1-(3,4-Dimeth­oxy­phen­yl)propan-1-one

Yang, B.; Han, C.; Song, X.; Chen, G.; Song, X.

doi:10.1107/S1600536811035173

organic compounds

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ISSN: 2056-9890

Volume 67| Part 10| October 2011| Page o2568

https://doi.org/10.1107/S1600536811035173

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1-(3,4-Dimethoxyphenyl)propan-1-one

Biao Yang,^a Changri Han,^a Xiaoping Song,^a Guangying Chen ^a ^* and Xinming Song ^a

^aKey Laboratory of Tropical Medicinal Plant Chemistry of the Ministry of Education, College of Chemistry & Chemical Engineering, Hainan Normal University, Haikou 571158, People's Republic of China
^*Correspondence e-mail: hchr116@hainnu.edu.cn, chgying123@163.com

(Received 27 March 2011; accepted 29 August 2011; online 14 September 2011)

The title compound, C₁₁H₁₄O₃, was isolated from the stems of Trigonostemon xyphophylloides, which belongs to Trigonostemon genus of Euphorbiaceae. The plants in this genus were used in folk medicine, such as for the treatment of diseases caused by viruses and fungi. The limited investigation of the chemistry of this plant prompted an examination of constituents of its twigs, from which the title compound was isolated. The molecule is approximately planar with an r.m.s. deviation of 0.1237Å. In the crystal, intermolecular C—H⋯O hydrogen bonds connect the molecules into a two-dimensional network structure with an R₂²(12) graph-set motif.

Related literature

For the medicinal and botanical background to the title compound, see: Zdero et al. (1990 ); Lopes et al. (1996 ). For weak hydrogen bonds, see: Steiner (1996 ).

Experimental

Crystal data

C₁₁H₁₄O₃
M_r = 194.22
Monoclinic, P 2₁ /c
a = 8.9308 (9) Å
b = 13.8582 (14) Å
c = 8.5692 (8) Å
β = 102.427 (1)°
V = 1035.72 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.50 × 0.43 × 0.40 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.236, T_max = 0.965
5082 measured reflections
1827 independent reflections
1265 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.122
S = 1.04
1827 reflections
131 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11C⋯O2ⁱ	0.96	2.66	3.607 (2)	171
C8—H8⋯O1ⁱⁱ	0.93	2.50	3.419 (3)	171
Symmetry codes: (i) -x, -y+1, -z+1; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus; 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.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811035173/nr2005sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811035173/nr2005Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811035173/nr2005Isup3.cml

checkCIF report

Comment top

The title compound was isolated from plants such as Pteronia camphorata (Zdero et al., 1990) and Virola surinamensis (Lopes et al., 1996). In our ongoing studies of natural products with biological activity we isolated the compound from the 75% EtOH extract of the stems of Trigonostemon xyphophylloides, a plant used as a folk medicine which were collected from Jianfengling County, Hainan Province, P.R. China. We have undertaken the X-ray crystal structure analysis of the title compound in order to establish its molecular structure and relative stereochemistry.

The molecular structure of (I) is shown in Fig.1. All nonhydrogen atom are coplanar, the mean deviation is 0.1237Å and the largest deviation being -0.3235 (20)Å for atom O1.In the crystal, molecules are linked by intermolecular C–H···O hydrogen bonds into two dimensional network structure (Steiner, 1996) (Fig.2). There are two intermolecular C–H···O hydrogen bonds C8–H8···O1 and C11c–H11c···O2, each adjacent C11c–H11c···O2 form a ring of twelve atoms with with an R² ₂(12) graphset motif.

Related literature top

For the medicinal and botanical background to the title compound, see: Zdero et al. (1990); Lopes et al. (1996). For weak hydrogen bonds, see: Steiner (1996).

Experimental top

Air-dried stems of Trigonostemon xyphophylloides (5.9 kg) were ground and percolated (3 × 2.5 h) with 75% EtOH at 60°C, which was suspended in 1.5 L water and then partitioned with petroleum ether, chloroform, ethyl acetate and n-BuOH, successively, yielding a petroleum ether extract, a chloroform extract, an ethyl acetate extract and a n-BuOH extract, respectively. The petroleum ether extract was subjected to a silica gel CC column using petroleum ether as first eluent and then increasing the polarity with EtOAc, to afford 20 fractions (A—T). Fraction D was further separated by column chromatography with a gradient of petroleum ether-EtOAc to give the title compound. The crude product was dissolved in small amount of ethyl acetate to obtain single crystals suitable for X-ray analysis by slow evaporation of ethyl acetate solution at 298 K.

Structure description top

For the medicinal and botanical background to the title compound, see: Zdero et al. (1990); Lopes et al. (1996). For weak hydrogen bonds, see: Steiner (1996).

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); 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).

Figures top

	Fig. 1. View of the title compound without the hydrogen atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the molecular packing.

1-(3,4-Dimethoxyphenyl)propan-1-one top

Crystal data top

C₁₁H₁₄O₃	F(000) = 416
M_r = 194.22	D_x = 1.246 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1875 reflections
a = 8.9308 (9) Å	θ = 2.4–23.9°
b = 13.8582 (14) Å	µ = 0.09 mm⁻¹
c = 8.5692 (8) Å	T = 298 K
β = 102.427 (1)°	Block, colourless
V = 1035.72 (18) Å³	0.50 × 0.43 × 0.40 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	1827 independent reflections
Radiation source: fine-focus sealed tube	1265 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
φ and ω scans	θ_max = 25.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −10→9
T_min = 0.236, T_max = 0.965	k = −11→16
5082 measured reflections	l = −9→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)] = 0.041	H-atom parameters constrained
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0535P)² + 0.2478P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max < 0.001
1827 reflections	Δρ_max = 0.16 e Å⁻³
131 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0080 (18)

Crystal data top

C₁₁H₁₄O₃	V = 1035.72 (18) Å³
M_r = 194.22	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.9308 (9) Å	µ = 0.09 mm⁻¹
b = 13.8582 (14) Å	T = 298 K
c = 8.5692 (8) Å	0.50 × 0.43 × 0.40 mm
β = 102.427 (1)°

Data collection top

Bruker APEXII CCD diffractometer	1827 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1265 reflections with I > 2σ(I)
T_min = 0.236, T_max = 0.965	R_int = 0.024
5082 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	Δρ_max = 0.16 e Å⁻³
1827 reflections	Δρ_min = −0.18 e Å⁻³
131 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	0.6568 (2)	0.70399 (12)	0.1437 (3)	0.1020 (7)
O2	0.21582 (15)	0.66963 (10)	0.42215 (18)	0.0649 (4)
O3	0.16048 (14)	0.48733 (10)	0.42736 (17)	0.0602 (4)
C1	0.9079 (2)	0.60873 (18)	0.0925 (3)	0.0775 (7)
H1A	0.9509	0.6544	0.1740	0.116*
H1B	0.8682	0.6422	−0.0058	0.116*
H1C	0.9859	0.5642	0.0773	0.116*
C2	0.7796 (2)	0.55404 (15)	0.1427 (3)	0.0578 (5)
H2A	0.7366	0.5081	0.0597	0.069*
H2B	0.8214	0.5179	0.2392	0.069*
C3	0.6546 (2)	0.61841 (15)	0.1727 (3)	0.0560 (5)
C4	0.52728 (19)	0.57857 (13)	0.2399 (2)	0.0463 (5)
C5	0.4315 (2)	0.64333 (13)	0.2967 (2)	0.0497 (5)
H5	0.4492	0.7093	0.2916	0.060*
C6	0.31209 (19)	0.61142 (13)	0.3597 (2)	0.0478 (5)
C7	0.28263 (19)	0.51162 (14)	0.3649 (2)	0.0478 (5)
C8	0.3772 (2)	0.44743 (13)	0.3093 (2)	0.0511 (5)
H8	0.3589	0.3815	0.3125	0.061*
C9	0.4994 (2)	0.48095 (13)	0.2487 (2)	0.0509 (5)
H9	0.5636	0.4370	0.2134	0.061*
C10	0.2320 (3)	0.77064 (14)	0.4052 (3)	0.0708 (7)
H10A	0.2190	0.7864	0.2940	0.106*
H10B	0.3322	0.7903	0.4614	0.106*
H10C	0.1557	0.8036	0.4487	0.106*
C11	0.1190 (3)	0.38787 (15)	0.4241 (3)	0.0670 (6)
H11A	0.2027	0.3511	0.4847	0.101*
H11B	0.0958	0.3654	0.3155	0.101*
H11C	0.0305	0.3801	0.4697	0.101*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0941 (13)	0.0551 (10)	0.182 (2)	0.0115 (8)	0.0862 (13)	0.0284 (11)
O2	0.0603 (8)	0.0511 (8)	0.0924 (11)	0.0016 (7)	0.0363 (8)	−0.0055 (7)
O3	0.0537 (8)	0.0536 (8)	0.0801 (10)	−0.0069 (6)	0.0291 (7)	0.0014 (7)
C1	0.0584 (13)	0.0816 (16)	0.1011 (19)	−0.0035 (12)	0.0364 (13)	−0.0103 (14)
C2	0.0530 (11)	0.0600 (12)	0.0648 (13)	0.0022 (9)	0.0220 (10)	−0.0019 (10)
C3	0.0530 (11)	0.0478 (12)	0.0714 (14)	0.0016 (9)	0.0226 (10)	0.0058 (10)
C4	0.0426 (10)	0.0462 (10)	0.0516 (11)	0.0049 (8)	0.0134 (8)	0.0046 (9)
C5	0.0467 (10)	0.0423 (10)	0.0612 (12)	0.0010 (8)	0.0144 (9)	0.0043 (9)
C6	0.0421 (10)	0.0477 (11)	0.0547 (12)	0.0044 (8)	0.0127 (8)	−0.0013 (9)
C7	0.0425 (10)	0.0509 (11)	0.0511 (11)	−0.0024 (8)	0.0126 (8)	0.0016 (9)
C8	0.0524 (11)	0.0408 (10)	0.0608 (12)	−0.0021 (9)	0.0135 (9)	0.0021 (9)
C9	0.0490 (10)	0.0446 (11)	0.0617 (12)	0.0059 (8)	0.0175 (9)	0.0000 (9)
C10	0.0690 (14)	0.0526 (13)	0.0963 (18)	0.0069 (10)	0.0303 (13)	−0.0095 (11)
C11	0.0650 (13)	0.0597 (13)	0.0828 (16)	−0.0167 (11)	0.0300 (11)	−0.0014 (12)

Geometric parameters (Å, º) top

O1—C3	1.213 (2)	C4—C5	1.398 (2)
O2—C6	1.369 (2)	C5—C6	1.368 (2)
O2—C10	1.418 (2)	C5—H5	0.9300
O3—C7	1.357 (2)	C6—C7	1.410 (3)
O3—C11	1.426 (2)	C7—C8	1.381 (3)
C1—C2	1.511 (3)	C8—C9	1.385 (3)
C1—H1A	0.9600	C8—H8	0.9300
C1—H1B	0.9600	C9—H9	0.9300
C1—H1C	0.9600	C10—H10A	0.9600
C2—C3	1.494 (3)	C10—H10B	0.9600
C2—H2A	0.9700	C10—H10C	0.9600
C2—H2B	0.9700	C11—H11A	0.9600
C3—C4	1.487 (3)	C11—H11B	0.9600
C4—C9	1.381 (2)	C11—H11C	0.9600

C6—O2—C10	117.08 (15)	C5—C6—C7	119.73 (16)
C7—O3—C11	117.36 (15)	O2—C6—C7	115.37 (16)
C2—C1—H1A	109.5	O3—C7—C8	125.45 (17)
C2—C1—H1B	109.5	O3—C7—C6	115.27 (16)
H1A—C1—H1B	109.5	C8—C7—C6	119.27 (16)
C2—C1—H1C	109.5	C7—C8—C9	120.20 (17)
H1A—C1—H1C	109.5	C7—C8—H8	119.9
H1B—C1—H1C	109.5	C9—C8—H8	119.9
C3—C2—C1	112.94 (18)	C4—C9—C8	121.00 (17)
C3—C2—H2A	109.0	C4—C9—H9	119.5
C1—C2—H2A	109.0	C8—C9—H9	119.5
C3—C2—H2B	109.0	O2—C10—H10A	109.5
C1—C2—H2B	109.0	O2—C10—H10B	109.5
H2A—C2—H2B	107.8	H10A—C10—H10B	109.5
O1—C3—C4	119.34 (18)	O2—C10—H10C	109.5
O1—C3—C2	120.19 (18)	H10A—C10—H10C	109.5
C4—C3—C2	120.46 (17)	H10B—C10—H10C	109.5
C9—C4—C5	118.62 (16)	O3—C11—H11A	109.5
C9—C4—C3	123.16 (16)	O3—C11—H11B	109.5
C5—C4—C3	118.22 (16)	H11A—C11—H11B	109.5
C6—C5—C4	121.16 (17)	O3—C11—H11C	109.5
C6—C5—H5	119.4	H11A—C11—H11C	109.5
C4—C5—H5	119.4	H11B—C11—H11C	109.5
C5—C6—O2	124.90 (17)

C1—C2—C3—O1	6.0 (3)	C11—O3—C7—C8	−5.2 (3)
C1—C2—C3—C4	−173.37 (19)	C11—O3—C7—C6	175.36 (16)
O1—C3—C4—C9	167.5 (2)	C5—C6—C7—O3	−179.08 (15)
C2—C3—C4—C9	−13.1 (3)	O2—C6—C7—O3	1.6 (2)
O1—C3—C4—C5	−12.5 (3)	C5—C6—C7—C8	1.4 (3)
C2—C3—C4—C5	166.88 (18)	O2—C6—C7—C8	−177.89 (16)
C9—C4—C5—C6	−0.1 (3)	O3—C7—C8—C9	−179.64 (17)
C3—C4—C5—C6	179.88 (18)	C6—C7—C8—C9	−0.2 (3)
C4—C5—C6—O2	177.98 (17)	C5—C4—C9—C8	1.4 (3)
C4—C5—C6—C7	−1.3 (3)	C3—C4—C9—C8	−178.62 (18)
C10—O2—C6—C5	6.7 (3)	C7—C8—C9—C4	−1.2 (3)
C10—O2—C6—C7	−174.01 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O2ⁱ	0.96	2.66	3.607 (2)	171
C8—H8···O1ⁱⁱ	0.93	2.50	3.419 (3)	171

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₁H₁₄O₃
M_r	194.22
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.9308 (9), 13.8582 (14), 8.5692 (8)
β (°)	102.427 (1)
V (Å³)	1035.72 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.50 × 0.43 × 0.40

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.236, 0.965
No. of measured, independent and observed [I > 2σ(I)] reflections	5082, 1827, 1265
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.122, 1.04
No. of reflections	1827
No. of parameters	131
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18

Computer programs: APEX2 (Bruker, 2003), SAINT-Plus (Bruker, 2003), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···O2ⁱ	0.96	2.66	3.607 (2)	170.9
C8—H8···O1ⁱⁱ	0.93	2.50	3.419 (3)	171.4

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, y−1/2, −z+1/2.

Acknowledgements

This work was supported by the National Natural Science Foundation of China (20862005), the Program for New Century Excellent Talents in Universities (NCET-08–0656), the Natural Science Foundation of Hainan Province, China (No. 070207) and the University Graduate Student Innovation Science Research Project of Hainan Province (No. Hxwsy2008–17).

References

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