Anilinium 3,4-dihy-droxy-benzoate.

The asymmetric unit of the title salt, C(6)H(8)N(+)·C(7)H(5)O(4) (-), contains two anilinium cations and two 3,4-dihy-droxy-benzoate anions. An intra-moleculer O-H⋯O hydrogen bond occurs in each anion. In the crystal, O-H⋯O and N-H⋯O hydrogen bonds link the cations and anions into a three-dimensional array. The structure is further consolidated by weak C-H⋯O inter-actions.

Related literature

For the pharmacological activity of 3,4-dihy­droxy­benzoic acid derivatives, see: An et al. (2006 ▶); Lin et al. (2009 ▶). For related structures, see: Mazurek et al. (2007 ▶); Zhu (2010 ▶).

Experimental

Crystal data

C6H8N+·C7H5O4 −

M = 247.24

Triclinic,

a = 6.8638 (16) Å

b = 11.566 (3) Å

c = 15.400 (3) Å

α = 88.980 (3)°

β = 87.517 (2)°

γ = 76.302 (2)°

V = 1186.6 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.30 × 0.27 × 0.27 mm

Data collection

Bruker APEXII area-detector diffractometer

6128 measured reflections

4202 independent reflections

3317 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.109

S = 1.05

4202 reflections

332 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032758/pv2568sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032758/pv2568Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812032758/pv2568Isup3.cml

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

C6H8N+·C7H5O4−	Z = 4
Mr = 247.24	F(000) = 520
Triclinic, P1	Dx = 1.384 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.8638 (16) Å	Cell parameters from 2457 reflections
b = 11.566 (3) Å	θ = 2.2–27.3°
c = 15.400 (3) Å	µ = 0.10 mm−1
α = 88.980 (3)°	T = 296 K
β = 87.517 (2)°	Block, colorless
γ = 76.302 (2)°	0.30 × 0.27 × 0.27 mm
V = 1186.6 (5) Å3

Bruker APEXII area-detector diffractometer	3317 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Graphite monochromator	θmax = 25.2°, θmin = 1.8°
φ and ω scan	h = −8→8
6128 measured reflections	k = −13→11
4202 independent reflections	l = −18→17

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.109	w = 1/[σ2(Fo2) + (0.0508P)2 + 0.1856P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
4202 reflections	Δρmax = 0.18 e Å−3
332 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.077 (4)

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.

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.

	x	y	z	Uiso*/Ueq
C1	0.7332 (2)	0.75230 (15)	0.52005 (12)	0.0372 (4)
C2	0.7644 (3)	0.71776 (19)	0.60497 (14)	0.0546 (5)
H2	0.7840	0.7714	0.6461	0.065*
C3	0.7662 (3)	0.6010 (3)	0.6283 (2)	0.0825 (9)
H3	0.7869	0.5760	0.6856	0.099*
C4	0.7375 (4)	0.5222 (2)	0.5672 (3)	0.0927 (10)
H4	0.7389	0.4441	0.5831	0.111*
C5	0.7070 (3)	0.5584 (2)	0.4830 (2)	0.0780 (8)
H5	0.6887	0.5045	0.4419	0.094*
C6	0.7028 (3)	0.67478 (17)	0.45810 (15)	0.0518 (5)
H6	0.6801	0.6998	0.4009	0.062*
C7	0.7273 (2)	0.39504 (14)	0.11410 (10)	0.0289 (4)
C8	0.7123 (2)	0.32018 (14)	0.19329 (10)	0.0302 (4)
C9	0.7779 (3)	0.34600 (15)	0.27309 (10)	0.0367 (4)
H9	0.8273	0.4136	0.2790	0.044*
C10	0.7701 (2)	0.27142 (15)	0.34417 (10)	0.0363 (4)
H10	0.8132	0.2899	0.3975	0.044*
C11	0.6993 (2)	0.17023 (14)	0.33649 (10)	0.0309 (4)
C12	0.6287 (2)	0.14519 (14)	0.25711 (10)	0.0343 (4)
C13	0.6371 (2)	0.21926 (14)	0.18642 (10)	0.0328 (4)
H13	0.5917	0.2014	0.1334	0.039*
C14	0.2555 (2)	0.87609 (14)	0.38609 (10)	0.0295 (4)
C15	0.2338 (2)	0.80700 (14)	0.30781 (10)	0.0294 (4)
C16	0.3636 (3)	0.79873 (16)	0.23537 (11)	0.0432 (5)
H16	0.4660	0.8389	0.2341	0.052*
C17	0.3413 (3)	0.73098 (17)	0.16494 (12)	0.0465 (5)
H17	0.4290	0.7265	0.1167	0.056*
C18	0.1917 (2)	0.67006 (14)	0.16508 (10)	0.0322 (4)
C19	0.0601 (2)	0.67786 (14)	0.23739 (10)	0.0329 (4)
C20	0.0831 (2)	0.74530 (15)	0.30705 (10)	0.0349 (4)
H20	−0.0049	0.7498	0.3552	0.042*
C21	0.2207 (2)	0.24550 (15)	0.02540 (12)	0.0368 (4)
C22	0.1956 (3)	0.18707 (18)	0.10200 (14)	0.0498 (5)
H22	0.1788	0.2270	0.1547	0.060*
C23	0.1959 (3)	0.0664 (2)	0.09909 (18)	0.0691 (7)
H23	0.1786	0.0252	0.1501	0.083*
C24	0.2217 (3)	0.0089 (2)	0.0209 (2)	0.0729 (7)
H24	0.2253	−0.0719	0.0193	0.087*
C25	0.2423 (3)	0.0690 (2)	−0.05475 (18)	0.0655 (6)
H25	0.2572	0.0292	−0.1075	0.079*
C26	0.2411 (3)	0.18871 (17)	−0.05349 (13)	0.0474 (5)
H26	0.2538	0.2301	−0.1049	0.057*
O1	0.83712 (17)	0.46884 (10)	0.11452 (7)	0.0371 (3)
O2	0.63288 (17)	0.37944 (10)	0.04814 (7)	0.0381 (3)
O3	0.5524 (2)	0.04784 (12)	0.24703 (8)	0.0576 (4)
H3A	0.5288	0.0209	0.2949	0.086*
O4	0.68868 (18)	0.09263 (10)	0.40301 (7)	0.0392 (3)
H4A	0.7455	0.1102	0.4449	0.059*
O5	0.14211 (17)	0.87197 (11)	0.45229 (7)	0.0383 (3)
O6	0.38799 (17)	0.93671 (10)	0.38500 (7)	0.0372 (3)
O7	0.16366 (18)	0.60121 (11)	0.09808 (7)	0.0410 (3)
H7	0.2382	0.6096	0.0566	0.062*
O8	−0.0916 (2)	0.61981 (14)	0.24128 (8)	0.0564 (4)
H8	−0.0856	0.5798	0.1974	0.085*
N1	0.7354 (2)	0.87382 (11)	0.49340 (9)	0.0347 (3)
H1A	0.6996	0.9221	0.5387	0.052*
H1B	0.6496	0.8972	0.4513	0.052*
H1C	0.8585	0.8763	0.4740	0.052*
N2	0.2307 (2)	0.37032 (12)	0.02875 (9)	0.0370 (3)
H2A	0.1406	0.4082	0.0682	0.055*
H2B	0.2046	0.4042	−0.0231	0.055*
H2C	0.3529	0.3745	0.0432	0.055*

	U11	U22	U33	U12	U13	U23
C1	0.0258 (8)	0.0358 (9)	0.0509 (11)	−0.0102 (7)	0.0022 (7)	0.0026 (8)
C2	0.0380 (10)	0.0650 (13)	0.0617 (13)	−0.0145 (9)	−0.0075 (9)	0.0171 (11)
C3	0.0515 (13)	0.0844 (19)	0.110 (2)	−0.0161 (13)	−0.0126 (13)	0.0570 (17)
C4	0.0596 (15)	0.0493 (15)	0.170 (3)	−0.0166 (12)	−0.0026 (18)	0.0349 (19)
C5	0.0568 (14)	0.0410 (13)	0.140 (3)	−0.0210 (11)	0.0147 (15)	−0.0136 (15)
C6	0.0416 (10)	0.0434 (11)	0.0739 (14)	−0.0179 (9)	0.0088 (10)	−0.0121 (10)
C7	0.0303 (8)	0.0346 (9)	0.0250 (8)	−0.0139 (7)	0.0005 (6)	−0.0022 (7)
C8	0.0292 (8)	0.0353 (9)	0.0290 (9)	−0.0132 (7)	0.0003 (6)	−0.0009 (7)
C9	0.0468 (10)	0.0388 (9)	0.0323 (9)	−0.0250 (8)	−0.0057 (7)	0.0009 (7)
C10	0.0451 (10)	0.0438 (10)	0.0269 (9)	−0.0229 (8)	−0.0073 (7)	−0.0020 (7)
C11	0.0337 (8)	0.0351 (9)	0.0265 (8)	−0.0140 (7)	−0.0010 (6)	0.0026 (7)
C12	0.0437 (9)	0.0360 (9)	0.0294 (9)	−0.0216 (8)	−0.0024 (7)	−0.0010 (7)
C13	0.0399 (9)	0.0392 (9)	0.0248 (8)	−0.0196 (7)	−0.0042 (7)	−0.0016 (7)
C14	0.0329 (8)	0.0316 (8)	0.0273 (8)	−0.0140 (7)	−0.0031 (7)	0.0000 (6)
C15	0.0334 (8)	0.0314 (8)	0.0258 (8)	−0.0122 (7)	−0.0023 (6)	−0.0007 (6)
C16	0.0464 (10)	0.0548 (11)	0.0395 (10)	−0.0347 (9)	0.0064 (8)	−0.0117 (8)
C17	0.0532 (11)	0.0617 (12)	0.0349 (10)	−0.0360 (10)	0.0161 (8)	−0.0164 (9)
C18	0.0410 (9)	0.0333 (9)	0.0262 (8)	−0.0164 (7)	0.0000 (7)	−0.0051 (7)
C19	0.0358 (9)	0.0391 (9)	0.0298 (9)	−0.0212 (7)	0.0009 (7)	−0.0030 (7)
C20	0.0389 (9)	0.0458 (10)	0.0258 (8)	−0.0225 (8)	0.0063 (7)	−0.0079 (7)
C21	0.0274 (8)	0.0359 (9)	0.0493 (11)	−0.0110 (7)	−0.0035 (7)	−0.0008 (8)
C22	0.0452 (11)	0.0515 (12)	0.0556 (12)	−0.0172 (9)	−0.0061 (9)	0.0093 (9)
C23	0.0564 (13)	0.0617 (15)	0.0955 (19)	−0.0266 (11)	−0.0168 (13)	0.0341 (14)
C24	0.0565 (14)	0.0427 (13)	0.123 (2)	−0.0174 (11)	−0.0112 (14)	−0.0040 (14)
C25	0.0547 (13)	0.0544 (14)	0.0902 (18)	−0.0177 (11)	0.0034 (12)	−0.0263 (13)
C26	0.0394 (10)	0.0504 (12)	0.0551 (12)	−0.0160 (9)	0.0021 (8)	−0.0113 (9)
O1	0.0453 (7)	0.0425 (7)	0.0315 (6)	−0.0267 (6)	−0.0009 (5)	0.0008 (5)
O2	0.0431 (7)	0.0504 (7)	0.0280 (6)	−0.0251 (6)	−0.0055 (5)	0.0041 (5)
O3	0.1055 (11)	0.0573 (8)	0.0308 (7)	−0.0590 (8)	−0.0125 (7)	0.0049 (6)
O4	0.0561 (8)	0.0426 (7)	0.0276 (6)	−0.0279 (6)	−0.0103 (5)	0.0056 (5)
O5	0.0409 (6)	0.0545 (8)	0.0262 (6)	−0.0248 (6)	0.0026 (5)	−0.0082 (5)
O6	0.0449 (7)	0.0436 (7)	0.0317 (6)	−0.0269 (6)	−0.0016 (5)	−0.0054 (5)
O7	0.0540 (8)	0.0497 (7)	0.0290 (6)	−0.0322 (6)	0.0094 (5)	−0.0139 (5)
O8	0.0646 (9)	0.0825 (10)	0.0408 (8)	−0.0562 (8)	0.0168 (6)	−0.0242 (7)
N1	0.0354 (7)	0.0357 (8)	0.0353 (8)	−0.0127 (6)	−0.0002 (6)	−0.0032 (6)
N2	0.0379 (8)	0.0379 (8)	0.0373 (8)	−0.0132 (6)	−0.0005 (6)	−0.0023 (6)

C1—C2	1.371 (3)	C16—C17	1.384 (2)
C1—C6	1.376 (3)	C16—H16	0.9300
C1—N1	1.460 (2)	C17—C18	1.376 (2)
C2—C3	1.389 (3)	C17—H17	0.9300
C2—H2	0.9300	C18—O7	1.3619 (18)
C3—C4	1.374 (4)	C18—C19	1.394 (2)
C3—H3	0.9300	C19—O8	1.3646 (18)
C4—C5	1.364 (4)	C19—C20	1.374 (2)
C4—H4	0.9300	C20—H20	0.9300
C5—C6	1.387 (3)	C21—C22	1.374 (3)
C5—H5	0.9300	C21—C26	1.377 (3)
C6—H6	0.9300	C21—N2	1.463 (2)
C7—O1	1.2655 (17)	C22—C23	1.396 (3)
C7—O2	1.2663 (18)	C22—H22	0.9300
C7—C8	1.497 (2)	C23—C24	1.371 (4)
C8—C9	1.388 (2)	C23—H23	0.9300
C8—C13	1.391 (2)	C24—C25	1.364 (3)
C9—C10	1.389 (2)	C24—H24	0.9300
C9—H9	0.9300	C25—C26	1.383 (3)
C10—C11	1.378 (2)	C25—H25	0.9300
C10—H10	0.9300	C26—H26	0.9300
C11—O4	1.3609 (18)	O3—H3A	0.8200
C11—C12	1.394 (2)	O4—H4A	0.8200
C12—O3	1.3635 (18)	O7—H7	0.8200
C12—C13	1.381 (2)	O8—H8	0.8200
C13—H13	0.9300	N1—H1A	0.8900
C14—O5	1.2628 (19)	N1—H1B	0.8900
C14—O6	1.2722 (18)	N1—H1C	0.8900
C14—C15	1.490 (2)	N2—H2A	0.8900
C15—C16	1.387 (2)	N2—H2B	0.8900
C15—C20	1.389 (2)	N2—H2C	0.8900
C2—C1—C6	121.80 (18)	C15—C16—H16	119.8
C2—C1—N1	119.70 (17)	C18—C17—C16	121.12 (15)
C6—C1—N1	118.49 (16)	C18—C17—H17	119.4
C1—C2—C3	118.6 (2)	C16—C17—H17	119.4
C1—C2—H2	120.7	O7—C18—C17	123.75 (15)
C3—C2—H2	120.7	O7—C18—C19	117.17 (13)
C4—C3—C2	120.3 (3)	C17—C18—C19	119.08 (15)
C4—C3—H3	119.8	O8—C19—C20	118.75 (14)
C2—C3—H3	119.8	O8—C19—C18	121.81 (14)
C5—C4—C3	120.1 (2)	C20—C19—C18	119.44 (14)
C5—C4—H4	120.0	C19—C20—C15	122.05 (14)
C3—C4—H4	120.0	C19—C20—H20	119.0
C4—C5—C6	120.8 (3)	C15—C20—H20	119.0
C4—C5—H5	119.6	C22—C21—C26	121.61 (17)
C6—C5—H5	119.6	C22—C21—N2	118.65 (16)
C1—C6—C5	118.4 (2)	C26—C21—N2	119.72 (16)
C1—C6—H6	120.8	C21—C22—C23	118.6 (2)
C5—C6—H6	120.8	C21—C22—H22	120.7
O1—C7—O2	122.50 (13)	C23—C22—H22	120.7
O1—C7—C8	119.26 (13)	C24—C23—C22	119.9 (2)
O2—C7—C8	118.21 (13)	C24—C23—H23	120.1
C9—C8—C13	118.72 (14)	C22—C23—H23	120.1
C9—C8—C7	121.95 (14)	C25—C24—C23	120.7 (2)
C13—C8—C7	119.29 (14)	C25—C24—H24	119.6
C8—C9—C10	120.33 (15)	C23—C24—H24	119.6
C8—C9—H9	119.8	C24—C25—C26	120.4 (2)
C10—C9—H9	119.8	C24—C25—H25	119.8
C11—C10—C9	120.67 (15)	C26—C25—H25	119.8
C11—C10—H10	119.7	C21—C26—C25	118.8 (2)
C9—C10—H10	119.7	C21—C26—H26	120.6
O4—C11—C10	123.95 (14)	C25—C26—H26	120.6
O4—C11—C12	116.70 (13)	C12—O3—H3A	109.5
C10—C11—C12	119.33 (14)	C11—O4—H4A	109.5
O3—C12—C13	118.67 (14)	C18—O7—H7	109.5
O3—C12—C11	121.43 (14)	C19—O8—H8	109.5
C13—C12—C11	119.90 (14)	C1—N1—H1A	109.5
C12—C13—C8	121.02 (14)	C1—N1—H1B	109.5
C12—C13—H13	119.5	H1A—N1—H1B	109.5
C8—C13—H13	119.5	C1—N1—H1C	109.5
O5—C14—O6	121.70 (14)	H1A—N1—H1C	109.5
O5—C14—C15	118.76 (13)	H1B—N1—H1C	109.5
O6—C14—C15	119.54 (13)	C21—N2—H2A	109.5
C16—C15—C20	117.95 (14)	C21—N2—H2B	109.5
C16—C15—C14	122.22 (14)	H2A—N2—H2B	109.5
C20—C15—C14	119.81 (14)	C21—N2—H2C	109.5
C17—C16—C15	120.36 (15)	H2A—N2—H2C	109.5
C17—C16—H16	119.8	H2B—N2—H2C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O6i	0.89	1.99	2.856 (2)	165
N1—H1B···O4ii	0.89	2.44	2.824 (2)	107
N1—H1B···O6	0.89	2.06	2.912 (2)	161
N1—H1C···O5iii	0.89	1.95	2.831 (2)	170
N2—H2A···O1iv	0.89	2.13	2.937 (2)	150
N2—H2A···O7	0.89	2.33	2.821 (2)	115
N2—H2B···O1v	0.89	2.00	2.842 (2)	159
N2—H2C···O2	0.89	1.94	2.816 (2)	168
O3—H3A···O4	0.82	2.30	2.717 (2)	112
O3—H3A···O6vi	0.82	2.02	2.797 (2)	157
O4—H4A···O5vii	0.82	1.83	2.639 (2)	170
O7—H7···O2v	0.82	1.82	2.632 (2)	169
O8—H8···O1iv	0.82	2.00	2.776 (2)	158
O8—H8···O7	0.82	2.30	2.735 (2)	114
C20—H20···O5	0.93	2.48	2.791 (2)	100
C25—H25···O3viii	0.93	2.53	3.385 (3)	153

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O6i	0.89	1.99	2.856 (2)	165
N1—H1B⋯O4ii	0.89	2.44	2.824 (2)	107
N1—H1B⋯O6	0.89	2.06	2.912 (2)	161
N1—H1C⋯O5iii	0.89	1.95	2.831 (2)	170
N2—H2A⋯O1iv	0.89	2.13	2.937 (2)	150
N2—H2A⋯O7	0.89	2.33	2.821 (2)	115
N2—H2B⋯O1v	0.89	2.00	2.842 (2)	159
N2—H2C⋯O2	0.89	1.94	2.816 (2)	168
O3—H3A⋯O4	0.82	2.30	2.717 (2)	112
O3—H3A⋯O6vi	0.82	2.02	2.797 (2)	157
O4—H4A⋯O5vii	0.82	1.83	2.639 (2)	170
O7—H7⋯O2v	0.82	1.82	2.632 (2)	169
O8—H8⋯O1iv	0.82	2.00	2.776 (2)	158
O8—H8⋯O7	0.82	2.30	2.735 (2)	114
C25—H25⋯O3viii	0.93	2.53	3.385 (3)	153

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) ; (viii) .