PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1564.
Published online 2010 June 5. doi:  10.1107/S1600536810020453
PMCID: PMC3007079

3-Methyl-4H-chromen-4-one

Abstract

In the title chromenone derivative, C10H8O2, the two fused six-membered rings are coplanar, with a mean deviation of 0.0261 (1) Å from the plane through the non-H atoms of the rings. The carbonyl and methyl substituents of the pyran ring also lie close to that plane, with the O and C atoms deviating by 0.0557 (1) and 0.1405 (1) Å, respectively. In the crystal, weak C—H(...)O contacts form chains along the a axis.

Related literature

For the pharmaceutical applications of chromanone compounds, see: Shi et al. (2004 [triangle]). For related structures, see: Takikawa & Suzuki (2007 [triangle]); Patonay et al. (2002 [triangle]); Alaniz & Rovis, (2005 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1564-scheme1.jpg

Experimental

Crystal data

  • C10H8O2
  • M r = 160.16
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1564-efi1.jpg
  • a = 6.5284 (13) Å
  • b = 7.2210 (14) Å
  • c = 8.9834 (18) Å
  • α = 75.137 (2)°
  • β = 78.169 (2)°
  • γ = 80.895 (2)°
  • V = 398.12 (14) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 296 K
  • 0.12 × 0.10 × 0.08 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2001 [triangle]) T min = 0.989, T max = 0.993
  • 2771 measured reflections
  • 1394 independent reflections
  • 1143 reflections with I > 2σ(I)
  • R int = 0.014

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.116
  • S = 1.00
  • 1394 reflections
  • 111 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.14 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT-Plus (Bruker, 2001 [triangle]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810020453/sj5009sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810020453/sj5009Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

Financial support from the International Cooperation Program for Excellent Lectures of 2008 by Shandong Provincial Education Department is gratefully acknowledged.

supplementary crystallographic information

Comment

The synthesis of chromanone derivatives has attracted continuous research interest due to their applications as vasodilator, anti-hypertensive, bronchodilator, heptaprotective, anti-tumor, anti-mutagenic, geroprotective and anti-diabetic agents (Shi et al., 2004). Here, we describe the cystallization and structural characterization of the title compound.

As shown in Fig 1. the two fused six membered rings are coplanar with a mean deviation of 0.0261 (1) Å from the plane through the non-hydrogen atoms of the rings. The carbonyl and methyl substituents of the pyran ring also lie close to that plane with deviations of 0.0557 (1) and 0.1405 (1) Å, respectively. The C=O and C—O bond distances, 1.367 (2) and 1.231 (2)—1.355 (2) Å, respectively, are in the normal range compared to reported chromanone derivatives (Takikawa & Suzuki, 2007; Patonay et al., 2002; Alaniz & Rovis, 2005). In the crystal structure, chains along the a axis are formed via the weak C—H···O contacts.

Experimental

3-methyl-4H-chromen-4-one powder (10 mmoL, 1.60 g) was purchased from Jinan Henghua Science & Technology Co. Ltd., dissolved in 20 ml ethanol and evaporated in an open flask at room temperature. One week later, colorless block like crystals of the title compound suitable for the X-ray analysis were obained. Anal. C10H8O2: C, 74.93; H, 5.00%. Found: C, 74.86; H, 4.89%.

Refinement

Hydrogen atoms were placed in geometrically calculated positions (C—H 0.95 Å for aromatic and formyl, 0.99 Å for methylene and 0.98 Å for methyl) and included in the refinement in a riding motion approximation with Uiso(H) = 1.2Ueq(C) [for methyl groups Uiso(H) = 1.5Ueq(C)].

Figures

Fig. 1.
Structure of the title compound showing the atom numbering with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as spheres of arbitrary radius.
Fig. 2.
Crystal packing showing chains formed along the a axis via weak C—H···O contacts.

Crystal data

C10H8O2Z = 2
Mr = 160.16F(000) = 168
Triclinic, P1Dx = 1.336 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.5284 (13) ÅCell parameters from 1573 reflections
b = 7.2210 (14) Åθ = 2.4–28.4°
c = 8.9834 (18) ŵ = 0.09 mm1
α = 75.137 (2)°T = 296 K
β = 78.169 (2)°Block, colorless
γ = 80.895 (2)°0.12 × 0.10 × 0.08 mm
V = 398.12 (14) Å3

Data collection

Bruker APEXII CCD diffractometer1394 independent reflections
Radiation source: fine-focus sealed tube1143 reflections with I > 2σ(I)
graphiteRint = 0.014
[var phi] and ω scansθmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)h = −7→7
Tmin = 0.989, Tmax = 0.993k = −8→8
2771 measured reflectionsl = −10→10

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.116w = 1/[σ2(Fo2) + (0.065P)2 + 0.067P] where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1394 reflectionsΔρmax = 0.18 e Å3
111 parametersΔρmin = −0.13 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.032 (10)

Special details

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)

xyzUiso*/Ueq
C10.5883 (2)0.71757 (18)1.05339 (16)0.0417 (3)
C20.4277 (2)0.76708 (17)0.96592 (15)0.0390 (3)
C30.4728 (2)0.76636 (18)0.79936 (15)0.0427 (4)
C40.6928 (2)0.71855 (19)0.73797 (16)0.0455 (4)
C50.8332 (2)0.6710 (2)0.83389 (17)0.0503 (4)
H50.97260.63980.79050.060*
C60.7581 (3)0.7246 (3)0.56727 (18)0.0700 (5)
H6A0.90740.69030.54450.105*
H6B0.72220.85240.50780.105*
H6C0.68640.63500.54000.105*
C70.2263 (2)0.8210 (2)1.04176 (18)0.0506 (4)
H70.11500.85330.98640.061*
C80.1897 (3)0.8271 (2)1.19601 (19)0.0602 (4)
H80.05490.86461.24430.072*
C90.3541 (3)0.7771 (2)1.28035 (18)0.0607 (5)
H90.32910.78181.38510.073*
C100.5524 (3)0.7212 (2)1.21027 (17)0.0554 (4)
H100.66210.68591.26710.066*
O10.33452 (17)0.80490 (17)0.71782 (12)0.0648 (4)
O20.79069 (14)0.66418 (15)0.98916 (11)0.0522 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0424 (7)0.0398 (7)0.0441 (7)−0.0053 (5)−0.0089 (6)−0.0103 (5)
C20.0379 (7)0.0336 (6)0.0444 (7)−0.0056 (5)−0.0078 (5)−0.0057 (5)
C30.0444 (8)0.0392 (7)0.0440 (7)−0.0064 (6)−0.0133 (6)−0.0031 (5)
C40.0487 (8)0.0439 (7)0.0421 (7)−0.0055 (6)−0.0062 (6)−0.0080 (6)
C50.0397 (8)0.0574 (9)0.0522 (8)−0.0016 (6)−0.0028 (6)−0.0162 (7)
C60.0782 (12)0.0787 (12)0.0445 (9)−0.0009 (9)−0.0016 (8)−0.0108 (8)
C70.0418 (8)0.0482 (8)0.0594 (9)−0.0046 (6)−0.0063 (6)−0.0106 (6)
C80.0552 (9)0.0551 (9)0.0635 (10)−0.0085 (7)0.0104 (7)−0.0168 (7)
C90.0803 (12)0.0573 (9)0.0437 (8)−0.0141 (8)0.0018 (8)−0.0164 (7)
C100.0673 (10)0.0573 (9)0.0461 (8)−0.0084 (7)−0.0180 (7)−0.0129 (7)
O10.0559 (7)0.0849 (8)0.0544 (7)−0.0039 (6)−0.0253 (5)−0.0076 (5)
O20.0403 (6)0.0681 (7)0.0517 (6)0.0017 (5)−0.0162 (4)−0.0184 (5)

Geometric parameters (Å, °)

C1—O21.3668 (17)C6—H6A0.9600
C1—C21.3854 (19)C6—H6B0.9600
C1—C101.387 (2)C6—H6C0.9600
C2—C71.3967 (19)C7—C81.368 (2)
C2—C31.4657 (19)C7—H70.9300
C3—O11.2312 (16)C8—C91.388 (2)
C3—C41.450 (2)C8—H80.9300
C4—C51.332 (2)C9—C101.366 (2)
C4—C61.4961 (19)C9—H90.9300
C5—O21.3548 (17)C10—H100.9300
C5—H50.9300
O2—C1—C2121.70 (12)H6A—C6—H6B109.5
O2—C1—C10116.53 (12)C4—C6—H6C109.5
C2—C1—C10121.77 (14)H6A—C6—H6C109.5
C1—C2—C7117.46 (13)H6B—C6—H6C109.5
C1—C2—C3120.18 (13)C8—C7—C2121.23 (14)
C7—C2—C3122.34 (13)C8—C7—H7119.4
O1—C3—C4122.69 (13)C2—C7—H7119.4
O1—C3—C2122.50 (13)C7—C8—C9119.91 (15)
C4—C3—C2114.81 (11)C7—C8—H8120.0
C5—C4—C3119.62 (13)C9—C8—H8120.0
C5—C4—C6121.16 (14)C10—C9—C8120.34 (14)
C3—C4—C6119.22 (13)C10—C9—H9119.8
C4—C5—O2125.65 (13)C8—C9—H9119.8
C4—C5—H5117.2C9—C10—C1119.28 (14)
O2—C5—H5117.2C9—C10—H10120.4
C4—C6—H6A109.5C1—C10—H10120.4
C4—C6—H6B109.5C5—O2—C1117.89 (11)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.703.4374 (19)137
C7—H7···O2ii0.932.693.3820 (19)132

Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5009).

References

  • Alaniz, J. R. de & Rovis, T. (2005). J. Am. Chem. Soc.127, 6284—6289. [PubMed]
  • Bruker (2001). SAINT-Plus and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bruker (2004). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  • Patonay, T., Juhász-Tóth, É. & Bényei, A. (2002). Eur. J. Org. Chem. pp. 285—295.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Shi, G. F., Lu, R. H., Yang, Y. S., Li, C. L., Yang, A. M. & Cai, L. X. (2004). Chin. J. Struct. Chem.23, 1164–1169.
  • Takikawa, H. & Suzuki, K. (2007). Org. Lett.9, 2713—2716. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography