Literature DB >> 21202545

3-Methyl-5-(3-phenoxy-phen-yl)cyclo-hex-2-enone.

R T Sabapathy Mohan, S Kamatchi, M Subramanyam, A Thiruvalluvar, A Linden.   

Abstract

In the title mol-ecule, C(19)H(18)O(2), the cyclo-hexene 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.

Entities:  

Year:  2008        PMID： 21202545      PMCID： PMC2961611          DOI： 10.1107/S1600536808012956

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Pandiarajan et al. (2005 ▶).

Experimental

Crystal data

C19H18O2 M = 278.33 Orthorhombic, 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 ▶); 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 ▶). 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
C19H18O2Dx = 1.270 Mg m−3
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 mm−1
c = 17.6730 (5) ÅT = 160 (1) K
V = 2911.34 (17) Å3Tablet, colourless
Z = 80.20 × 0.15 × 0.08 mm
F000 = 1184
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 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 Å−3
191 parametersΔρmin = −0.38 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction correction: none
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.
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*
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)
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)
  2 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

2.  Synthesis and NMR spectral study of some t(3)-aryl-r(2),c(4)-bisethoxycarbonyl-t(5)-hydroxy-c(5)-methylcyclohexanones.

Authors:  K Pandiarajan; R T Sabapathy Mohan; R Gomathi; G Muthukumaran
Journal:  Magn Reson Chem       Date:  2005-05       Impact factor: 2.447
  2 in total

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