PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1105.
Published online 2010 April 17. doi:  10.1107/S1600536810013334
PMCID: PMC2979231

Isopropyl 3-(3,4-dihydroxy­phen­yl)-2-hydroxy­propanoate

Abstract

The title compound, C12H16O5, is a derivative of β-(3,4-dihydroxy­phen­yl)-α-hydr­oxy acid. The crystal packing is stabilized by inter­molecular O—H(...)O hydrogen bonds.

Related literature

For the anti­oxidant properties and vasorelaxant activity of the title compound, see: Tian et al. (2008 [triangle]); Wang et al. (2008 [triangle]). For the preparation, see: Zhang et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o1105-scheme1.jpg

Experimental

Crystal data

  • C12H16O5
  • M r = 240.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1105-efi1.jpg
  • a = 5.7691 (13) Å
  • b = 14.271 (3) Å
  • c = 14.955 (3) Å
  • β = 96.360 (3)°
  • V = 1223.7 (5) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 296 K
  • 0.38 × 0.27 × 0.18 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • 5934 measured reflections
  • 2174 independent reflections
  • 1598 reflections with I > 2σ(I)
  • R int = 0.029

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.106
  • S = 1.14
  • 2174 reflections
  • 159 parameters
  • H-atom parameters constrained
  • Δρmax = 0.18 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013334/jh2138sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013334/jh2138Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We are grateful for financial support from the Ministry of Education of Shaanxi Province (Nos. 08 J K476, 09 J K702), the National Natural Sciences Foundation of China (No. 20875074) and the West Light Foundation of the Chinese Academy of Sciences (No. 2007DF02).

supplementary crystallographic information

Comment

The antioxidant property (Tian et al., 2008) and vasorelaxant activity (Wang et al., 2008) of the title compound (I) is already described. At 296 K, X-ray structure analysis was carried out in order to structurally characterised (I). The molecular structure of the title compound and the atom-numbering scheme are shown in Fig.1. In the Fig.1, the hydrogen atoms are omitted for clarity. As shown in Fig.2, both the carbonyl oxygen and the hydroxyl oxygen form hydrogen bonds with the hydrogen of the hydroxyl in another moleculars. The distance of O1 and O4 is 2.7622 (14)/%A. The distance is longer than that between O2 and O3(2.7417/%A), shorter than O3 and O1(2.7832/%A). All the data, listed in table 1 suggest strong hydrogen bond interactions.

Experimental

The synthesis of the crude product was carried out according to reported methods(Zhang et al., 2009). The title compound was crystalised from ether and water at room temperature. Spectroscopic analysis: IR(KBr, χm-1): 3256, 2952, 1678, 1656; 1H NMR (DMSO, δ, p.p.m.): 12.389 (s, 1 H), 9.492 (s, 1 H), 9.316 (s, 1 H), 7.286—7.282 (d, 1 H), 7.196 (s, 1 H), 7.088—7.068 (m, 1 H), 6.797—6.781 (d, 1 H), 3.771 (s, 3 H), 1.985 (s, 3 H).

Refinement

H atoms bonded to N and O atoms were located in a difference map and refined with distance restraints of O—H = 0.8200 and N—H = 0.8600 Å, and with Uĩso~(H) = 1.2U~eq~(N,O). Other H atoms were positioned geometrically and refined using a riding model (including free rotation about the ethanol C—C bond), with C—H = 0.93–0.96 Å.

Figures

Fig. 1.
The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
Fig. 2.
The packing of (I), viewed down the a axis, molecules are connected by O—H···O hydrogen bonds shown as dashed lines.

Crystal data

C12H16O5Dx = 1.304 Mg m3
Mr = 240.25Melting point: 360 K
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 5.7691 (13) ÅCell parameters from 2102 reflections
b = 14.271 (3) Åθ = 2.7–25.9°
c = 14.955 (3) ŵ = 0.10 mm1
β = 96.360 (3)°T = 296 K
V = 1223.7 (5) Å3Block, colorless
Z = 40.38 × 0.27 × 0.18 mm
F(000) = 512

Data collection

Bruker SMART CCD area-detector diffractometer1598 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
graphiteθmax = 25.1°, θmin = 2.0°
phi and ω scansh = −6→6
5934 measured reflectionsk = −17→9
2174 independent reflectionsl = −17→17

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.14w = 1/[σ2(Fo2) + (0.0576P)2] where P = (Fo2 + 2Fc2)/3
2174 reflections(Δ/σ)max < 0.001
159 parametersΔρmax = 0.18 e Å3
0 restraintsΔρmin = −0.18 e Å3

Special details

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 > 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)

xyzUiso*/Ueq
O10.71641 (18)0.75521 (7)0.11545 (6)0.0508 (3)
H10.62200.73900.07330.076*
O21.09466 (18)0.79570 (7)0.22404 (8)0.0554 (3)
H21.23170.80590.24230.083*
O30.94395 (17)0.34163 (7)0.23630 (6)0.0457 (3)
H30.86480.32030.27380.068*
O40.5296 (2)0.29738 (8)0.04573 (8)0.0709 (4)
O50.77917 (17)0.20274 (7)0.12753 (6)0.0464 (3)
C10.8694 (2)0.68321 (10)0.13822 (9)0.0384 (4)
C21.0709 (2)0.70525 (10)0.19423 (10)0.0427 (4)
C31.2329 (3)0.63583 (11)0.21636 (11)0.0535 (4)
H3A1.36980.64990.25270.064*
C41.1939 (3)0.54492 (11)0.18498 (11)0.0518 (4)
H41.30580.49910.20040.062*
C50.9928 (2)0.52155 (10)0.13152 (9)0.0411 (4)
C60.8304 (3)0.59214 (10)0.10876 (9)0.0405 (4)
H60.69280.57770.07300.049*
C70.9418 (3)0.42345 (10)0.09809 (9)0.0461 (4)
H7A1.08810.39110.09390.055*
H7B0.85890.42650.03810.055*
C80.7973 (2)0.36720 (10)0.15824 (9)0.0395 (4)
H80.67270.40750.17600.047*
C90.6870 (3)0.28507 (11)0.10523 (10)0.0439 (4)
C100.6941 (3)0.12093 (10)0.07388 (10)0.0504 (4)
H100.52540.12660.05770.061*
C110.7441 (4)0.03703 (11)0.13364 (12)0.0705 (6)
H11A0.67080.04500.18770.106*
H11B0.90960.03080.14860.106*
H11C0.6840−0.01830.10270.106*
C120.8141 (4)0.11835 (14)−0.01037 (13)0.0812 (6)
H12A0.97980.11490.00540.122*
H12B0.77680.1741−0.04490.122*
H12C0.76250.0644−0.04540.122*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0510 (7)0.0484 (7)0.0490 (6)0.0097 (5)−0.0127 (5)−0.0090 (5)
O20.0500 (7)0.0482 (7)0.0644 (8)−0.0019 (5)−0.0092 (6)−0.0115 (5)
O30.0503 (6)0.0477 (7)0.0368 (5)−0.0044 (5)−0.0051 (5)0.0048 (4)
O40.0797 (9)0.0563 (8)0.0668 (8)0.0092 (6)−0.0370 (7)−0.0063 (6)
O50.0533 (6)0.0363 (6)0.0468 (6)0.0017 (5)−0.0070 (5)−0.0023 (4)
C10.0381 (8)0.0432 (9)0.0330 (7)0.0041 (6)0.0004 (6)0.0008 (6)
C20.0434 (9)0.0430 (10)0.0411 (8)−0.0032 (7)0.0023 (7)−0.0023 (6)
C30.0421 (9)0.0515 (11)0.0631 (10)−0.0005 (8)−0.0113 (7)0.0021 (8)
C40.0460 (9)0.0482 (10)0.0595 (10)0.0067 (8)−0.0022 (8)0.0076 (8)
C50.0464 (9)0.0416 (9)0.0360 (7)0.0005 (7)0.0076 (7)0.0052 (6)
C60.0415 (8)0.0470 (9)0.0321 (7)−0.0023 (7)−0.0006 (6)0.0000 (6)
C70.0558 (10)0.0454 (9)0.0376 (8)0.0036 (7)0.0073 (7)0.0008 (7)
C80.0418 (8)0.0389 (9)0.0369 (8)0.0040 (6)0.0001 (6)0.0003 (6)
C90.0472 (9)0.0419 (9)0.0404 (8)0.0041 (7)−0.0044 (7)0.0004 (6)
C100.0579 (10)0.0417 (9)0.0499 (9)−0.0054 (7)−0.0021 (7)−0.0093 (7)
C110.1035 (15)0.0405 (10)0.0672 (11)−0.0069 (10)0.0076 (11)−0.0050 (8)
C120.1136 (17)0.0685 (13)0.0647 (11)0.0007 (12)0.0244 (11)−0.0088 (10)

Geometric parameters (Å, °)

O1—C11.3725 (16)C5—C71.505 (2)
O1—H10.8200C6—H60.9300
O2—C21.3676 (17)C7—C81.5212 (19)
O2—H20.8200C7—H7A0.9700
O3—C81.4116 (16)C7—H7B0.9700
O3—H30.8200C8—C91.515 (2)
O4—C91.2119 (17)C8—H80.9800
O5—C91.3172 (17)C10—C111.503 (2)
O5—C101.4698 (17)C10—C121.504 (2)
C1—C61.3827 (19)C10—H100.9800
C1—C21.392 (2)C11—H11A0.9600
C2—C31.377 (2)C11—H11B0.9600
C3—C41.389 (2)C11—H11C0.9600
C3—H3A0.9300C12—H12A0.9600
C4—C51.375 (2)C12—H12B0.9600
C4—H40.9300C12—H12C0.9600
C5—C61.3920 (19)
C1—O1—H1109.5O3—C8—C9114.28 (11)
C2—O2—H2109.5O3—C8—C7107.94 (11)
C8—O3—H3109.5C9—C8—C7108.95 (11)
C9—O5—C10117.99 (11)O3—C8—H8108.5
O1—C1—C6123.19 (12)C9—C8—H8108.5
O1—C1—C2116.83 (13)C7—C8—H8108.5
C6—C1—C2119.97 (13)O4—C9—O5124.32 (14)
O2—C2—C3124.07 (13)O4—C9—C8120.62 (14)
O2—C2—C1117.15 (13)O5—C9—C8115.04 (12)
C3—C2—C1118.78 (14)O5—C10—C11106.12 (12)
C2—C3—C4120.72 (14)O5—C10—C12108.65 (14)
C2—C3—H3A119.6C11—C10—C12113.75 (15)
C4—C3—H3A119.6O5—C10—H10109.4
C5—C4—C3121.15 (15)C11—C10—H10109.4
C5—C4—H4119.4C12—C10—H10109.4
C3—C4—H4119.4C10—C11—H11A109.5
C4—C5—C6117.93 (14)C10—C11—H11B109.5
C4—C5—C7122.71 (14)H11A—C11—H11B109.5
C6—C5—C7119.37 (13)C10—C11—H11C109.5
C1—C6—C5121.41 (13)H11A—C11—H11C109.5
C1—C6—H6119.3H11B—C11—H11C109.5
C5—C6—H6119.3C10—C12—H12A109.5
C5—C7—C8113.23 (11)C10—C12—H12B109.5
C5—C7—H7A108.9H12A—C12—H12B109.5
C8—C7—H7A108.9C10—C12—H12C109.5
C5—C7—H7B108.9H12A—C12—H12C109.5
C8—C7—H7B108.9H12B—C12—H12C109.5
H7A—C7—H7B107.7
O1—C1—C2—O22.23 (19)C4—C5—C7—C893.95 (16)
C6—C1—C2—O2−177.37 (13)C6—C5—C7—C8−85.35 (15)
O1—C1—C2—C3−177.87 (13)C5—C7—C8—O3−74.53 (15)
C6—C1—C2—C32.5 (2)C5—C7—C8—C9160.84 (12)
O2—C2—C3—C4178.56 (15)C10—O5—C9—O43.3 (2)
C1—C2—C3—C4−1.3 (2)C10—O5—C9—C8−174.98 (12)
C2—C3—C4—C5−0.4 (2)O3—C8—C9—O4167.89 (15)
C3—C4—C5—C60.8 (2)C7—C8—C9—O4−71.30 (18)
C3—C4—C5—C7−178.48 (14)O3—C8—C9—O5−13.79 (18)
O1—C1—C6—C5178.33 (12)C7—C8—C9—O5107.02 (14)
C2—C1—C6—C5−2.1 (2)C9—O5—C10—C11−156.25 (14)
C4—C5—C6—C10.41 (19)C9—O5—C10—C1281.06 (17)
C7—C5—C6—C1179.74 (13)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.962.7621 (14)164
O2—H2···O3ii0.821.932.7417 (15)169
O3—H3···O1iii0.822.002.7832 (14)160

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+5/2, y+1/2, −z+1/2; (iii) −x+3/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2138).

References

  • Bruker (1997). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Tian, J., Li, G., Liu, Z., Zhang, S., Qu, G., Jiang, W. & Fu, F. (2008). Neurosci. Lett.442, 279–283. [PubMed]
  • Wang, S., Zang, W., Kong, S., Yu, X., Sun, L., Zhao, X., Wang, S. & Zheng, X. (2008). Eur. J. Pharmacol.579, 283–288. [PubMed]
  • Zhang, Q., Dong, Y., Nan, Y., Cai, X. & Zheng, X. (2009). Youji Huaxue, 29, 1466–1469.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography