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

Akhazzane, M.; Zouihri, H.; Bennani, A.K.; Kerbal, A.; Al Houari, G.

doi:10.1107/S1600536811022793

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1700

doi:10.1107/S1600536811022793

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

Mohamed Akhazzane,^a ^* Hafid Zouihri,^b A. Kella Bennani,^a 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, and ^bLaboratoires de Diffraction des Rayons X, Centre National pour la Recherche, Scientifique et Technique, Rabat, Morocco
^*Correspondence e-mail: makhazzane@yahoo.com

(Received 8 June 2011; accepted 13 June 2011; online 18 June 2011)

In the title compound, C₁₉H₁₈O, the exocyclic C=C double bond has an E configuration. The ethyl substituent on the cyclohexanone ring is in an axial position. The cyclohexanone ring adopts a half-chair conformation, presumably due to conjugation in the benzene ring.

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 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₉H₁₈O
M_r = 262.33
Monoclinic, P 2₁ /n
a = 11.7997 (8) Å
b = 8.9020 (6) Å
c = 13.9912 (9) Å
β = 94.214 (4)°
V = 1465.68 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 296 K
0.24 × 0.13 × 0.10 mm

Data collection

Bruker APEXII CCD detector diffractometer
12738 measured reflections
2870 independent reflections
1776 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.139
S = 1.06
2870 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.15 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: 10.1107/S1600536811022793/fj2430sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811022793/fj2430Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811022793/fj2430Isup3.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) and 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.

The cyclohexanone ring in the dihydronaphthalene fused-ring system adopts a half-chair conformation, presumably due to conjugation of the planar annulated benzo ring,, with the puckering parameters of: Q(2) = 0.403 (2) Å, Phi(2) = 75.0 (3)°, Q(3) = -0.255 (2) Å (Cremer & Pople, 1975). The dihedral angle between the benzene ring and the napthyl ring system is 64.87 (9)°.

In the title compound, as shown in Fig. 1, all bond lengths and angles are normal and comparable with those reported for the related structure [Akhazzane et al., (2010)].

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). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The synthesis of (2E)-2-benzylidene-4-ethyl-3,4-dihydronaphthalen-1(2H)-onewas achieved using the method reported by Kerbal and al. [Kerbal et al. (1988)]. i.e. by a condensation of para tolylaldehyde with 4-ethyl-3,4-dihydronaphthalen-1(2H)-one in an alkaline medium in methanol.

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. Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

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

Crystal data top

C₁₉H₁₈O	F(000) = 560
M_r = 262.33	D_x = 1.189 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 317 reflections
a = 11.7997 (8) Å	θ = 2.3–25.7°
b = 8.9020 (6) Å	µ = 0.07 mm⁻¹
c = 13.9912 (9) Å	T = 296 K
β = 94.214 (4)°	Prism, colourless
V = 1465.68 (17) Å³	0.24 × 0.13 × 0.10 mm
Z = 4

Data collection top

Bruker APEXII CCD detector diffractometer	1776 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 26.0°, θ_min = 2.2°
ω and ϕ scans	h = −14→14
12738 measured reflections	k = −10→10
2870 independent reflections	l = −17→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0502P)² + 0.4678P] where P = (F_o² + 2F_c²)/3
2870 reflections	(Δ/σ)_max < 0.001
182 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₉H₁₈O	V = 1465.68 (17) Å³
M_r = 262.33	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.7997 (8) Å	µ = 0.07 mm⁻¹
b = 8.9020 (6) Å	T = 296 K
c = 13.9912 (9) Å	0.24 × 0.13 × 0.10 mm
β = 94.214 (4)°

Data collection top

Bruker APEXII CCD detector diffractometer	1776 reflections with I > 2σ(I)
12738 measured reflections	R_int = 0.039
2870 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 1.06	Δρ_max = 0.15 e Å⁻³
2870 reflections	Δρ_min = −0.15 e Å⁻³
182 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
C1	0.38673 (16)	0.3632 (2)	0.90220 (14)	0.0475 (5)
C2	0.36836 (19)	0.5147 (3)	0.91678 (16)	0.0644 (6)
C3	0.2891 (2)	0.5643 (3)	0.97699 (17)	0.0704 (7)
C4	0.2262 (2)	0.4615 (3)	1.02507 (17)	0.0699 (7)
C5	0.24340 (18)	0.3114 (3)	1.01251 (14)	0.0583 (6)
C6	0.32381 (16)	0.2594 (2)	0.95135 (13)	0.0466 (5)
C7	0.33731 (16)	0.0969 (2)	0.93682 (13)	0.0478 (5)
C8	0.42994 (15)	0.0467 (2)	0.87708 (13)	0.0437 (5)
C9	0.52038 (16)	0.1607 (2)	0.86272 (15)	0.0512 (5)
C10	0.46780 (16)	0.3104 (2)	0.83054 (14)	0.0498 (5)
C11	0.40543 (18)	0.3027 (3)	0.73028 (15)	0.0611 (6)
C12	0.4811 (2)	0.2601 (4)	0.65044 (17)	0.0861 (9)
C13	0.41996 (16)	−0.0882 (2)	0.83653 (13)	0.0482 (5)
C14	0.49530 (16)	−0.1640 (2)	0.77224 (13)	0.0472 (5)
C15	0.61293 (17)	−0.1592 (3)	0.78482 (15)	0.0598 (6)
C16	0.6781 (2)	−0.2362 (3)	0.72341 (19)	0.0748 (8)
C17	0.6287 (2)	−0.3177 (3)	0.64874 (17)	0.0734 (7)
C18	0.5129 (2)	−0.3237 (3)	0.63530 (17)	0.0752 (7)
C19	0.4468 (2)	−0.2491 (3)	0.69728 (16)	0.0652 (6)
H10	0.5290	0.3845	0.8288	0.060*
H11A	0.3445	0.2298	0.7315	0.073*
H11B	0.3712	0.3998	0.7154	0.073*
H12A	0.5471	0.3234	0.6539	0.129*
H12B	0.4396	0.2730	0.5894	0.129*
H12C	0.5041	0.1571	0.6579	0.129*
H13	0.3561	−0.1426	0.8508	0.058*
H15	0.6480	−0.1038	0.8350	0.072*
H16	0.7569	−0.2327	0.7329	0.090*
H17	0.6735	−0.3687	0.6074	0.088*
H18	0.4787	−0.3781	0.5843	0.090*
H19	0.3681	−0.2561	0.6885	0.078*
H2	0.4106	0.5847	0.8851	0.077*
H3	0.2779	0.6667	0.9853	0.085*
H4	0.1724	0.4946	1.0657	0.084*
H5	0.2011	0.2426	1.0450	0.070*
H9A	0.5691	0.1247	0.8148	0.061*
H9B	0.5667	0.1746	0.9222	0.061*
O1	0.27360 (13)	0.00631 (18)	0.97155 (11)	0.0699 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0455 (11)	0.0539 (13)	0.0434 (11)	0.0016 (9)	0.0058 (9)	0.0034 (9)
C2	0.0697 (14)	0.0580 (16)	0.0668 (15)	0.0008 (12)	0.0151 (12)	0.0043 (12)
C3	0.0805 (16)	0.0593 (15)	0.0728 (16)	0.0096 (13)	0.0141 (13)	−0.0093 (13)
C4	0.0745 (15)	0.0776 (19)	0.0604 (14)	0.0122 (13)	0.0237 (12)	−0.0098 (13)
C5	0.0609 (13)	0.0687 (16)	0.0477 (12)	0.0046 (11)	0.0202 (10)	0.0003 (11)
C6	0.0452 (11)	0.0569 (13)	0.0385 (11)	0.0031 (9)	0.0091 (9)	0.0007 (9)
C7	0.0460 (11)	0.0583 (14)	0.0406 (11)	−0.0012 (10)	0.0125 (9)	0.0046 (9)
C8	0.0390 (10)	0.0517 (13)	0.0415 (11)	0.0037 (9)	0.0108 (8)	0.0068 (9)
C9	0.0396 (10)	0.0578 (14)	0.0576 (13)	−0.0016 (9)	0.0132 (9)	0.0027 (10)
C10	0.0418 (10)	0.0553 (13)	0.0539 (12)	−0.0042 (9)	0.0145 (9)	0.0058 (10)
C11	0.0566 (12)	0.0771 (16)	0.0518 (13)	0.0029 (12)	0.0188 (10)	0.0121 (11)
C12	0.0870 (18)	0.117 (2)	0.0579 (15)	0.0054 (17)	0.0310 (14)	0.0036 (15)
C13	0.0418 (10)	0.0578 (14)	0.0464 (11)	−0.0009 (9)	0.0129 (9)	0.0064 (10)
C14	0.0487 (11)	0.0531 (13)	0.0410 (11)	0.0027 (9)	0.0111 (9)	0.0064 (9)
C15	0.0518 (12)	0.0729 (16)	0.0548 (13)	0.0125 (11)	0.0040 (10)	−0.0029 (11)
C16	0.0555 (13)	0.092 (2)	0.0790 (18)	0.0205 (13)	0.0213 (13)	−0.0014 (15)
C17	0.0875 (19)	0.0762 (18)	0.0607 (15)	0.0159 (14)	0.0341 (14)	0.0019 (13)
C18	0.0938 (19)	0.0823 (19)	0.0514 (14)	0.0004 (15)	0.0187 (13)	−0.0119 (13)
C19	0.0594 (13)	0.0794 (17)	0.0577 (14)	−0.0041 (12)	0.0104 (11)	−0.0069 (12)
O1	0.0714 (10)	0.0649 (10)	0.0790 (11)	−0.0055 (8)	0.0427 (9)	0.0053 (8)

Geometric parameters (Å, º) top

C1—C6	1.398 (3)	C11—H11B	0.9700
C1—C2	1.383 (3)	C11—H11A	0.9700
C2—H2	0.9300	C11—C12	1.528 (3)
C2—C3	1.376 (3)	C12—H12C	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C3—C4	1.384 (3)	C12—H12A	0.9600
C4—H4	0.9300	C13—H13	0.9300
C5—H5	0.9300	C13—C14	1.474 (3)
C5—C4	1.365 (3)	C13—C8	1.330 (3)
C6—C5	1.402 (3)	C14—C15	1.387 (3)
C7—C8	1.492 (2)	C14—C19	1.383 (3)
C7—C6	1.471 (3)	C15—H15	0.9300
C7—O1	1.227 (2)	C15—C16	1.377 (3)
C8—C9	1.497 (3)	C16—H16	0.9300
C9—H9B	0.9700	C16—C17	1.367 (4)
C9—H9A	0.9700	C17—H17	0.9300
C10—H10	0.9800	C18—H18	0.9300
C10—C11	1.537 (3)	C18—C17	1.366 (4)
C10—C9	1.524 (3)	C19—H19	0.9300
C10—C1	1.511 (3)	C19—C18	1.379 (3)

C6—C1—C10	120.39 (18)	C18—C17—C16	119.5 (2)
C2—C1—C10	120.99 (18)	C19—C18—H18	120.0
C2—C1—C6	118.53 (18)	C17—C18—H18	120.0
C11—C10—H10	108.1	C17—C18—C19	120.1 (2)
C9—C10—H10	108.1	C14—C19—H19	119.4
C1—C10—H10	108.1	C18—C19—H19	119.4
C9—C10—C11	112.82 (18)	C18—C19—C14	121.2 (2)
C1—C10—C11	109.61 (16)	C1—C2—H2	119.2
C1—C10—C9	109.87 (16)	C3—C2—H2	119.2
H11A—C11—H11B	107.6	C3—C2—C1	121.6 (2)
C10—C11—H11B	108.7	C4—C3—H3	120.0
C12—C11—H11B	108.7	C2—C3—H3	120.0
C10—C11—H11A	108.7	C2—C3—C4	119.9 (2)
C12—C11—H11A	108.7	C3—C4—H4	120.2
C12—C11—C10	114.33 (19)	C5—C4—H4	120.2
H12B—C12—H12C	109.5	C5—C4—C3	119.6 (2)
H12A—C12—H12C	109.5	C6—C5—H5	119.5
C11—C12—H12C	109.5	C4—C5—H5	119.5
H12A—C12—H12B	109.5	C4—C5—C6	121.0 (2)
C11—C12—H12B	109.5	C5—C6—C7	119.61 (18)
C11—C12—H12A	109.5	C1—C6—C7	121.03 (17)
C14—C13—H13	115.3	C1—C6—C5	119.3 (2)
C8—C13—H13	115.3	C6—C7—C8	117.57 (16)
C8—C13—C14	129.46 (18)	O1—C7—C8	121.35 (19)
C15—C14—C13	123.46 (19)	O1—C7—C6	121.07 (17)
C19—C14—C13	118.62 (18)	C7—C8—C9	115.53 (17)
C19—C14—C15	117.88 (19)	C13—C8—C9	126.63 (17)
C14—C15—H15	119.8	C13—C8—C7	117.63 (17)
C16—C15—H15	119.8	H9A—C9—H9B	108.1
C16—C15—C14	120.4 (2)	C10—C9—H9B	109.5
C15—C16—H16	119.5	C8—C9—H9B	109.5
C17—C16—H16	119.5	C10—C9—H9A	109.5
C17—C16—C15	120.9 (2)	C8—C9—H9A	109.5
C16—C17—H17	120.3	C8—C9—C10	110.72 (16)
C18—C17—H17	120.3

Experimental details

Crystal data
Chemical formula	C₁₉H₁₈O
M_r	262.33
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	11.7997 (8), 8.9020 (6), 13.9912 (9)
β (°)	94.214 (4)
V (Å³)	1465.68 (17)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.24 × 0.13 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	12738, 2870, 1776
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.139, 1.06
No. of reflections	2870
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.15

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