Bis(2-amino-thia-zolium) succinate succinic acid.

In the title compound, 2C(3)H(5)N(2)S(+)·C(4)H(4)O(4) (2-)·C(4)H(6)O(4), the thia-zolium ring is almost planar, with the maximum deviation from planarity being 0.0056 (8) Å for the C atom carrying the amine substituent. The N atom of the 2-amino-thia-zole mol-ecule is protonated. Both the anion and the acid lie across inversion centres. The crystal packing is consolidated by inter-molecular O-H⋯O, N-H⋯O and C-H⋯O hydrogen bonds. Mol-ecules are stacked down the b axis.

Related literature

For the structure of 2-amino­thia­zole, see: Caranoni & Reboul (1982 ▶). For applications of 2-amino­thia­zole, see: Saarnivaara & Matilla (1974 ▶); Windholz (2001 ▶). For the structure of succinic acid, see: Gopalan et al. (2000 ▶); Leviel et al. (1981 ▶). For applications of succinic acid, see: Sauer et al. (2008 ▶); Song & Lee (2006 ▶); Zeikus et al. (1999 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

2C3H5N2S+·C4H4O4 2−·C4H6O4

M = 436.46

Monoclinic,

a = 10.1680 (2) Å

b = 5.1012 (1) Å

c = 18.3850 (4) Å

β = 105.961 (1)°

V = 916.85 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.34 mm−1

T = 100 K

0.58 × 0.42 × 0.32 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.826, T max = 0.897

16689 measured reflections

3691 independent reflections

3442 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.077

S = 1.04

3691 reflections

167 parameters

All H-atom parameters refined

Δρmax = 0.45 e Å−3

Δρmin = −0.35 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/S1600536809007004/sj2582sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809007004/sj2582Isup2.hkl

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

2C3H5N2S+·C4H4O42−·C4H6O4	F(000) = 456
Mr = 436.46	Dx = 1.581 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9994 reflections
a = 10.1680 (2) Å	θ = 2.3–40.1°
b = 5.1012 (1) Å	µ = 0.34 mm−1
c = 18.3850 (4) Å	T = 100 K
β = 105.961 (1)°	Block, yellow
V = 916.85 (3) Å3	0.58 × 0.42 × 0.32 mm
Z = 2

Bruker SMART APEXII CCD area-detector diffractometer	3691 independent reflections
Radiation source: fine-focus sealed tube	3442 reflections with I > 2σ(I)
graphite	Rint = 0.022
φ and ω scans	θmax = 34.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −16→16
Tmin = 0.826, Tmax = 0.897	k = −7→7
16689 measured reflections	l = −28→24

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)] = 0.027	Hydrogen site location: difference Fourier map
wR(F2) = 0.077	All H-atom parameters refined
S = 1.04	w = 1/[σ2(Fo2) + (0.0423P)2 + 0.2556P] where P = (Fo2 + 2Fc2)/3
3691 reflections	(Δ/σ)max = 0.001
167 parameters	Δρmax = 0.45 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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

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
S1	0.398521 (18)	0.38496 (4)	0.154349 (10)	0.01603 (6)
O1	0.64045 (5)	0.89655 (11)	0.12963 (3)	0.01367 (10)
O2	0.77343 (5)	1.19344 (12)	0.09559 (3)	0.01562 (10)
O3	0.80012 (6)	0.57645 (12)	0.00894 (3)	0.01703 (11)
O4	0.99583 (6)	0.66022 (12)	0.09808 (3)	0.01646 (11)
N1	0.52407 (6)	0.60443 (12)	0.27794 (3)	0.01361 (11)
N2	0.63526 (6)	0.22575 (14)	0.25269 (4)	0.01565 (12)
C1	0.32820 (7)	0.66562 (16)	0.18253 (4)	0.01749 (13)
C2	0.40776 (7)	0.75502 (15)	0.24905 (4)	0.01599 (13)
C3	0.53433 (7)	0.39842 (14)	0.23509 (4)	0.01261 (12)
C4	0.66461 (6)	1.05440 (14)	0.08264 (4)	0.01101 (11)
C5	0.56100 (7)	1.09079 (14)	0.00653 (4)	0.01307 (12)
C6	0.91584 (7)	0.70771 (13)	0.03682 (4)	0.01173 (11)
C7	0.93722 (7)	0.91684 (14)	−0.01673 (4)	0.01291 (12)
H1	0.2400 (13)	0.731 (3)	0.1506 (7)	0.027 (3)*
H2	0.3948 (13)	0.900 (2)	0.2779 (7)	0.023 (3)*
H7A	0.8557 (13)	1.025 (3)	−0.0314 (7)	0.023 (3)*
H7B	0.9449 (13)	0.826 (3)	−0.0630 (7)	0.025 (3)*
H1N2	0.7022 (15)	0.248 (3)	0.2933 (8)	0.035 (4)*
H2N2	0.6384 (13)	0.100 (3)	0.2197 (7)	0.025 (3)*
H1C5	0.6093 (14)	1.070 (3)	−0.0333 (8)	0.030 (3)*
H2C5	0.5330 (13)	1.280 (3)	0.0047 (8)	0.030 (3)*
H1N1	0.5877 (14)	0.640 (3)	0.3188 (8)	0.031 (3)*
H1O3	0.7940 (17)	0.447 (4)	0.0401 (9)	0.052 (5)*

	U11	U22	U33	U12	U13	U23
S1	0.01505 (8)	0.01672 (9)	0.01227 (8)	−0.00239 (5)	−0.00303 (6)	0.00025 (5)
O1	0.0141 (2)	0.0152 (2)	0.0103 (2)	−0.00308 (17)	0.00095 (16)	0.00264 (16)
O2	0.0127 (2)	0.0175 (2)	0.0136 (2)	−0.00582 (18)	−0.00159 (17)	0.00353 (18)
O3	0.0150 (2)	0.0181 (3)	0.0151 (2)	−0.00693 (18)	−0.00061 (18)	0.00485 (19)
O4	0.0145 (2)	0.0178 (2)	0.0146 (2)	−0.00236 (18)	−0.00011 (18)	0.00380 (19)
N1	0.0128 (2)	0.0147 (3)	0.0116 (2)	0.00017 (19)	0.00047 (19)	−0.00062 (19)
N2	0.0141 (2)	0.0176 (3)	0.0128 (2)	0.0022 (2)	−0.0003 (2)	−0.0030 (2)
C1	0.0137 (3)	0.0171 (3)	0.0189 (3)	−0.0001 (2)	−0.0001 (2)	0.0044 (3)
C2	0.0141 (3)	0.0152 (3)	0.0179 (3)	0.0014 (2)	0.0031 (2)	0.0022 (2)
C3	0.0119 (3)	0.0143 (3)	0.0102 (2)	−0.0016 (2)	0.0008 (2)	0.0004 (2)
C4	0.0106 (2)	0.0116 (3)	0.0097 (2)	−0.0009 (2)	0.00098 (19)	0.0002 (2)
C5	0.0115 (2)	0.0153 (3)	0.0101 (2)	−0.0035 (2)	−0.0009 (2)	0.0027 (2)
C6	0.0113 (2)	0.0111 (3)	0.0127 (3)	−0.0006 (2)	0.0032 (2)	0.0002 (2)
C7	0.0129 (3)	0.0129 (3)	0.0122 (3)	−0.0022 (2)	0.0023 (2)	0.0018 (2)

S1—C3	1.7285 (7)	N2—H2N2	0.888 (13)
S1—C1	1.7416 (9)	C1—C2	1.3468 (11)
O1—C4	1.2538 (8)	C1—H1	0.986 (13)
O2—C4	1.2802 (8)	C2—H2	0.941 (13)
O3—C6	1.3281 (8)	C4—C5	1.5139 (9)
O3—H1O3	0.887 (18)	C5—C5i	1.5135 (14)
O4—C6	1.2185 (8)	C5—H1C5	0.993 (14)
N1—C3	1.3346 (9)	C5—H2C5	1.003 (14)
N1—C2	1.3877 (9)	C6—C7	1.5075 (10)
N1—H1N1	0.864 (14)	C7—C7ii	1.5153 (14)
N2—C3	1.3233 (9)	C7—H7A	0.970 (13)
N2—H1N2	0.868 (15)	C7—H7B	0.989 (13)
C3—S1—C1	90.47 (3)	O1—C4—C5	119.82 (6)
C6—O3—H1O3	109.7 (10)	O2—C4—C5	116.75 (6)
C3—N1—C2	113.99 (6)	C5i—C5—C4	113.78 (7)
C3—N1—H1N1	121.0 (9)	C5i—C5—H1C5	111.6 (8)
C2—N1—H1N1	125.0 (9)	C4—C5—H1C5	108.0 (8)
C3—N2—H1N2	119.6 (10)	C5i—C5—H2C5	111.7 (8)
C3—N2—H2N2	118.9 (8)	C4—C5—H2C5	105.5 (8)
H1N2—N2—H2N2	121.0 (13)	H1C5—C5—H2C5	105.7 (11)
C2—C1—S1	110.81 (6)	O4—C6—O3	123.50 (6)
C2—C1—H1	130.3 (8)	O4—C6—C7	124.39 (6)
S1—C1—H1	118.9 (8)	O3—C6—C7	112.10 (6)
C1—C2—N1	113.33 (7)	C6—C7—C7ii	112.82 (7)
C1—C2—H2	129.5 (8)	C6—C7—H7A	108.6 (7)
N1—C2—H2	117.2 (8)	C7ii—C7—H7A	110.8 (8)
N2—C3—N1	124.12 (6)	C6—C7—H7B	106.9 (8)
N2—C3—S1	124.49 (5)	C7ii—C7—H7B	110.7 (7)
N1—C3—S1	111.38 (5)	H7A—C7—H7B	106.8 (10)
O1—C4—O2	123.42 (6)
C3—S1—C1—C2	0.33 (6)	C1—S1—C3—N1	−0.78 (6)
S1—C1—C2—N1	0.18 (9)	O1—C4—C5—C5i	−4.29 (11)
C3—N1—C2—C1	−0.80 (9)	O2—C4—C5—C5i	176.67 (8)
C2—N1—C3—N2	−178.46 (7)	O4—C6—C7—C7ii	−5.84 (12)
C2—N1—C3—S1	1.04 (8)	O3—C6—C7—C7ii	175.31 (7)
C1—S1—C3—N2	178.72 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O1iii	0.868 (15)	1.974 (15)	2.8156 (9)	163.0 (14)
N2—H2N2···O1iv	0.889 (14)	1.959 (13)	2.8297 (9)	165.7 (13)
N1—H1N1···O2iii	0.865 (14)	1.823 (14)	2.6868 (8)	176.2 (15)
O3—H1O3···O2iv	0.888 (19)	1.696 (19)	2.5820 (8)	176.5 (19)
C1—H1···O4v	0.985 (13)	2.431 (14)	3.3086 (10)	148.2 (12)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O1i	0.868 (15)	1.974 (15)	2.8156 (9)	163.0 (14)
N2—H2N2⋯O1ii	0.889 (14)	1.959 (13)	2.8297 (9)	165.7 (13)
N1—H1N1⋯O2i	0.865 (14)	1.823 (14)	2.6868 (8)	176.2 (15)
O3—H1O3⋯O2ii	0.888 (19)	1.696 (19)	2.5820 (8)	176.5 (19)
C1—H1⋯O4iii	0.985 (13)	2.431 (14)	3.3086 (10)	148.2 (12)

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