3,4-Dihy­droxy­phenethyl acetate

Shen, F.; Zhu, J.; Wang, L.; Wang, K.; Yang, W.

doi:10.1107/S1600536811026730

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o1996

doi:10.1107/S1600536811026730

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3,4-Dihydroxyphenethyl acetate

Fei Shen,^a Jing Zhu,^b Lu-lu Wang,^b Kai Wang ^b and Wen-ge Yang ^b ^*

^aJiangsu Engineering Technology Research Center of, Polypeptide Pharmaceutical, Nanjing 210009, People's Republic of China, and ^bState Key Laboratory of Materials-Oriented Chemical Engineering, School of Pharmaceutical Sciences, Nanjing University of Technology, Xinmofan Road No. 5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: chemywg@126.com

(Received 14 June 2011; accepted 5 July 2011; online 9 July 2011)

In the title compound, C₁₀H₁₂O₄, the dihedral angle between the acetate group and the aromatic ring is 20.47 (10)°. In the crystal, molecules are linked by O—H⋯O hydrogen bonds, forming [001] chains. Weak C—H⋯O interactions consolidate the packing.

Related literature

For the synthesis, see: Bovicelli et al. (2007 ).

Experimental

Crystal data

C₁₀H₁₂O₄
M_r = 196.20
Monoclinic, P 2₁ /n
a = 11.088 (2) Å
b = 7.7100 (15) Å
c = 12.687 (3) Å
β = 114.50 (3)°
V = 986.9 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.970, T_max = 0.990
3672 measured reflections
1819 independent reflections
1439 reflections with I > 2σ(I)
R_int = 0.025
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.146
S = 1.01
1819 reflections
129 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2ⁱ	0.82	2.11	2.827 (2)	145
O2—H2A⋯O4ⁱⁱ	0.82	1.89	2.7138 (19)	179
C10—H10A⋯O1ⁱⁱⁱ	0.96	2.36	3.316 (3)	177
Symmetry codes: (i) -x+2, -y, -z; (ii) -x+2, -y, -z+1; (iii) x, y, z+1.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026730/hb5912sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026730/hb5912Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026730/hb5912Isup3.cml

checkCIF report

Related literature top

For the synthesis, see: Bovicelli et al. (2007).

Experimental top

The title compound was prepared by the literature method (Bovicelli et al. 2007). Colourless blocks of (I) were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with displacement ellipsoids drawn at 30% probability levels.
	Fig. 2. A practical packing diagram of the title compound. Hydron bonds are shown as dashed lines.

3,4-Dihydroxyphenethyl acetate top

Crystal data top

C₁₀H₁₂O₄	F(000) = 416
M_r = 196.20	D_x = 1.320 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 11.088 (2) Å	Cell parameters from 25 reflections
b = 7.7100 (15) Å	θ = 9–13°
c = 12.687 (3) Å	µ = 0.10 mm⁻¹
β = 114.50 (3)°	T = 293 K
V = 986.9 (3) Å³	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1439 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.025
Graphite monochromator	θ_max = 25.4°, θ_min = 2.1°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = −9→9
T_min = 0.970, T_max = 0.990	l = −15→13
3672 measured reflections	3 standard reflections every 200 reflections
1819 independent reflections	intensity decay: 1%

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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.146	w = 1/[σ²(F_o²) + (0.1P)² + 0.110P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1819 reflections	Δρ_max = 0.28 e Å⁻³
129 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Extinction correction: SHELXS97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.113 (13)

Crystal data top

C₁₀H₁₂O₄	V = 986.9 (3) Å³
M_r = 196.20	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.088 (2) Å	µ = 0.10 mm⁻¹
b = 7.7100 (15) Å	T = 293 K
c = 12.687 (3) Å	0.30 × 0.20 × 0.10 mm
β = 114.50 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1439 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.025
T_min = 0.970, T_max = 0.990	3 standard reflections every 200 reflections
3672 measured reflections	intensity decay: 1%
1819 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.01	Δρ_max = 0.28 e Å⁻³
1819 reflections	Δρ_min = −0.21 e Å⁻³
129 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
O1	0.82657 (16)	0.1555 (2)	−0.06613 (11)	0.0744 (5)
H1A	0.8814	0.0814	−0.0619	0.112*
C1	0.61846 (18)	0.1594 (2)	0.09171 (14)	0.0500 (5)
H1B	0.5326	0.1915	0.0787	0.060*
O2	0.99568 (12)	0.0172 (2)	0.13823 (10)	0.0600 (4)
H2A	1.0401	−0.0162	0.2045	0.090*
C2	0.6604 (2)	0.1768 (3)	0.00363 (14)	0.0551 (5)
H2B	0.6023	0.2195	−0.0681	0.066*
O3	0.67398 (12)	0.1071 (2)	0.48254 (10)	0.0591 (4)
C3	0.78691 (19)	0.1315 (2)	0.02105 (14)	0.0493 (5)
O4	0.85894 (13)	0.0936 (2)	0.64219 (11)	0.0667 (5)
C4	0.87258 (17)	0.0653 (2)	0.12809 (14)	0.0444 (4)
C5	0.83054 (17)	0.0485 (2)	0.21595 (13)	0.0435 (4)
H5A	0.8886	0.0053	0.2875	0.052*
C6	0.70253 (17)	0.0951 (2)	0.19887 (14)	0.0425 (4)
C7	0.65213 (17)	0.0689 (3)	0.29153 (14)	0.0498 (5)
H7A	0.5705	0.1339	0.2703	0.060*
H7B	0.6312	−0.0529	0.2934	0.060*
C8	0.74690 (17)	0.1231 (2)	0.41116 (15)	0.0490 (5)
H8A	0.8242	0.0483	0.4398	0.059*
H8B	0.7757	0.2418	0.4109	0.059*
C9	0.73987 (17)	0.0917 (2)	0.59542 (15)	0.0497 (5)
C10	0.6508 (2)	0.0698 (4)	0.65552 (17)	0.0706 (7)
H10A	0.6997	0.0906	0.7369	0.106*
H10B	0.6163	−0.0463	0.6439	0.106*
H10C	0.5788	0.1508	0.6246	0.106*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0785 (10)	0.1125 (13)	0.0404 (7)	0.0258 (9)	0.0327 (7)	0.0154 (7)
C1	0.0448 (9)	0.0593 (11)	0.0435 (9)	0.0051 (8)	0.0162 (8)	−0.0028 (7)
O2	0.0493 (7)	0.0940 (11)	0.0420 (7)	0.0130 (7)	0.0241 (6)	0.0090 (6)
C2	0.0565 (11)	0.0675 (12)	0.0346 (9)	0.0115 (9)	0.0122 (8)	0.0035 (8)
O3	0.0406 (7)	0.1006 (11)	0.0383 (7)	0.0101 (6)	0.0185 (5)	0.0056 (6)
C3	0.0586 (11)	0.0581 (11)	0.0337 (8)	0.0033 (8)	0.0217 (8)	−0.0002 (7)
O4	0.0414 (8)	0.1125 (12)	0.0430 (7)	0.0016 (7)	0.0144 (6)	0.0054 (7)
C4	0.0455 (9)	0.0515 (10)	0.0373 (8)	0.0000 (7)	0.0184 (7)	−0.0019 (7)
C5	0.0462 (9)	0.0501 (9)	0.0344 (8)	0.0020 (7)	0.0169 (7)	0.0041 (7)
C6	0.0436 (9)	0.0458 (9)	0.0386 (9)	−0.0013 (7)	0.0176 (7)	−0.0026 (7)
C7	0.0469 (10)	0.0627 (11)	0.0443 (10)	0.0003 (8)	0.0235 (8)	0.0026 (8)
C8	0.0439 (9)	0.0641 (11)	0.0438 (9)	0.0065 (8)	0.0231 (8)	0.0074 (8)
C9	0.0414 (10)	0.0702 (12)	0.0380 (9)	0.0037 (8)	0.0170 (7)	−0.0026 (8)
C10	0.0529 (12)	0.1190 (19)	0.0459 (11)	−0.0016 (12)	0.0264 (9)	−0.0075 (11)

Geometric parameters (Å, º) top

O1—C3	1.362 (2)	C4—C5	1.381 (2)
O1—H1A	0.8200	C5—C6	1.391 (2)
C1—C6	1.383 (2)	C5—H5A	0.9300
C1—C2	1.384 (2)	C6—C7	1.510 (2)
C1—H1B	0.9300	C7—C8	1.503 (3)
O2—C4	1.368 (2)	C7—H7A	0.9700
O2—H2A	0.8200	C7—H7B	0.9700
C2—C3	1.371 (3)	C8—H8A	0.9700
C2—H2B	0.9300	C8—H8B	0.9700
O3—C9	1.316 (2)	C9—C10	1.487 (2)
O3—C8	1.448 (2)	C10—H10A	0.9600
C3—C4	1.392 (2)	C10—H10B	0.9600
O4—C9	1.202 (2)	C10—H10C	0.9600

C3—O1—H1A	109.5	C8—C7—C6	114.80 (14)
C6—C1—C2	120.88 (16)	C8—C7—H7A	108.6
C6—C1—H1B	119.6	C6—C7—H7A	108.6
C2—C1—H1B	119.6	C8—C7—H7B	108.6
C4—O2—H2A	109.5	C6—C7—H7B	108.6
C3—C2—C1	120.62 (16)	H7A—C7—H7B	107.5
C3—C2—H2B	119.7	O3—C8—C7	105.67 (13)
C1—C2—H2B	119.7	O3—C8—H8A	110.6
C9—O3—C8	119.11 (13)	C7—C8—H8A	110.6
O1—C3—C2	119.20 (16)	O3—C8—H8B	110.6
O1—C3—C4	121.50 (17)	C7—C8—H8B	110.6
C2—C3—C4	119.29 (16)	H8A—C8—H8B	108.7
O2—C4—C5	123.78 (16)	O4—C9—O3	122.44 (17)
O2—C4—C3	116.22 (15)	O4—C9—C10	125.14 (16)
C5—C4—C3	119.99 (16)	O3—C9—C10	112.42 (15)
C4—C5—C6	120.92 (16)	C9—C10—H10A	109.5
C4—C5—H5A	119.5	C9—C10—H10B	109.5
C6—C5—H5A	119.5	H10A—C10—H10B	109.5
C1—C6—C5	118.30 (15)	C9—C10—H10C	109.5
C1—C6—C7	119.81 (15)	H10A—C10—H10C	109.5
C5—C6—C7	121.82 (15)	H10B—C10—H10C	109.5

C6—C1—C2—C3	−0.5 (3)	C2—C1—C6—C7	−176.88 (17)
C1—C2—C3—O1	−177.86 (17)	C4—C5—C6—C1	−0.2 (3)
C1—C2—C3—C4	0.9 (3)	C4—C5—C6—C7	176.70 (15)
O1—C3—C4—O2	−3.4 (3)	C1—C6—C7—C8	−138.32 (18)
C2—C3—C4—O2	177.79 (17)	C5—C6—C7—C8	44.8 (2)
O1—C3—C4—C5	177.72 (17)	C9—O3—C8—C7	158.48 (17)
C2—C3—C4—C5	−1.0 (3)	C6—C7—C8—O3	173.27 (15)
O2—C4—C5—C6	−178.03 (16)	C8—O3—C9—O4	1.5 (3)
C3—C4—C5—C6	0.7 (3)	C8—O3—C9—C10	−177.75 (18)
C2—C1—C6—C5	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	2.11	2.827 (2)	145
O2—H2A···O4ⁱⁱ	0.82	1.89	2.7138 (19)	179
C10—H10A···O1ⁱⁱⁱ	0.96	2.36	3.316 (3)	177

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

Experimental details

Crystal data
Chemical formula	C₁₀H₁₂O₄
M_r	196.20
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.088 (2), 7.7100 (15), 12.687 (3)
β (°)	114.50 (3)
V (Å³)	986.9 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.970, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	3672, 1819, 1439
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.604

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.146, 1.01
No. of reflections	1819
No. of parameters	129
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.21

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2ⁱ	0.82	2.11	2.827 (2)	145
O2—H2A···O4ⁱⁱ	0.82	1.89	2.7138 (19)	179
C10—H10A···O1ⁱⁱⁱ	0.96	2.36	3.316 (3)	177

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

Acknowledgements

This research work was supported financially by the Program of Six Talent Tops Foundation of Jiangsu Province (2009 NO 2009118) and the Natural Science Basic Research Program of Higher Education in Jiangsu Province (08 K J A530002).

References

Bovicelli, P., Antonioletti, R., Mancini, S., Causio, S., Borioni, G., Ammendola, S. & Barontini, M. (2007). Synth. Commun. 37, 4245–4252. Web of Science CrossRef CAS Google Scholar
Enraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar