2-Amino-1,3-thia-zolium dihydrogen phosphate.

In the title compound, C(3)H(5)N(2)S(+)·H(2)PO(4) (-), the dihydrogen phosphate anions form infinite chains along [001] via short O-H⋯O hydrogen bonds. The 2-amino-thia-zolium cations inter-connect these chains into a three-dimensional network by short linear or bifurcated N-H⋯O and weak C-H⋯O hydrogen bonds.

Related literature

For metal complexes of 2-amino­thia­zole and its derivatives used in medicine, see: De et al. (2008 ▶); Aridoss et al. (2009 ▶); Cukurovali et al. (2006 ▶); Franklin et al. (2008 ▶); Li et al. (2009 ▶); Alexandru et al. (2010 ▶); Mura et al. (2005 ▶). For the use of 2-amino­thia­zole in the decontamination of aqueous media or ethanol fuel, see: Cristante et al. (2006 ▶, 2007 ▶); Takeuchi et al. (2007 ▶). For uses of 2-amino­thia­zole and its derivatives as anti­corrosive films, see: Ciftci et al. (2011 ▶); Solmaz (2011 ▶). For non-linear optical properties and for structural properties of closely related compounds, see: Yesilel et al. (2008 ▶); Matulková et al. (2007 ▶, 2008 ▶, 2011a ▶,b ▶).

Experimental

Crystal data

C3H5N2S+·H2PO4 −

M = 198.14

Monoclinic,

a = 9.7581 (2) Å

b = 9.8826 (2) Å

c = 8.2794 (1) Å

β = 90.680 (2)°

V = 798.37 (2) Å3

Z = 4

Cu Kα radiation

μ = 5.35 mm−1

T = 120 K

0.47 × 0.17 × 0.13 mm

Data collection

Agilent Xcalibur Atlas Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010 ▶) T min = 0.453, T max = 1.000

7670 measured reflections

1419 independent reflections

1389 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.070

S = 1.07

1419 reflections

100 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrysAlis PRO (Agilent, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681104935X/im2339sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681104935X/im2339Isup2.hkl

Supplementary material file. DOI: 10.1107/S160053681104935X/im2339Isup3.cml

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

C3H5N2S+·H2PO4−	F(000) = 408
Mr = 198.14	Dx = 1.648 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 6931 reflections
a = 9.7581 (2) Å	θ = 4.5–66.8°
b = 9.8826 (2) Å	µ = 5.35 mm−1
c = 8.2794 (1) Å	T = 120 K
β = 90.680 (2)°	Plate, colourless
V = 798.37 (2) Å3	0.47 × 0.17 × 0.13 mm
Z = 4

Agilent Xcalibur Atlas Gemini ultra diffractometer	1419 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	1389 reflections with I > 2σ(I)
mirror	Rint = 0.025
Detector resolution: 10.3874 pixels mm-1	θmax = 66.9°, θmin = 4.5°
Rotation method data acquisition using ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2010)	k = −11→11
Tmin = 0.453, Tmax = 1.000	l = −9→7
7670 measured reflections

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: inferred from neighbouring sites
wR(F2) = 0.070	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0339P)2 + 0.5451P] where P = (Fo2 + 2Fc2)/3
1419 reflections	(Δ/σ)max = 0.001
100 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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. The hydrogen atoms were be localized from the difference Fourier map. Despite of that,all hydrogen atoms connected to C were constrained to ideal positions. The distance in N—H and O—H groups were left unrestrained. The isotropic temperature parameters of hydrogen atoms were calculated as 1.2*Ueq of the parent atom.

	x	y	z	Uiso*/Ueq
C1	0.66442 (17)	0.80237 (17)	0.1326 (2)	0.0234 (4)
C2	0.85753 (17)	0.75229 (19)	−0.0086 (2)	0.0283 (4)
H1C2	0.9367	0.7716	−0.0657	0.034*
C3	0.81429 (18)	0.62710 (18)	0.0206 (2)	0.0301 (4)
H1C3	0.8591	0.5492	−0.0132	0.036*
N1	0.57066 (15)	0.87839 (15)	0.20091 (19)	0.0303 (4)
H1N1	0.5829	0.9648	0.2168	0.036*
H2N1	0.5099	0.8487	0.2540	0.036*
N2	0.77265 (14)	0.85134 (15)	0.05485 (17)	0.0237 (3)
H1N2	0.7837	0.9509	0.0454	0.028*
O1	0.66404 (15)	0.33219 (15)	0.06047 (15)	0.0400 (4)
H1O1	0.6636	0.3367	−0.0481	0.048*
O2	0.65458 (14)	0.14664 (14)	0.25914 (15)	0.0338 (3)
O3	0.80601 (12)	0.12283 (11)	0.01267 (14)	0.0243 (3)
O4	0.87030 (12)	0.28418 (13)	0.23071 (15)	0.0301 (3)
H1O4	0.8469	0.3189	0.3326	0.036*
P1	0.74805 (4)	0.21447 (4)	0.14002 (5)	0.02120 (14)
S1	0.66311 (4)	0.62775 (4)	0.13014 (5)	0.02763 (15)

	U11	U22	U33	U12	U13	U23
C1	0.0219 (8)	0.0251 (9)	0.0234 (9)	−0.0034 (6)	0.0016 (6)	−0.0005 (6)
C2	0.0210 (8)	0.0331 (9)	0.0310 (9)	0.0010 (7)	0.0049 (7)	−0.0035 (8)
C3	0.0220 (9)	0.0288 (10)	0.0398 (10)	0.0024 (7)	0.0051 (7)	−0.0049 (7)
N1	0.0277 (8)	0.0262 (8)	0.0373 (9)	−0.0053 (6)	0.0157 (7)	−0.0039 (6)
N2	0.0216 (7)	0.0245 (7)	0.0250 (7)	−0.0023 (5)	0.0050 (5)	−0.0015 (6)
O1	0.0515 (9)	0.0436 (8)	0.0247 (7)	0.0265 (7)	−0.0028 (6)	−0.0091 (6)
O2	0.0347 (7)	0.0371 (7)	0.0300 (7)	−0.0138 (6)	0.0155 (5)	−0.0113 (6)
O3	0.0287 (6)	0.0216 (6)	0.0227 (6)	0.0031 (5)	0.0089 (5)	0.0001 (4)
O4	0.0228 (6)	0.0444 (8)	0.0231 (6)	−0.0071 (5)	0.0070 (5)	−0.0071 (5)
P1	0.0201 (2)	0.0230 (2)	0.0207 (2)	0.00071 (15)	0.00549 (16)	−0.00254 (15)
S1	0.0252 (2)	0.0228 (2)	0.0351 (3)	−0.00293 (15)	0.00515 (18)	−0.00053 (16)

C1—N1	1.317 (2)	N1—H2N1	0.7980
C1—N2	1.334 (2)	N2—H1N2	0.9934
C1—S1	1.726 (2)	O1—P1	1.564 (1)
C2—C3	1.330 (3)	O1—H1O1	0.8996
C2—N2	1.389 (2)	O2—P1	1.508 (1)
C2—H1C2	0.9300	O3—P1	1.505 (1)
C3—S1	1.741 (2)	O4—P1	1.562 (1)
C3—H1C3	0.9300	O4—H1O4	0.9413
N1—H1N1	0.8718
N1—C1—N2	123.9 (2)	C1—N2—C2	113.9 (2)
N1—C1—S1	124.79 (13)	C1—N2—H1N2	119.0
N2—C1—S1	111.3 (2)	C2—N2—H1N2	127.1
C3—C2—N2	113.3 (2)	P1—O1—H1O1	117.0
C3—C2—H1C2	123.4	P1—O4—H1O4	113.5
N2—C2—H1C2	123.4	O3—P1—O2	115.19 (7)
C2—C3—S1	111.3 (1)	O3—P1—O4	108.11 (7)
C2—C3—H1C3	124.3	O2—P1—O4	110.24 (7)
S1—C3—H1C3	124.3	O3—P1—O1	110.61 (7)
C1—N1—H1N1	121.9	O2—P1—O1	106.73 (8)
C1—N1—H2N1	123.4	O4—P1—O1	105.54 (8)
H1N1—N1—H2N1	112.3	C1—S1—C3	90.21 (8)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O2i	0.87	1.96	2.815 (2)	167
N1—H2N1···O1ii	0.80	2.31	3.076 (2)	162
N1—H2N1···O2ii	0.80	2.56	3.194 (2)	137
N2—H1N2···O3i	0.99	1.73	2.726 (2)	175
O1—H1O1···O2iii	0.90	1.61	2.504 (2)	176
O4—H1O4···O3iv	0.94	1.65	2.593 (2)	179
C2—H1C2···O4v	0.93	2.40	3.268 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O2i	0.87	1.96	2.815 (2)	167
N1—H2N1⋯O1ii	0.80	2.31	3.076 (2)	162
N1—H2N1⋯O2ii	0.80	2.56	3.194 (2)	137
N2—H1N2⋯O3i	0.99	1.73	2.726 (2)	175
O1—H1O1⋯O2iii	0.90	1.61	2.504 (2)	176
O4—H1O4⋯O3iv	0.94	1.65	2.593 (2)	179
C2—H1C2⋯O4v	0.93	2.40	3.268 (2)	155

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