Methyl gallate.

THE CRYSTAL STRUCTURE OF THE TITLE COMPOUND (SYSTEMATIC NAME: methyl 3,4,5-trihydroxy-benzoate), C(8)H(8)O(5), is composed of essentially planar mol-ecules [maximum departures from the mean carbon and oxygen skeleton plane of 0.0348 (10) Å]. The H atoms of the three hydroxyl groups, which function as hydrogen-bond donors and acceptors simultaneously, are oriented in the same direction around the aromatic ring. In addition to two intra-molecular hydrogen bonds, each mol-ecule is hydrogen bonded to six others, creating a three-dimensional hydrogen-bonded network.

Related literature

For natural extracts containing gallic acid methyl ester, see: Saxena et al. (1994 ▶); Schmidt et al. (2003 ▶); Hawas (2007 ▶). For studies concerning anti­oxidant activity, see: Aruoma et al. (1993 ▶); Schmidt et al. (2003 ▶); Hawas (2007 ▶). For studies concerning anti­cancer properties, see: Fiuza et al. (2004 ▶) and for anti­microbial properties, see: Saxena et al. (1994 ▶); Landete et al. (2007 ▶). For cocrystals containing gallic acid methyl ester, see: Sekine et al. (2003 ▶); Martin et al. (1986 ▶). Similar gallate ester conformations are found in Parkin et al. (2002 ▶); Okabe & Kyoyama (2002a ▶); Nomura et al. (2000 ▶); Mizuguchi et al. (2005 ▶). For structures with similar hydroxyl arrangements, see: Hitachi et al. (2005 ▶); Okabe et al. (2001 ▶); Okabe & Kyoyama (2002b ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C8H8O5

M = 184.14

Monoclinic,

a = 7.6963 (2) Å

b = 9.9111 (2) Å

c = 10.5625 (2) Å

β = 95.9930 (10)°

V = 801.29 (3) Å3

Z = 4

Cu Kα radiation

μ = 1.12 mm−1

T = 100 (2) K

0.31 × 0.23 × 0.21 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: numerical (SADABS; Sheldrick, 2004 ▶) T min = 0.723, T max = 0.799

8192 measured reflections

1352 independent reflections

1311 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.093

S = 0.69

1352 reflections

121 parameters

All H-atom parameters refined

Δρmax = 0.23 e Å−3

Δρmin = −0.20 e Å−3

Data collection: APEX2 (Bruker , 2004 ▶); cell refinement: SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: WinGX (Farrugia, 1999 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809001123/rz2286sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809001123/rz2286Isup2.hkl

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

C8H8O5	F(000) = 384
Mr = 184.14	Dx = 1.526 Mg m−3
Monoclinic, P21/n	Melting point: 474 K
Hall symbol: -P 2yn	Cu Kα radiation, λ = 1.54178 Å
a = 7.6963 (2) Å	Cell parameters from 1352 reflections
b = 9.9111 (2) Å	θ = 6.1–67.0°
c = 10.5625 (2) Å	µ = 1.12 mm−1
β = 95.993 (1)°	T = 100 K
V = 801.29 (3) Å3	Rhombic prism, colourless
Z = 4	0.31 × 0.23 × 0.21 mm

Bruker SMART APEXII CCD diffractometer	1352 independent reflections
Radiation source: fine-focus sealed tube	1311 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω and ψ scans	θmax = 67.0°, θmin = 6.1°
Absorption correction: numerical (SADABS; Sheldrick, 2004)	h = −8→9
Tmin = 0.723, Tmax = 0.799	k = −11→11
8192 measured reflections	l = −12→12

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)] = 0.033	Hydrogen site location: difference Fourier map
wR(F2) = 0.093	All H-atom parameters refined
S = 0.69	w = 1/[σ2(Fo2) + (0.0834P)2 + 0.9466P] where P = (Fo2 + 2Fc2)/3
1352 reflections	(Δ/σ)max = 0.004
121 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.20 e Å−3
32 constraints

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.

	x	y	z	Uiso*/Ueq
O1	0.14003 (11)	1.05605 (9)	0.77633 (8)	0.0145 (2)
O2	0.29090 (12)	0.99023 (9)	0.61631 (8)	0.0156 (3)
O3	−0.38148 (12)	0.74067 (10)	0.72722 (9)	0.0189 (3)
H3	−0.4389	0.6742	0.6963	0.028*
O4	−0.33530 (12)	0.58249 (9)	0.52444 (9)	0.0167 (2)
H4	−0.314	0.5462	0.4559	0.025*
O5	−0.05442 (13)	0.61740 (10)	0.39075 (9)	0.0185 (3)
H5	0.0127	0.6524	0.3422	0.028*
C7	0.15489 (17)	0.98352 (13)	0.68447 (12)	0.0121 (3)
C1	0.02736 (17)	0.87858 (13)	0.63777 (12)	0.0126 (3)
C2	−0.11958 (17)	0.85957 (13)	0.70290 (12)	0.0126 (3)
H2	−0.1378	0.9145	0.774	0.015*
C3	−0.23803 (17)	0.75983 (13)	0.66260 (12)	0.0129 (3)
C4	−0.21306 (17)	0.67861 (13)	0.55808 (12)	0.0129 (3)
C5	−0.06683 (17)	0.69987 (13)	0.49284 (12)	0.0134 (3)
C6	0.05370 (16)	0.79838 (13)	0.53249 (12)	0.0134 (3)
H6	0.1539	0.8116	0.4885	0.016*
C8	0.42258 (18)	1.09026 (14)	0.65644 (13)	0.0182 (3)
H8A	0.5161	1.0867	0.6003	0.027*
H8B	0.4712	1.0715	0.7441	0.027*
H8C	0.3695	1.1802	0.6521	0.027*

	U11	U22	U33	U12	U13	U23
O1	0.0147 (5)	0.0147 (5)	0.0141 (5)	0.0011 (4)	0.0010 (4)	−0.0023 (4)
O2	0.0135 (5)	0.0186 (5)	0.0153 (5)	−0.0048 (4)	0.0040 (4)	−0.0030 (4)
O3	0.0171 (5)	0.0206 (5)	0.0209 (5)	−0.0067 (4)	0.0108 (4)	−0.0070 (4)
O4	0.0188 (5)	0.0180 (5)	0.0141 (5)	−0.0071 (4)	0.0058 (4)	−0.0043 (4)
O5	0.0237 (5)	0.0196 (5)	0.0140 (5)	−0.0080 (4)	0.0103 (4)	−0.0057 (4)
C1	0.0135 (6)	0.0127 (6)	0.0114 (6)	0.0019 (5)	0.0004 (5)	0.0028 (5)
C2	0.0147 (7)	0.0130 (6)	0.0104 (6)	0.0023 (5)	0.0021 (5)	−0.0002 (5)
C3	0.0127 (6)	0.0147 (6)	0.0120 (6)	0.0012 (5)	0.0041 (5)	0.0025 (5)
C4	0.0137 (6)	0.0123 (6)	0.0124 (6)	−0.0012 (5)	0.0000 (5)	0.0022 (5)
C5	0.0176 (7)	0.0129 (6)	0.0100 (6)	0.0012 (5)	0.0032 (5)	0.0002 (5)
C6	0.0127 (6)	0.0159 (7)	0.0121 (6)	0.0004 (5)	0.0040 (5)	0.0024 (5)
C7	0.0129 (7)	0.0122 (6)	0.0111 (6)	0.0037 (5)	0.0006 (5)	0.0030 (5)
C8	0.0157 (7)	0.0203 (7)	0.0185 (7)	−0.0071 (5)	0.0015 (6)	−0.0010 (5)

O1—C7	1.2225 (16)	C1—C6	1.3988 (19)
O2—C7	1.3327 (15)	C2—C3	1.3815 (18)
O2—C8	1.4491 (16)	C2—H2	0.95
O3—C3	1.3705 (15)	C3—C4	1.3957 (18)
O3—H3	0.84	C4—C5	1.3956 (18)
O4—C4	1.3598 (16)	C5—C6	1.3813 (18)
O4—H4	0.84	C6—H6	0.95
O5—C5	1.3644 (16)	C8—H8A	0.98
O5—H5	0.84	C8—H8B	0.98
C7—C1	1.4790 (19)	C8—H8C	0.98
C1—C2	1.3965 (17)
C7—O2—C8	116.16 (10)	O4—C4—C5	123.25 (11)
C3—O3—H3	109.5	O4—C4—C3	117.52 (11)
C4—O4—H4	109.5	C5—C4—C3	119.22 (12)
C5—O5—H5	109.5	O5—C5—C6	124.25 (11)
O1—C7—O2	122.91 (12)	O5—C5—C4	115.24 (12)
O1—C7—C1	124.36 (11)	C6—C5—C4	120.51 (11)
O2—C7—C1	112.72 (11)	C5—C6—C1	119.62 (12)
C2—C1—C6	120.47 (12)	C5—C6—H6	120.2
C2—C1—C7	118.29 (11)	C1—C6—H6	120.2
C6—C1—C7	121.24 (12)	O2—C8—H8A	109.5
C3—C2—C1	119.15 (12)	O2—C8—H8B	109.5
C3—C2—H2	120.4	H8A—C8—H8B	109.5
C1—C2—H2	120.4	O2—C8—H8C	109.5
O3—C3—C2	119.06 (11)	H8A—C8—H8C	109.5
O3—C3—C4	119.91 (12)	H8B—C8—H8C	109.5
C2—C3—C4	121.03 (12)
C8—O2—C7—O1	−0.42 (18)	C2—C3—C4—O4	179.88 (11)
C8—O2—C7—C1	−179.68 (10)	O3—C3—C4—C5	179.65 (11)
O1—C7—C1—C2	−0.53 (19)	C2—C3—C4—C5	−0.7 (2)
O2—C7—C1—C2	178.71 (11)	O4—C4—C5—O5	0.45 (19)
O1—C7—C1—C6	−179.44 (12)	C3—C4—C5—O5	−178.97 (11)
O2—C7—C1—C6	−0.19 (17)	O4—C4—C5—C6	−179.37 (11)
C6—C1—C2—C3	0.47 (19)	C3—C4—C5—C6	1.21 (19)
C7—C1—C2—C3	−178.44 (11)	O5—C5—C6—C1	179.28 (12)
C1—C2—C3—O3	179.52 (11)	C4—C5—C6—C1	−0.92 (19)
C1—C2—C3—C4	−0.17 (19)	C2—C1—C6—C5	0.07 (19)
O3—C3—C4—O4	0.19 (18)	C7—C1—C6—C5	178.95 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O4	0.84	2.25	2.7075 (13)	115
O4—H4···O5	0.84	2.29	2.7247 (12)	112
O4—H4···O1i	0.84	2.15	2.9470 (13)	159
O3—H3···O1ii	0.84	1.99	2.7007 (12)	142
O5—H5···O3iii	0.84	1.86	2.6859 (12)	166

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3⋯O4	0.84	2.25	2.7075 (13)	115
O4—H4⋯O5	0.84	2.29	2.7247 (12)	112
O4—H4⋯O1i	0.84	2.15	2.9470 (13)	159
O3—H3⋯O1ii	0.84	1.99	2.7007 (12)	142
O5—H5⋯O3iii	0.84	1.86	2.6859 (12)	166

Symmetry codes: (i) ; (ii) ; (iii) .