Bis(2,3-diamino-pyridinium) succinate trihydrate.

In the title salt, 2C(5)H(8)N(3) (+)·C(4)H(4)O(4) (2-)·3H(2)O, the asymmetric unit contains a protonated 2,3-diamino-pyridinium cation, half of a succinate dianion (disposed about a centre of inversion), and one and a half water mol-ecules. One of the water mol-ecules is disordered over two sites with occupancies of 0.670 (17) and 0.330 (17). The other water mol-ecule has an occupancy of 0.5 (from refinement). The pyridine N atom of the 2,3-diamino-pyridine mol-ecule is protonated. The protonated N atom and one of the 2-amino H atoms are hydrogen bonded to the succinate anion through a pair of N-H⋯O hydrogen bonds, forming an R(2) (2)(8) ring motif. In the crystal, mol-ecules are consolidated into a three-dimensional network by N-H⋯O and O-H⋯O inter-actions.

Related literature

For substituted pyridines, see: Pozharski et al. (1997 ▶); Katritzky et al. (1996 ▶); Jeffrey & Saenger (1991 ▶); Jeffrey (1997 ▶); Scheiner (1997 ▶). For related structures, see: De Cires-Mejias et al. (2004 ▶); Fun & Balasubramani (2009 ▶); Balasubramani & Fun (2009a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

2C5H8N3 +·C4H4O4 2−·3H2O

M = 195.20

Monoclinic,

a = 12.7159 (4) Å

b = 3.9024 (1) Å

c = 18.7734 (6) Å

β = 94.933 (2)°

V = 928.13 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 100 K

0.17 × 0.13 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.981, T max = 0.993

10934 measured reflections

2121 independent reflections

1364 reflections with I > 2σ(I)

R int = 0.056

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.129

S = 1.06

2121 reflections

178 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 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/S1600536809026439/tk2489sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809026439/tk2489Isup2.hkl

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

2C5H8N3+·C4H4O42−·3H2O	F(000) = 416
Mr = 195.20	Dx = 1.397 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2108 reflections
a = 12.7159 (4) Å	θ = 2.2–30.0°
b = 3.9024 (1) Å	µ = 0.11 mm−1
c = 18.7734 (6) Å	T = 100 K
β = 94.933 (2)°	Block, brown
V = 928.13 (5) Å3	0.17 × 0.13 × 0.06 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2121 independent reflections
Radiation source: fine-focus sealed tube	1364 reflections with I > 2σ(I)
graphite	Rint = 0.056
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
Tmin = 0.981, Tmax = 0.993	k = −4→5
10934 measured reflections	l = −24→21

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.041P)2 + 0.7373P] where P = (Fo2 + 2Fc2)/3
2121 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.26 e Å−3
0 restraints	Δρmin = −0.24 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	Occ. (<1)
O1	0.02464 (12)	0.7567 (4)	0.37851 (8)	0.0251 (4)
O2	0.18198 (12)	0.6548 (5)	0.43615 (8)	0.0264 (4)
N1	0.25383 (14)	0.2963 (5)	0.33114 (10)	0.0204 (5)
N2	0.10876 (15)	0.4334 (6)	0.25459 (12)	0.0243 (5)
N3	0.20743 (19)	0.1167 (7)	0.14153 (12)	0.0328 (6)
C1	0.20422 (17)	0.2863 (6)	0.26523 (12)	0.0201 (5)
C2	0.25526 (17)	0.1188 (6)	0.20981 (12)	0.0221 (6)
C3	0.35320 (18)	−0.0256 (7)	0.22796 (13)	0.0243 (6)
C4	0.40151 (18)	−0.0059 (7)	0.29740 (13)	0.0248 (6)
C5	0.35068 (18)	0.1562 (7)	0.34840 (13)	0.0241 (6)
C6	0.08824 (17)	0.7727 (6)	0.43321 (12)	0.0207 (5)
C7	0.05630 (18)	0.9358 (7)	0.50147 (12)	0.0207 (5)
O1WA	0.3424 (4)	0.840 (3)	0.5375 (3)	0.082 (3)	0.670 (17)
H1WA	0.3803	0.6625	0.5341	0.123*	0.670 (17)
H2WA	0.2898	0.8222	0.5066	0.123*	0.670 (17)
O1WB	0.3443 (6)	0.583 (4)	0.5327 (3)	0.039 (4)	0.330 (17)
H1WB	0.3312	0.7954	0.5365	0.058*	0.330 (17)
H2WB	0.3173	0.5182	0.4919	0.058*	0.330 (17)
O2W	0.4593 (3)	0.248 (2)	0.5467 (3)	0.110 (3)	0.50
H1W2	0.5119	0.3543	0.5322	0.165*	0.50
H2W2	0.4462	0.0794	0.5187	0.165*	0.50
H4A	0.4676 (19)	−0.100 (7)	0.3090 (12)	0.027 (7)*
H5A	0.3781 (17)	0.185 (6)	0.3960 (13)	0.022 (6)*
H3A	0.3854 (18)	−0.140 (7)	0.1902 (13)	0.030 (7)*
H7B	0.0722 (17)	0.759 (6)	0.5381 (12)	0.020 (6)*
H7A	0.1062 (18)	1.118 (7)	0.5145 (12)	0.026 (7)*
H2N2	0.076 (2)	0.445 (8)	0.2102 (16)	0.047 (9)*
H1N3	0.142 (2)	0.154 (7)	0.1337 (14)	0.037 (8)*
H1N2	0.0799 (19)	0.537 (7)	0.2905 (14)	0.028 (7)*
H2N3	0.239 (2)	−0.022 (8)	0.1105 (15)	0.045 (9)*
H1N1	0.2213 (19)	0.418 (7)	0.3676 (13)	0.030 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0211 (8)	0.0345 (11)	0.0203 (8)	0.0028 (8)	0.0054 (7)	−0.0005 (7)
O2	0.0188 (8)	0.0361 (11)	0.0253 (9)	0.0030 (8)	0.0074 (7)	−0.0010 (8)
N1	0.0177 (10)	0.0213 (12)	0.0235 (10)	−0.0029 (9)	0.0084 (8)	−0.0007 (9)
N2	0.0203 (11)	0.0296 (13)	0.0239 (11)	0.0020 (10)	0.0066 (9)	−0.0041 (10)
N3	0.0263 (13)	0.0450 (16)	0.0277 (12)	0.0052 (12)	0.0056 (10)	−0.0071 (11)
C1	0.0172 (11)	0.0179 (13)	0.0259 (12)	−0.0052 (10)	0.0067 (9)	0.0016 (10)
C2	0.0219 (12)	0.0213 (14)	0.0242 (12)	−0.0050 (11)	0.0074 (10)	−0.0006 (10)
C3	0.0229 (12)	0.0215 (15)	0.0304 (13)	−0.0033 (11)	0.0134 (10)	−0.0025 (11)
C4	0.0153 (12)	0.0234 (14)	0.0366 (14)	−0.0026 (11)	0.0067 (10)	0.0008 (12)
C5	0.0204 (12)	0.0251 (15)	0.0269 (13)	−0.0031 (11)	0.0028 (10)	0.0024 (11)
C6	0.0219 (12)	0.0185 (14)	0.0229 (12)	−0.0022 (11)	0.0082 (10)	0.0049 (10)
C7	0.0207 (12)	0.0212 (14)	0.0204 (12)	−0.0003 (11)	0.0035 (10)	0.0027 (11)
O1WA	0.068 (3)	0.111 (8)	0.061 (3)	−0.030 (3)	−0.026 (2)	0.022 (3)
O1WB	0.031 (4)	0.064 (9)	0.020 (3)	0.009 (4)	−0.002 (2)	−0.009 (3)
O2W	0.039 (3)	0.210 (8)	0.078 (4)	−0.015 (4)	−0.016 (3)	−0.006 (4)

O1—C6	1.253 (3)	C4—H4A	0.93 (2)
O2—C6	1.274 (3)	C5—H5A	0.94 (2)
N1—C1	1.340 (3)	C6—C7	1.517 (3)
N1—C5	1.361 (3)	C7—C7i	1.513 (4)
N1—H1N1	0.96 (3)	C7—H7B	0.98 (2)
N2—C1	1.342 (3)	C7—H7A	0.97 (3)
N2—H2N2	0.90 (3)	O1WA—H1WA	0.8500
N2—H1N2	0.89 (3)	O1WA—H2WA	0.8501
N3—C2	1.371 (3)	O1WA—H1WB	0.2257
N3—H1N3	0.85 (3)	O1WB—H1WA	0.5518
N3—H2N3	0.91 (3)	O1WB—H2WA	1.2381
C1—C2	1.431 (3)	O1WB—H1WB	0.8500
C2—C3	1.383 (3)	O1WB—H2WB	0.8502
C3—C4	1.395 (3)	O2W—H1W2	0.8500
C3—H3A	0.96 (3)	O2W—H2W2	0.8501
C4—C5	1.357 (3)
C1—N1—C5	123.6 (2)	C4—C5—H5A	124.5 (14)
C1—N1—H1N1	118.5 (14)	N1—C5—H5A	115.7 (14)
C5—N1—H1N1	117.9 (14)	O1—C6—O2	123.6 (2)
C1—N2—H2N2	120.3 (18)	O1—C6—C7	120.8 (2)
C1—N2—H1N2	120.5 (15)	O2—C6—C7	115.61 (19)
H2N2—N2—H1N2	119 (2)	C7i—C7—C6	115.4 (2)
C2—N3—H1N3	120.8 (18)	C7i—C7—H7B	113.3 (13)
C2—N3—H2N3	114.7 (17)	C6—C7—H7B	104.0 (13)
H1N3—N3—H2N3	118 (3)	C7i—C7—H7A	111.3 (14)
N1—C1—N2	118.2 (2)	C6—C7—H7A	107.7 (14)
N1—C1—C2	118.5 (2)	H7B—C7—H7A	104.4 (18)
N2—C1—C2	123.2 (2)	H1WA—O1WA—H2WA	107.4
N3—C2—C3	123.1 (2)	H1WA—O1WA—H1WB	73.7
N3—C2—C1	119.4 (2)	H2WA—O1WA—H1WB	54.6
C3—C2—C1	117.5 (2)	H1WA—O1WB—H2WA	91.7
C2—C3—C4	121.5 (2)	H1WA—O1WB—H1WB	67.4
C2—C3—H3A	116.1 (14)	H2WA—O1WB—H1WB	35.9
C4—C3—H3A	122.3 (14)	H1WA—O1WB—H2WB	118.6
C5—C4—C3	119.1 (2)	H2WA—O1WB—H2WB	72.5
C5—C4—H4A	119.8 (15)	H1WB—O1WB—H2WB	107.4
C3—C4—H4A	121.1 (15)	H1W2—O2W—H2W2	107.4
C4—C5—N1	119.7 (2)
C5—N1—C1—N2	180.0 (2)	C1—C2—C3—C4	−0.8 (4)
C5—N1—C1—C2	0.2 (3)	C2—C3—C4—C5	0.6 (4)
N1—C1—C2—N3	−177.7 (2)	C3—C4—C5—N1	0.0 (4)
N2—C1—C2—N3	2.6 (4)	C1—N1—C5—C4	−0.4 (4)
N1—C1—C2—C3	0.4 (3)	O1—C6—C7—C7i	1.6 (4)
N2—C1—C2—C3	−179.4 (2)	O2—C6—C7—C7i	−177.9 (3)
N3—C2—C3—C4	177.2 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N2···O1ii	0.90 (3)	2.14 (3)	2.978 (3)	155 (3)
N3—H1N3···O1ii	0.85 (3)	2.14 (3)	2.993 (3)	176 (3)
N3—H2N3···O1WAiii	0.91 (3)	2.34 (3)	3.243 (6)	172 (2)
O1WA—H2WA···O2	0.85	1.93	2.764 (5)	165
N2—H1N2···O1	0.89 (3)	2.04 (3)	2.929 (3)	175 (2)
N1—H1N1···O2	0.96 (3)	1.69 (3)	2.643 (3)	171 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N2⋯O1i	0.90 (3)	2.14 (3)	2.978 (3)	155 (3)
N3—H1N3⋯O1i	0.85 (3)	2.14 (3)	2.993 (3)	176 (3)
N3—H2N3⋯O1WAii	0.91 (3)	2.34 (3)	3.243 (6)	172 (2)
O1WA—H2WA⋯O2	0.85	1.93	2.764 (5)	165
N2—H1N2⋯O1	0.89 (3)	2.04 (3)	2.929 (3)	175 (2)
N1—H1N1⋯O2	0.96 (3)	1.69 (3)	2.643 (3)	171 (2)

Symmetry codes: (i) ; (ii) .