1-(4-Hydr­oxy-3,5-dimethoxy­phen­yl)ethanone

He, J.; Yang, J.

doi:10.1107/S1600536809046285

organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3030

doi:10.1107/S1600536809046285

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1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone

Jun He ^a ^* and Jin-cheng Yang ^b

^aDepartment of Pharmacognosy, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China, and ^bDepartment of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China
^*Correspondence e-mail: netkiller119@gmail.com

(Received 30 October 2009; accepted 3 November 2009; online 7 November 2009)

In the title molecule, C₁₀H₁₂O₄, the non-H atoms are essentially coplanar (r.m.s. deviation = 0.033 Å). In the crystal, molecules are linked into chains along [001] by O—H⋯O hydrogen bonds.

Related literature

For the use of the title compound to promote genetic transformation in plant tissue culture and genetic engineering, see: Mathews et al. (1990 ); Sheikholeslam & Weeks (1987 ).

Experimental

Crystal data

C₁₀H₁₂O₄
M_r = 196.20
Tetragonal, I 4₁ c d
a = 14.977 (2) Å
c = 17.142 (3) Å
V = 3845.5 (11) Å³
Z = 16
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 113 K
0.32 × 0.26 × 0.21 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.967, T_max = 0.978
14812 measured reflections
1178 independent reflections
1157 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.077
S = 1.16
1178 reflections
132 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4ⁱ	0.84	1.96	2.7210 (17)	151
Symmetry code: (i) $[-x+1, y, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046285/ci2962sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809046285/ci2962Isup2.hkl

checkCIF report

Comment top

The title compound is an important plant phenolic used in bioresearch. In plant tissue culture and genetic engineering, it is used to promote genetic transformation (Sheikholeslam & Weeks, 1987; Mathews et al., 1990). We herein report its crystal structure.

All of the non-H atoms of the title molecule (Fig.1) are essentially coplanar. In the crystal structure, adjacent molecules are linked into chains along the [001] by O—H···.O hydrogen bonds.

Related literature top

For the use of the title compound to promote genetic transformation in plant tissue culture and genetic engineering, see: Mathews et al. (1990); Sheikholeslam & Weeks (1987).

Experimental top

Single crystals suitable for X-ray analysis were grown by slow evaporation at room temperature of an acetone solution of commerical 1-(4-hydroxy-3,5-dimethoxyphenyl)ethanone.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level.

1-(4-Hydroxy-3,5-dimethoxyphenyl)ethanone top

Crystal data top

C₁₀H₁₂O₄	D_x = 1.356 Mg m⁻³
M_r = 196.20	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁cd	Cell parameters from 6429 reflections
Hall symbol: I 4bw -2c	θ = 3.0–27.9°
a = 14.977 (2) Å	µ = 0.11 mm⁻¹
c = 17.142 (3) Å	T = 113 K
V = 3845.5 (11) Å³	Block, colourless
Z = 16	0.32 × 0.26 × 0.21 mm
F(000) = 1664

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1178 independent reflections
Radiation source: rotating anode	1157 reflections with I > 2σ(I)
Confocal monochromator	R_int = 0.031
Detector resolution: 7.31 pixels mm^-1	θ_max = 27.9°, θ_min = 3.1°
ω and ϕ scans	h = −19→19
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −15→19
T_min = 0.967, T_max = 0.978	l = −22→22
14812 measured reflections

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)] = 0.028	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0561P)²] where P = (F_o² + 2F_c²)/3
S = 1.16	(Δ/σ)_max = 0.001
1178 reflections	Δρ_max = 0.17 e Å⁻³
132 parameters	Δρ_min = −0.16 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0083 (13)

Crystal data top

C₁₀H₁₂O₄	Z = 16
M_r = 196.20	Mo Kα radiation
Tetragonal, I4₁cd	µ = 0.11 mm⁻¹
a = 14.977 (2) Å	T = 113 K
c = 17.142 (3) Å	0.32 × 0.26 × 0.21 mm
V = 3845.5 (11) Å³

Data collection top

Rigaku Saturn CCD area-detector diffractometer	1178 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	1157 reflections with I > 2σ(I)
T_min = 0.967, T_max = 0.978	R_int = 0.031
14812 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	1 restraint
wR(F²) = 0.077	H-atom parameters constrained
S = 1.16	Δρ_max = 0.17 e Å⁻³
1178 reflections	Δρ_min = −0.16 e Å⁻³
132 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
O2	0.58678 (8)	0.08820 (8)	0.37342 (8)	0.0259 (3)
O1	0.42294 (7)	0.15165 (9)	0.39717 (6)	0.0245 (3)
H1	0.4621	0.1342	0.4288	0.037*
O3	0.31210 (7)	0.18800 (7)	0.28362 (6)	0.0231 (3)
C5	0.56661 (11)	0.09497 (10)	0.23142 (9)	0.0198 (3)
H5	0.6250	0.0733	0.2210	0.024*
O4	0.48863 (8)	0.12870 (8)	0.03437 (7)	0.0285 (3)
C3	0.42301 (10)	0.14750 (10)	0.18508 (9)	0.0199 (3)
H3	0.3842	0.1617	0.1430	0.024*
C4	0.50917 (11)	0.11554 (10)	0.17016 (9)	0.0193 (3)
C2	0.39445 (10)	0.15836 (10)	0.26140 (9)	0.0190 (3)
C6	0.53803 (10)	0.10625 (10)	0.30770 (9)	0.0195 (3)
C8	0.53803 (11)	0.10552 (10)	0.08750 (9)	0.0215 (3)
C1	0.45208 (11)	0.13863 (10)	0.32347 (9)	0.0190 (3)
C9	0.62896 (12)	0.06734 (13)	0.07049 (11)	0.0279 (4)
H9A	0.6386	0.0660	0.0140	0.042*
H9B	0.6327	0.0066	0.0914	0.042*
H9C	0.6748	0.1047	0.0951	0.042*
C7	0.67612 (11)	0.05852 (12)	0.36300 (10)	0.0267 (4)
H7A	0.6762	0.0026	0.3333	0.040*
H7B	0.7038	0.0485	0.4141	0.040*
H7C	0.7100	0.1040	0.3345	0.040*
C10	0.25044 (11)	0.20807 (13)	0.22248 (11)	0.0308 (4)
H10A	0.2760	0.2539	0.1883	0.046*
H10B	0.1945	0.2302	0.2451	0.046*
H10C	0.2385	0.1539	0.1921	0.046*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0226 (6)	0.0370 (7)	0.0181 (5)	0.0070 (5)	−0.0037 (4)	−0.0010 (5)
O1	0.0238 (6)	0.0353 (7)	0.0143 (5)	0.0054 (5)	−0.0008 (5)	0.0001 (5)
O3	0.0180 (5)	0.0319 (6)	0.0194 (5)	0.0033 (4)	−0.0006 (4)	0.0006 (5)
C5	0.0195 (7)	0.0195 (7)	0.0204 (7)	−0.0004 (5)	0.0021 (6)	−0.0002 (6)
O4	0.0277 (6)	0.0412 (7)	0.0166 (5)	0.0004 (5)	0.0010 (5)	−0.0004 (5)
C3	0.0217 (7)	0.0200 (7)	0.0179 (7)	−0.0021 (5)	−0.0026 (6)	0.0005 (6)
C4	0.0224 (8)	0.0186 (7)	0.0169 (7)	−0.0032 (6)	0.0012 (6)	−0.0010 (6)
C2	0.0190 (7)	0.0185 (7)	0.0195 (7)	0.0000 (5)	0.0007 (6)	−0.0012 (6)
C6	0.0208 (8)	0.0205 (7)	0.0172 (7)	0.0004 (5)	−0.0038 (6)	−0.0001 (5)
C8	0.0244 (8)	0.0214 (7)	0.0187 (7)	−0.0053 (6)	0.0029 (6)	−0.0004 (6)
C1	0.0205 (7)	0.0202 (7)	0.0163 (7)	−0.0009 (6)	0.0006 (6)	−0.0003 (6)
C9	0.0279 (8)	0.0357 (9)	0.0201 (7)	0.0022 (7)	0.0058 (7)	−0.0009 (7)
C7	0.0206 (7)	0.0305 (8)	0.0290 (8)	0.0050 (6)	−0.0041 (7)	−0.0018 (7)
C10	0.0220 (8)	0.0439 (10)	0.0264 (8)	0.0054 (7)	−0.0049 (7)	0.0022 (8)

Geometric parameters (Å, º) top

O2—C6	1.3695 (19)	C4—C8	1.489 (2)
O2—C7	1.421 (2)	C2—C1	1.402 (2)
O1—C1	1.3508 (19)	C6—C1	1.402 (2)
O1—H1	0.84	C8—C9	1.506 (2)
O3—C2	1.3650 (18)	C9—H9A	0.98
O3—C10	1.429 (2)	C9—H9B	0.98
C5—C6	1.386 (2)	C9—H9C	0.98
C5—C4	1.392 (2)	C7—H7A	0.98
C5—H5	0.95	C7—H7B	0.98
O4—C8	1.224 (2)	C7—H7C	0.98
C3—C2	1.386 (2)	C10—H10A	0.98
C3—C4	1.400 (2)	C10—H10B	0.98
C3—H3	0.95	C10—H10C	0.98

C6—O2—C7	117.41 (13)	O1—C1—C6	121.81 (13)
C1—O1—H1	109.5	O1—C1—C2	118.72 (13)
C2—O3—C10	116.60 (12)	C6—C1—C2	119.47 (14)
C6—C5—C4	119.59 (14)	C8—C9—H9A	109.5
C6—C5—H5	120.2	C8—C9—H9B	109.5
C4—C5—H5	120.2	H9A—C9—H9B	109.5
C2—C3—C4	119.80 (14)	C8—C9—H9C	109.5
C2—C3—H3	120.1	H9A—C9—H9C	109.5
C4—C3—H3	120.1	H9B—C9—H9C	109.5
C5—C4—C3	120.50 (14)	O2—C7—H7A	109.5
C5—C4—C8	121.08 (14)	O2—C7—H7B	109.5
C3—C4—C8	118.41 (14)	H7A—C7—H7B	109.5
O3—C2—C3	125.47 (13)	O2—C7—H7C	109.5
O3—C2—C1	114.41 (13)	H7A—C7—H7C	109.5
C3—C2—C1	120.12 (13)	H7B—C7—H7C	109.5
O2—C6—C5	125.96 (14)	O3—C10—H10A	109.5
O2—C6—C1	113.53 (13)	O3—C10—H10B	109.5
C5—C6—C1	120.51 (14)	H10A—C10—H10B	109.5
O4—C8—C4	120.27 (14)	O3—C10—H10C	109.5
O4—C8—C9	120.71 (15)	H10A—C10—H10C	109.5
C4—C8—C9	119.02 (15)	H10B—C10—H10C	109.5

C6—C5—C4—C3	0.0 (2)	C5—C4—C8—O4	−175.79 (15)
C6—C5—C4—C8	179.10 (14)	C3—C4—C8—O4	3.3 (2)
C2—C3—C4—C5	−0.3 (2)	C5—C4—C8—C9	3.6 (2)
C2—C3—C4—C8	−179.40 (14)	C3—C4—C8—C9	−177.28 (14)
C10—O3—C2—C3	0.9 (2)	O2—C6—C1—O1	1.2 (2)
C10—O3—C2—C1	−179.30 (13)	C5—C6—C1—O1	−178.92 (15)
C4—C3—C2—O3	−179.32 (14)	O2—C6—C1—C2	−178.90 (14)
C4—C3—C2—C1	0.9 (2)	C5—C6—C1—C2	1.0 (2)
C7—O2—C6—C5	2.7 (2)	O3—C2—C1—O1	−1.1 (2)
C7—O2—C6—C1	−177.48 (13)	C3—C2—C1—O1	178.65 (15)
C4—C5—C6—O2	179.47 (15)	O3—C2—C1—C6	178.98 (13)
C4—C5—C6—C1	−0.4 (2)	C3—C2—C1—C6	−1.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.84	1.96	2.7210 (17)	151

Symmetry code: (i) −x+1, y, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂O₄
M_r	196.20
Crystal system, space group	Tetragonal, I4₁cd
Temperature (K)	113
a, c (Å)	14.977 (2), 17.142 (3)
V (Å³)	3845.5 (11)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.32 × 0.26 × 0.21

Data collection
Diffractometer	Rigaku Saturn CCD area-detector diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.967, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	14812, 1178, 1157
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.658

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.077, 1.16
No. of reflections	1178
No. of parameters	132
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.16

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4ⁱ	0.84	1.96	2.7210 (17)	151

Symmetry code: (i) −x+1, y, z+1/2.

Acknowledgements

The authors thank Mr Zhi-Hua Mao of Sichuan University for his help with the X-ray data collection.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Sheikholeslam, S. N. & Weeks, D. P. (1987). Plant Mol. Biol. 8, 291–298. CrossRef CAS PubMed Web of Science Google Scholar
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