organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

1-(2,4-Di­chloro­phen­yl)-4,4-di­methyl­pent-1-en-3-one

aCollege of Chemistry and Chemical Engineering, Hunan University, 410082 Changsha, People's Republic of China
*Correspondence e-mail: axhu0731@yahoo.com.cn

(Received 28 August 2008; accepted 17 September 2008; online 20 September 2008)

In the title compound, C13H14Cl2O, the carbonyl and ethenyl groups are coplanar with the aromatic ring. There are four molecules in the asymmetric unit and all atoms in the molecule lie on mirror planes. The mol­ecules are packed in an offset face-to-face arrangement showing ππ stacking inter­actions involving the benzene rings [centroid–centroid distance = 3.564 (2) Å].

Related literature

For related compounds, see: Wang et al. (2008[Wang, Y., Hu, A.-X., Cao, G., Li, G.-X., Zhang, J.-Y., Xia, L., Ou, X.-M. & Xu, J.-B. (2008). Chin. J. Org. Chem. 28, 443-448.]).

[Scheme 1]

Experimental

Crystal data
  • C13H14Cl2O

  • Mr = 257.14

  • Orthorhombic, P n m a

  • a = 11.2553 (7) Å

  • b = 7.0458 (4) Å

  • c = 15.4969 (9) Å

  • V = 1228.94 (13) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.50 mm−1

  • T = 173 (2) K

  • 0.47 × 0.39 × 0.15 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.798, Tmax = 0.928

  • 6162 measured reflections

  • 1444 independent reflections

  • 1227 reflections with I > 2σ(I)

  • Rint = 0.021

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.085

  • S = 1.07

  • 1444 reflections

  • 95 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2001[Bruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2003[Bruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Phenyl-4,4-dimethylpentan-3-one derivatives are important intermediates in medicinal industry (Wang et al., 2006). Herein we report the synthesis and crystal structure of 1-(2,4-dichlorophen-yl)-4,4-dimethylpentan-3-one.

Related literature top

A series of related compounds was designed and synthesized by Wang et al. (2006).

Experimental top

3,3-dimethylbutan-2-one(0.0105 mol) was added dropwise into a solution of 2,4-dichlorobenzaldehyde (0.01 mol) and 60 ml ethanol. Then 0.1 g 50% NaOH solution as catalyst was added and the reaction was stirred at 333 K for 5 h . The solvent was evaporated to about half volume, then cooled to 277 K and the precipitate formed.This was filtered and dried to give the desired product (yield: 94.7%). Crystals suitable for X-ray structure determination were obtained by slow evaporation of an ethanol solution at room temperature.

Refinement top

The methyl H atoms were positioned geometrically (C—H=0.98 Å) and torsion angles refined to fit the electron density [Uiso(H) = 1.5Ueq(C)]. Other H atoms were placed in calculated position (methylene C—H = 0.95Å and aromatic C—H=0.95 Å) and refined as riding [Uiso(H) = 1.2Ueq(C)].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular structure showing 30% probability displacement ellipsoids.H atoms are omitted for clarity.
[Figure 2] Fig. 2. Packing diagram showing ππ stacking interactions.
1-(2,4-Dichlorophenyl)-4,4-dimethylpent-1-en-3-one top
Crystal data top
C13H14Cl2ODx = 1.390 Mg m3
Mr = 257.14Melting point: 385 K
Orthorhombic, PnmaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2nCell parameters from 3552 reflections
a = 11.2553 (7) Åθ = 2.2–27.0°
b = 7.0458 (4) ŵ = 0.50 mm1
c = 15.4969 (9) ÅT = 173 K
V = 1228.94 (13) Å3Block, colorless
Z = 40.47 × 0.39 × 0.15 mm
F(000) = 536
Data collection top
Bruker SMART 1000 CCD
diffractometer
1444 independent reflections
Radiation source: fine-focus sealed tube1227 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
ω scansθmax = 27.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1214
Tmin = 0.798, Tmax = 0.928k = 89
6162 measured reflectionsl = 1914
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.085H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0391P)2 + 0.6612P]
where P = (Fo2 + 2Fc2)/3
1444 reflections(Δ/σ)max < 0.001
95 parametersΔρmax = 0.28 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C13H14Cl2OV = 1228.94 (13) Å3
Mr = 257.14Z = 4
Orthorhombic, PnmaMo Kα radiation
a = 11.2553 (7) ŵ = 0.50 mm1
b = 7.0458 (4) ÅT = 173 K
c = 15.4969 (9) Å0.47 × 0.39 × 0.15 mm
Data collection top
Bruker SMART 1000 CCD
diffractometer
1444 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
1227 reflections with I > 2σ(I)
Tmin = 0.798, Tmax = 0.928Rint = 0.021
6162 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0320 restraints
wR(F2) = 0.085H-atom parameters constrained
S = 1.07Δρmax = 0.28 e Å3
1444 reflectionsΔρmin = 0.36 e Å3
95 parameters
Special details top

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) top
xyzUiso*/UeqOcc. (<1)
Cl10.73794 (5)0.25000.45333 (4)0.03276 (17)
Cl20.34147 (5)0.25000.26347 (3)0.03138 (17)
C10.57275 (19)0.25000.61286 (13)0.0239 (4)
H10.65710.25000.61490.029*
C20.51505 (19)0.25000.68766 (13)0.0265 (5)
H20.43070.25000.68690.032*
C30.57686 (18)0.25000.77240 (13)0.0225 (4)
C40.49783 (18)0.25000.85260 (12)0.0227 (4)
C50.5740 (2)0.25000.93380 (14)0.0314 (5)
H5A0.61630.15180.93470.047*0.50
H5B0.52250.25000.98480.047*
H5C0.62520.36250.93400.047*0.50
C60.41949 (13)0.0709 (2)0.85096 (10)0.0285 (3)
H6A0.36700.07510.80050.043*
H6B0.37140.06560.90360.043*
H6C0.47010.04210.84770.043*
C70.51674 (18)0.25000.52726 (13)0.0224 (4)
C80.58317 (17)0.25000.45064 (13)0.0217 (4)
C90.53111 (19)0.25000.36945 (13)0.0244 (4)
H90.57850.25000.31870.029*
C100.40892 (19)0.25000.36426 (13)0.0241 (4)
C110.33861 (18)0.25000.43745 (15)0.0267 (5)
H110.25440.25000.43290.032*
C120.39335 (19)0.25000.51767 (14)0.0265 (5)
H120.34510.25000.56800.032*
O10.68512 (13)0.25000.77742 (10)0.0323 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0204 (3)0.0528 (4)0.0251 (3)0.0000.00297 (19)0.000
Cl20.0291 (3)0.0413 (3)0.0237 (3)0.0000.0039 (2)0.000
C10.0243 (10)0.0245 (10)0.0228 (10)0.0000.0018 (8)0.000
C20.0232 (10)0.0337 (12)0.0225 (10)0.0000.0004 (8)0.000
C30.0221 (10)0.0236 (10)0.0218 (10)0.0000.0009 (8)0.000
C40.0202 (9)0.0284 (11)0.0195 (9)0.0000.0007 (8)0.000
C50.0256 (11)0.0463 (14)0.0223 (10)0.0000.0029 (9)0.000
C60.0269 (7)0.0303 (8)0.0285 (8)0.0032 (6)0.0043 (6)0.0008 (6)
C70.0238 (10)0.0204 (10)0.0229 (10)0.0000.0011 (8)0.000
C80.0190 (9)0.0209 (10)0.0252 (10)0.0000.0019 (8)0.000
C90.0276 (11)0.0240 (10)0.0217 (10)0.0000.0039 (8)0.000
C100.0286 (11)0.0220 (10)0.0217 (10)0.0000.0019 (8)0.000
C110.0205 (10)0.0311 (12)0.0285 (11)0.0000.0005 (8)0.000
C120.0256 (11)0.0310 (11)0.0228 (10)0.0000.0055 (8)0.000
O10.0200 (7)0.0468 (10)0.0301 (8)0.0000.0026 (6)0.000
Geometric parameters (Å, º) top
Cl1—C81.742 (2)C5—H5C0.9800
Cl2—C101.737 (2)C6—H6A0.9800
C1—C21.329 (3)C6—H6B0.9800
C1—C71.469 (3)C6—H6C0.9800
C1—H10.9500C7—C121.397 (3)
C2—C31.486 (3)C7—C81.403 (3)
C2—H20.9500C8—C91.388 (3)
C3—O11.221 (2)C9—C101.378 (3)
C3—C41.528 (3)C9—H90.9500
C4—C51.522 (3)C10—C111.383 (3)
C4—C61.5398 (19)C11—C121.387 (3)
C4—C6i1.5398 (19)C11—H110.9500
C5—H5A0.8400C12—H120.9500
C5—H5B0.9799
C2—C1—C7125.3 (2)H6A—C6—H6B109.5
C2—C1—H1117.3C4—C6—H6C109.5
C7—C1—H1117.3H6A—C6—H6C109.5
C1—C2—C3122.83 (19)H6B—C6—H6C109.5
C1—C2—H2118.6C12—C7—C8116.09 (18)
C3—C2—H2118.6C12—C7—C1121.53 (19)
O1—C3—C2121.57 (19)C8—C7—C1122.39 (18)
O1—C3—C4121.93 (18)C9—C8—C7122.84 (19)
C2—C3—C4116.50 (17)C9—C8—Cl1116.34 (15)
C5—C4—C3110.15 (17)C7—C8—Cl1120.82 (15)
C5—C4—C6109.64 (11)C10—C9—C8118.32 (19)
C3—C4—C6108.65 (11)C10—C9—H9120.8
C5—C4—C6i109.64 (11)C8—C9—H9120.8
C3—C4—C6i108.65 (11)C9—C10—C11121.55 (19)
C6—C4—C6i110.09 (17)C9—C10—Cl2119.27 (16)
C4—C5—H5A109.5C11—C10—Cl2119.17 (16)
C4—C5—H5B109.5C10—C11—C12118.73 (19)
H5A—C5—H5B108.7C10—C11—H11120.6
C4—C5—H5C109.4C12—C11—H11120.6
H5A—C5—H5C109.5C11—C12—C7122.5 (2)
H5B—C5—H5C110.2C11—C12—H12118.8
C4—C6—H6A109.5C7—C12—H12118.8
C4—C6—H6B109.5
C7—C1—C2—C3180.0C1—C7—C8—C9180.0
C1—C2—C3—O10.0C12—C7—C8—Cl1180.0
C1—C2—C3—C4180.0C1—C7—C8—Cl10.0
O1—C3—C4—C50.0C7—C8—C9—C100.0
C2—C3—C4—C5180.0Cl1—C8—C9—C10180.0
O1—C3—C4—C6120.11 (11)C8—C9—C10—C110.0
C2—C3—C4—C659.89 (11)C8—C9—C10—Cl2180.0
O1—C3—C4—C6i120.11 (11)C9—C10—C11—C120.0
C2—C3—C4—C6i59.89 (11)Cl2—C10—C11—C12180.0
C2—C1—C7—C120.0C10—C11—C12—C70.0
C2—C1—C7—C8180.0C8—C7—C12—C110.0
C12—C7—C8—C90.0C1—C7—C12—C11180.0
Symmetry code: (i) x, y+1/2, z.

Experimental details

Crystal data
Chemical formulaC13H14Cl2O
Mr257.14
Crystal system, space groupOrthorhombic, Pnma
Temperature (K)173
a, b, c (Å)11.2553 (7), 7.0458 (4), 15.4969 (9)
V3)1228.94 (13)
Z4
Radiation typeMo Kα
µ (mm1)0.50
Crystal size (mm)0.47 × 0.39 × 0.15
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2004)
Tmin, Tmax0.798, 0.928
No. of measured, independent and
observed [I > 2σ(I)] reflections
6162, 1444, 1227
Rint0.021
(sin θ/λ)max1)0.639
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.085, 1.07
No. of reflections1444
No. of parameters95
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.36

Computer programs: SMART (Bruker, 2001), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

The authors express their thanks to the National Key Technology R&D Program (No. 2006BAE01A01-4)

References

First citationBruker (2001). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2003). SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationSheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWang, Y., Hu, A.-X., Cao, G., Li, G.-X., Zhang, J.-Y., Xia, L., Ou, X.-M. & Xu, J.-B. (2008). Chin. J. Org. Chem. 28, 443–448.  CAS Google Scholar

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