6-Meth­oxy-4-methyl-2H-chromen-2-one

Fun, H.-K.; Goh, J.H.; Wu, D.; Zhang, Y.

doi:10.1107/S1600536810051652

organic compounds

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ISSN: 2056-9890

Volume 67| Part 1| January 2011| Page o136

https://doi.org/10.1107/S1600536810051652

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6-Methoxy-4-methyl-2H-chromen-2-one

Hoong-Kun Fun,^a ^*‡ Jia Hao Goh,^a § Dongdong Wu ^b and Yan Zhang ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bSchool of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: hkfun@usm.my

(Received 8 December 2010; accepted 9 December 2010; online 15 December 2010)

The whole molecule of the title coumarin derivative, C₁₁H₁₀O₃, is approximately planar, with a maximum deviation of 0.116 (3) Å from the least-squares plane defined by all non-H atoms. In the crystal, adjacent molecules are linked into chains along [011] via intermolecular C—H⋯O hydrogen bonds.

Related literature

For general background to and applications of the title coumarin derivative, see: Grimm & Girard (2006 ); Maresca et al. (2010 ); Parvez & Hadda (2010 ); Raj & Wenge (1998 ); Yao & Deng (2000 ). For related coumarin structures, see: Asad et al. (2010 ); Saidi et al. (2007 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₁₁H₁₀O₃
M_r = 190.19
Triclinic, $[P \overline 1]$
a = 7.2554 (2) Å
b = 8.0880 (2) Å
c = 8.5450 (2) Å
α = 112.988 (1)°
β = 90.234 (1)°
γ = 93.873 (1)°
V = 460.31 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.40 × 0.35 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.962, T_max = 0.994
10271 measured reflections
2793 independent reflections
1675 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.066
wR(F²) = 0.218
S = 1.09
2793 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.70 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯O2ⁱ	0.93	2.56	3.471 (2)	165
Symmetry code: (i) x, y-1, z-1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810051652/is2642sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810051652/is2642Isup2.hkl

checkCIF report

Comment top

Coumarin is the mother-nuclear structure of many natural products and the importance of coumarin and its analogous compounds which exhibit useful pharmaceutical activities are well-known. Some substituted coumarin and their derivatives have been reported as food constituents, anti-oxidants, stabilizers, immunomodulatory substances, inhibitors of some enzymes, fluorescent markers in analysis, lasers, and in clinical use (Parvez & Hadda, 2010; Maresca et al., 2010; Grimm & Girard, 2006). In addition, 4-substituted coumarins have shown many pharmaceutical activities such as anti-bacterial, anti-fungal, anthelmintic, insecticidal, hypnotic and other biological activities, and most precisely 4-methyl-coumarins have been correlated to several beneficial pharmacological effects too (Yao & Deng, 2000; Raj & Wenge, 1998). In view of the importance of the coumarin derivatives, the crystal structure of the title compound is reported in this paper.

The title coumarin derivative (Fig. 1) has an approximately planar molecular structure, with the methoxy-O atom (C10) deviating -0.116 (3) Å from the least-squares plane defined by all non-hydrogen atoms. All bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to those related coumarin structures (Asad et al., 2010; Saidi et al., 2007). In the crystal packing (Fig. 2), adjacent molecules are linked into one-dimensional chains propagating along the [011] direction via intermolecular C8—H8A···O2 hydrogen bonds.

Related literature top

For general background to and applications of the title coumarin derivative, see: Grimm & Girard (2006); Maresca et al. (2010); Parvez & Hadda (2010); Raj & Wenge (1998); Yao & Deng (2000). For related coumarin structures, see: Asad et al. (2010); Saidi et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound was obtained in the photoreaction of 4-(chloromethyl)-6-methoxy-2H-chromen-2-one in visible light. The compound was purified by flash column chromatography. Good quality single crystals suitable for X-ray analysis were obtained from slow evaporation of a 1:1 solution of acetone and petroleum ether.

Structure description top

For general background to and applications of the title coumarin derivative, see: Grimm & Girard (2006); Maresca et al. (2010); Parvez & Hadda (2010); Raj & Wenge (1998); Yao & Deng (2000). For related coumarin structures, see: Asad et al. (2010); Saidi et al. (2007). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); 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) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title coumarin derivative, showing the atomic numbering scheme. Displacement ellipsoids for non-hydrogen atoms are drawn at the 50 % probability level.
	Fig. 2. The crystal structure of the title compound, viewed along the a axis, showing one-dimensional chains propagating along the [011] direction. Intermolecular hydrogen bonds are shown as dashed lines.

6-Methoxy-4-methyl-2H-chromen-2-one top

Crystal data top

C₁₁H₁₀O₃	Z = 2
M_r = 190.19	F(000) = 200
Triclinic, P1	D_x = 1.372 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2554 (2) Å	Cell parameters from 3241 reflections
b = 8.0880 (2) Å	θ = 2.6–30.0°
c = 8.5450 (2) Å	µ = 0.10 mm⁻¹
α = 112.988 (1)°	T = 293 K
β = 90.234 (1)°	Plate, yellow
γ = 93.873 (1)°	0.40 × 0.35 × 0.06 mm
V = 460.31 (2) Å³

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2793 independent reflections
Radiation source: fine-focus sealed tube	1675 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 30.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.962, T_max = 0.994	k = −11→11
10271 measured reflections	l = −11→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.218	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0991P)² + 0.086P] where P = (F_o² + 2F_c²)/3
2793 reflections	(Δ/σ)_max < 0.001
129 parameters	Δρ_max = 0.70 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₁₁H₁₀O₃	γ = 93.873 (1)°
M_r = 190.19	V = 460.31 (2) Å³
Triclinic, P1	Z = 2
a = 7.2554 (2) Å	Mo Kα radiation
b = 8.0880 (2) Å	µ = 0.10 mm⁻¹
c = 8.5450 (2) Å	T = 293 K
α = 112.988 (1)°	0.40 × 0.35 × 0.06 mm
β = 90.234 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2793 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1675 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.994	R_int = 0.021
10271 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	0 restraints
wR(F²) = 0.218	H-atom parameters constrained
S = 1.09	Δρ_max = 0.70 e Å⁻³
2793 reflections	Δρ_min = −0.20 e Å⁻³
129 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
O1	0.19469 (16)	0.53037 (17)	0.87871 (16)	0.0508 (4)
O2	0.6197 (2)	1.09931 (18)	1.34611 (17)	0.0638 (4)
O3	0.1468 (2)	0.2933 (2)	0.63843 (19)	0.0679 (5)
C1	0.3087 (2)	0.6718 (2)	0.9894 (2)	0.0417 (4)
C2	0.2327 (3)	0.7819 (3)	1.1396 (2)	0.0512 (5)
H2A	0.1101	0.7603	1.1617	0.061*
C3	0.3402 (3)	0.9229 (3)	1.2551 (2)	0.0527 (5)
H3A	0.2901	0.9974	1.3559	0.063*
C4	0.5250 (3)	0.9555 (2)	1.2222 (2)	0.0472 (4)
C5	0.5999 (2)	0.8469 (2)	1.0726 (2)	0.0438 (4)
H5A	0.7225	0.8696	1.0510	0.053*
C6	0.4917 (2)	0.7016 (2)	0.9521 (2)	0.0384 (4)
C7	0.5603 (2)	0.5807 (2)	0.7919 (2)	0.0414 (4)
C8	0.4450 (2)	0.4441 (2)	0.6875 (2)	0.0463 (4)
H8A	0.4895	0.3663	0.5851	0.056*
C9	0.2564 (3)	0.4127 (2)	0.7264 (2)	0.0475 (4)
C10	0.8119 (3)	1.1270 (3)	1.3272 (3)	0.0695 (6)
H10C	0.8624	1.2287	1.4242	0.104*
H10D	0.8317	1.1495	1.2260	0.104*
H10A	0.8718	1.0217	1.3187	0.104*
C11	0.7558 (3)	0.6091 (3)	0.7459 (3)	0.0573 (5)
H11D	0.7824	0.5119	0.6419	0.086*
H11A	0.8387	0.6128	0.8352	0.086*
H11B	0.7713	0.7209	0.7311	0.086*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0352 (6)	0.0577 (8)	0.0514 (8)	0.0001 (5)	0.0021 (5)	0.0132 (6)
O2	0.0694 (10)	0.0531 (8)	0.0488 (8)	0.0036 (7)	−0.0011 (7)	−0.0017 (6)
O3	0.0523 (8)	0.0717 (9)	0.0622 (9)	−0.0130 (7)	−0.0092 (7)	0.0103 (8)
C1	0.0368 (8)	0.0467 (9)	0.0413 (9)	0.0056 (7)	0.0016 (7)	0.0164 (7)
C2	0.0411 (9)	0.0600 (11)	0.0516 (11)	0.0141 (8)	0.0130 (8)	0.0193 (9)
C3	0.0579 (11)	0.0553 (11)	0.0413 (10)	0.0187 (9)	0.0120 (8)	0.0125 (8)
C4	0.0541 (11)	0.0434 (9)	0.0394 (9)	0.0087 (8)	−0.0003 (8)	0.0104 (7)
C5	0.0400 (9)	0.0467 (9)	0.0416 (9)	0.0039 (7)	0.0031 (7)	0.0139 (7)
C6	0.0362 (8)	0.0418 (8)	0.0367 (8)	0.0073 (6)	0.0023 (6)	0.0141 (7)
C7	0.0384 (9)	0.0457 (9)	0.0387 (9)	0.0068 (7)	0.0042 (7)	0.0145 (7)
C8	0.0461 (10)	0.0480 (9)	0.0388 (9)	0.0059 (7)	0.0031 (7)	0.0102 (7)
C9	0.0429 (9)	0.0511 (10)	0.0440 (10)	0.0006 (8)	−0.0033 (7)	0.0144 (8)
C10	0.0654 (14)	0.0596 (12)	0.0646 (14)	−0.0073 (10)	−0.0111 (11)	0.0060 (10)
C11	0.0466 (10)	0.0633 (12)	0.0508 (11)	0.0045 (9)	0.0119 (8)	0.0100 (9)

Geometric parameters (Å, º) top

O1—C9	1.377 (2)	C5—H5A	0.9300
O1—C1	1.381 (2)	C6—C7	1.450 (2)
O2—C4	1.367 (2)	C7—C8	1.348 (2)
O2—C10	1.417 (3)	C7—C11	1.500 (2)
O3—C9	1.206 (2)	C8—C9	1.438 (3)
C1—C2	1.387 (2)	C8—H8A	0.9300
C1—C6	1.394 (2)	C10—H10C	0.9600
C2—C3	1.370 (3)	C10—H10D	0.9600
C2—H2A	0.9300	C10—H10A	0.9600
C3—C4	1.400 (3)	C11—H11D	0.9600
C3—H3A	0.9300	C11—H11A	0.9600
C4—C5	1.376 (2)	C11—H11B	0.9600
C5—C6	1.407 (2)

C9—O1—C1	121.54 (14)	C8—C7—C11	121.52 (15)
C4—O2—C10	117.77 (15)	C6—C7—C11	119.97 (15)
O1—C1—C2	116.85 (15)	C7—C8—C9	123.28 (16)
O1—C1—C6	121.51 (15)	C7—C8—H8A	118.4
C2—C1—C6	121.65 (16)	C9—C8—H8A	118.4
C3—C2—C1	119.36 (17)	O3—C9—O1	116.69 (17)
C3—C2—H2A	120.3	O3—C9—C8	126.37 (18)
C1—C2—H2A	120.3	O1—C9—C8	116.95 (15)
C2—C3—C4	120.41 (16)	O2—C10—H10C	109.5
C2—C3—H3A	119.8	O2—C10—H10D	109.5
C4—C3—H3A	119.8	H10C—C10—H10D	109.5
O2—C4—C5	124.24 (17)	O2—C10—H10A	109.5
O2—C4—C3	115.58 (16)	H10C—C10—H10A	109.5
C5—C4—C3	120.18 (17)	H10D—C10—H10A	109.5
C4—C5—C6	120.30 (16)	C7—C11—H11D	109.5
C4—C5—H5A	119.8	C7—C11—H11A	109.5
C6—C5—H5A	119.8	H11D—C11—H11A	109.5
C1—C6—C5	118.10 (15)	C7—C11—H11B	109.5
C1—C6—C7	118.22 (15)	H11D—C11—H11B	109.5
C5—C6—C7	123.68 (15)	H11A—C11—H11B	109.5
C8—C7—C6	118.51 (15)

C9—O1—C1—C2	−179.81 (14)	C2—C1—C6—C7	−179.76 (15)
C9—O1—C1—C6	−0.2 (3)	C4—C5—C6—C1	−0.1 (3)
O1—C1—C2—C3	179.14 (15)	C4—C5—C6—C7	−179.79 (14)
C6—C1—C2—C3	−0.4 (3)	C1—C6—C7—C8	−0.8 (2)
C1—C2—C3—C4	−0.1 (3)	C5—C6—C7—C8	178.89 (15)
C10—O2—C4—C5	−6.8 (3)	C1—C6—C7—C11	179.31 (16)
C10—O2—C4—C3	173.65 (17)	C5—C6—C7—C11	−1.0 (3)
C2—C3—C4—O2	−179.84 (16)	C6—C7—C8—C9	0.4 (3)
C2—C3—C4—C5	0.6 (3)	C11—C7—C8—C9	−179.67 (17)
O2—C4—C5—C6	−179.97 (15)	C1—O1—C9—O3	179.91 (15)
C3—C4—C5—C6	−0.4 (3)	C1—O1—C9—C8	−0.2 (3)
O1—C1—C6—C5	−178.98 (14)	C7—C8—C9—O3	179.99 (18)
C2—C1—C6—C5	0.6 (3)	C7—C8—C9—O1	0.1 (3)
O1—C1—C6—C7	0.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.93	2.56	3.471 (2)	165

Symmetry code: (i) x, y−1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₀O₃
M_r	190.19
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	7.2554 (2), 8.0880 (2), 8.5450 (2)
α, β, γ (°)	112.988 (1), 90.234 (1), 93.873 (1)
V (Å³)	460.31 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.35 × 0.06

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.962, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	10271, 2793, 1675
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.716

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.218, 1.09
No. of reflections	2793
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.70, −0.20

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···O2ⁱ	0.93	2.56	3.471 (2)	165

Symmetry code: (i) x, y−1, z−1.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Thomson Reuters ResearcherID: C-7576-2009.

Acknowledgements

HKF and JHG thank Universiti Sains Malaysia (USM) for a Research University Grant (No. 1001/PFIZIK/811160). Financial support from the Fok Ying Tung Education Foundation (114012) is also acknowledged.

References

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