Literature DB >> 21202585

3-Methyl-5-(4-methyl-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(14)H(16)O, the cyclo-hexene ring adopts an envelope conformation, with all substituents equatorial. Mol-ecules are linked by C-H⋯O hydrogen bonds. A C-H⋯π inter-action involving the benzene ring is also found in the crystal structure. The H atoms of both methyl groups are disordered equally over two positions.

Entities:  

Year:  2008        PMID： 21202585      PMCID： PMC2961522          DOI： 10.1107/S1600536808013822

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


Related literature

For related literature, see: Padmavathi et al. (2000 ▶).

Experimental

Crystal data

C14H16O M = 200.27 Monoclinic, a = 5.2623 (3) Å b = 11.1583 (7) Å c = 19.3341 (11) Å β = 94.994 (4)° V = 1130.96 (12) Å3 Z = 4 Mo Kα radiation μ = 0.07 mm−1 T = 160 (1) K 0.25 × 0.18 × 0.18 mm

Data collection

Nonius KappaCCD area-detector diffractometer Absorption correction: none 16716 measured reflections 2002 independent reflections 1316 reflections with I > 2σ(I) R int = 0.085

Refinement

R[F 2 > 2σ(F 2)] = 0.072 wR(F 2) = 0.231 S = 1.09 2002 reflections 137 parameters H-atom parameters constrained Δρmax = 0.48 e Å−3 Δρmin = −0.30 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/S1600536808013822/wn2260sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536808013822/wn2260Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H16OF000 = 432
Mr = 200.27Dx = 1.176 Mg m−3
Monoclinic, P21/nMelting point: 315 K
Hall symbol: -P 2ynMo Kα radiation λ = 0.71073 Å
a = 5.2623 (3) ÅCell parameters from 2105 reflections
b = 11.1583 (7) Åθ = 2.0–25.0º
c = 19.3341 (11) ŵ = 0.07 mm−1
β = 94.994 (4)ºT = 160 (1) K
V = 1130.96 (12) Å3Prism, colourless
Z = 40.25 × 0.18 × 0.18 mm
Nonius KappaCCD area-detector diffractometer2002 independent reflections
Radiation source: Nonius FR590 sealed tube generator1316 reflections with I > 2σ(I)
Monochromator: horizontally mounted graphite crystalRint = 0.085
Detector resolution: 9 pixels mm-1θmax = 25.0º
T = 160(1) Kθmin = 3.7º
ω scans with κ offsetsh = 0→6
Absorption correction: nonek = 0→13
16716 measured reflectionsl = −22→22
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.072  w = 1/[σ2(Fo2) + (0.1423P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.231(Δ/σ)max < 0.001
S = 1.09Δρmax = 0.48 e Å−3
2002 reflectionsΔρmin = −0.30 e Å−3
137 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.16 (2)
Secondary atom site location: difference Fourier map
Experimental. Solvent used: ? Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.728 (3) Frames collected: 237 Seconds exposure per frame: 18 Degrees rotation per frame: 1.8 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*/UeqOcc. (<1)
O10.8289 (3)0.60964 (17)0.42477 (10)0.0480 (7)
C10.6687 (5)0.5310 (2)0.41187 (13)0.0380 (9)
C20.6807 (5)0.4150 (3)0.44740 (14)0.0392 (9)
C30.5102 (5)0.3288 (2)0.43313 (13)0.0373 (9)
C40.2974 (5)0.3417 (2)0.37608 (13)0.0397 (9)
C50.3519 (5)0.4399 (2)0.32304 (14)0.0410 (9)
C60.4432 (5)0.5523 (3)0.36013 (15)0.0446 (10)
C110.1274 (5)0.4579 (2)0.26887 (14)0.0399 (9)
C120.0467 (5)0.3630 (3)0.22587 (15)0.0449 (10)
C13−0.1517 (5)0.3746 (3)0.17411 (15)0.0437 (10)
C14−0.2758 (5)0.4829 (2)0.16303 (13)0.0386 (9)
C15−0.1973 (5)0.5781 (2)0.20557 (14)0.0412 (9)
C16−0.0006 (5)0.5656 (2)0.25810 (14)0.0411 (9)
C21−0.4928 (5)0.4965 (3)0.10693 (15)0.0505 (10)
C310.5112 (6)0.2145 (2)0.47430 (15)0.0496 (10)
H20.816240.400750.482160.0471*
H4A0.272080.264200.351560.0476*
H4B0.137300.361480.396960.0476*
H50.497010.410210.297610.0492*
H6A0.490290.611870.325520.0536*
H6B0.301950.586440.384490.0536*
H120.130070.287790.232100.0539*
H13−0.202630.307440.146040.0525*
H15−0.279320.653530.198800.0494*
H160.046710.632150.287050.0493*
H21A−0.556560.578990.106750.0758*0.500
H21B−0.431590.478010.061680.0758*0.500
H21C−0.630660.441170.116000.0758*0.500
H21D−0.522650.419790.082870.0758*0.500
H21E−0.647620.520770.127940.0758*0.500
H21F−0.448550.557610.073620.0758*0.500
H31A0.370720.163090.455560.0744*0.500
H31B0.673700.172790.471170.0744*0.500
H31C0.489900.233120.522990.0744*0.500
H31D0.652160.216240.510920.0744*0.500
H31E0.349180.206540.495310.0744*0.500
H31F0.532980.146210.443490.0744*0.500
U11U22U33U12U13U23
O10.0439 (12)0.0548 (13)0.0434 (13)−0.0079 (10)−0.0074 (9)0.0016 (9)
C10.0331 (15)0.0480 (17)0.0324 (15)−0.0016 (13)0.0006 (12)−0.0033 (12)
C20.0340 (14)0.0505 (17)0.0324 (15)0.0048 (13)−0.0014 (12)0.0012 (12)
C30.0368 (15)0.0427 (16)0.0323 (15)0.0072 (12)0.0025 (12)−0.0009 (12)
C40.0379 (16)0.0433 (17)0.0370 (16)0.0007 (12)−0.0012 (12)0.0020 (12)
C50.0421 (16)0.0400 (16)0.0393 (16)0.0006 (12)−0.0052 (13)0.0000 (12)
C60.0429 (16)0.0458 (17)0.0432 (17)−0.0035 (13)−0.0076 (13)0.0081 (13)
C110.0393 (16)0.0390 (16)0.0399 (16)−0.0028 (12)−0.0043 (12)0.0024 (12)
C120.0485 (17)0.0373 (16)0.0463 (18)0.0028 (12)−0.0114 (14)−0.0005 (12)
C130.0471 (17)0.0418 (17)0.0406 (17)−0.0031 (13)−0.0058 (13)−0.0043 (12)
C140.0366 (15)0.0468 (17)0.0315 (15)−0.0018 (12)−0.0024 (11)0.0029 (12)
C150.0403 (16)0.0424 (16)0.0395 (17)0.0052 (12)−0.0049 (13)0.0046 (12)
C160.0449 (16)0.0360 (16)0.0409 (17)−0.0035 (12)−0.0042 (13)−0.0015 (12)
C210.0443 (17)0.065 (2)0.0398 (17)0.0002 (15)−0.0103 (13)0.0021 (14)
C310.0583 (19)0.0449 (17)0.0441 (17)0.0061 (14)−0.0038 (14)0.0024 (13)
O1—C11.227 (3)C5—H51.0000
C1—C21.464 (4)C6—H6A0.9900
C1—C61.503 (4)C6—H6B0.9900
C2—C31.328 (4)C12—H120.9500
C3—C41.509 (4)C13—H130.9500
C3—C311.503 (3)C15—H150.9500
C4—C51.545 (3)C16—H160.9500
C5—C61.503 (4)C21—H21A0.9800
C5—C111.522 (4)C21—H21B0.9800
C11—C121.390 (4)C21—H21C0.9800
C11—C161.385 (3)C21—H21D0.9800
C12—C131.388 (4)C21—H21E0.9800
C13—C141.381 (4)C21—H21F0.9800
C14—C151.384 (3)C31—H31A0.9800
C14—C211.513 (4)C31—H31B0.9800
C15—C161.393 (4)C31—H31C0.9800
C2—H20.9500C31—H31D0.9800
C4—H4A0.9900C31—H31E0.9800
C4—H4B0.9900C31—H31F0.9800
O1···C31i3.387 (3)H4B···H2v2.5000
O1···H6Bii2.6800H5···C22.9700
O1···H13iii2.6500H5···C14ii3.0700
O1···H2iv2.4800H6A···C15ii2.9800
O1···H31Ci2.6800H6A···C162.8400
O1···H31Ei2.7800H6A···H162.4000
C1···C16ii3.594 (4)H6A···C12iii2.9700
C1···C2i3.467 (4)H6A···C13iii3.0500
C1···C3i3.579 (4)H6A···H12iii2.3200
C2···C1i3.467 (4)H6A···H13iii2.4900
C2···C2i3.468 (4)H6B···O1v2.6800
C3···C1i3.579 (4)H6B···C162.8100
C16···C1v3.594 (4)H6B···H162.2700
C31···O1i3.387 (3)H12···C42.9100
C1···H31Ci3.0600H12···H4A2.3800
C2···H52.9700H12···H6Avi2.3200
C2···H4Bii2.7400H12···H16vi2.4800
C4···H122.9100H13···H21D2.3500
C6···H162.5700H13···O1vi2.6500
C12···H21Cii2.9600H13···H6Avi2.4900
C12···H4A2.8300H15···H21A2.3500
C12···H6Avi2.9700H16···C62.5700
C13···H6Avi3.0500H16···H6A2.4000
C14···H5v3.0700H16···H6B2.2700
C15···H6Av2.9800H16···H12iii2.4800
C16···H6A2.8400H21A···H152.3500
C16···H6B2.8100H21A···H4Avii2.5200
C21···H31Biii3.0700H21C···C12v2.9600
C21···H31Avii2.9100H21D···H132.3500
C31···H21Fvi3.1000H21F···C31iii3.1000
H2···H4Bii2.5000H31A···H4A2.3200
H2···H31D2.3200H31A···C21viii2.9100
H2···O1iv2.4800H31B···C21vi3.0700
H4A···C122.8300H31C···O1i2.6800
H4A···H122.3800H31C···C1i3.0600
H4A···H31A2.3200H31D···H22.3200
H4A···H31F2.5200H31E···O1i2.7800
H4A···H21Aviii2.5200H31F···H4A2.5200
H4B···C2v2.7400
O1—C1—C2122.4 (2)C15—C16—H16119.00
O1—C1—C6120.7 (2)C14—C21—H21A109.00
C2—C1—C6116.8 (2)C14—C21—H21B109.00
C1—C2—C3122.8 (2)C14—C21—H21C109.00
C2—C3—C4121.9 (2)C14—C21—H21D109.00
C2—C3—C31122.2 (2)C14—C21—H21E109.00
C4—C3—C31115.9 (2)C14—C21—H21F109.00
C3—C4—C5112.6 (2)H21A—C21—H21B109.00
C4—C5—C6110.2 (2)H21A—C21—H21C110.00
C4—C5—C11111.9 (2)H21A—C21—H21D141.00
C6—C5—C11114.5 (2)H21A—C21—H21E56.00
C1—C6—C5112.8 (2)H21A—C21—H21F56.00
C5—C11—C12119.3 (2)H21B—C21—H21C109.00
C5—C11—C16123.8 (2)H21B—C21—H21D56.00
C12—C11—C16116.9 (2)H21B—C21—H21E141.00
C11—C12—C13122.1 (3)H21B—C21—H21F56.00
C12—C13—C14120.6 (3)H21C—C21—H21D56.00
C13—C14—C15117.8 (2)H21C—C21—H21E56.00
C13—C14—C21121.1 (2)H21C—C21—H21F141.00
C15—C14—C21121.1 (2)H21D—C21—H21E109.00
C14—C15—C16121.4 (2)H21D—C21—H21F109.00
C11—C16—C15121.2 (2)H21E—C21—H21F110.00
C1—C2—H2119.00C3—C31—H31A109.00
C3—C2—H2119.00C3—C31—H31B109.00
C3—C4—H4A109.00C3—C31—H31C109.00
C3—C4—H4B109.00C3—C31—H31D109.00
C5—C4—H4A109.00C3—C31—H31E109.00
C5—C4—H4B109.00C3—C31—H31F109.00
H4A—C4—H4B108.00H31A—C31—H31B109.00
C4—C5—H5107.00H31A—C31—H31C109.00
C6—C5—H5107.00H31A—C31—H31D141.00
C11—C5—H5107.00H31A—C31—H31E56.00
C1—C6—H6A109.00H31A—C31—H31F56.00
C1—C6—H6B109.00H31B—C31—H31C109.00
C5—C6—H6A109.00H31B—C31—H31D56.00
C5—C6—H6B109.00H31B—C31—H31E141.00
H6A—C6—H6B108.00H31B—C31—H31F56.00
C11—C12—H12119.00H31C—C31—H31D56.00
C13—C12—H12119.00H31C—C31—H31E56.00
C12—C13—H13120.00H31C—C31—H31F141.00
C14—C13—H13120.00H31D—C31—H31E109.00
C14—C15—H15119.00H31D—C31—H31F109.00
C16—C15—H15119.00H31E—C31—H31F109.00
C11—C16—H16119.00
O1—C1—C2—C3−179.1 (3)C4—C5—C11—C16120.6 (3)
C6—C1—C2—C33.3 (4)C6—C5—C11—C12172.5 (2)
O1—C1—C6—C5149.3 (2)C6—C5—C11—C16−5.7 (4)
C2—C1—C6—C5−33.1 (3)C5—C11—C12—C13−178.0 (3)
C1—C2—C3—C43.3 (4)C16—C11—C12—C130.4 (4)
C1—C2—C3—C31−174.4 (2)C5—C11—C16—C15177.0 (2)
C2—C3—C4—C519.3 (3)C12—C11—C16—C15−1.3 (4)
C31—C3—C4—C5−162.8 (2)C11—C12—C13—C140.6 (4)
C3—C4—C5—C6−47.3 (3)C12—C13—C14—C15−0.7 (4)
C3—C4—C5—C11−175.9 (2)C12—C13—C14—C21−179.8 (3)
C4—C5—C6—C154.2 (3)C13—C14—C15—C16−0.3 (4)
C11—C5—C6—C1−178.6 (2)C21—C14—C15—C16178.9 (2)
C4—C5—C11—C12−61.2 (3)C14—C15—C16—C111.3 (4)
D—H···AD—HH···AD···AD—H···A
C2—H2···O1iv0.952.483.425 (3)173
C5—H5···Cgii1.002.943.818 (3)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C2—H2⋯O1i0.952.483.425 (3)173
C5—H5⋯Cgii1.002.943.818 (3)147

Symmetry codes: (i) ; (ii) . Cg is the centroid of the bezene ring.

  1 in total

1.  A short history of SHELX.

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

1.  2-Iodo-3-(4-meth-oxy-anilino)-5,5-dimethyl-cyclo-hex-2-en-1-one.

Authors:  S Paramasivam; G Bhaskar; P R Seshadri; P T Perumal
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-25
  1 in total

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