Experimental. Crystal data. C 19 H 18 O 2 M r = Orthorhombic, Pbca a = (3) Å b = (7) Å c = (5) Å.

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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Methyl-5-(3-phenoxyphenyl)cyclohex- 2-enone R. T. Sabapathy Mohan, a S. Kamatchi, a M. Subramanyam, b A. Thiruvalluvar b * and A. Linden c a Department of Chemistry, Annamalai University, Annamalai Nagar , Tamil Nadu, India, b PG Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur , Tamil Nadu, India, and c Institute of Organic Chemistry, University of Zürich, Winterthurerstrasse 190, CH-8057 Zürich, Switzerland Correspondence athiru@vsnl.net Received 29 April 2008; accepted 1 May 2008 Experimental Crystal data C 19 H 18 O 2 M r = Orthorhombic, Pbca a = (3) Å b = (7) Å c = (5) Å Data collection Nonius KappaCCD area-detector diffractometer Absorption correction: none measured reflections Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections V = (17) Å 3 Z =8 Mo K radiation = 0.08 mm 1 T = 160 (1) K mm 2566 independent reflections 1708 reflections with I > 2(I) R int = parameters H-atom parameters constrained max = 1.03 e Å 3 min = 0.38 e Å 3 Key indicators: single-crystal X-ray study; T = 160 K; mean (C C) = Å; R factor = 0.070; wr factor = 0.199; data-to-parameter ratio = In the title molecule, C 19 H 18 O 2, the cyclohexene ring adopts an envelope conformation, with all substituents equatorial. The dihedral angle between the benzene and phenyl rings is (16). No classical hydrogen bonds are found in the crystal structure. Related literature For related literature, see: Pandiarajan et al. (2005). Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2003). 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 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 New York: Academic Press. Pandiarajan, K., Sabapathy Mohan, R. T., Gomathi, R. & Muthukumaran, G. (2005). Magn. Reson. Chem. 43, Sheldrick, G. M. (2008). Acta Cryst. A64, Spek, A. L. (2003). J. Appl. Cryst. 36, o1020 Mohan et al. doi: /s Acta Cryst. (2008). E64, o1020

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3 Acta Cryst. (2008). E64, o1020 [ doi: /s ] 3-Methyl-5-(3-phenoxyphenyl)cyclohex-2-enone R. T. S. Mohan, S. Kamatchi, M. Subramanyam, A. Thiruvalluvar and A. Linden 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 (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 = Å and U iso (H) = xu eq (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. sup-1

4 3-Methyl-5-(3-phenoxyphenyl)cyclohex-2-enone Crystal data C 19 H 18 O 2 M r = Orthorhombic, Pbca Hall symbol: -P 2ac 2ab D x = Mg m 3 Melting point: 478 K Mo Kα radiation λ = Å a = (3) Å θ = º b = (7) Å c = (5) Å V = (17) Å 3 Z = 8 F 000 = 1184 Cell parameters from 2911 reflections µ = 0.08 mm 1 T = 160 (1) K Tablet, colourless mm Data collection Nonius KappaCCD area-detector diffractometer Radiation source: Nonius FR590 sealed tube generator Monochromator: horizontally mounted graphite crystal 2566 independent reflections 1708 reflections with I > 2σ(I) R int = Detector resolution: 9 pixels mm -1 θ max = 25.1º T = 160(1) K θ min = 2.4º ω scans with κ offsets Absorption correction: none h = k = measured reflections l = Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = Secondary atom site location: difference Fourier map Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o 2 ) + (0.0847P) P] where P = (F o 2 + 2F c 2 )/3 S = 1.04 (Δ/σ) max < reflections Δρ max = 1.04 e Å parameters Δρ min = 0.38 e Å 3 Primary atom site location: structure-invariant direct methods Extinction correction: none sup-2

5 Special details Experimental. Solvent used:? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (.): (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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R- factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq O (3) (15) (14) (9) O (2) (13) (15) (9) C (3) (19) (2) (11) C (3) (19) (19) (11) C (3) (18) (19) (10) C (3) (18) (17) (10) C (4) (2) (2) (12) C (4) (2) (2) (12) C (3) (2) (17) (13) C (4) (2) (18) (11) C (3) (19) (17) (10) C (3) (18) (17) (10) C (3) (2) (18) (11) C (4) (2) (18) (14) C (3) (19) (19) (11) C (3) (2) (2) (11) C (4) (2) (2) (11) C (4) (19) (2) (11) C (4) (2) (2) (11) C (3) (2) (19) (11) C (3) (2) (2) (12) H * H4A * H4B * H * H6A * H6B * H * H * H * sup-3

6 H * H * H * H * H * H * H31A * H31B * H31C * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (17) (16) (16) (13) (13) (14) O (15) (14) (18) (12) (13) (12) C (18) (18) (2) (15) (15) (17) C (17) (19) (2) (14) (15) (16) C (16) (18) (19) (14) (14) (15) C (16) (18) (17) (14) (13) (14) C (2) (2) (2) (19) (17) (18) C (2) (2) (2) (17) (18) (17) C (18) (3) (17) (17) (14) (17) C (2) (19) (19) (18) (17) (15) C (17) (19) (18) (15) (14) (14) C (17) (19) (18) (14) (14) (14) C (2) (2) (18) (17) (15) (16) C (2) (3) (19) (19) (15) (17) C (17) (18) (2) (15) (16) (16) C (18) (2) (2) (16) (16) (17) C (2) (2) (19) (18) (17) (16) C (2) (19) (2) (15) (17) (16) C (19) (2) (2) (17) (17) (18) C (19) (2) (19) (16) (16) (16) C (2) (2) (2) (17) (17) (18) Geometric parameters (Å, ) O1 C (4) C24 C (5) O13 C (4) C25 C (5) O13 C (4) C2 H C1 C (5) C4 H4A C1 C (5) C4 H4B C2 C (5) C5 H C3 C (4) C6 H6A C3 C (5) C6 H6B C4 C (5) C12 H C5 C (5) C14 H C5 C (5) C15 H C11 C (5) C16 H sup-4

7 C11 C (5) C22 H C12 C (5) C23 H C13 C (4) C24 H C14 C (4) C25 H C15 C (5) C26 H C21 C (5) C31 H31A C21 C (4) C31 H31B C22 C (5) C31 H31C C23 C (5) O1 H23 i H4A C23 x O1 H15 ii H4A C24 x O13 H6B iii H4B C26 viii C2 C6 iv (5) H4B H31B C6 C2 iii (5) H5 C C14 C (4) H5 H C22 C (4) H5 C12 iv C24 C31 v (5) H5 C13 iv C31 C24 vi (5) H6A C C1 H6A iv H6A H C2 H6A iv H6A C1 iii C2 H6B iv H6A C2 iii C2 H H6B O13 iv C2 H14 vi H6B C2 iii C6 H H12 C C12 H5 iii H12 H6A C12 H4A H12 C22 x C12 H6A H14 C C13 H H14 C C13 H5 iii H14 C C14 H24 vii H14 C2 v C14 H16 iii H15 H23 vii C15 H23 vii H15 O1 xi C15 H26 iv H16 H C16 H25 viii H16 C14 iv C16 H26 iv H22 C C21 H31B ix H23 O1 xii C21 H H23 C15 xiii C22 H H23 H15 xiii C22 H12 x H24 C14 xiii C23 H4A x H25 C16 ix C24 H4A x H26 C15 iii C24 H31A v H26 C16 iii C26 H4B ix H31A H sup-5

8 C26 H H31A C24 vi H2 H31A H31B C21 viii H4A C H31B H4B C13 O13 C (2) C5 C4 H4A O1 C1 C (3) C5 C4 H4B O1 C1 C (3) H4A C4 H4B C2 C1 C (3) C4 C5 H C1 C2 C (3) C6 C5 H C2 C3 C (3) C11 C5 H C2 C3 C (3) C1 C6 H6A C4 C3 C (3) C1 C6 H6B C3 C4 C (3) C5 C6 H6A C4 C5 C (3) C5 C6 H6B C4 C5 C (3) H6A C6 H6B C6 C5 C (3) C11 C12 H C1 C6 C (3) C13 C12 H C5 C11 C (3) C13 C14 H C5 C11 C (3) C15 C14 H C12 C11 C (3) C14 C15 H C11 C12 C (3) C16 C15 H O13 C13 C (3) C11 C16 H O13 C13 C (3) C15 C16 H C12 C13 C (3) C21 C22 H C13 C14 C (3) C23 C22 H C14 C15 C (3) C22 C23 H C11 C16 C (3) C24 C23 H O13 C21 C (3) C23 C24 H O13 C21 C (3) C25 C24 H C22 C21 C (3) C24 C25 H C21 C22 C (3) C26 C25 H C22 C23 C (3) C21 C26 H C23 C24 C (3) C25 C26 H C24 C25 C (3) C3 C31 H31A C21 C26 C (3) C3 C31 H31B C1 C2 H C3 C31 H31C C3 C2 H H31A C31 H31B C3 C4 H4A H31A C31 H31C C3 C4 H4B H31B C31 H31C C21 O13 C13 C (3) C6 C5 C11 C (3) C21 O13 C13 C (4) C5 C11 C12 C (3) C13 O13 C21 C (4) C16 C11 C12 C (5) C13 O13 C21 C (3) C5 C11 C16 C (3) O1 C1 C2 C (3) C12 C11 C16 C (5) C6 C1 C2 C3 3.8 (5) C11 C12 C13 O (3) O1 C1 C6 C (3) C11 C12 C13 C (5) C2 C1 C6 C (4) O13 C13 C14 C (3) C1 C2 C3 C4 1.6 (5) C12 C13 C14 C (5) C1 C2 C3 C (3) C13 C14 C15 C (5) sup-6

9 C2 C3 C4 C (4) C14 C15 C16 C (5) C31 C3 C4 C (3) O13 C21 C22 C (3) C3 C4 C5 C (4) C26 C21 C22 C (5) C3 C4 C5 C (3) O13 C21 C26 C (3) C4 C5 C6 C (4) C22 C21 C26 C (5) C11 C5 C6 C (3) C21 C22 C23 C (5) C4 C5 C11 C (4) C22 C23 C24 C (5) C4 C5 C11 C (3) C23 C24 C25 C (5) C6 C5 C11 C (4) C24 C25 C26 C (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. sup-7

10 Fig. 1 sup-8