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

Hao, L.; Chen, J.; Zhang, X.

doi:10.1107/S1600536810020453

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1564

doi:10.1107/S1600536810020453

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

Lujiang Hao,^a ^* Jiangkui Chen ^a and Xiaofei Zhang ^a

^aShandong Provincial Key Laboratory of Microbial Engineering, Shandong Institute of Light Industry, Jinan 250353, People's Republic of China
^*Correspondence e-mail: lujianghao001@yahoo.com.cn

(Received 15 May 2010; accepted 29 May 2010; online 5 June 2010)

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 ). For related structures, see: Takikawa & Suzuki (2007 ); Patonay et al. (2002 ); Alaniz & Rovis, (2005 ).

Experimental

Crystal data

C₁₀H₈O₂
M_r = 160.16
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.116
S = 1.00
1394 reflections
111 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O1ⁱ	0.93	2.70	3.4374 (19)	137
C7—H7⋯O2ⁱⁱ	0.93	2.69	3.3820 (19)	132
Symmetry codes: (i) x+1, y, z; (ii) x-1, y, z.

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

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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%.

Computing details top

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

Figures top

	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.

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

Crystal data top

C₁₀H₈O₂	Z = 2
M_r = 160.16	F(000) = 168
Triclinic, P1	D_x = 1.336 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.5284 (13) Å	Cell parameters from 1573 reflections
b = 7.2210 (14) Å	θ = 2.4–28.4°
c = 8.9834 (18) Å	µ = 0.09 mm⁻¹
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 top

Bruker APEXII CCD diffractometer	1394 independent reflections
Radiation source: fine-focus sealed tube	1143 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −7→7
T_min = 0.989, T_max = 0.993	k = −8→8
2771 measured reflections	l = −10→10

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.116	w = 1/[σ²(F_o²) + (0.065P)² + 0.067P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1394 reflections	Δρ_max = 0.18 e Å⁻³
111 parameters	Δρ_min = −0.14 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.032 (10)

Crystal data top

C₁₀H₈O₂	γ = 80.895 (2)°
M_r = 160.16	V = 398.12 (14) Å³
Triclinic, P1	Z = 2
a = 6.5284 (13) Å	Mo Kα radiation
b = 7.2210 (14) Å	µ = 0.09 mm⁻¹
c = 8.9834 (18) Å	T = 296 K
α = 75.137 (2)°	0.12 × 0.10 × 0.08 mm
β = 78.169 (2)°

Data collection top

Bruker APEXII CCD diffractometer	1394 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	1143 reflections with I > 2σ(I)
T_min = 0.989, T_max = 0.993	R_int = 0.014
2771 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
1394 reflections	Δρ_min = −0.14 e Å⁻³
111 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

	x	y	z	U_iso*/U_eq
C1	0.5883 (2)	0.71757 (18)	1.05339 (16)	0.0417 (3)
C2	0.4277 (2)	0.76708 (17)	0.96592 (15)	0.0390 (3)
C3	0.4728 (2)	0.76636 (18)	0.79936 (15)	0.0427 (4)
C4	0.6928 (2)	0.71855 (19)	0.73797 (16)	0.0455 (4)
C5	0.8332 (2)	0.6710 (2)	0.83389 (17)	0.0503 (4)
H5	0.9726	0.6398	0.7905	0.060*
C6	0.7581 (3)	0.7246 (3)	0.56727 (18)	0.0700 (5)
H6A	0.9074	0.6903	0.5445	0.105*
H6B	0.7222	0.8524	0.5078	0.105*
H6C	0.6864	0.6350	0.5400	0.105*
C7	0.2263 (2)	0.8210 (2)	1.04176 (18)	0.0506 (4)
H7	0.1150	0.8533	0.9864	0.061*
C8	0.1897 (3)	0.8271 (2)	1.19601 (19)	0.0602 (4)
H8	0.0549	0.8646	1.2443	0.072*
C9	0.3541 (3)	0.7771 (2)	1.28035 (18)	0.0607 (5)
H9	0.3291	0.7818	1.3851	0.073*
C10	0.5524 (3)	0.7212 (2)	1.21027 (17)	0.0554 (4)
H10	0.6621	0.6859	1.2671	0.066*
O1	0.33452 (17)	0.80490 (17)	0.71782 (12)	0.0648 (4)
O2	0.79069 (14)	0.66418 (15)	0.98916 (11)	0.0522 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0424 (7)	0.0398 (7)	0.0441 (7)	−0.0053 (5)	−0.0089 (6)	−0.0103 (5)
C2	0.0379 (7)	0.0336 (6)	0.0444 (7)	−0.0056 (5)	−0.0078 (5)	−0.0057 (5)
C3	0.0444 (8)	0.0392 (7)	0.0440 (7)	−0.0064 (6)	−0.0133 (6)	−0.0031 (5)
C4	0.0487 (8)	0.0439 (7)	0.0421 (7)	−0.0055 (6)	−0.0062 (6)	−0.0080 (6)
C5	0.0397 (8)	0.0574 (9)	0.0522 (8)	−0.0016 (6)	−0.0028 (6)	−0.0162 (7)
C6	0.0782 (12)	0.0787 (12)	0.0445 (9)	−0.0009 (9)	−0.0016 (8)	−0.0108 (8)
C7	0.0418 (8)	0.0482 (8)	0.0594 (9)	−0.0046 (6)	−0.0063 (6)	−0.0106 (6)
C8	0.0552 (9)	0.0551 (9)	0.0635 (10)	−0.0085 (7)	0.0104 (7)	−0.0168 (7)
C9	0.0803 (12)	0.0573 (9)	0.0437 (8)	−0.0141 (8)	0.0018 (8)	−0.0164 (7)
C10	0.0673 (10)	0.0573 (9)	0.0461 (8)	−0.0084 (7)	−0.0180 (7)	−0.0129 (7)
O1	0.0559 (7)	0.0849 (8)	0.0544 (7)	−0.0039 (6)	−0.0253 (5)	−0.0076 (5)
O2	0.0403 (6)	0.0681 (7)	0.0517 (6)	0.0017 (5)	−0.0162 (4)	−0.0184 (5)

Geometric parameters (Å, º) top

C1—O2	1.3668 (17)	C6—H6A	0.9600
C1—C2	1.3854 (19)	C6—H6B	0.9600
C1—C10	1.387 (2)	C6—H6C	0.9600
C2—C7	1.3967 (19)	C7—C8	1.368 (2)
C2—C3	1.4657 (19)	C7—H7	0.9300
C3—O1	1.2312 (16)	C8—C9	1.388 (2)
C3—C4	1.450 (2)	C8—H8	0.9300
C4—C5	1.332 (2)	C9—C10	1.366 (2)
C4—C6	1.4961 (19)	C9—H9	0.9300
C5—O2	1.3548 (17)	C10—H10	0.9300
C5—H5	0.9300

O2—C1—C2	121.70 (12)	H6A—C6—H6B	109.5
O2—C1—C10	116.53 (12)	C4—C6—H6C	109.5
C2—C1—C10	121.77 (14)	H6A—C6—H6C	109.5
C1—C2—C7	117.46 (13)	H6B—C6—H6C	109.5
C1—C2—C3	120.18 (13)	C8—C7—C2	121.23 (14)
C7—C2—C3	122.34 (13)	C8—C7—H7	119.4
O1—C3—C4	122.69 (13)	C2—C7—H7	119.4
O1—C3—C2	122.50 (13)	C7—C8—C9	119.91 (15)
C4—C3—C2	114.81 (11)	C7—C8—H8	120.0
C5—C4—C3	119.62 (13)	C9—C8—H8	120.0
C5—C4—C6	121.16 (14)	C10—C9—C8	120.34 (14)
C3—C4—C6	119.22 (13)	C10—C9—H9	119.8
C4—C5—O2	125.65 (13)	C8—C9—H9	119.8
C4—C5—H5	117.2	C9—C10—C1	119.28 (14)
O2—C5—H5	117.2	C9—C10—H10	120.4
C4—C6—H6A	109.5	C1—C10—H10	120.4
C4—C6—H6B	109.5	C5—O2—C1	117.89 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.70	3.4374 (19)	137
C7—H7···O2ⁱⁱ	0.93	2.69	3.3820 (19)	132

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

Experimental details

Crystal data
Chemical formula	C₁₀H₈O₂
M_r	160.16
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.5284 (13), 7.2210 (14), 8.9834 (18)
α, β, γ (°)	75.137 (2), 78.169 (2), 80.895 (2)
V (Å³)	398.12 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.12 × 0.10 × 0.08

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.989, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	2771, 1394, 1143
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.116, 1.00
No. of reflections	1394
No. of parameters	111
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.14

Computer programs: APEX2 (Bruker, 2004), SAINT-Plus (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O1ⁱ	0.93	2.70	3.4374 (19)	136.8
C7—H7···O2ⁱⁱ	0.93	2.69	3.3820 (19)	132.0

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

Acknowledgements

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

References

Alaniz, J. R. de & Rovis, T. (2005). J. Am. Chem. Soc. 127, 6284—6289. Google Scholar
Bruker (2001). SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2004). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Patonay, T., Juhász-Tóth, É. & Bényei, A. (2002). Eur. J. Org. Chem. pp. 285—295. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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. CAS Google Scholar
Takikawa, H. & Suzuki, K. (2007). Org. Lett. 9, 2713—2716. Web of Science CSD CrossRef Google Scholar