3-(4-Hy­droxy-3-meth­oxy­phen­yl)acrylic acid–2,3,5,6-tetra­methyl­pyrazine (2/1)

Zaiyou Tan; Erjia Zhu; Lin Luo; Zhuohui Lin; Ruisi Yan

doi:10.1107/S1600536811000961

. 2011 Jan 15;67(Pt 2):o424. doi: 10.1107/S1600536811000961

3-(4-Hydroxy-3-methoxyphenyl)acrylic acid–2,3,5,6-tetramethylpyrazine (2/1)

Zaiyou Tan ^a,^*, Erjia Zhu ^a, Lin Luo ^a, Zhuohui Lin ^a, Ruisi Yan ^a

PMCID: PMC3051719 PMID: 21523092

Abstract

The asymmetric unit of the title compound, C₈H₁₂N₂·2C₁₀H₁₀O₄, contains a tetramethylpyrazine molecule, situated about an inversion center, and two substituted acrylic acid derivatives. The dihedral angle between the phenyl and pyrazine rings is 69.45 (9)°. In the crystal, intermolecular O—H⋯O, O—H⋯N hydrogen bonds and weak C—H⋯O interactions lead to the formation of a supramolecular network. The acrylic acid side chain is positionally disordered [occupancy ratio 0.852 (7):0.148 (7)].

Related literature

For the synthesis of the title compound, see: Tan (2004 ▶). For the biological properties of the title compound, see: Tan et al. (2003 ▶).

Experimental

Crystal data

0.5C₈H₁₂N₂·C₁₀H₁₀O₄
M _r = 262.28
Monoclinic,
a = 9.4696 (7) Å
b = 5.7641 (4) Å
c = 24.3737 (15) Å
β = 93.654 (6)°
V = 1327.70 (16) Å³
Z = 4
Cu Kα radiation
μ = 0.80 mm⁻¹
T = 100 K
0.20 × 0.05 × 0.05 mm

Data collection

Oxford Diffraction Xcalibur Onyx Nova diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T _min = 0.953, T _max = 0.961
4780 measured reflections
2398 independent reflections
2004 reflections with I > 2σi(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.054
wR(F ²) = 0.156
S = 1.09
2398 reflections
208 parameters
4 restraints
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.40 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000961/su2237sup1.cif

e-67-0o424-sup1.cif^{(19.6KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000961/su2237Isup2.hkl

e-67-0o424-Isup2.hkl^{(117.9KB, hkl)}

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O1ⁱ	0.84	1.79	2.613 (5)	167
O4—H4⋯N1	0.82	1.97	2.749 (2)	158
C3—H3B⋯O4ⁱⁱ	0.98	2.58	3.553 (3)	174
C14—H14B⋯O4ⁱⁱ	0.98	2.59	3.465 (2)	148

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

The authors acknowledge financial support from the Science and Technology Project of the Government of Guangdong Province, China (grant No. 2009B080701025) and thank Professor Xiaopeng Hu of Sun Yat-Sen University for his help.

supplementary crystallographic information

Comment

The title compound, tetramethylpyrazine ferulate is a pharmacologically significant compound which we found in some prescriptions of traditional Chinese medicine, and which are used to treat stroke patients. In both the invivo and invitro experiments, tetramethylpyrazine ferulate has a remarkable inhibitory effect on ADP induced platelet aggregation (Tan et al., 2003). In order to study further its pharmacological effects the title compound was synthesized by the reaction of 3-(4-hydroxy-3-methoxyphenyl)-2-acrylicacid with tetrathylpyrazine, and its crystal structure is reported on herein.

X-ray crystallographic analysis confirmed the molecular structure and the atom connectivity for the title compound, as illustrated in Fig. 1. The dihedral angle between the mean planes of the pyrazine ring and phenyl ring (C8—C13) is 69.45 (9)°.

In the crystal intermolecular O—H···N hydrogen bonds and weak C—H···O interactions are observed, leading to the formation of a supra-molecular network (Table 1).

Experimental

The title compound was synthesized according to the published procedure (Tan, 2004). Tetramethylpyrazine (2.8 g) was heated with 3-(4-hydroxy-3-methoxyphenyl)-2-acrylicacid (4.0 g) in acetone (45 ml). After refluxing at 333 K for 1 h, the reaction mixture was left to stand for several days, and yellow crystals were finally isolated.