Bis(2,6-diamino-pyridinium) tartrate monohydrate.

In the title compound, 2C(5)H(8)N(3) (+)·C(4)H(4)O(6) (2-)·H(2)O, the two cations are essentially planar [maximum deviations = 0.023 (1) and 0.026 (1) Å]. In one of the cations, the protonated N atom and one of the amino group H atoms are hydrogen bonded to one of the carboxyl groups of the dianion through a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. In the crystal structure, the tartrate anions and water mol-ecules are linked into chains along the c axis by inter-molecular O-H⋯O and C-H⋯O hydrogen bonds. The cations further link the anions and water mol-ecules into a three-dimensional extended structure by a network of N-H⋯O hydrogen bonds. The crystal structure is also stabilized by weak inter-molecular π-π inter-actions [centroid-centroid distance = 3.6950 (6) Å].

Related literature

For related structures, see: Al-Dajani, Abdallah et al. (2009 ▶); Al-Dajani, Salhin et al. (2009 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For bond-length data, see: Allen et al. (1987 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

2C5H8N3 +·C4H4O6 2−·H2O

M = 386.38

Monoclinic,

a = 14.4722 (2) Å

b = 15.7270 (2) Å

c = 7.8419 (1) Å

β = 96.916 (1)°

V = 1771.86 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.44 × 0.33 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.950, T max = 0.970

55803 measured reflections

8384 independent reflections

5761 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.137

S = 1.04

8384 reflections

332 parameters

All H-atom parameters refined

Δρmax = 0.33 e Å−3

Δρmin = −0.24 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809044663/hb5185sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809044663/hb5185Isup2.hkl

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

2C5H8N3+·C4H4O62−·H2O	F(000) = 816
Mr = 386.38	Dx = 1.448 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9979 reflections
a = 14.4722 (2) Å	θ = 2.6–33.1°
b = 15.7270 (2) Å	µ = 0.12 mm−1
c = 7.8419 (1) Å	T = 296 K
β = 96.916 (1)°	Block, brown
V = 1771.86 (4) Å3	0.44 × 0.33 × 0.26 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	8384 independent reflections
Radiation source: fine-focus sealed tube	5761 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 36.1°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −23→23
Tmin = 0.950, Tmax = 0.970	k = −25→24
55803 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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0645P)2 + 0.1774P] where P = (Fo2 + 2Fc2)/3
8384 reflections	(Δ/σ)max < 0.001
332 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

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	0.14121 (5)	0.62179 (5)	0.37307 (9)	0.03748 (15)
O2	0.33130 (5)	0.69021 (5)	0.36761 (10)	0.03834 (16)
O3	0.09223 (6)	0.78743 (6)	0.35992 (11)	0.0505 (2)
O4	0.19983 (6)	0.82535 (5)	0.57216 (9)	0.04158 (17)
O5	0.28815 (5)	0.55133 (5)	0.71274 (9)	0.04001 (16)
O6	0.36515 (6)	0.53101 (5)	0.48798 (9)	0.04409 (18)
C1	0.15720 (6)	0.77090 (6)	0.47338 (11)	0.03144 (17)
C2	0.18625 (6)	0.67770 (6)	0.49999 (10)	0.02824 (15)
C3	0.29147 (6)	0.66622 (6)	0.51725 (10)	0.02834 (15)
C4	0.31696 (6)	0.57521 (6)	0.57453 (10)	0.02985 (16)
N1	0.39658 (5)	0.44405 (5)	0.90954 (9)	0.02900 (14)
N2	0.47289 (7)	0.39813 (7)	0.68421 (11)	0.0423 (2)
N3	0.31436 (7)	0.50158 (7)	1.11702 (12)	0.0429 (2)
C5	0.46341 (6)	0.39419 (6)	0.85246 (11)	0.03136 (17)
C6	0.51647 (7)	0.34231 (7)	0.97048 (14)	0.0404 (2)
C7	0.49815 (8)	0.34277 (7)	1.13904 (14)	0.0427 (2)
C8	0.43089 (8)	0.39418 (7)	1.19503 (12)	0.0395 (2)
C9	0.38033 (6)	0.44752 (6)	1.07627 (10)	0.03057 (16)
N4	0.07411 (6)	0.29439 (6)	0.34459 (12)	0.03809 (18)
N5	0.05279 (8)	0.15005 (7)	0.31936 (18)	0.0562 (3)
N6	0.07972 (10)	0.44052 (8)	0.3524 (2)	0.0649 (3)
C10	0.10707 (7)	0.21441 (7)	0.37940 (14)	0.0394 (2)
C11	0.19414 (8)	0.20559 (8)	0.47490 (18)	0.0504 (3)
C12	0.24392 (8)	0.27782 (10)	0.52373 (19)	0.0564 (3)
C13	0.20988 (9)	0.35831 (9)	0.48473 (18)	0.0534 (3)
C14	0.12190 (8)	0.36637 (7)	0.39441 (15)	0.0426 (2)
O1W	0.11303 (7)	0.52769 (6)	0.82780 (15)	0.0559 (2)
H1O1	0.1548 (11)	0.6424 (10)	0.272 (2)	0.057 (4)*
H1O2	0.2904 (13)	0.6826 (10)	0.278 (2)	0.067 (5)*
H1N1	0.3619 (9)	0.4801 (8)	0.8319 (18)	0.044 (3)*
H1N2	0.5253 (12)	0.3800 (10)	0.650 (2)	0.062 (4)*
H2N2	0.4425 (9)	0.4390 (9)	0.6238 (18)	0.045 (3)*
H1N3	0.2911 (11)	0.5406 (11)	1.038 (2)	0.065 (5)*
H2N3	0.3161 (12)	0.5144 (10)	1.224 (2)	0.067 (5)*
H1N4	0.0176 (12)	0.2971 (10)	0.276 (2)	0.059 (4)*
H1N5	0.0716 (12)	0.1009 (12)	0.338 (2)	0.068 (5)*
H2N5	−0.0001 (12)	0.1605 (10)	0.253 (2)	0.059 (4)*
H1N6	0.0204 (12)	0.4416 (10)	0.302 (2)	0.060 (4)*
H2N6	0.1102 (14)	0.4860 (12)	0.389 (3)	0.079 (5)*
H2A	0.1657 (8)	0.6614 (7)	0.6076 (14)	0.030 (3)*
H3A	0.3165 (9)	0.7015 (7)	0.6120 (16)	0.034 (3)*
H6A	0.5634 (12)	0.3070 (10)	0.937 (2)	0.063 (4)*
H7A	0.5370 (10)	0.3053 (9)	1.2187 (18)	0.050 (4)*
H8A	0.4196 (10)	0.3943 (9)	1.3120 (19)	0.051 (4)*
H11A	0.2168 (12)	0.1515 (11)	0.498 (2)	0.067 (5)*
H12A	0.3045 (13)	0.2700 (11)	0.588 (2)	0.075 (5)*
H13A	0.2436 (12)	0.4097 (11)	0.514 (2)	0.069 (5)*
H1W1	0.1128 (16)	0.5645 (16)	0.907 (3)	0.102 (7)*
H2W1	0.1669 (15)	0.5349 (13)	0.785 (3)	0.087 (6)*

	U11	U22	U33	U12	U13	U23
O1	0.0370 (3)	0.0357 (4)	0.0381 (3)	−0.0092 (3)	−0.0024 (3)	−0.0016 (3)
O2	0.0333 (3)	0.0438 (4)	0.0384 (3)	−0.0046 (3)	0.0061 (3)	0.0108 (3)
O3	0.0395 (4)	0.0544 (5)	0.0547 (5)	0.0125 (3)	−0.0065 (3)	0.0098 (4)
O4	0.0576 (4)	0.0305 (3)	0.0367 (3)	0.0000 (3)	0.0057 (3)	−0.0021 (3)
O5	0.0451 (4)	0.0428 (4)	0.0335 (3)	0.0128 (3)	0.0100 (3)	0.0117 (3)
O6	0.0569 (4)	0.0413 (4)	0.0360 (3)	0.0153 (3)	0.0133 (3)	0.0013 (3)
C1	0.0326 (4)	0.0333 (4)	0.0292 (3)	0.0048 (3)	0.0066 (3)	0.0038 (3)
C2	0.0298 (4)	0.0285 (4)	0.0261 (3)	−0.0009 (3)	0.0020 (3)	0.0011 (3)
C3	0.0292 (4)	0.0281 (4)	0.0269 (3)	−0.0014 (3)	−0.0002 (3)	0.0004 (3)
C4	0.0315 (4)	0.0315 (4)	0.0257 (3)	0.0023 (3)	−0.0001 (3)	0.0008 (3)
N1	0.0305 (3)	0.0292 (4)	0.0266 (3)	0.0036 (3)	0.0006 (2)	0.0020 (2)
N2	0.0456 (5)	0.0480 (5)	0.0346 (4)	0.0104 (4)	0.0100 (3)	0.0000 (4)
N3	0.0471 (5)	0.0488 (5)	0.0331 (4)	0.0141 (4)	0.0064 (3)	−0.0019 (4)
C5	0.0311 (4)	0.0300 (4)	0.0325 (4)	0.0013 (3)	0.0018 (3)	−0.0028 (3)
C6	0.0396 (5)	0.0367 (5)	0.0431 (5)	0.0124 (4)	−0.0028 (4)	−0.0020 (4)
C7	0.0485 (5)	0.0359 (5)	0.0398 (5)	0.0078 (4)	−0.0106 (4)	0.0039 (4)
C8	0.0483 (5)	0.0411 (5)	0.0274 (4)	0.0037 (4)	−0.0022 (3)	0.0033 (3)
C9	0.0322 (4)	0.0317 (4)	0.0270 (3)	−0.0004 (3)	0.0004 (3)	−0.0007 (3)
N4	0.0290 (4)	0.0349 (4)	0.0485 (4)	0.0013 (3)	−0.0029 (3)	−0.0015 (3)
N5	0.0403 (5)	0.0351 (5)	0.0901 (9)	0.0016 (4)	−0.0046 (5)	−0.0084 (5)
N6	0.0575 (7)	0.0332 (5)	0.0982 (10)	−0.0015 (5)	−0.0145 (6)	0.0028 (5)
C10	0.0319 (4)	0.0352 (5)	0.0508 (5)	0.0024 (4)	0.0031 (4)	−0.0024 (4)
C11	0.0376 (5)	0.0459 (7)	0.0651 (7)	0.0093 (5)	−0.0048 (5)	0.0021 (5)
C12	0.0339 (5)	0.0639 (8)	0.0670 (8)	0.0027 (5)	−0.0123 (5)	−0.0004 (6)
C13	0.0413 (6)	0.0490 (7)	0.0661 (8)	−0.0081 (5)	−0.0095 (5)	−0.0043 (5)
C14	0.0388 (5)	0.0365 (5)	0.0512 (6)	−0.0026 (4)	−0.0003 (4)	−0.0007 (4)
O1W	0.0539 (5)	0.0414 (5)	0.0734 (6)	−0.0122 (4)	0.0114 (4)	−0.0059 (4)

O1—C2	1.4257 (11)	C6—H6A	0.938 (17)
O1—H1O1	0.901 (16)	C7—C8	1.3773 (16)
O2—C3	1.4194 (10)	C7—H7A	0.984 (15)
O2—H1O2	0.868 (19)	C8—C9	1.3937 (13)
O3—C1	1.2418 (12)	C8—H8A	0.951 (14)
O4—C1	1.2644 (12)	N4—C14	1.3591 (14)
O5—C4	1.2643 (10)	N4—C10	1.3613 (13)
O6—C4	1.2426 (11)	N4—H1N4	0.923 (17)
C1—C2	1.5322 (13)	N5—C10	1.3319 (15)
C2—C3	1.5231 (12)	N5—H1N5	0.827 (18)
C2—H2A	0.962 (11)	N5—H2N5	0.888 (17)
C3—C4	1.5318 (12)	N6—C14	1.3390 (16)
C3—H3A	0.962 (12)	N6—H1N6	0.901 (18)
N1—C9	1.3572 (11)	N6—H2N6	0.87 (2)
N1—C5	1.3620 (11)	C10—C11	1.3930 (16)
N1—H1N1	0.933 (14)	C11—C12	1.3747 (19)
N2—C5	1.3443 (12)	C11—H11A	0.922 (18)
N2—H1N2	0.881 (17)	C12—C13	1.379 (2)
N2—H2N2	0.884 (14)	C12—H12A	0.963 (19)
N3—C9	1.3453 (13)	C13—C14	1.3862 (16)
N3—H1N3	0.907 (17)	C13—H13A	0.959 (17)
N3—H2N3	0.859 (18)	O1W—H1W1	0.85 (3)
C5—C6	1.3931 (13)	O1W—H2W1	0.89 (2)
C6—C7	1.3790 (15)
C2—O1—H1O1	105.3 (10)	C8—C7—C6	122.24 (9)
C3—O2—H1O2	108.9 (11)	C8—C7—H7A	121.3 (8)
O3—C1—O4	124.66 (9)	C6—C7—H7A	116.4 (8)
O3—C1—C2	118.00 (9)	C7—C8—C9	118.34 (9)
O4—C1—C2	117.31 (8)	C7—C8—H8A	121.2 (9)
O1—C2—C3	110.92 (7)	C9—C8—H8A	120.4 (9)
O1—C2—C1	113.58 (7)	N3—C9—N1	117.68 (8)
C3—C2—C1	112.37 (7)	N3—C9—C8	123.52 (9)
O1—C2—H2A	106.5 (7)	N1—C9—C8	118.79 (8)
C3—C2—H2A	107.6 (7)	C14—N4—C10	123.92 (9)
C1—C2—H2A	105.4 (7)	C14—N4—H1N4	120.8 (10)
O2—C3—C2	113.34 (7)	C10—N4—H1N4	115.1 (10)
O2—C3—C4	112.54 (7)	C10—N5—H1N5	118.6 (12)
C2—C3—C4	109.86 (7)	C10—N5—H2N5	119.8 (11)
O2—C3—H3A	109.4 (7)	H1N5—N5—H2N5	121.5 (16)
C2—C3—H3A	106.2 (7)	C14—N6—H1N6	120.4 (11)
C4—C3—H3A	104.9 (7)	C14—N6—H2N6	115.8 (13)
O6—C4—O5	124.53 (9)	H1N6—N6—H2N6	123.2 (17)
O6—C4—C3	119.58 (8)	N5—C10—N4	116.98 (10)
O5—C4—C3	115.86 (8)	N5—C10—C11	124.84 (11)
C9—N1—C5	123.51 (8)	N4—C10—C11	118.18 (10)
C9—N1—H1N1	117.5 (8)	C12—C11—C10	118.51 (11)
C5—N1—H1N1	118.9 (8)	C12—C11—H11A	123.0 (11)
C5—N2—H1N2	118.3 (11)	C10—C11—H11A	118.4 (11)
C5—N2—H2N2	117.2 (9)	C11—C12—C13	122.37 (11)
H1N2—N2—H2N2	117.8 (13)	C11—C12—H12A	116.9 (11)
C9—N3—H1N3	118.8 (10)	C13—C12—H12A	120.7 (11)
C9—N3—H2N3	116.2 (11)	C12—C13—C14	118.61 (11)
H1N3—N3—H2N3	118.1 (15)	C12—C13—H13A	124.2 (10)
N2—C5—N1	117.16 (8)	C14—C13—H13A	117.1 (10)
N2—C5—C6	124.46 (9)	N6—C14—N4	116.97 (10)
N1—C5—C6	118.38 (8)	N6—C14—C13	124.67 (11)
C7—C6—C5	118.65 (9)	N4—C14—C13	118.36 (11)
C7—C6—H6A	119.9 (10)	H1W1—O1W—H2W1	106 (2)
C5—C6—H6A	121.5 (10)
O3—C1—C2—O1	7.58 (11)	C5—C6—C7—C8	−1.59 (17)
O4—C1—C2—O1	−174.21 (7)	C6—C7—C8—C9	−0.26 (17)
O3—C1—C2—C3	134.52 (9)	C5—N1—C9—N3	177.76 (9)
O4—C1—C2—C3	−47.27 (10)	C5—N1—C9—C8	−3.54 (14)
O1—C2—C3—O2	65.36 (10)	C7—C8—C9—N3	−178.63 (10)
C1—C2—C3—O2	−62.99 (9)	C7—C8—C9—N1	2.75 (15)
O1—C2—C3—C4	−61.50 (9)	C14—N4—C10—N5	−178.83 (11)
C1—C2—C3—C4	170.15 (7)	C14—N4—C10—C11	1.42 (17)
O2—C3—C4—O6	−2.16 (12)	N5—C10—C11—C12	177.88 (13)
C2—C3—C4—O6	125.14 (9)	N4—C10—C11—C12	−2.39 (19)
O2—C3—C4—O5	176.12 (8)	C10—C11—C12—C13	1.4 (2)
C2—C3—C4—O5	−56.57 (10)	C11—C12—C13—C14	0.6 (2)
C9—N1—C5—N2	−178.91 (9)	C10—N4—C14—N6	−179.17 (12)
C9—N1—C5—C6	1.66 (14)	C10—N4—C14—C13	0.63 (17)
N2—C5—C6—C7	−178.45 (10)	C12—C13—C14—N6	178.15 (14)
N1—C5—C6—C7	0.93 (15)	C12—C13—C14—N4	−1.64 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O4i	0.900 (16)	1.840 (16)	2.7315 (10)	170.9 (15)
O2—H1O2···O4i	0.871 (17)	1.957 (17)	2.8260 (11)	175.6 (15)
N1—H1N1···O5	0.933 (13)	1.740 (13)	2.6660 (11)	171.4 (13)
N2—H1N2···O2ii	0.882 (17)	2.369 (17)	3.2254 (13)	163.7 (14)
N2—H1N2···O6ii	0.882 (17)	2.461 (17)	3.0531 (13)	125.0 (13)
N2—H2N2···O6	0.884 (14)	2.048 (14)	2.9306 (13)	176.7 (12)
N3—H1N3···O5	0.908 (16)	2.552 (16)	3.2431 (12)	133.4 (13)
N3—H1N3···O4iii	0.908 (16)	2.519 (17)	3.1842 (13)	130.5 (13)
N3—H2N3···O6iv	0.860 (16)	2.122 (16)	2.9499 (12)	161.3 (16)
N4—H1N4···O3v	0.924 (17)	1.810 (17)	2.7294 (12)	172.5 (15)
N5—H1N5···O1Wvi	0.827 (19)	2.114 (19)	2.9265 (15)	167.7 (15)
N5—H2N5···O1v	0.888 (17)	2.243 (17)	3.0557 (14)	152.0 (14)
N5—H2N5···O3v	0.888 (17)	2.503 (16)	3.2154 (15)	137.8 (13)
N6—H1N6···O1Wvii	0.901 (17)	2.127 (17)	3.0131 (18)	167.5 (14)
N6—H2N6···O1	0.87 (2)	2.189 (19)	2.9851 (15)	152 (2)
O1W—H1W1···O3iii	0.85 (2)	2.37 (3)	2.9371 (13)	125 (2)
O1W—H1W1···O4iii	0.85 (2)	2.42 (2)	3.1642 (13)	146 (2)
O1W—H2W1···O5	0.89 (2)	1.93 (2)	2.8153 (13)	175 (2)
C2—H2A···O3iii	0.963 (11)	2.490 (11)	3.3232 (12)	144.8 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O1⋯O4i	0.900 (16)	1.840 (16)	2.7315 (10)	170.9 (15)
O2—H1O2⋯O4i	0.871 (17)	1.957 (17)	2.8260 (11)	175.6 (15)
N1—H1N1⋯O5	0.933 (13)	1.740 (13)	2.6660 (11)	171.4 (13)
N2—H1N2⋯O2ii	0.882 (17)	2.369 (17)	3.2254 (13)	163.7 (14)
N2—H1N2⋯O6ii	0.882 (17)	2.461 (17)	3.0531 (13)	125.0 (13)
N2—H2N2⋯O6	0.884 (14)	2.048 (14)	2.9306 (13)	176.7 (12)
N3—H1N3⋯O5	0.908 (16)	2.552 (16)	3.2431 (12)	133.4 (13)
N3—H1N3⋯O4iii	0.908 (16)	2.519 (17)	3.1842 (13)	130.5 (13)
N3—H2N3⋯O6iv	0.860 (16)	2.122 (16)	2.9499 (12)	161.3 (16)
N4—H1N4⋯O3v	0.924 (17)	1.810 (17)	2.7294 (12)	172.5 (15)
N5—H1N5⋯O1Wvi	0.827 (19)	2.114 (19)	2.9265 (15)	167.7 (15)
N5—H2N5⋯O1v	0.888 (17)	2.243 (17)	3.0557 (14)	152.0 (14)
N5—H2N5⋯O3v	0.888 (17)	2.503 (16)	3.2154 (15)	137.8 (13)
N6—H1N6⋯O1Wvii	0.901 (17)	2.127 (17)	3.0131 (18)	167.5 (14)
N6—H2N6⋯O1	0.87 (2)	2.189 (19)	2.9851 (15)	152 (2)
O1W—H1W1⋯O3iii	0.85 (2)	2.37 (3)	2.9371 (13)	125 (2)
O1W—H1W1⋯O4iii	0.85 (2)	2.42 (2)	3.1642 (13)	146 (2)
O1W—H2W1⋯O5	0.89 (2)	1.93 (2)	2.8153 (13)	175 (2)
C2—H2A⋯O3iii	0.963 (11)	2.490 (11)	3.3232 (12)	144.8 (9)

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