Gallic acid pyridine monosolvate.

IN THE TITLE COMPOUND (SYSTENATIC NAME: 3,4,5-trihy-droxy-benzoic acid pyridine monosolvate), C(5)H(5)N·C(7)H(6)O(5), the gallic acid mol-ecule is essentially planar (r.m.s deviation = 0.0766 Å for non-H atoms) and is linked to the pyridine mol-ecule by an O-H⋯N hydrogen bond. An intra-molecular O-H⋯O hydrogen bond occurs in the gallic acid mol-ecule. The gallic acid and pyridine mean planes make a dihedral angle 12.6 (3)°. Inter-molecular O-H⋯O and O-H⋯N hydrogen bonding involving the hy-droxy and carboxyl groups and the pyridine mol-ecule, and π-π inter-actions between inversion-related pyridines [centroid-centroid distance = 3.459 (6) Å] and between pyridine and benzene rings [centroid-centroid distance = 3.548 (6) Å], lead to a three-dimensional network in the crystal.

Related literature

For the biological activity of gallic acid, see: Souza et al. (2011 ▶); Ozcelik et al. (2011 ▶); Liu et al. (2011 ▶). For previous reports on the crystal structures of gallic acid monohydrate and gallic acid monopyridine solvate, see: Clarke et al. (2011 ▶); Jiang et al. (2000 ▶). For π–π inter­actions in natural flavonoids, see: Jiang et al. (2002 ▶, 2009 ▶).

Experimental

Crystal data

C5H5N·C7H6O5

M = 249.22

Monoclinic,

a = 9.335 (1) Å

b = 10.435 (2) Å

c = 11.8581 (15) Å

β = 107.632 (8)°

V = 1100.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 293 K

0.34 × 0.20 × 0.12 mm

Data collection

Bruker SMART CCD 1000 diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.821, T max = 0.986

2601 measured reflections

1944 independent reflections

1031 reflections with I > 2σ(I)

R int = 0.057

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.172

S = 1.02

1944 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.36 e Å−3

Δρmin = −0.30 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 1998 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: XP in SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811043868/pk2351sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043868/pk2351Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043868/pk2351Isup3.cml

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

C5H5N·C7H6O5	F(000) = 520
Mr = 249.22	Dx = 1.504 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2601 reflections
a = 9.335 (1) Å	θ = 2.5–25.0°
b = 10.435 (2) Å	µ = 0.12 mm−1
c = 11.8581 (15) Å	T = 293 K
β = 107.632 (8)°	Prism, colorless
V = 1100.9 (3) Å3	0.34 × 0.20 × 0.12 mm
Z = 4

Bruker SMART CCD 1000 diffractometer	1944 independent reflections
Radiation source: fine-focus sealed tube	1031 reflections with I > 2σ(I)
graphite	Rint = 0.057
ω scan	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −1→11
Tmin = 0.821, Tmax = 0.986	k = −1→12
2601 measured reflections	l = −14→13

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)] = 0.066	H-atom parameters constrained
wR(F2) = 0.172	w = 1/[σ2(Fo2) + (0.0724P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
1944 reflections	Δρmax = 0.36 e Å−3
166 parameters	Δρmin = −0.30 e Å−3
0 restraints	Extinction correction: SHELXTL (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.026 (5)

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
O1	0.2507 (3)	0.4817 (3)	0.5719 (2)	0.0455 (9)
H1A	0.1613	0.4918	0.5650	0.068*
O2	0.0218 (3)	0.5026 (3)	0.3644 (3)	0.0478 (9)
H2A	−0.0003	0.5559	0.3111	0.09 (2)*
O3	0.0523 (3)	0.3953 (3)	0.1596 (2)	0.0443 (9)
H3A	0.0722	0.3559	0.1064	0.026 (12)*
O4	0.6443 (3)	0.2100 (3)	0.4836 (2)	0.0447 (9)
H4A	0.7301	0.2041	0.4794	0.067*
O5	0.5775 (3)	0.1955 (3)	0.2878 (2)	0.0372 (8)
C1	0.4139 (4)	0.3050 (4)	0.3759 (3)	0.0272 (10)
C2	0.3957 (4)	0.3632 (4)	0.4761 (3)	0.0335 (10)
H2B	0.4718	0.3581	0.5478	0.040*
C3	0.2654 (4)	0.4285 (4)	0.4696 (3)	0.0319 (10)
C4	0.1511 (4)	0.4397 (4)	0.3634 (3)	0.0293 (10)
C5	0.1690 (4)	0.3824 (4)	0.2629 (3)	0.0299 (10)
C6	0.2988 (4)	0.3151 (4)	0.2682 (3)	0.0308 (10)
H6A	0.3096	0.2768	0.2004	0.037*
C7	0.5536 (4)	0.2314 (4)	0.3809 (3)	0.0298 (10)
N1	0.9126 (4)	0.1750 (4)	0.4402 (4)	0.0467 (10)
C8	1.1809 (5)	0.0925 (5)	0.4259 (5)	0.0508 (13)
H8A	1.2731	0.0630	0.4216	0.061*
C9	1.1691 (5)	0.1366 (5)	0.5296 (5)	0.0544 (14)
H9A	1.2532	0.1387	0.5962	0.065*
C10	1.0337 (6)	0.1779 (5)	0.5367 (4)	0.0516 (14)
H10A	1.0251	0.2082	0.6082	0.062*
C11	0.9235 (6)	0.1326 (5)	0.3370 (4)	0.0529 (14)
H11A	0.8389	0.1312	0.2708	0.063*
C12	1.0599 (6)	0.0908 (5)	0.3285 (4)	0.0542 (14)
H12A	1.0685	0.0619	0.2567	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0410 (17)	0.066 (2)	0.0299 (16)	0.0120 (17)	0.0106 (13)	−0.0052 (16)
O2	0.0428 (18)	0.065 (2)	0.0382 (17)	0.0205 (18)	0.0164 (14)	0.0152 (18)
O3	0.0319 (16)	0.067 (2)	0.0288 (16)	0.0128 (16)	0.0009 (13)	−0.0029 (17)
O4	0.0269 (15)	0.071 (2)	0.0322 (16)	0.0146 (17)	0.0036 (13)	0.0038 (16)
O5	0.0367 (16)	0.051 (2)	0.0277 (15)	0.0034 (15)	0.0150 (12)	−0.0043 (15)
C1	0.024 (2)	0.032 (2)	0.026 (2)	−0.0016 (19)	0.0081 (17)	0.0049 (18)
C2	0.027 (2)	0.044 (3)	0.024 (2)	−0.001 (2)	−0.0009 (17)	−0.002 (2)
C3	0.036 (2)	0.036 (3)	0.026 (2)	−0.001 (2)	0.0132 (19)	−0.0036 (19)
C4	0.027 (2)	0.035 (3)	0.026 (2)	0.009 (2)	0.0088 (17)	0.0079 (19)
C5	0.022 (2)	0.038 (3)	0.026 (2)	−0.003 (2)	0.0023 (17)	0.0054 (19)
C6	0.026 (2)	0.043 (3)	0.0227 (19)	−0.005 (2)	0.0056 (16)	0.0005 (19)
C7	0.0213 (19)	0.039 (3)	0.026 (2)	−0.005 (2)	0.0024 (17)	0.003 (2)
N1	0.036 (2)	0.043 (3)	0.065 (3)	0.0048 (19)	0.021 (2)	0.005 (2)
C8	0.042 (3)	0.039 (3)	0.078 (4)	0.006 (2)	0.028 (3)	0.013 (3)
C9	0.037 (3)	0.054 (3)	0.060 (3)	−0.008 (3)	−0.003 (2)	0.011 (3)
C10	0.067 (3)	0.048 (3)	0.047 (3)	−0.012 (3)	0.028 (3)	−0.009 (3)
C11	0.054 (3)	0.048 (3)	0.043 (3)	−0.003 (3)	−0.006 (2)	0.012 (3)
C12	0.077 (4)	0.049 (3)	0.049 (3)	0.004 (3)	0.038 (3)	0.002 (3)

O1—C3	1.379 (5)	C4—C5	1.388 (5)
O1—H1A	0.8200	C5—C6	1.385 (5)
O2—C4	1.377 (5)	C6—H6A	0.9300
O2—H2A	0.8200	N1—C11	1.333 (6)
O3—C5	1.378 (4)	N1—C10	1.343 (6)
O3—H3A	0.8200	C8—C9	1.348 (7)
O4—C7	1.275 (4)	C8—C12	1.349 (7)
O4—H4A	0.8200	C8—H8A	0.9300
O5—C7	1.248 (4)	C9—C10	1.362 (7)
C1—C2	1.391 (5)	C9—H9A	0.9300
C1—C6	1.402 (5)	C10—H10A	0.9300
C1—C7	1.499 (5)	C11—C12	1.379 (7)
C2—C3	1.375 (5)	C11—H11A	0.9300
C2—H2B	0.9300	C12—H12A	0.9300
C3—C4	1.387 (5)
C3—O1—H1A	109.5	C1—C6—H6A	120.1
C4—O2—H2A	109.5	O5—C7—O4	123.2 (4)
C5—O3—H3A	109.5	O5—C7—C1	120.3 (3)
C7—O4—H4A	109.5	O4—C7—C1	116.5 (3)
C2—C1—C6	119.2 (4)	C11—N1—C10	120.8 (4)
C2—C1—C7	121.3 (3)	C9—C8—C12	120.4 (5)
C6—C1—C7	119.5 (3)	C9—C8—H8A	119.8
C3—C2—C1	120.2 (3)	C12—C8—H8A	119.8
C3—C2—H2B	119.9	C8—C9—C10	119.9 (5)
C1—C2—H2B	119.9	C8—C9—H9A	120.1
C2—C3—O1	118.2 (3)	C10—C9—H9A	120.1
C2—C3—C4	121.1 (4)	N1—C10—C9	119.8 (4)
O1—C3—C4	120.7 (4)	N1—C10—H10A	120.1
O2—C4—C3	117.9 (4)	C9—C10—H10A	120.1
O2—C4—C5	123.1 (3)	N1—C11—C12	120.0 (5)
C3—C4—C5	118.9 (4)	N1—C11—H11A	120.0
O3—C5—C6	122.3 (4)	C12—C11—H11A	120.0
O3—C5—C4	116.9 (4)	C8—C12—C11	119.1 (5)
C6—C5—C4	120.7 (3)	C8—C12—H12A	120.5
C5—C6—C1	119.8 (4)	C11—C12—H12A	120.5
C5—C6—H6A	120.1
C6—C1—C2—C3	0.9 (6)	C4—C5—C6—C1	−0.2 (6)
C7—C1—C2—C3	−179.0 (4)	C2—C1—C6—C5	−0.2 (6)
C1—C2—C3—O1	178.3 (4)	C7—C1—C6—C5	179.7 (4)
C1—C2—C3—C4	−1.2 (6)	C2—C1—C7—O5	−169.7 (4)
C2—C3—C4—O2	177.8 (4)	C6—C1—C7—O5	10.4 (6)
O1—C3—C4—O2	−1.6 (6)	C2—C1—C7—O4	9.5 (6)
C2—C3—C4—C5	0.8 (6)	C6—C1—C7—O4	−170.3 (4)
O1—C3—C4—C5	−178.7 (4)	C12—C8—C9—C10	1.0 (8)
O2—C4—C5—O3	2.7 (6)	C11—N1—C10—C9	−0.4 (7)
C3—C4—C5—O3	179.6 (4)	C8—C9—C10—N1	−0.2 (8)
O2—C4—C5—C6	−177.0 (4)	C10—N1—C11—C12	0.2 (7)
C3—C4—C5—C6	−0.1 (7)	C9—C8—C12—C11	−1.2 (8)
O3—C5—C6—C1	−179.9 (4)	N1—C11—C12—C8	0.6 (7)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2i	0.82	2.12	2.869 (3)	152.
O1—H1A···O2	0.82	2.34	2.736 (4)	110.
O2—H2A···O5ii	0.82	1.87	2.675 (4)	166.
O3—H3A···O4iii	0.82	1.91	2.718 (3)	169.
O4—H4A···N1	0.82	1.92	2.730 (4)	169.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O2i	0.82	2.12	2.869 (3)	152
O1—H1A⋯O2	0.82	2.34	2.736 (4)	110
O2—H2A⋯O5ii	0.82	1.87	2.675 (4)	166
O3—H3A⋯O4iii	0.82	1.91	2.718 (3)	169
O4—H4A⋯N1	0.82	1.92	2.730 (4)	169

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