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

Tan, Z.; Zhu, E.; Luo, L.; Lin, Z.; Yan, R.

doi:10.1107/S1600536811000961

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o424

doi:10.1107/S1600536811000961

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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 and Ruisi Yan ^a

^aDepartment of Physical Chemistry, Guangdong Pharmaceutical University, Guangzhou, Guangdong 510006, People's Republic of China
^*Correspondence e-mail: tanzaiyou@yahoo.com.cn

(Received 10 December 2010; accepted 7 January 2011; online 15 January 2011)

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, P 2₁ /n
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.054
wR(F²) = 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

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
Symmetry codes: (i) -x, -y+1, -z; (ii) x, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

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

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

checkCIF report

Comment top

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).

Related literature top

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

Experimental top

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.

Computing details top

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

Figures top

Fig. 1. A view of the centrosymmmetric tetramethylpyrazine molecule and one of the ferulate molecules of the title compound. Displacement ellipsoids are drawn at the 50% probability level [Symmetry code: (a) = -x, -y, -z + 1; only the major component of the disordered acrylicacid side chain is shown].

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

Crystal data top

0.5C₈H₁₂N₂·C₁₀H₁₀O₄	F(000) = 556
M_r = 262.28	D_x = 1.312 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2yn	Cell parameters from 2625 reflections
a = 9.4696 (7) Å	θ = 3.6–71.3°
b = 5.7641 (4) Å	µ = 0.80 mm⁻¹
c = 24.3737 (15) Å	T = 100 K
β = 93.654 (6)°	Plate, yellow
V = 1327.70 (16) Å³	0.20 × 0.05 × 0.05 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Onyx Nova diffractometer	2398 independent reflections
Radiation source: fine-focus sealed tube	2004 reflections with I > 2σi(I)
Graphite monochromator	R_int = 0.030
Detector resolution: 8.2417 pixels mm^-1	θ_max = 68.2°, θ_min = 3.6°
ω scans	h = −6→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −6→6
T_min = 0.953, T_max = 0.961	l = −29→29
4780 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0848P)² + 0.4876P] where P = (F_o² + 2F_c²)/3
2398 reflections	(Δ/σ)_max = 0.003
208 parameters	Δρ_max = 0.63 e Å⁻³
4 restraints	Δρ_min = −0.40 e Å⁻³

Crystal data top

0.5C₈H₁₂N₂·C₁₀H₁₀O₄	V = 1327.70 (16) Å³
M_r = 262.28	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 9.4696 (7) Å	µ = 0.80 mm⁻¹
b = 5.7641 (4) Å	T = 100 K
c = 24.3737 (15) Å	0.20 × 0.05 × 0.05 mm
β = 93.654 (6)°

Data collection top

Oxford Diffraction Xcalibur Onyx Nova diffractometer	2398 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2004 reflections with I > 2σi(I)
T_min = 0.953, T_max = 0.961	R_int = 0.030
4780 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	4 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.09	Δρ_max = 0.63 e Å⁻³
2398 reflections	Δρ_min = −0.40 e Å⁻³
208 parameters

Special details top

Experimental. CrysAlisPro (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	Occ. (<1)
O1	−0.0744 (5)	0.5740 (6)	0.06036 (17)	0.0523 (10)	0.852 (7)
O2	0.0563 (4)	0.2666 (5)	0.03930 (15)	0.0489 (9)	0.852 (7)
O3	−0.11323 (15)	0.0544 (3)	0.33773 (5)	0.0432 (4)
O4	0.04554 (15)	−0.3292 (2)	0.35223 (6)	0.0444 (5)
C5	−0.0143 (5)	0.3836 (9)	0.07299 (14)	0.0391 (11)	0.852 (7)
C6	−0.0257 (2)	0.2939 (4)	0.12865 (9)	0.0392 (7)	0.852 (7)
C7	0.0333 (2)	0.1014 (4)	0.14611 (9)	0.0506 (7)
C8	0.0286 (2)	−0.0041 (4)	0.20015 (8)	0.0404 (6)
C9	−0.0448 (2)	0.0919 (3)	0.24314 (8)	0.0375 (6)
C10	−0.04259 (19)	−0.0175 (3)	0.29389 (7)	0.0334 (5)
C11	0.03695 (19)	−0.2208 (3)	0.30294 (7)	0.0347 (5)
C12	0.1057 (2)	−0.3180 (4)	0.26015 (8)	0.0395 (6)
C13	0.1010 (2)	−0.2104 (4)	0.20929 (8)	0.0416 (6)
C14	−0.2088 (2)	0.2438 (4)	0.32912 (9)	0.0462 (7)
O1A	−0.051 (2)	0.484 (4)	0.0621 (8)	0.045 (6)	0.148 (7)
O2A	0.1074 (19)	0.249 (3)	0.0201 (7)	0.054 (5)	0.148 (7)
C5A	0.028 (3)	0.322 (5)	0.0629 (11)	0.0391 (11)	0.148 (7)
C6A	0.0587 (13)	0.162 (2)	0.1065 (5)	0.038 (4)	0.148 (7)
N1	0.00905 (17)	−0.1036 (3)	0.44970 (6)	0.0393 (5)
C1	0.0891 (2)	0.0814 (4)	0.46363 (8)	0.0383 (6)
C2	−0.0802 (2)	−0.1871 (3)	0.48531 (8)	0.0378 (6)
C3	0.1847 (2)	0.1711 (4)	0.42178 (9)	0.0479 (7)
C4	−0.1659 (2)	−0.3952 (4)	0.46761 (10)	0.0503 (7)
H4	0.01920	−0.24080	0.37590	0.0670*
H6	−0.07890	0.38050	0.15330	0.0470*	0.852 (7)
H2	0.05430	0.33540	0.00890	0.0730*	0.852 (7)
H14A	−0.27540	0.20980	0.29770	0.0690*
H14B	−0.15560	0.38480	0.32160	0.0690*
H14C	−0.26120	0.26690	0.36210	0.0690*
H7	0.08590	0.01970	0.12040	0.0610*	0.852 (7)
H9	−0.09610	0.23230	0.23740	0.0450*
H12	0.15630	−0.45930	0.26570	0.0470*
H13	0.14830	−0.27930	0.18020	0.0500*
H6AA	0.13470	0.06810	0.09570	0.0450*	0.148 (7)
H6AB	−0.05690	0.17360	0.14590	0.0610*	0.148 (7)
H2A	0.09850	0.34570	−0.00580	0.0810*	0.148 (7)
H3A	0.20300	0.04760	0.39550	0.0720*
H3B	0.13940	0.30260	0.40220	0.0720*
H3C	0.27440	0.22170	0.44030	0.0720*
H4A	−0.12420	−0.46860	0.43620	0.0750*
H4B	−0.26310	−0.34730	0.45700	0.0750*
H4C	−0.16650	−0.50610	0.49810	0.0750*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0654 (19)	0.053 (2)	0.0387 (12)	0.0041 (16)	0.0046 (11)	0.0104 (15)
O2	0.0630 (18)	0.0519 (12)	0.0320 (15)	−0.0025 (11)	0.0044 (11)	0.0042 (11)
O3	0.0487 (8)	0.0467 (8)	0.0339 (7)	0.0155 (6)	0.0009 (6)	0.0038 (6)
O4	0.0586 (9)	0.0409 (8)	0.0337 (7)	0.0124 (6)	0.0032 (6)	0.0103 (6)
C5	0.046 (2)	0.045 (2)	0.0266 (16)	−0.0126 (18)	0.0039 (12)	−0.0014 (14)
C6	0.0447 (13)	0.0429 (13)	0.0302 (12)	−0.0046 (10)	0.0036 (9)	−0.0014 (9)
C7	0.0541 (12)	0.0586 (14)	0.0381 (12)	−0.0193 (11)	−0.0043 (9)	0.0034 (10)
C8	0.0428 (10)	0.0473 (11)	0.0304 (9)	−0.0178 (9)	−0.0024 (8)	0.0015 (8)
C9	0.0425 (10)	0.0327 (9)	0.0357 (10)	−0.0048 (8)	−0.0090 (8)	0.0055 (7)
C10	0.0367 (9)	0.0343 (9)	0.0286 (9)	0.0002 (7)	−0.0027 (7)	0.0003 (7)
C11	0.0366 (9)	0.0357 (10)	0.0312 (9)	−0.0006 (7)	−0.0018 (7)	0.0046 (7)
C12	0.0372 (10)	0.0422 (11)	0.0389 (10)	0.0010 (8)	0.0017 (8)	−0.0008 (8)
C13	0.0409 (10)	0.0502 (12)	0.0339 (10)	−0.0076 (9)	0.0043 (8)	−0.0041 (8)
C14	0.0463 (11)	0.0405 (11)	0.0516 (12)	0.0110 (9)	0.0011 (9)	−0.0011 (9)
O1A	0.054 (10)	0.050 (15)	0.034 (7)	0.014 (10)	0.025 (7)	0.024 (10)
O2A	0.071 (10)	0.057 (7)	0.035 (7)	0.008 (7)	0.011 (6)	0.015 (6)
C5A	0.046 (2)	0.045 (2)	0.0266 (16)	−0.0126 (18)	0.0039 (12)	−0.0014 (14)
C6A	0.037 (7)	0.042 (8)	0.034 (8)	0.011 (5)	0.003 (5)	0.012 (6)
N1	0.0404 (8)	0.0450 (9)	0.0322 (8)	0.0081 (7)	−0.0007 (7)	0.0108 (7)
C1	0.0365 (9)	0.0450 (11)	0.0331 (9)	0.0087 (8)	0.0010 (7)	0.0140 (8)
C2	0.0356 (9)	0.0446 (11)	0.0327 (9)	0.0072 (8)	−0.0007 (7)	0.0122 (8)
C3	0.0478 (11)	0.0549 (13)	0.0420 (11)	0.0058 (9)	0.0107 (9)	0.0151 (9)
C4	0.0486 (12)	0.0520 (13)	0.0498 (12)	−0.0011 (10)	0.0002 (10)	0.0051 (10)

Geometric parameters (Å, º) top

O1—C5	1.265 (6)	C11—C12	1.383 (3)
O1A—C5A	1.20 (4)	C12—C13	1.384 (3)
O2—C5	1.283 (6)	C6—H6	0.9500
O2A—C5A	1.39 (3)	C6A—H6AA	0.9500
O3—C14	1.425 (3)	C7—H7	0.9500
O3—C10	1.361 (2)	C7—H6AB	0.9500
O4—C11	1.352 (2)	C9—H9	0.9500
O2—H2	0.8400	C12—H12	0.9500
O2A—H2A	0.8400	C13—H13	0.9500
O4—H4	0.8200	C14—H14B	0.9800
N1—C1	1.340 (3)	C14—H14C	0.9800
N1—C2	1.339 (2)	C14—H14A	0.9800
C5—C6	1.462 (4)	C1—C3	1.498 (3)
C5A—C6A	1.42 (3)	C1—C2ⁱ	1.393 (3)
C6—C7	1.302 (3)	C2—C4	1.496 (3)
C6A—C7	1.068 (12)	C3—H3A	0.9800
C7—C8	1.454 (3)	C3—H3B	0.9800
C8—C13	1.384 (3)	C3—H3C	0.9800
C8—C9	1.407 (3)	C4—H4A	0.9800
C9—C10	1.387 (3)	C4—H4B	0.9800
C10—C11	1.403 (2)	C4—H4C	0.9800

C10—O3—C14	117.19 (15)	C8—C7—H7	116.00
C5—O2—H2	109.00	C8—C7—H6AB	96.00
C5A—O2A—H2A	109.00	C10—C9—H9	120.00
C11—O4—H4	110.00	C8—C9—H9	120.00
C1—N1—C2	119.49 (16)	C13—C12—H12	120.00
O2—C5—C6	118.7 (4)	C11—C12—H12	120.00
O1—C5—C6	118.3 (4)	C8—C13—H13	119.00
O1—C5—O2	123.0 (4)	C12—C13—H13	119.00
O1A—C5A—O2A	126 (2)	H14A—C14—H14C	109.00
O2A—C5A—C6A	106 (2)	H14B—C14—H14C	110.00
O1A—C5A—C6A	128 (2)	H14A—C14—H14B	109.00
C5—C6—C7	123.3 (3)	O3—C14—H14A	109.00
C5A—C6A—C7	147.1 (16)	O3—C14—H14B	109.00
C6A—C7—C8	167.7 (7)	O3—C14—H14C	109.00
C6—C7—C8	128.0 (2)	N1—C1—C3	117.31 (18)
C9—C8—C13	118.77 (18)	N1—C1—C2ⁱ	120.61 (17)
C7—C8—C13	117.51 (18)	C2ⁱ—C1—C3	122.06 (19)
C7—C8—C9	123.72 (19)	N1—C2—C4	117.03 (17)
C8—C9—C10	120.34 (17)	N1—C2—C1ⁱ	119.90 (17)
O3—C10—C9	125.55 (16)	C1ⁱ—C2—C4	123.07 (18)
O3—C10—C11	114.63 (15)	C1—C3—H3A	110.00
C9—C10—C11	119.82 (16)	C1—C3—H3B	109.00
O4—C11—C12	118.58 (16)	C1—C3—H3C	109.00
C10—C11—C12	119.59 (17)	H3A—C3—H3B	109.00
O4—C11—C10	121.81 (15)	H3A—C3—H3C	109.00
C11—C12—C13	120.3 (2)	H3B—C3—H3C	109.00
C8—C13—C12	121.10 (19)	C2—C4—H4A	109.00
C7—C6—H6	118.00	C2—C4—H4B	109.00
C5—C6—H6	118.00	C2—C4—H4C	109.00
C5A—C6A—H6AA	107.00	H4A—C4—H4B	110.00
C7—C6A—H6AA	106.00	H4A—C4—H4C	109.00
C6—C7—H7	116.00	H4B—C4—H4C	109.00
C6A—C7—H6AB	96.00

C14—O3—C10—C9	6.9 (3)	C7—C8—C13—C12	177.84 (19)
C14—O3—C10—C11	−172.83 (16)	C8—C9—C10—C11	2.1 (3)
C1—N1—C2—C4	−179.50 (18)	C8—C9—C10—O3	−177.59 (18)
C2—N1—C1—C2ⁱ	0.0 (3)	O3—C10—C11—O4	−2.3 (3)
C1—N1—C2—C1ⁱ	0.0 (3)	O3—C10—C11—C12	175.86 (17)
C2—N1—C1—C3	−178.63 (17)	C9—C10—C11—O4	177.98 (17)
O2—C5—C6—C7	0.6 (6)	C9—C10—C11—C12	−3.8 (3)
O1—C5—C6—C7	−179.2 (4)	C10—C11—C12—C13	2.7 (3)
C5—C6—C7—C8	−179.8 (3)	O4—C11—C12—C13	−179.10 (17)
C6—C7—C8—C9	0.3 (3)	C11—C12—C13—C8	0.3 (3)
C6—C7—C8—C13	−179.6 (2)	N1—C1—C2ⁱ—N1ⁱ	0.0 (3)
C7—C8—C9—C10	−179.05 (18)	N1—C1—C2ⁱ—C4ⁱ	−179.47 (18)
C9—C8—C13—C12	−2.1 (3)	C3—C1—C2ⁱ—N1ⁱ	178.56 (18)
C13—C8—C9—C10	0.9 (3)	C3—C1—C2ⁱ—C4ⁱ	−0.9 (3)

Symmetry code: (i) −x, −y, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O1ⁱⁱ	0.84	1.79	2.613 (5)	167
O4—H4···O3	0.82	2.28	2.685 (2)	111
O4—H4···N1	0.82	1.97	2.749 (2)	158
C3—H3B···O4ⁱⁱⁱ	0.98	2.58	3.553 (3)	174
C14—H14B···O4ⁱⁱⁱ	0.98	2.59	3.465 (2)	148

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

Experimental details

Crystal data
Chemical formula	0.5C₈H₁₂N₂·C₁₀H₁₀O₄
M_r	262.28
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	9.4696 (7), 5.7641 (4), 24.3737 (15)
β (°)	93.654 (6)
V (Å³)	1327.70 (16)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.20 × 0.05 × 0.05

Data collection
Diffractometer	Oxford Diffraction Xcalibur Onyx Nova diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.953, 0.961
No. of measured, independent and observed [I > 2σi(I)] reflections	4780, 2398, 2004
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.156, 1.09
No. of reflections	2398
No. of parameters	208
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.40

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

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

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

Acknowledgements

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.

References

Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Tan, Z. (2004). China Patent No. ZL00114239.9. Google Scholar
Tan, Z., Jiang, T., Tang, C., Luo, J., Tan, H. & Chen, R. (2003). J. Chin. New Drugs, 12, 529-531. CAS Google Scholar

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Volume 67| Part 2| February 2011| Page o424

doi:10.1107/S1600536811000961

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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