedral angle of 72.92 (6)°.The cyclohexyl ring of the 3,4-dihydronaphthalen-1(2H)-one is distorted from a classical chair conformation, presumably due to conjugation of the planar annulated benzo ring (r.m.s. deviation 0.32 (13) A °). In the crystal, molecules are connected through C—H···O hydrogen bonds.

Related literature top

For general background to dipolar-1,3 cycloaddition reactions, see: Kerbal et al. (1988), Bennani et al. (2007); Al Houari et al. (2008). For a related structure, see: Al Houari et al. (2005).

Experimental top

The synthesis of 2-(4-methoxybenzylidene)-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one was achieved using the method reported by Kerbal et al. (1988), i.e. by a condensation of para anisaldehyde with 4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one in an alkaline medium in methanol.

Structure description top

For general background to dipolar-1,3 cycloaddition reactions, see: Kerbal et al. (1988), Bennani et al. (2007); Al Houari et al. (2008). For a related structure, see: Al Houari et al. (2005).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Two independent molecules of the title compound showing the atom-labelling scheme and 30% probability displacement ellipsoids.
	Fig. 2. Partial packing view.

2-(4-Methoxybenzylidene)-4,4-dimethyl-3,4-dihydronaphthalen-1(2H)-one top

Crystal data top

C₂₀H₂₀O₂	F(000) = 624
M_r = 292.36	D_x = 1.260 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1852 reflections
a = 11.8587 (3) Å	θ = 1.5–25.7°
b = 8.7536 (2) Å	µ = 0.08 mm⁻¹
c = 14.9392 (4) Å	T = 190 K
β = 96.527 (1)°	Block, colourless
V = 1540.73 (7) Å³	0.19 × 0.15 × 0.13 mm
Z = 4

Data collection top

Bruker APEXII CCD detector diffractometer	2709 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.029
Graphite monochromator	θ_max = 26.4°, θ_min = 2.7°
ω and φ scans	h = −14→14
15082 measured reflections	k = −10→10
3159 independent reflections	l = −18→18

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0577P)² + 0.2729P] where P = (F_o² + 2F_c²)/3
3159 reflections	(Δ/σ)_max = 0.001
202 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₂₀H₂₀O₂	V = 1540.73 (7) Å³
M_r = 292.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.8587 (3) Å	µ = 0.08 mm⁻¹
b = 8.7536 (2) Å	T = 190 K
c = 14.9392 (4) Å	0.19 × 0.15 × 0.13 mm
β = 96.527 (1)°

Data collection top

Bruker APEXII CCD detector diffractometer	2709 reflections with I > 2σ(I)
15082 measured reflections	R_int = 0.029
3159 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.08	Δρ_max = 0.21 e Å⁻³
3159 reflections	Δρ_min = −0.22 e Å⁻³
202 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.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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
C6	0.04770 (10)	1.19124 (13)	0.42407 (7)	0.0258 (2)
C10	0.25868 (10)	1.19809 (13)	0.41294 (7)	0.0269 (3)
C9	0.25676 (9)	1.03468 (13)	0.37763 (7)	0.0270 (3)
C5	0.16041 (10)	1.26897 (13)	0.43710 (7)	0.0265 (3)
C14	−0.07348 (9)	0.83891 (13)	0.29360 (7)	0.0257 (2)
C19	−0.04025 (10)	0.69666 (13)	0.32854 (8)	0.0291 (3)
H19	0.0014	0.6914	0.3851	0.035*
C15	−0.13830 (10)	0.84177 (13)	0.20924 (8)	0.0292 (3)
H15	−0.1640	0.9350	0.1849	0.035*
C8	0.15580 (9)	0.94675 (12)	0.40857 (8)	0.0268 (3)
H8A	0.1489	0.8489	0.3779	0.032*
H8B	0.1706	0.9271	0.4727	0.032*
C16	−0.16482 (10)	0.70964 (13)	0.16147 (8)	0.0301 (3)
H16	−0.2070	0.7146	0.1051	0.036*
C7	0.04589 (9)	1.03173 (12)	0.39000 (7)	0.0246 (2)
C18	−0.06740 (10)	0.56202 (13)	0.28164 (8)	0.0296 (3)
H18	−0.0445	0.4683	0.3068	0.036*
C17	−0.12881 (10)	0.56856 (12)	0.19710 (8)	0.0267 (3)
C13	−0.04948 (9)	0.98441 (13)	0.34094 (7)	0.0264 (3)
H13	−0.1092	1.0539	0.3362	0.032*
C11	0.36517 (10)	0.94804 (15)	0.41279 (9)	0.0371 (3)
H11A	0.4291	0.9941	0.3892	0.056*
H11B	0.3585	0.8434	0.3937	0.056*
H11C	0.3757	0.9524	0.4774	0.056*
C4	0.16424 (12)	1.42072 (14)	0.46707 (8)	0.0349 (3)
H4	0.0994	1.4656	0.4850	0.042*
C1	0.35781 (11)	1.28557 (16)	0.41635 (9)	0.0373 (3)
H1	0.4238	1.2414	0.4000	0.045*
C3	0.26285 (13)	1.50403 (15)	0.47021 (9)	0.0423 (3)
H3	0.2648	1.6048	0.4900	0.051*
C20	−0.12557 (12)	0.29770 (14)	0.17537 (10)	0.0400 (3)
H20A	−0.0442	0.2929	0.1850	0.060*
H20B	−0.1533	0.2225	0.1315	0.060*
H20C	−0.1561	0.2779	0.2311	0.060*
C2	0.35928 (13)	1.43660 (16)	0.44363 (10)	0.0448 (4)
H2	0.4256	1.4934	0.4441	0.054*
C12	0.24585 (12)	1.04047 (16)	0.27413 (8)	0.0393 (3)
H12A	0.1760	1.0898	0.2519	0.059*
H12B	0.2463	0.9384	0.2507	0.059*
H12C	0.3085	1.0968	0.2552	0.059*
O2	−0.15974 (8)	0.44573 (9)	0.14344 (6)	0.0359 (2)
O1	−0.03919 (7)	1.26029 (9)	0.43670 (6)	0.0340 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C6	0.0308 (6)	0.0244 (5)	0.0221 (5)	0.0023 (4)	0.0030 (4)	0.0019 (4)
C10	0.0296 (6)	0.0296 (6)	0.0204 (5)	−0.0040 (5)	−0.0016 (4)	0.0033 (4)
C9	0.0256 (6)	0.0295 (6)	0.0261 (6)	0.0004 (4)	0.0036 (4)	−0.0003 (4)
C5	0.0337 (6)	0.0247 (6)	0.0203 (5)	−0.0026 (5)	0.0005 (4)	0.0011 (4)
C14	0.0221 (5)	0.0262 (6)	0.0288 (6)	−0.0014 (4)	0.0036 (4)	−0.0002 (4)
C19	0.0300 (6)	0.0299 (6)	0.0264 (6)	−0.0019 (5)	−0.0012 (5)	0.0036 (5)
C15	0.0296 (6)	0.0245 (6)	0.0328 (6)	0.0021 (5)	0.0000 (5)	0.0042 (5)
C8	0.0263 (6)	0.0218 (5)	0.0319 (6)	0.0014 (4)	0.0021 (5)	0.0008 (4)
C16	0.0328 (6)	0.0306 (6)	0.0258 (6)	−0.0017 (5)	−0.0018 (5)	0.0018 (5)
C7	0.0256 (6)	0.0229 (5)	0.0255 (5)	0.0000 (4)	0.0042 (4)	0.0022 (4)
C18	0.0324 (6)	0.0229 (6)	0.0336 (6)	−0.0001 (4)	0.0036 (5)	0.0056 (5)
C17	0.0280 (6)	0.0247 (6)	0.0283 (6)	−0.0041 (4)	0.0071 (4)	−0.0014 (4)
C13	0.0257 (6)	0.0240 (6)	0.0297 (6)	0.0023 (4)	0.0041 (4)	0.0016 (4)
C11	0.0269 (6)	0.0397 (7)	0.0452 (7)	0.0031 (5)	0.0067 (5)	0.0022 (6)
C4	0.0503 (8)	0.0267 (6)	0.0265 (6)	−0.0013 (5)	−0.0014 (5)	−0.0019 (5)
C1	0.0312 (6)	0.0418 (7)	0.0374 (7)	−0.0077 (5)	−0.0030 (5)	0.0062 (6)
C3	0.0624 (9)	0.0276 (6)	0.0333 (7)	−0.0121 (6)	−0.0102 (6)	−0.0015 (5)
C20	0.0513 (8)	0.0238 (6)	0.0469 (8)	−0.0035 (5)	0.0143 (6)	−0.0020 (5)
C2	0.0457 (8)	0.0421 (8)	0.0423 (8)	−0.0204 (6)	−0.0140 (6)	0.0082 (6)
C12	0.0462 (8)	0.0442 (8)	0.0282 (6)	−0.0006 (6)	0.0074 (6)	−0.0039 (5)
O2	0.0481 (5)	0.0256 (4)	0.0338 (5)	−0.0052 (4)	0.0031 (4)	−0.0038 (3)
O1	0.0330 (5)	0.0291 (4)	0.0403 (5)	0.0058 (4)	0.0066 (4)	−0.0032 (4)

Geometric parameters (Å, º) top

C6—O1	1.2275 (13)	C7—C13	1.3414 (16)
C6—C7	1.4855 (15)	C18—C17	1.3855 (17)
C6—C5	1.4927 (16)	C18—H18	0.9300
C10—C1	1.3990 (17)	C17—O2	1.3661 (14)
C10—C5	1.4031 (16)	C13—H13	0.9300
C10—C9	1.5239 (16)	C11—H11A	0.9600
C9—C11	1.5330 (16)	C11—H11B	0.9600
C9—C12	1.5377 (16)	C11—H11C	0.9600
C9—C8	1.5381 (15)	C4—C3	1.3745 (19)
C5—C4	1.4009 (16)	C4—H4	0.9300
C14—C19	1.3898 (16)	C1—C2	1.383 (2)
C14—C15	1.3999 (16)	C1—H1	0.9300
C14—C13	1.4689 (15)	C3—C2	1.385 (2)
C19—C18	1.3901 (16)	C3—H3	0.9300
C19—H19	0.9300	C20—O2	1.4237 (15)
C15—C16	1.3766 (16)	C20—H20A	0.9600
C15—H15	0.9300	C20—H20B	0.9600
C8—C7	1.4990 (15)	C20—H20C	0.9600
C8—H8A	0.9700	C2—H2	0.9300
C8—H8B	0.9700	C12—H12A	0.9600
C16—C17	1.3925 (16)	C12—H12B	0.9600
C16—H16	0.9300	C12—H12C	0.9600

O1—C6—C7	122.40 (10)	C19—C18—H18	120.3
O1—C6—C5	120.69 (10)	O2—C17—C18	125.49 (10)
C7—C6—C5	116.80 (9)	O2—C17—C16	115.05 (10)
C1—C10—C5	117.88 (11)	C18—C17—C16	119.45 (10)
C1—C10—C9	120.38 (11)	C7—C13—C14	129.49 (10)
C5—C10—C9	121.60 (10)	C7—C13—H13	115.3
C10—C9—C11	111.52 (9)	C14—C13—H13	115.3
C10—C9—C12	108.26 (10)	C9—C11—H11A	109.5
C11—C9—C12	109.40 (10)	C9—C11—H11B	109.5
C10—C9—C8	110.32 (9)	H11A—C11—H11B	109.5
C11—C9—C8	107.49 (9)	C9—C11—H11C	109.5
C12—C9—C8	109.83 (10)	H11A—C11—H11C	109.5
C4—C5—C10	120.26 (11)	H11B—C11—H11C	109.5
C4—C5—C6	118.02 (11)	C3—C4—C5	120.70 (13)
C10—C5—C6	121.50 (10)	C3—C4—H4	119.7
C19—C14—C15	117.22 (10)	C5—C4—H4	119.7
C19—C14—C13	124.40 (10)	C2—C1—C10	121.09 (13)
C15—C14—C13	118.32 (10)	C2—C1—H1	119.5
C14—C19—C18	122.06 (10)	C10—C1—H1	119.5
C14—C19—H19	119.0	C4—C3—C2	119.43 (12)
C18—C19—H19	119.0	C4—C3—H3	120.3
C16—C15—C14	121.43 (10)	C2—C3—H3	120.3
C16—C15—H15	119.3	O2—C20—H20A	109.5
C14—C15—H15	119.3	O2—C20—H20B	109.5
C7—C8—C9	112.72 (9)	H20A—C20—H20B	109.5
C7—C8—H8A	109.0	O2—C20—H20C	109.5
C9—C8—H8A	109.0	H20A—C20—H20C	109.5
C7—C8—H8B	109.0	H20B—C20—H20C	109.5
C9—C8—H8B	109.0	C1—C2—C3	120.59 (12)
H8A—C8—H8B	107.8	C1—C2—H2	119.7
C15—C16—C17	120.32 (10)	C3—C2—H2	119.7
C15—C16—H16	119.8	C9—C12—H12A	109.5
C17—C16—H16	119.8	C9—C12—H12B	109.5
C13—C7—C6	117.12 (10)	H12A—C12—H12B	109.5
C13—C7—C8	127.53 (10)	C9—C12—H12C	109.5
C6—C7—C8	115.13 (9)	H12A—C12—H12C	109.5
C17—C18—C19	119.48 (10)	H12B—C12—H12C	109.5
C17—C18—H18	120.3	C17—O2—C20	118.20 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.44	2.8034 (15)	104

Experimental details

Crystal data
Chemical formula	C₂₀H₂₀O₂
M_r	292.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	190
a, b, c (Å)	11.8587 (3), 8.7536 (2), 14.9392 (4)
β (°)	96.527 (1)
V (Å³)	1540.73 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.19 × 0.15 × 0.13

Data collection
Diffractometer	Bruker APEXII CCD detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15082, 3159, 2709
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.626

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.08
No. of reflections	3159
No. of parameters	202
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O1	0.93	2.44	2.8034 (15)	104

Acknowledgements

The authors thinks the CNRST, Morocco, for making this work possible.

References

Al Houari, G., Kerbal, A., Bennani, B., Baba, M. F., Daoudi, M. & Ben Hadda, T. (2008). Arkivok, pp. 42–50. Google Scholar
Al Houari, G., Kerbal, A., El Bali, B. & Bolte, M. (2005). Acta Cryst. E61, o3330–o3331. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bennani, B., Kerbal, A., Daoudi, M., Filali Baba, B., Al Houari, G., Jalbout, A. F., Mimouni, M., Benazza, M., Demailly, G., Akkurt, M., Öztürk Yıldırım, S. & Ben Hadda, T. (2007). Arkivok, pp. 19–40. CrossRef Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Kerbal, A., Tshiamala, K., Vebrel, J. & Laude, B. (1988). Bull. Soc. Chim. Belg. 97, 149–161. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar