PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3067.
Published online 2010 November 6. doi:  10.1107/S1600536810044387
PMCID: PMC3011461

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

Abstract

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 [triangle]), Bennani et al. (2007 [triangle]); Al Houari et al. (2008 [triangle]). For a related structure, see: Al Houari et al. (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3067-scheme1.jpg

Experimental

Crystal data

  • C20H20O2
  • M r = 292.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3067-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.108
  • S = 1.08
  • 3159 reflections
  • 202 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.22 e Å−3

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

Supplementary Material

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044387/ds2066Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

All H atoms were fixed geometrically and treated as riding with C—H = 0.97 Å (methyne) and 0.93Å (aromatic) with Uiso(H) = 1.2Ueq(C).

Figures

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

Crystal data

C20H20O2F(000) = 624
Mr = 292.36Dx = 1.260 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1852 reflections
a = 11.8587 (3) Åθ = 1.5–25.7°
b = 8.7536 (2) ŵ = 0.08 mm1
c = 14.9392 (4) ÅT = 190 K
β = 96.527 (1)°Block, colourless
V = 1540.73 (7) Å30.19 × 0.15 × 0.13 mm
Z = 4

Data collection

Bruker APEXII CCD detector diffractometer2709 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 26.4°, θmin = 2.7°
ω and [var phi] scansh = −14→14
15082 measured reflectionsk = −10→10
3159 independent reflectionsl = −18→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.08w = 1/[σ2(Fo2) + (0.0577P)2 + 0.2729P] where P = (Fo2 + 2Fc2)/3
3159 reflections(Δ/σ)max = 0.001
202 parametersΔρmax = 0.21 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

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)

xyzUiso*/Ueq
C60.04770 (10)1.19124 (13)0.42407 (7)0.0258 (2)
C100.25868 (10)1.19809 (13)0.41294 (7)0.0269 (3)
C90.25676 (9)1.03468 (13)0.37763 (7)0.0270 (3)
C50.16041 (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)
H190.00140.69140.38510.035*
C15−0.13830 (10)0.84177 (13)0.20924 (8)0.0292 (3)
H15−0.16400.93500.18490.035*
C80.15580 (9)0.94675 (12)0.40857 (8)0.0268 (3)
H8A0.14890.84890.37790.032*
H8B0.17060.92710.47270.032*
C16−0.16482 (10)0.70964 (13)0.16147 (8)0.0301 (3)
H16−0.20700.71460.10510.036*
C70.04589 (9)1.03173 (12)0.39000 (7)0.0246 (2)
C18−0.06740 (10)0.56202 (13)0.28164 (8)0.0296 (3)
H18−0.04450.46830.30680.036*
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)
H13−0.10921.05390.33620.032*
C110.36517 (10)0.94804 (15)0.41279 (9)0.0371 (3)
H11A0.42910.99410.38920.056*
H11B0.35850.84340.39370.056*
H11C0.37570.95240.47740.056*
C40.16424 (12)1.42072 (14)0.46707 (8)0.0349 (3)
H40.09941.46560.48500.042*
C10.35781 (11)1.28557 (16)0.41635 (9)0.0373 (3)
H10.42381.24140.40000.045*
C30.26285 (13)1.50403 (15)0.47021 (9)0.0423 (3)
H30.26481.60480.49000.051*
C20−0.12557 (12)0.29770 (14)0.17537 (10)0.0400 (3)
H20A−0.04420.29290.18500.060*
H20B−0.15330.22250.13150.060*
H20C−0.15610.27790.23110.060*
C20.35928 (13)1.43660 (16)0.44363 (10)0.0448 (4)
H20.42561.49340.44410.054*
C120.24585 (12)1.04047 (16)0.27413 (8)0.0393 (3)
H12A0.17601.08980.25190.059*
H12B0.24630.93840.25070.059*
H12C0.30851.09680.25520.059*
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)

U11U22U33U12U13U23
C60.0308 (6)0.0244 (5)0.0221 (5)0.0023 (4)0.0030 (4)0.0019 (4)
C100.0296 (6)0.0296 (6)0.0204 (5)−0.0040 (5)−0.0016 (4)0.0033 (4)
C90.0256 (6)0.0295 (6)0.0261 (6)0.0004 (4)0.0036 (4)−0.0003 (4)
C50.0337 (6)0.0247 (6)0.0203 (5)−0.0026 (5)0.0005 (4)0.0011 (4)
C140.0221 (5)0.0262 (6)0.0288 (6)−0.0014 (4)0.0036 (4)−0.0002 (4)
C190.0300 (6)0.0299 (6)0.0264 (6)−0.0019 (5)−0.0012 (5)0.0036 (5)
C150.0296 (6)0.0245 (6)0.0328 (6)0.0021 (5)0.0000 (5)0.0042 (5)
C80.0263 (6)0.0218 (5)0.0319 (6)0.0014 (4)0.0021 (5)0.0008 (4)
C160.0328 (6)0.0306 (6)0.0258 (6)−0.0017 (5)−0.0018 (5)0.0018 (5)
C70.0256 (6)0.0229 (5)0.0255 (5)0.0000 (4)0.0042 (4)0.0022 (4)
C180.0324 (6)0.0229 (6)0.0336 (6)−0.0001 (4)0.0036 (5)0.0056 (5)
C170.0280 (6)0.0247 (6)0.0283 (6)−0.0041 (4)0.0071 (4)−0.0014 (4)
C130.0257 (6)0.0240 (6)0.0297 (6)0.0023 (4)0.0041 (4)0.0016 (4)
C110.0269 (6)0.0397 (7)0.0452 (7)0.0031 (5)0.0067 (5)0.0022 (6)
C40.0503 (8)0.0267 (6)0.0265 (6)−0.0013 (5)−0.0014 (5)−0.0019 (5)
C10.0312 (6)0.0418 (7)0.0374 (7)−0.0077 (5)−0.0030 (5)0.0062 (6)
C30.0624 (9)0.0276 (6)0.0333 (7)−0.0121 (6)−0.0102 (6)−0.0015 (5)
C200.0513 (8)0.0238 (6)0.0469 (8)−0.0035 (5)0.0143 (6)−0.0020 (5)
C20.0457 (8)0.0421 (8)0.0423 (8)−0.0204 (6)−0.0140 (6)0.0082 (6)
C120.0462 (8)0.0442 (8)0.0282 (6)−0.0006 (6)0.0074 (6)−0.0039 (5)
O20.0481 (5)0.0256 (4)0.0338 (5)−0.0052 (4)0.0031 (4)−0.0038 (3)
O10.0330 (5)0.0291 (4)0.0403 (5)0.0058 (4)0.0066 (4)−0.0032 (4)

Geometric parameters (Å, °)

C6—O11.2275 (13)C7—C131.3414 (16)
C6—C71.4855 (15)C18—C171.3855 (17)
C6—C51.4927 (16)C18—H180.9300
C10—C11.3990 (17)C17—O21.3661 (14)
C10—C51.4031 (16)C13—H130.9300
C10—C91.5239 (16)C11—H11A0.9600
C9—C111.5330 (16)C11—H11B0.9600
C9—C121.5377 (16)C11—H11C0.9600
C9—C81.5381 (15)C4—C31.3745 (19)
C5—C41.4009 (16)C4—H40.9300
C14—C191.3898 (16)C1—C21.383 (2)
C14—C151.3999 (16)C1—H10.9300
C14—C131.4689 (15)C3—C21.385 (2)
C19—C181.3901 (16)C3—H30.9300
C19—H190.9300C20—O21.4237 (15)
C15—C161.3766 (16)C20—H20A0.9600
C15—H150.9300C20—H20B0.9600
C8—C71.4990 (15)C20—H20C0.9600
C8—H8A0.9700C2—H20.9300
C8—H8B0.9700C12—H12A0.9600
C16—C171.3925 (16)C12—H12B0.9600
C16—H160.9300C12—H12C0.9600
O1—C6—C7122.40 (10)C19—C18—H18120.3
O1—C6—C5120.69 (10)O2—C17—C18125.49 (10)
C7—C6—C5116.80 (9)O2—C17—C16115.05 (10)
C1—C10—C5117.88 (11)C18—C17—C16119.45 (10)
C1—C10—C9120.38 (11)C7—C13—C14129.49 (10)
C5—C10—C9121.60 (10)C7—C13—H13115.3
C10—C9—C11111.52 (9)C14—C13—H13115.3
C10—C9—C12108.26 (10)C9—C11—H11A109.5
C11—C9—C12109.40 (10)C9—C11—H11B109.5
C10—C9—C8110.32 (9)H11A—C11—H11B109.5
C11—C9—C8107.49 (9)C9—C11—H11C109.5
C12—C9—C8109.83 (10)H11A—C11—H11C109.5
C4—C5—C10120.26 (11)H11B—C11—H11C109.5
C4—C5—C6118.02 (11)C3—C4—C5120.70 (13)
C10—C5—C6121.50 (10)C3—C4—H4119.7
C19—C14—C15117.22 (10)C5—C4—H4119.7
C19—C14—C13124.40 (10)C2—C1—C10121.09 (13)
C15—C14—C13118.32 (10)C2—C1—H1119.5
C14—C19—C18122.06 (10)C10—C1—H1119.5
C14—C19—H19119.0C4—C3—C2119.43 (12)
C18—C19—H19119.0C4—C3—H3120.3
C16—C15—C14121.43 (10)C2—C3—H3120.3
C16—C15—H15119.3O2—C20—H20A109.5
C14—C15—H15119.3O2—C20—H20B109.5
C7—C8—C9112.72 (9)H20A—C20—H20B109.5
C7—C8—H8A109.0O2—C20—H20C109.5
C9—C8—H8A109.0H20A—C20—H20C109.5
C7—C8—H8B109.0H20B—C20—H20C109.5
C9—C8—H8B109.0C1—C2—C3120.59 (12)
H8A—C8—H8B107.8C1—C2—H2119.7
C15—C16—C17120.32 (10)C3—C2—H2119.7
C15—C16—H16119.8C9—C12—H12A109.5
C17—C16—H16119.8C9—C12—H12B109.5
C13—C7—C6117.12 (10)H12A—C12—H12B109.5
C13—C7—C8127.53 (10)C9—C12—H12C109.5
C6—C7—C8115.13 (9)H12A—C12—H12C109.5
C17—C18—C19119.48 (10)H12B—C12—H12C109.5
C17—C18—H18120.3C17—O2—C20118.20 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C13—H13···O10.932.442.8034 (15)104

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2066).

References

  • Al Houari, G., Kerbal, A., Bennani, B., Baba, M. F., Daoudi, M. & Ben Hadda, T. (2008). Arkivok, pp. 42–50.
  • Al Houari, G., Kerbal, A., El Bali, B. & Bolte, M. (2005). Acta Cryst. E61, o3330–o3331.
  • 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.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kerbal, A., Tshiamala, K., Vebrel, J. & Laude, B. (1988). Bull. Soc. Chim. Belg.97, 149–161.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Westrip, S. P. (2010). J. Appl. Cryst.43, 920–925.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography