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Acta Crystallogr Sect E Struct Rep Online. 2008 June 1; 64(Pt 6): o1020.
Published online 2008 May 10. doi:  10.1107/S1600536808012956
PMCID: PMC2961611

3-Methyl-5-(3-phenoxy­phen­yl)cyclo­hex-2-enone

Abstract

In the title mol­ecule, C19H18O2, the cyclo­hexene ring adopts an envelope conformation, with all substituents equatorial. The dihedral angle between the benzene and phenyl rings is 83.75 (16)°. No classical hydrogen bonds are found in the crystal structure.

Related literature

For related literature, see: Pandiarajan et al. (2005 [triangle]).

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Object name is e-64-o1020-scheme1.jpg

Experimental

Crystal data

  • C19H18O2
  • M r = 278.33
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1020-efi1.jpg
  • a = 9.6002 (3) Å
  • b = 17.1594 (7) Å
  • c = 17.6730 (5) Å
  • V = 2911.34 (17) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.08 mm−1
  • T = 160 (1) K
  • 0.20 × 0.15 × 0.08 mm

Data collection

  • Nonius KappaCCD area-detector diffractometer
  • Absorption correction: none
  • 32821 measured reflections
  • 2566 independent reflections
  • 1708 reflections with I > 2σ(I)
  • R int = 0.115

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.198
  • S = 1.04
  • 2566 reflections
  • 191 parameters
  • H-atom parameters constrained
  • Δρmax = 1.03 e Å−3
  • Δρmin = −0.38 e Å−3

Data collection: COLLECT (Nonius, 2000 [triangle]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 [triangle]); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: PLATON (Spek, 2003 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012956/wn2258sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012956/wn2258Isup2.hkl

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

Acknowledgments

AT thanks the UGC, India, for the award of a Minor Research Project [file No. MRP-2355/06 (UGC-SERO), link No. 2355, 10/01/2007].

supplementary crystallographic information

Comment

The present X-ray diffraction study was undertaken to determine how the conformation of the system is affected by the substitution of a methyl group at position 3 and a phenoxyphenyl group at position 5 of the cyclohexenone ring. The molecular structure of the title compound, with atomic numbering scheme, is shown in Fig. 1. The cyclohexene ring adopts an envelope conformation, with all substituents equatorial. The dihedral angle between the benzene and phenyl rings is 83.75 (16)°. No classical hydrogen bonds are found in the crystal structure.

Experimental

The title compound was prepared according to the general procedure reported by Pandiarajan et al. (2005). A mixture of 2,4-bis(ethoxycarbonyl)-5-hydroxy-5-methyl-3,3'-phenoxy phenylcyclohexanone (4.40 g, 0.01 mol) in glacial acetic acid (25 ml) and concentrated hydrochloric acid (50 ml) was refluxed for 12 h. After completion of the reaction, the reaction mixture was neutralized with aqueous ammonia and separated by using chloroform. The product was purified by column chromatography (benzene-EtOAc, 9.5:0.5 v/v). The yield of the isolated product was 2.08 g (75%).

Refinement

H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–1.00 Å and Uiso(H) = xUeq(carrier atom), where x = 1.5 for methyl and 1.2 for all other C atoms. The maximum residual electron density peak is located 1.08 Å from C5.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme and displacement ellipsoids drawn at the 40% probability level. Hydrogen atoms are represented by spheres of arbitrary radius.

Crystal data

C19H18O2Dx = 1.270 Mg m3
Mr = 278.33Melting point: 478 K
Orthorhombic, PbcaMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 2911 reflections
a = 9.6002 (3) Åθ = 2.0–25.0º
b = 17.1594 (7) ŵ = 0.08 mm1
c = 17.6730 (5) ÅT = 160 (1) K
V = 2911.34 (17) Å3Tablet, colourless
Z = 80.20 × 0.15 × 0.08 mm
F000 = 1184

Data collection

Nonius KappaCCD area-detector diffractometer2566 independent reflections
Radiation source: Nonius FR590 sealed tube generator1708 reflections with I > 2σ(I)
Monochromator: horizontally mounted graphite crystalRint = 0.115
Detector resolution: 9 pixels mm-1θmax = 25.1º
T = 160(1) Kθmin = 2.4º
ω scans with κ offsetsh = −11→11
Absorption correction: nonek = −20→20
32821 measured reflectionsl = −21→21

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.070H-atom parameters constrained
wR(F2) = 0.198  w = 1/[σ2(Fo2) + (0.0847P)2 + 2.668P] where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
2566 reflectionsΔρmax = 1.04 e Å3
191 parametersΔρmin = −0.38 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

Special details

Experimental. Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.560 (2) Frames collected: 270 Seconds exposure per frame: 114 Degrees rotation per frame: 1.2 Crystal-Detector distance (mm): 30.0
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
O1−0.0247 (3)−0.18365 (15)0.28956 (14)0.0629 (9)
O130.5599 (2)0.05049 (13)0.11517 (15)0.0591 (9)
C1−0.0118 (3)−0.14143 (19)0.2341 (2)0.0455 (11)
C2−0.1041 (3)−0.14696 (19)0.16869 (19)0.0451 (11)
C3−0.0947 (3)−0.09996 (18)0.10876 (19)0.0413 (10)
C40.0161 (3)−0.03832 (18)0.10374 (17)0.0395 (10)
C50.0737 (4)−0.0131 (2)0.1805 (2)0.0567 (12)
C60.1045 (4)−0.0818 (2)0.2293 (2)0.0550 (12)
C110.1921 (3)0.0452 (2)0.17330 (17)0.0493 (13)
C120.3246 (4)0.0212 (2)0.14640 (18)0.0514 (11)
C130.4298 (3)0.07684 (19)0.13841 (17)0.0412 (10)
C140.4052 (3)0.15345 (18)0.15702 (17)0.0399 (10)
C150.2749 (3)0.1745 (2)0.18305 (18)0.0478 (11)
C160.1706 (4)0.1217 (2)0.19066 (18)0.0523 (14)
C210.6445 (3)0.10391 (19)0.07643 (19)0.0450 (11)
C220.6069 (3)0.1299 (2)0.0053 (2)0.0490 (11)
C230.6939 (4)0.1795 (2)−0.0331 (2)0.0512 (11)
C240.8177 (4)0.20337 (19)−0.0009 (2)0.0485 (11)
C250.8541 (4)0.1771 (2)0.0703 (2)0.0517 (11)
C260.7668 (3)0.1271 (2)0.10933 (19)0.0472 (11)
C31−0.1933 (3)−0.1052 (2)0.0437 (2)0.0547 (12)
H2−0.17441−0.185940.168810.0541*
H4A0.09381−0.058320.072420.0474*
H4B−0.022960.007860.077740.0474*
H5−0.003880.015450.206140.0677*
H6A0.18905−0.107910.209660.0662*
H6B0.12561−0.063100.280980.0662*
H120.34146−0.031810.134010.0619*
H140.476760.191320.152030.0479*
H150.257850.227370.196000.0576*
H160.081810.138190.208210.0627*
H220.521620.11346−0.016840.0588*
H230.668720.19757−0.082070.0616*
H240.877650.23777−0.027550.0582*
H250.939400.193320.092520.0622*
H260.791330.109110.158380.0566*
H31A−0.26101−0.146800.053160.0820*
H31B−0.24236−0.055470.037890.0820*
H31C−0.14127−0.11674−0.002670.0820*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0680 (17)0.0558 (16)0.0649 (16)−0.0136 (13)0.0041 (13)0.0168 (14)
O130.0528 (15)0.0379 (14)0.0866 (18)0.0057 (12)0.0163 (13)0.0127 (12)
C10.0423 (18)0.0383 (18)0.056 (2)0.0021 (15)0.0055 (15)0.0018 (17)
C20.0354 (17)0.0379 (19)0.062 (2)−0.0055 (14)0.0070 (15)−0.0097 (16)
C30.0336 (16)0.0369 (18)0.0533 (19)0.0012 (14)0.0011 (14)−0.0100 (15)
C40.0351 (16)0.0394 (18)0.0440 (17)−0.0002 (14)−0.0006 (13)−0.0026 (14)
C50.054 (2)0.063 (2)0.053 (2)−0.0137 (19)−0.0044 (17)0.0033 (18)
C60.060 (2)0.044 (2)0.061 (2)−0.0104 (17)−0.0137 (18)0.0118 (17)
C110.0363 (18)0.077 (3)0.0347 (17)−0.0184 (17)−0.0048 (14)0.0115 (17)
C120.072 (2)0.0363 (19)0.0459 (19)−0.0121 (18)−0.0090 (17)0.0034 (15)
C130.0388 (17)0.0402 (19)0.0446 (18)−0.0023 (15)0.0004 (14)0.0055 (14)
C140.0372 (17)0.0372 (19)0.0452 (18)−0.0040 (14)−0.0012 (14)0.0045 (14)
C150.047 (2)0.055 (2)0.0415 (18)0.0008 (17)0.0018 (15)0.0035 (16)
C160.048 (2)0.067 (3)0.0420 (19)0.0032 (19)0.0000 (15)0.0037 (17)
C210.0392 (17)0.0357 (18)0.060 (2)0.0048 (15)0.0081 (16)0.0010 (16)
C220.0410 (18)0.047 (2)0.059 (2)0.0015 (16)−0.0023 (16)−0.0042 (17)
C230.056 (2)0.050 (2)0.0476 (19)0.0128 (18)0.0041 (17)−0.0002 (16)
C240.050 (2)0.0376 (19)0.058 (2)0.0036 (15)0.0159 (17)0.0008 (16)
C250.0421 (19)0.053 (2)0.060 (2)0.0040 (17)−0.0005 (17)−0.0115 (18)
C260.0466 (19)0.049 (2)0.0461 (19)0.0116 (16)0.0019 (16)0.0005 (16)
C310.050 (2)0.048 (2)0.066 (2)−0.0049 (17)−0.0103 (17)−0.0078 (18)

Geometric parameters (Å, °)

O1—C11.225 (4)C24—C251.382 (5)
O13—C131.390 (4)C25—C261.384 (5)
O13—C211.403 (4)C2—H20.9500
C1—C21.460 (5)C4—H4A0.9900
C1—C61.517 (5)C4—H4B0.9900
C2—C31.334 (5)C5—H51.0000
C3—C41.503 (4)C6—H6A0.9900
C3—C311.492 (5)C6—H6B0.9900
C4—C51.528 (5)C12—H120.9500
C5—C61.490 (5)C14—H140.9500
C5—C111.520 (5)C15—H150.9500
C11—C121.419 (5)C16—H160.9500
C11—C161.364 (5)C22—H220.9500
C12—C131.397 (5)C23—H230.9500
C13—C141.376 (4)C24—H240.9500
C14—C151.381 (4)C25—H250.9500
C15—C161.357 (5)C26—H260.9500
C21—C221.382 (5)C31—H31A0.9800
C21—C261.369 (4)C31—H31B0.9800
C22—C231.372 (5)C31—H31C0.9800
C23—C241.380 (5)
O1···H23i2.6700H4A···C23x2.9900
O1···H15ii2.7200H4A···C24x2.9200
O13···H6Biii2.7500H4B···C26viii2.9300
C2···C6iv3.511 (5)H4B···H31B2.4700
C6···C2iii3.511 (5)H5···C23.0200
C14···C223.332 (4)H5···H162.2600
C22···C143.332 (4)H5···C12iv3.0800
C24···C31v3.583 (5)H5···C13iv3.0100
C31···C24vi3.583 (5)H6A···C122.8000
C1···H6Aiv3.0900H6A···H122.3700
C2···H6Aiv3.0000H6A···C1iii3.0900
C2···H6Biv3.1000H6A···C2iii3.0000
C2···H53.0200H6B···O13iv2.7500
C2···H14vi3.0500H6B···C2iii3.1000
C6···H122.9600H12···C62.9600
C12···H5iii3.0800H12···H6A2.3700
C12···H4A2.9100H12···C22x3.0200
C12···H6A2.8000H14···C212.5700
C13···H222.9500H14···C223.0700
C13···H5iii3.0100H14···C263.0900
C14···H24vii2.9600H14···C2v3.0500
C14···H16iii2.9400H15···H23vii2.5400
C15···H23vii3.0100H15···O1xi2.7200
C15···H26iv3.0200H16···H52.2600
C16···H25viii3.0700H16···C14iv2.9400
C16···H26iv2.9200H22···C132.9500
C21···H31Bix3.0200H23···O1xii2.6700
C21···H142.5700H23···C15xiii3.0100
C22···H143.0700H23···H15xiii2.5400
C22···H12x3.0200H24···C14xiii2.9600
C23···H4Ax2.9900H25···C16ix3.0700
C24···H4Ax2.9200H26···C15iii3.0200
C24···H31Av2.8000H26···C16iii2.9200
C26···H4Bix2.9300H31A···H22.3100
C26···H143.0900H31A···C24vi2.8000
H2···H31A2.3100H31B···C21viii3.0200
H4A···C122.9100H31B···H4B2.4700
C13—O13—C21116.9 (2)C5—C4—H4A109.00
O1—C1—C2122.3 (3)C5—C4—H4B109.00
O1—C1—C6121.2 (3)H4A—C4—H4B108.00
C2—C1—C6116.5 (3)C4—C5—H5106.00
C1—C2—C3123.3 (3)C6—C5—H5106.00
C2—C3—C4121.3 (3)C11—C5—H5106.00
C2—C3—C31122.2 (3)C1—C6—H6A109.00
C4—C3—C31116.5 (3)C1—C6—H6B109.00
C3—C4—C5113.8 (3)C5—C6—H6A109.00
C4—C5—C6111.2 (3)C5—C6—H6B109.00
C4—C5—C11112.5 (3)H6A—C6—H6B108.00
C6—C5—C11114.9 (3)C11—C12—H12121.00
C1—C6—C5114.8 (3)C13—C12—H12121.00
C5—C11—C12120.5 (3)C13—C14—H14120.00
C5—C11—C16120.1 (3)C15—C14—H14120.00
C12—C11—C16119.4 (3)C14—C15—H15119.00
C11—C12—C13118.9 (3)C16—C15—H15119.00
O13—C13—C12117.2 (3)C11—C16—H16120.00
O13—C13—C14122.4 (3)C15—C16—H16120.00
C12—C13—C14120.3 (3)C21—C22—H22120.00
C13—C14—C15119.0 (3)C23—C22—H22120.00
C14—C15—C16121.8 (3)C22—C23—H23120.00
C11—C16—C15120.6 (3)C24—C23—H23120.00
O13—C21—C22120.2 (3)C23—C24—H24120.00
O13—C21—C26118.6 (3)C25—C24—H24120.00
C22—C21—C26121.1 (3)C24—C25—H25120.00
C21—C22—C23119.4 (3)C26—C25—H25120.00
C22—C23—C24120.3 (3)C21—C26—H26120.00
C23—C24—C25119.8 (3)C25—C26—H26120.00
C24—C25—C26120.2 (3)C3—C31—H31A109.00
C21—C26—C25119.2 (3)C3—C31—H31B109.00
C1—C2—H2118.00C3—C31—H31C109.00
C3—C2—H2118.00H31A—C31—H31B109.00
C3—C4—H4A109.00H31A—C31—H31C109.00
C3—C4—H4B109.00H31B—C31—H31C109.00
C21—O13—C13—C12153.1 (3)C6—C5—C11—C16−125.0 (3)
C21—O13—C13—C14−30.3 (4)C5—C11—C12—C13178.1 (3)
C13—O13—C21—C22−67.2 (4)C16—C11—C12—C130.0 (5)
C13—O13—C21—C26115.2 (3)C5—C11—C16—C15−178.7 (3)
O1—C1—C2—C3177.8 (3)C12—C11—C16—C15−0.6 (5)
C6—C1—C2—C3−3.8 (5)C11—C12—C13—O13177.2 (3)
O1—C1—C6—C5−153.3 (3)C11—C12—C13—C140.6 (5)
C2—C1—C6—C528.3 (4)O13—C13—C14—C15−177.0 (3)
C1—C2—C3—C41.6 (5)C12—C13—C14—C15−0.5 (5)
C1—C2—C3—C31−178.0 (3)C13—C14—C15—C16−0.1 (5)
C2—C3—C4—C5−23.1 (4)C14—C15—C16—C110.7 (5)
C31—C3—C4—C5156.5 (3)O13—C21—C22—C23−177.2 (3)
C3—C4—C5—C645.7 (4)C26—C21—C22—C230.3 (5)
C3—C4—C5—C11176.2 (3)O13—C21—C26—C25177.2 (3)
C4—C5—C6—C1−48.6 (4)C22—C21—C26—C25−0.3 (5)
C11—C5—C6—C1−177.8 (3)C21—C22—C23—C24−0.2 (5)
C4—C5—C11—C12−71.7 (4)C22—C23—C24—C250.1 (5)
C4—C5—C11—C16106.4 (3)C23—C24—C25—C26−0.1 (5)
C6—C5—C11—C1256.9 (4)C24—C25—C26—C210.2 (5)

Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) −x, y−1/2, −z+1/2; (iii) x+1/2, y, −z+1/2; (iv) x−1/2, y, −z+1/2; (v) −x+1/2, y+1/2, z; (vi) −x+1/2, y−1/2, z; (vii) x−1/2, −y+1/2, −z; (viii) x−1, y, z; (ix) x+1, y, z; (x) −x+1, −y, −z; (xi) −x, y+1/2, −z+1/2; (xii) −x+1/2, −y, z−1/2; (xiii) x+1/2, −y+1/2, −z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WN2258).

References

  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Nonius (2000). COLLECT Nonius BV, Delft, The Netherlands.
  • Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press.
  • Pandiarajan, K., Sabapathy Mohan, R. T., Gomathi, R. & Muthukumaran, G. (2005). Magn. Reson. Chem.43, 430–434. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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