3-Benzyl-2H-chromen-2-one

Li, G.-Q.; Li, Y.-L.; Jiang, T.; Jiang, R.-W.; Wang, G.-C.

doi:10.1107/S1600536812014298

organic compounds

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ISSN: 2056-9890

Volume 68| Part 5| May 2012| Page o1504

doi:10.1107/S1600536812014298

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3-Benzyl-2H-chromen-2-one

Guo-Qiang Li,^a Yao-Lan Li,^a Tao Jiang,^b Ren-Wang Jiang ^a and Guo-Cai Wang ^a ^*

^aGuangdong Province Key Laboratory of Pharmacodynamic Constituents of Traditional Chinese Medicine and New Drugs Research, Institute of Traditional Chinese Medicine and Natural Products, Jinan University, Guangzhou 510632, People's Republic of China, and ^bResearch Center for Harmful Algae and Aquatic Environment, Jinan University, Guangzhou 510632, People's Republic of China
^*Correspondence e-mail: wang_guocai@hotmail.com

(Received 27 March 2012; accepted 2 April 2012; online 21 April 2012)

The title compound, C₁₆H₁₂O₂, is a coumarin which was isolated from stones of the Chinese traditional medicine Clausena lansium. The pyrone ring is almost planar, with a mean deviation of 0.0135 (4) Å. The benzene ring (A) of the benzopyrone unit forms dihedral angles of 1.82 (5) and 72.86 (2)° with the pyrone ring and the substituent benzene ring, respectively. The crystal structure is stabilized by weak π–π stacking interactions, with a minimum centroid–centroid distance between benzene rings of 3.6761 (7) Å.

Related literature

For general background to the isolation of the title compound, see: Wisanu et al. (2010 , 2012 ). For the biological activity of Clausena lansium, see: Adebajo et al. (2009 ).

Experimental

Crystal data

C₁₆H₁₂O₂
M_r = 236.26
Monoclinic, P 2₁ /c
a = 11.7704 (4) Å
b = 8.2809 (4) Å
c = 12.4652 (6) Å
β = 108.151 (2)°
V = 1154.52 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 150 K
0.86 × 0.23 × 0.21 mm

Data collection

Bruker SMART CCD 1000 diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.982
8002 measured reflections
2475 independent reflections
2050 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.093
S = 1.08
2475 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Data collection: SAINT (Bruker, 1998 ); cell refinement: SMART (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812014298/zs2199sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812014298/zs2199Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812014298/zs2199Isup3.cml

checkCIF report

Comment top

The title compound, C₁₆H₁₂O₂ (systematic name:3-benzylchromen-2-one), is a coumarin which was isolated from stones of the Chinese traditional medicine Clausena lansium. This plant is a rich source of coumarin (Wisanu et al., 2010; Wisanu et al., 2012). The biological activity of Clausena lansium have been studied (Adebajo et al., 2009). In this study, we report the crystal structure of the title compound (Fig. 1) comprises two benzene rings (A and C) and a pyrone ring (B), which is almost planar with a mean deviation 0.0135 (4) Å. The ring A of the benzopyrone unit forms dihedral angles of 1.82 (5) and 72.86 (2)° with the ring B and the ring C, respectively. The molecules are stacked parallel to the c axis giving weak π–π interactions between benzene rings (Fig. 2), with a minimum centroid–centroid distance of 3.6761 (7) Å.

Related literature top

For general background to the isolation of the title compound, see: Wisanu et al. (2010, 2012). For the biological activity of Clausena lansium, see: Adebajo et al. (2009).

Experimental top

The title compound was isolated from stones of the traditional chinese medicine Clausena lansium, 5 kg of which was extracted with 95% ethanol at room temperature, then concentrated by rotary evaporation. The crude extract was suspended in distilled water and partitioned with petroleum ether, ethyl acetate and n-butanol. The title compound (8 mg) was isolated from the petroleum ether fraction using silica gel column chromatography. Crystals of the title compound were obtained after slow evaporation of an ethyl acetate solution at room temperature.

Computing details top

Data collection: SAINT (Bruker, 1998); cell refinement: SMART (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of the title compound showing 50% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. The packing of the title compound, viewed down the c axis.

3-Benzyl-2H-chromen-2-one top

Crystal data top

C₁₆H₁₂O₂	F(000) = 496
M_r = 236.26	D_x = 1.359 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.710747 Å
a = 11.7704 (4) Å	Cell parameters from 8002 reflections
b = 8.2809 (4) Å	θ = 3–27.5°
c = 12.4652 (6) Å	µ = 0.09 mm⁻¹
β = 108.151 (2)°	T = 150 K
V = 1154.52 (9) Å³	Prism, colourless
Z = 4	0.86 × 0.23 × 0.21 mm

Data collection top

Bruker SMART CCD 1000 diffractometer	2475 independent reflections
Radiation source: fine-focus sealed tube	2050 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ω scans	θ_max = 27.0°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→13
T_min = 0.928, T_max = 0.982	k = −10→10
8002 measured reflections	l = −12→15

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.093	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0426P)² + 0.2137P] where P = (F_o² + 2F_c²)/3
2475 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.24 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₆H₁₂O₂	V = 1154.52 (9) Å³
M_r = 236.26	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.7704 (4) Å	µ = 0.09 mm⁻¹
b = 8.2809 (4) Å	T = 150 K
c = 12.4652 (6) Å	0.86 × 0.23 × 0.21 mm
β = 108.151 (2)°

Data collection top

Bruker SMART CCD 1000 diffractometer	2475 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2050 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.982	R_int = 0.033
8002 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.093	H-atom parameters constrained
S = 1.08	Δρ_max = 0.24 e Å⁻³
2475 reflections	Δρ_min = −0.18 e Å⁻³
163 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	0.38027 (9)	0.35804 (12)	0.36947 (9)	0.0229 (2)
C2	0.35856 (9)	0.38688 (11)	0.47770 (9)	0.0206 (2)
C3	0.43498 (9)	0.32578 (12)	0.57355 (9)	0.0213 (2)
H3	0.4219	0.3477	0.6436	0.026*
C4	0.53617 (9)	0.22788 (12)	0.57215 (9)	0.0206 (2)
C5	0.61806 (10)	0.16006 (13)	0.66886 (10)	0.0260 (3)
H5	0.6099	0.1803	0.7411	0.031*
C6	0.71066 (10)	0.06388 (13)	0.65934 (10)	0.0287 (3)
H6	0.7660	0.0191	0.7252	0.034*
C7	0.72314 (10)	0.03238 (12)	0.55376 (11)	0.0271 (3)
H7	0.7868	−0.0342	0.5482	0.033*
C8	0.64344 (9)	0.09730 (12)	0.45677 (10)	0.0251 (2)
H8	0.6511	0.0752	0.3846	0.030*
C9	0.55206 (9)	0.19552 (12)	0.46798 (9)	0.0206 (2)
C10	0.24760 (9)	0.48264 (12)	0.47378 (10)	0.0244 (2)
H10A	0.2366	0.5706	0.4177	0.029*
H10B	0.2586	0.5325	0.5485	0.029*
C11	0.13605 (9)	0.37716 (12)	0.44253 (9)	0.0216 (2)
C12	0.09172 (10)	0.31780 (13)	0.52614 (10)	0.0285 (3)
H12	0.1305	0.3453	0.6029	0.034*
C13	−0.00877 (11)	0.21854 (14)	0.49858 (11)	0.0323 (3)
H13	−0.0383	0.1794	0.5565	0.039*
C14	−0.06579 (10)	0.17677 (13)	0.38743 (11)	0.0296 (3)
H14	−0.1344	0.1092	0.3687	0.036*
C15	−0.02205 (10)	0.23422 (14)	0.30374 (11)	0.0307 (3)
H15	−0.0604	0.2051	0.2273	0.037*
C16	0.07789 (9)	0.33453 (13)	0.33096 (10)	0.0272 (3)
H16	0.1066	0.3742	0.2727	0.033*
O1	0.47592 (6)	0.26132 (9)	0.36983 (6)	0.02389 (19)
O2	0.32169 (7)	0.41253 (10)	0.27881 (7)	0.0331 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0211 (5)	0.0238 (5)	0.0243 (6)	−0.0041 (4)	0.0078 (4)	0.0014 (4)
C2	0.0205 (5)	0.0186 (5)	0.0242 (6)	−0.0052 (4)	0.0092 (4)	−0.0015 (4)
C3	0.0233 (5)	0.0221 (5)	0.0209 (6)	−0.0049 (4)	0.0102 (4)	−0.0034 (4)
C4	0.0204 (5)	0.0199 (5)	0.0221 (6)	−0.0050 (4)	0.0076 (4)	−0.0012 (4)
C5	0.0273 (6)	0.0286 (5)	0.0217 (6)	−0.0024 (4)	0.0072 (4)	−0.0003 (4)
C6	0.0246 (6)	0.0268 (5)	0.0318 (7)	−0.0005 (4)	0.0045 (5)	0.0045 (5)
C7	0.0231 (5)	0.0199 (5)	0.0401 (7)	−0.0018 (4)	0.0126 (5)	−0.0016 (4)
C8	0.0262 (6)	0.0237 (5)	0.0294 (6)	−0.0053 (4)	0.0143 (5)	−0.0050 (4)
C9	0.0201 (5)	0.0199 (5)	0.0221 (6)	−0.0053 (4)	0.0071 (4)	−0.0006 (4)
C10	0.0238 (6)	0.0203 (5)	0.0292 (6)	−0.0012 (4)	0.0086 (4)	−0.0014 (4)
C11	0.0198 (5)	0.0179 (5)	0.0276 (6)	0.0031 (4)	0.0079 (4)	0.0001 (4)
C12	0.0312 (6)	0.0310 (6)	0.0254 (6)	−0.0042 (5)	0.0121 (5)	−0.0067 (5)
C13	0.0358 (6)	0.0343 (6)	0.0338 (7)	−0.0070 (5)	0.0207 (5)	−0.0034 (5)
C14	0.0224 (6)	0.0297 (6)	0.0372 (7)	−0.0056 (4)	0.0101 (5)	−0.0021 (5)
C15	0.0264 (6)	0.0368 (6)	0.0247 (6)	−0.0043 (5)	0.0020 (5)	0.0011 (5)
C16	0.0253 (6)	0.0307 (6)	0.0250 (6)	−0.0020 (4)	0.0067 (4)	0.0066 (4)
O1	0.0247 (4)	0.0297 (4)	0.0191 (4)	−0.0007 (3)	0.0094 (3)	0.0003 (3)
O2	0.0314 (4)	0.0432 (5)	0.0240 (5)	0.0019 (4)	0.0077 (3)	0.0089 (4)

Geometric parameters (Å, º) top

C1—C2	1.4687 (15)	C8—C9	1.3898 (15)
C1—O1	1.3805 (13)	C9—O1	1.3834 (13)
C1—O2	1.2128 (13)	C10—H10A	0.9900
C2—C3	1.3502 (15)	C10—H10B	0.9900
C2—C10	1.5157 (14)	C10—C11	1.5231 (14)
C3—H3	0.9500	C11—C12	1.3925 (15)
C3—C4	1.4453 (14)	C11—C16	1.3908 (16)
C4—C5	1.4050 (15)	C12—H12	0.9500
C4—C9	1.3944 (16)	C12—C13	1.3927 (16)
C5—H5	0.9500	C13—H13	0.9500
C5—C6	1.3845 (16)	C13—C14	1.3821 (18)
C6—H6	0.9500	C14—H14	0.9500
C6—C7	1.3937 (17)	C14—C15	1.3836 (17)
C7—H7	0.9500	C15—H15	0.9500
C7—C8	1.3871 (16)	C15—C16	1.3930 (15)
C8—H8	0.9500	C16—H16	0.9500

O1—C1—C2	117.80 (9)	O1—C9—C8	116.75 (10)
O2—C1—C2	125.76 (10)	C2—C10—H10A	109.2
O2—C1—O1	116.43 (10)	C2—C10—H10B	109.2
C1—C2—C10	116.75 (9)	C2—C10—C11	111.95 (8)
C3—C2—C1	119.56 (9)	H10A—C10—H10B	107.9
C3—C2—C10	123.67 (10)	C11—C10—H10A	109.2
C2—C3—H3	119.2	C11—C10—H10B	109.2
C2—C3—C4	121.59 (10)	C12—C11—C10	120.34 (10)
C4—C3—H3	119.2	C16—C11—C10	121.18 (10)
C5—C4—C3	124.16 (10)	C16—C11—C12	118.46 (10)
C9—C4—C3	117.98 (10)	C11—C12—H12	119.6
C9—C4—C5	117.84 (10)	C11—C12—C13	120.74 (11)
C4—C5—H5	119.9	C13—C12—H12	119.6
C6—C5—C4	120.29 (11)	C12—C13—H13	119.8
C6—C5—H5	119.9	C14—C13—C12	120.33 (11)
C5—C6—H6	119.8	C14—C13—H13	119.8
C5—C6—C7	120.40 (11)	C13—C14—H14	120.3
C7—C6—H6	119.8	C13—C14—C15	119.42 (11)
C6—C7—H7	119.7	C15—C14—H14	120.3
C8—C7—C6	120.58 (10)	C14—C15—H15	119.8
C8—C7—H7	119.7	C14—C15—C16	120.38 (11)
C7—C8—H8	120.9	C16—C15—H15	119.8
C7—C8—C9	118.28 (11)	C11—C16—C15	120.67 (11)
C9—C8—H8	120.9	C11—C16—H16	119.7
C8—C9—C4	122.59 (10)	C15—C16—H16	119.7
O1—C9—C4	120.66 (9)	C1—O1—C9	122.30 (9)

C1—C2—C3—C4	−1.97 (14)	C7—C8—C9—O1	178.51 (9)
C1—C2—C10—C11	82.11 (11)	C8—C9—O1—C1	178.61 (9)
C2—C1—O1—C9	−1.63 (13)	C9—C4—C5—C6	−0.30 (15)
C2—C3—C4—C5	−179.48 (9)	C10—C2—C3—C4	176.63 (9)
C2—C3—C4—C9	−1.02 (14)	C10—C11—C12—C13	−178.67 (10)
C2—C10—C11—C12	98.80 (12)	C10—C11—C16—C15	178.15 (10)
C2—C10—C11—C16	−79.60 (12)	C11—C12—C13—C14	0.32 (18)
C3—C2—C10—C11	−96.53 (12)	C12—C11—C16—C15	−0.27 (16)
C3—C4—C5—C6	178.17 (9)	C12—C13—C14—C15	0.10 (18)
C3—C4—C9—C8	−177.27 (9)	C13—C14—C15—C16	−0.60 (18)
C3—C4—C9—O1	2.74 (14)	C14—C15—C16—C11	0.70 (17)
C4—C5—C6—C7	−0.46 (16)	C16—C11—C12—C13	−0.23 (16)
C4—C9—O1—C1	−1.39 (14)	O1—C1—C2—C3	3.29 (14)
C5—C4—C9—C8	1.30 (15)	O1—C1—C2—C10	−175.41 (8)
C5—C4—C9—O1	−178.70 (8)	O2—C1—C2—C3	−176.32 (10)
C5—C6—C7—C8	0.27 (16)	O2—C1—C2—C10	4.98 (15)
C6—C7—C8—C9	0.68 (15)	O2—C1—O1—C9	178.02 (9)
C7—C8—C9—C4	−1.49 (15)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₂O₂
M_r	236.26
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	11.7704 (4), 8.2809 (4), 12.4652 (6)
β (°)	108.151 (2)
V (Å³)	1154.52 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.86 × 0.23 × 0.21

Data collection
Diffractometer	Bruker SMART CCD 1000 diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.982
No. of measured, independent and observed [I > 2σ(I)] reflections	8002, 2475, 2050
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.093, 1.08
No. of reflections	2475
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.18

Computer programs: SAINT (Bruker, 1998), SMART (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Acknowledgements

This work was supported by the National Natural Science Foundation of China (No. 41106090) and the Natural Science Foundation of Guangdong Province (No. S2011040003113)

References

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