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

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ISSN: 2056-9890

3-[(E)-2-(2-Meth­­oxy­phen­yl)vin­yl]-5,5-di­methyl­cyclo­hex-2-enone

aCenter of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India, and bDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Tamilnadu, India
*Correspondence e-mail: shirai2011@gmail.com

(Received 23 March 2014; accepted 24 March 2014; online 2 April 2014)

The title compound, C17H20O2, has an E conformation about the bridging C=C bond. The cyclo­hexene ring adopts an envelope conformation with the dimethyl-substituted C atom as the flap. Its mean plane makes a dihedral angle of 7.20 (12)° with the benzene ring. In the crystal, neighbouring mol­ecules are connected via C—H⋯O hydrogen bonds, forming chains running along the a-axis direction.

Related literature

For the pharmacological activity of cyclo­hexa­none derivatives, see: Puetz et al. (2003[Puetz, C., Buschmann, H. & Koegel, B. (2003). US Patent Appl. No. 20030096811.]); Rajveer et al. (2010[Rajveer, C., Stephenrathinaraj, B., Sudharshini, S., Kumaraswamy, D., Bhupendra, S. & Choudhury, P. K. (2010). Res. J. Pharm. Bio. Chem. Sci. 1, 99-107.]). For related structures, see: Fatima et al. (2013[Fatima, Z., Senthilkumar, G., Vadivel, A., Manikandan, H. & Velmurugan, D. (2013). Acta Cryst. E69, o1121.]); Hema et al. (2006[Hema, R., Parthasarathi, V., Ravikumar, K., Pandiarajan, K. & Murugavel, K. (2006). Acta Cryst. E62, o703-o705.]). For ring puckering parametes, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data
  • C17H20O2

  • Mr = 256.33

  • Monoclinic, P 21 /n

  • a = 7.208 (4) Å

  • b = 13.824 (7) Å

  • c = 15.022 (8) Å

  • β = 92.13 (2)°

  • V = 1495.8 (14) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.07 mm−1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.986

  • 10491 measured reflections

  • 3517 independent reflections

  • 2489 reflections with I > 2σ(I)

  • Rint = 0.054

Refinement
  • R[F2 > 2σ(F2)] = 0.085

  • wR(F2) = 0.283

  • S = 1.06

  • 3517 reflections

  • 175 parameters

  • H-atom parameters constrained

  • Δρmax = 0.65 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C14—H14B⋯O1i 0.97 2.62 3.554 (4) 161
Symmetry code: (i) x+1, y, z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Cyclohexanone is an aliphatic cyclic ketone. Cyclohexanone derivatives have potent pharmacological activity in the treatment of a broad spectrum of medical conditions (Puetz et al., 2003). The cyclohexanone moiety constitutes an important structural feature in several anti-inflammatory, analgesic, local anesthetic and antihistaminic drugs (Rajveer et al., 2010). As part of our studies in this area (Fatima et al., 2013; Hema et al., 2006), we have undertaken a single-crystal structure determination of the title compound.

In the title compound, Fig. 1, the cyclohexene ring (C9—C14) adopts an envelope conformation with atom C13 as the flap: puckering parameters (Cremer & Pople, 1975) are Q = 0.464 (3) Å, θ = 52.3 (4) °, and ϕ = 232.2 (4) °. Its mean plane makes a dihedral angle of 7.20 (12)° with the benzene ring (C1—C6).

In the crystal, hydrogen bonded chains running along the a-axis direction are generated by connecting neighbouring molecules via C—H···O hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For the pharmacological activity of cyclohexanone derivatives, see: Puetz et al. (2003); Rajveer et al. (2010). For related structures, see: Fatima et al. (2013); Hema et al. (2006). For ring puckering parametes, see: Cremer & Pople (1975).

Experimental top

A mixture of isophorone (0.01 mol), 2-methoxybezaldehyde (0.01 mol) and sodium hydroxide solution (10 ml, 10%) in ethanol (25 ml) was stirred at room temperature until the starting material disappeared. The resulting mixture was poured into crushed ice and the precipitate was filtered off, dried and recrystallized from ethanol giving p. colourless block-like crystals [Yield = 93%; M.p. = 373-375 K].

Refinement top

The H atoms were placed in calculated positions and refined as riding atoms: C—H = 0.93 - 0.97 Å with Uiso(H) = 1.5Ueq(C-methyl ) and = 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title molecule, with atom labelling. The displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. The crystal packing of the title compound viewed along the b axis. The hydrogen bonds are shown as dashed lines (see Table 1 for details; H-atoms not involved in hydrogen bonding have been excluded for clarity).
3-[(E)-2-(2-Methoxyphenyl)vinyl]-5,5-dimethylcyclohex-2-enone top
Crystal data top
C17H20O2F(000) = 552
Mr = 256.33Dx = 1.138 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3517 reflections
a = 7.208 (4) Åθ = 2.0–28.6°
b = 13.824 (7) ŵ = 0.07 mm1
c = 15.022 (8) ÅT = 293 K
β = 92.13 (2)°Block, colourless
V = 1495.8 (14) Å30.30 × 0.25 × 0.20 mm
Z = 4
Data collection top
Bruker SMART APEXII area-detector
diffractometer
3517 independent reflections
Radiation source: fine-focus sealed tube2489 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.054
ω and ϕ scansθmax = 28.6°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
h = 99
Tmin = 0.978, Tmax = 0.986k = 1817
10491 measured reflectionsl = 1911
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)] = 0.085Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.283H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.1498P)2 + 0.8245P]
where P = (Fo2 + 2Fc2)/3
3517 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.65 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C17H20O2V = 1495.8 (14) Å3
Mr = 256.33Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.208 (4) ŵ = 0.07 mm1
b = 13.824 (7) ÅT = 293 K
c = 15.022 (8) Å0.30 × 0.25 × 0.20 mm
β = 92.13 (2)°
Data collection top
Bruker SMART APEXII area-detector
diffractometer
3517 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2008)
2489 reflections with I > 2σ(I)
Tmin = 0.978, Tmax = 0.986Rint = 0.054
10491 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0850 restraints
wR(F2) = 0.283H-atom parameters constrained
S = 1.06Δρmax = 0.65 e Å3
3517 reflectionsΔρmin = 0.27 e Å3
175 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*/Ueq
C11.4696 (5)0.6141 (2)0.2237 (2)0.0617 (8)
H11.53760.65520.18840.074*
C21.2899 (4)0.5897 (2)0.1978 (2)0.0533 (7)
H21.23770.61470.14510.064*
C31.1846 (4)0.52740 (19)0.25024 (18)0.0472 (6)
C41.2616 (4)0.49045 (18)0.33219 (18)0.0452 (6)
C51.4433 (4)0.51557 (18)0.35727 (18)0.0464 (6)
H51.49510.49150.41040.056*
C61.5515 (4)0.5767 (2)0.3041 (2)0.0617 (8)
H61.67320.59200.32130.074*
C71.1621 (4)0.42686 (18)0.39463 (18)0.0479 (6)
H71.23210.40880.44520.057*
C80.9882 (4)0.39088 (18)0.39058 (18)0.0500 (7)
H80.91430.40490.34010.060*
C90.9055 (3)0.33023 (16)0.46110 (16)0.0411 (6)
C100.7259 (4)0.29964 (19)0.45218 (19)0.0496 (7)
H100.65850.31530.40020.060*
C110.6334 (3)0.24317 (19)0.5206 (2)0.0499 (7)
C120.7438 (4)0.22367 (19)0.60826 (18)0.0459 (6)
H12A0.69870.16440.63450.055*
H12B0.72190.27600.64950.055*
C130.9558 (3)0.21429 (15)0.59556 (15)0.0369 (5)
C141.0219 (3)0.30514 (16)0.54545 (16)0.0396 (5)
H14A1.02000.36000.58570.048*
H14B1.14950.29520.52920.048*
C150.9938 (4)0.12099 (17)0.54174 (19)0.0480 (6)
H15A0.95320.06570.57440.072*
H15B1.12440.11570.53230.072*
H15C0.92720.12390.48530.072*
C161.0603 (5)0.2081 (2)0.68771 (18)0.0563 (8)
H16A1.03540.26520.72160.084*
H16B1.19130.20310.67930.084*
H16C1.01870.15210.71920.084*
C170.9273 (5)0.5303 (3)0.1418 (2)0.0736 (10)
H17A0.92710.59970.13890.110*
H17B0.80230.50680.13440.110*
H17C1.00080.50480.09520.110*
O10.4730 (3)0.2135 (2)0.5081 (2)0.0762 (8)
O21.0044 (3)0.49973 (15)0.22679 (13)0.0569 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0701 (18)0.0601 (16)0.0560 (17)0.0103 (15)0.0175 (15)0.0004 (14)
C20.0659 (16)0.0489 (13)0.0464 (14)0.0038 (12)0.0184 (13)0.0005 (11)
C30.0542 (14)0.0450 (12)0.0426 (13)0.0002 (11)0.0037 (12)0.0020 (10)
C40.0477 (13)0.0433 (12)0.0448 (13)0.0021 (10)0.0033 (11)0.0035 (10)
C50.0477 (13)0.0468 (12)0.0445 (13)0.0005 (10)0.0014 (11)0.0020 (10)
C60.0517 (14)0.0652 (17)0.069 (2)0.0135 (13)0.0093 (15)0.0085 (15)
C70.0576 (14)0.0416 (12)0.0446 (13)0.0017 (11)0.0024 (12)0.0073 (10)
C80.0646 (16)0.0446 (12)0.0404 (13)0.0084 (12)0.0033 (12)0.0079 (10)
C90.0488 (12)0.0367 (10)0.0375 (12)0.0056 (9)0.0005 (10)0.0036 (9)
C100.0490 (13)0.0494 (13)0.0495 (14)0.0067 (11)0.0090 (12)0.0045 (11)
C110.0390 (12)0.0479 (13)0.0627 (17)0.0036 (10)0.0002 (12)0.0098 (12)
C120.0479 (13)0.0456 (12)0.0448 (13)0.0035 (10)0.0127 (11)0.0038 (10)
C130.0432 (11)0.0346 (10)0.0327 (11)0.0005 (9)0.0005 (9)0.0022 (8)
C140.0409 (11)0.0376 (11)0.0401 (12)0.0020 (9)0.0014 (10)0.0062 (9)
C150.0581 (14)0.0363 (11)0.0497 (14)0.0092 (10)0.0051 (12)0.0005 (10)
C160.0710 (18)0.0579 (15)0.0392 (13)0.0071 (13)0.0096 (13)0.0101 (11)
C170.084 (2)0.083 (2)0.0520 (18)0.0015 (19)0.0171 (17)0.0147 (16)
O10.0395 (10)0.0955 (18)0.0935 (19)0.0095 (11)0.0002 (11)0.0084 (14)
O20.0559 (11)0.0680 (12)0.0461 (11)0.0088 (9)0.0081 (9)0.0163 (9)
Geometric parameters (Å, º) top
C1—C21.381 (4)C11—O11.234 (3)
C1—C61.421 (5)C11—C121.537 (4)
C1—H10.9300C12—C131.553 (4)
C2—C31.408 (4)C12—H12A0.9700
C2—H20.9300C12—H12B0.9700
C3—O21.387 (3)C13—C141.548 (3)
C3—C41.426 (4)C13—C151.552 (3)
C4—C51.393 (4)C13—C161.553 (3)
C4—C71.489 (4)C14—H14A0.9700
C5—C61.416 (4)C14—H14B0.9700
C5—H50.9300C15—H15A0.9600
C6—H60.9300C15—H15B0.9600
C7—C81.348 (4)C15—H15C0.9600
C7—H70.9300C16—H16A0.9600
C8—C91.493 (4)C16—H16B0.9600
C8—H80.9300C16—H16C0.9600
C9—C101.364 (4)C17—O21.437 (3)
C9—C141.533 (3)C17—H17A0.9600
C10—C111.470 (4)C17—H17B0.9600
C10—H100.9300C17—H17C0.9600
C2—C1—C6120.4 (3)C13—C12—H12A109.0
C2—C1—H1119.8C11—C12—H12B109.0
C6—C1—H1119.8C13—C12—H12B109.0
C1—C2—C3120.7 (3)H12A—C12—H12B107.8
C1—C2—H2119.7C14—C13—C15111.0 (2)
C3—C2—H2119.7C14—C13—C12108.29 (18)
O2—C3—C2123.0 (2)C15—C13—C12109.07 (19)
O2—C3—C4116.8 (2)C14—C13—C16109.30 (19)
C2—C3—C4120.1 (3)C15—C13—C16109.2 (2)
C5—C4—C3118.4 (3)C12—C13—C16110.0 (2)
C5—C4—C7116.5 (2)C9—C14—C13114.63 (19)
C3—C4—C7125.0 (2)C9—C14—H14A108.6
C4—C5—C6121.8 (3)C13—C14—H14A108.6
C4—C5—H5119.1C9—C14—H14B108.6
C6—C5—H5119.1C13—C14—H14B108.6
C5—C6—C1118.5 (3)H14A—C14—H14B107.6
C5—C6—H6120.8C13—C15—H15A109.5
C1—C6—H6120.8C13—C15—H15B109.5
C8—C7—C4131.2 (2)H15A—C15—H15B109.5
C8—C7—H7114.4C13—C15—H15C109.5
C4—C7—H7114.4H15A—C15—H15C109.5
C7—C8—C9124.8 (2)H15B—C15—H15C109.5
C7—C8—H8117.6C13—C16—H16A109.5
C9—C8—H8117.6C13—C16—H16B109.5
C10—C9—C8120.5 (2)H16A—C16—H16B109.5
C10—C9—C14119.9 (2)C13—C16—H16C109.5
C8—C9—C14119.5 (2)H16A—C16—H16C109.5
C9—C10—C11123.3 (2)H16B—C16—H16C109.5
C9—C10—H10118.3O2—C17—H17A109.5
C11—C10—H10118.3O2—C17—H17B109.5
O1—C11—C10121.1 (3)H17A—C17—H17B109.5
O1—C11—C12121.6 (3)O2—C17—H17C109.5
C10—C11—C12117.3 (2)H17A—C17—H17C109.5
C11—C12—C13113.0 (2)H17B—C17—H17C109.5
C11—C12—H12A109.0C3—O2—C17118.2 (2)
C6—C1—C2—C30.1 (5)C8—C9—C10—C11177.4 (2)
C1—C2—C3—O2179.2 (3)C14—C9—C10—C110.6 (4)
C1—C2—C3—C41.4 (4)C9—C10—C11—O1176.8 (3)
O2—C3—C4—C5179.1 (2)C9—C10—C11—C123.7 (4)
C2—C3—C4—C51.6 (4)O1—C11—C12—C13148.6 (3)
O2—C3—C4—C71.5 (4)C10—C11—C12—C1331.9 (3)
C2—C3—C4—C7177.9 (3)C11—C12—C13—C1453.3 (3)
C3—C4—C5—C60.4 (4)C11—C12—C13—C1567.5 (3)
C7—C4—C5—C6179.2 (3)C11—C12—C13—C16172.7 (2)
C4—C5—C6—C11.0 (4)C10—C9—C14—C1324.0 (3)
C2—C1—C6—C51.1 (5)C8—C9—C14—C13158.0 (2)
C5—C4—C7—C8179.3 (3)C15—C13—C14—C970.0 (3)
C3—C4—C7—C80.2 (5)C12—C13—C14—C949.6 (3)
C4—C7—C8—C9177.6 (3)C16—C13—C14—C9169.5 (2)
C7—C8—C9—C10177.9 (3)C2—C3—O2—C174.8 (4)
C7—C8—C9—C140.0 (4)C4—C3—O2—C17175.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O1i0.972.623.554 (4)161
Symmetry code: (i) x+1, y, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C14—H14B···O1i0.972.623.554 (4)161.4
Symmetry code: (i) x+1, y, z.
 

Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and ZF thanks the UGC for a meritorious fellowship.

References

First citationBruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
First citationCremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358.  CrossRef CAS Web of Science
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals
First citationFatima, Z., Senthilkumar, G., Vadivel, A., Manikandan, H. & Velmurugan, D. (2013). Acta Cryst. E69, o1121.  CSD CrossRef IUCr Journals
First citationHema, R., Parthasarathi, V., Ravikumar, K., Pandiarajan, K. & Murugavel, K. (2006). Acta Cryst. E62, o703–o705.  Web of Science CSD CrossRef CAS IUCr Journals
First citationPuetz, C., Buschmann, H. & Koegel, B. (2003). US Patent Appl. No. 20030096811.
First citationRajveer, C., Stephenrathinaraj, B., Sudharshini, S., Kumaraswamy, D., Bhupendra, S. & Choudhury, P. K. (2010). Res. J. Pharm. Bio. Chem. Sci. 1, 99–107.  CAS
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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