Bis(2-amino­thia­zolium) succinate succinic acid

Fun, H.-K.; John, J.; Jebas, S.R.; Balasubramanian, T.

doi:10.1107/S1600536809007004

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o744

doi:10.1107/S1600536809007004

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Bis(2-aminothiazolium) succinate succinic acid

Hoong-Kun Fun,^a ^* Jain John,^b Samuel Robinson Jebas ^a ‡ and T. Balasubramanian ^b

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and ^bDepartment of Physics, National Institute of Technology, Tiruchirappalli 620 015, India
^*Correspondence e-mail: hkfun@usm.my

(Received 20 February 2009; accepted 25 February 2009; online 14 March 2009)

In the title compound, 2C₃H₅N₂S⁺·C₄H₄O₄²⁻·C₄H₆O₄, the thiazolium 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-aminothiazole molecule is protonated. Both the anion and the acid lie across inversion centres. The crystal packing is consolidated by intermolecular O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds. Molecules 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⁺·C₄H₄O₄²⁻·C₄H₆O₄
M_r = 436.46
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.027
wR(F²) = 0.077
S = 1.04
3691 reflections
167 parameters
All H-atom parameters refined
Δρ_max = 0.45 e Å⁻³
Δρ_min = −0.35 e Å⁻³

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) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y-1, z; (iii) x-1, y, z.

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809007004/sj2582sup1.cif

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

checkCIF report

Comment top

2-Aminothiazole derivatives have shown heribicidal, anti-inflammatory, anti-microbial and antiparasitic activities (Saarnivaara & Matilla, 1974). 2-Aminothiazole is listed as a thyroid inhibitor (Windholz, 2001). The orthorhombic form of 2-amino-1,3-thiazole has been reported (Caranoni & Reboul, 1982). Succinic acid is a dicarboxylic acid and is a precursor for many chemicals of industrial importance (Zeikus et al., 1999; Song & Lee, 2006). Succinic acid derivatives are mostly used in chemicals, food and pharmaceuticals (Sauer et al., 2008). The crystal structure of succinic acid has been reported (Gopalan et al., 2000; Leviel et al. 1981). Due to all these important properties, the title compound (I) has been synthesized and is reported here.

The asymmetric unit of (I) (Fig. 1) contains one molecule of protonated 2-aminothiazole, a half molecule of succinate and a half molecule of succinic acid. The anion and the acid lie across different inversion centres [symmetry codes (i) -x + 1, -y + 2, -z and (ii) -x + 2, -y + 2, -z respectively]. The thiazolium ring is planar with the maximum deviation from planarity being 0.0056 (8)Å for atom C3. The ring nitrogen of the 2-aminothiazole molecule is protonated thereby leading to a widening of the corresponding internal angle (C2–N1–C3) of the thiazolium ring to 113.99 (6)° [which is 109.4 (5)° in the unprotonated form of 2-aminothiazole] and an increase in the bond lengths of N1–C3 to 1.334 (9)Å and N1–C2 to 1.387 (9)Å [which are 1.298 (6)Å and 1.375 (6)Å respectively in its uncomplexed form] (Caranoni & Reboul, 1982). An increase in the C1–S1–C3 bond angle to 90.47 (3)° [which is 88.6 (3)° in the unprotonated form] and a decrease in the S1–C3–N1 bond angle to 111.38 (5)° [which is 114.9 (5)° in the uncomplexed form of 2-aminothiazole] (Caranoni & Reboul, 1982) are also observed.

The bond lengths and bond angles of the succinate and succinic acid are found to have normal values (Gopalan et al., 2000; Leviel & Auvert, 1981). The crystal packing is consolidated by O—H···O, N—H···O and C—H···O intermolecular hydrogen bonds (Table 1) together with intermolecular [O—Oⁱ = 2.5820 (8) Å; O—N^ii-iii = 2.6868 (8) to 2.8297 (9) Å, short contacts [symmetry code: (i) x,-1 + y,z; (ii) 3/2 - x,1/2 + y,1/2 - z; (iii) x,1 + y,z]. Molecules are stacked down the b axis(Fig.2).

Related literature top

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 top

2- Aminothiazole (0.100 g, 1 mmol) and succinic acid (0.118 g, 1 mmol) were dissolved in ethanol (25 ml) in a 1:1 molar ratio. The clear brown solution obtained was refluxed for 6 h at a temperature of 323 K. Brown coloured crystals were harvested after two weeks on slow evaporation of the solvent.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom numbering scheme. [symmetry operators used to generate equivalent atoms are (i) -x + 1, -y + 2, -z and (ii) -x + 2, -y + 2, -z for the anion and acid respectively].
	Fig. 2. The crystal packing of the title compound, viewed along the b axis. Dashed lines indicate the hydrogen bonding.

Bis(2-aminothiazolium) succinate succinic acid solvate top

Crystal data top

2C₃H₅N₂S⁺·C₄H₄O₄²⁻·C₄H₆O₄	F(000) = 456
M_r = 436.46	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0423P)² + 0.2556P] where P = (F_o² + 2F_c²)/3
3691 reflections	(Δ/σ)_max = 0.001
167 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

2C₃H₅N₂S⁺·C₄H₄O₄²⁻·C₄H₆O₄	V = 916.85 (3) Å³
M_r = 436.46	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1680 (2) Å	µ = 0.34 mm⁻¹
b = 5.1012 (1) Å	T = 100 K
c = 18.3850 (4) Å	0.58 × 0.42 × 0.32 mm
β = 105.961 (1)°

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	3691 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3442 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.897	R_int = 0.022
16689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.027	0 restraints
wR(F²) = 0.077	All H-atom parameters refined
S = 1.04	Δρ_max = 0.45 e Å⁻³
3691 reflections	Δρ_min = −0.35 e Å⁻³
167 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+2, −z.

Hydrogen-bond geometry (Å, º) top

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···O1^iv	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···O2^iv	0.888 (19)	1.696 (19)	2.5820 (8)	176.5 (19)
C1—H1···O4^v	0.985 (13)	2.431 (14)	3.3086 (10)	148.2 (12)

Symmetry codes: (iii) −x+3/2, y−1/2, −z+1/2; (iv) x, y−1, z; (v) x−1, y, z.

Experimental details

Crystal data
Chemical formula	2C₃H₅N₂S⁺·C₄H₄O₄²⁻·C₄H₆O₄
M_r	436.46
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.1680 (2), 5.1012 (1), 18.3850 (4)
β (°)	105.961 (1)
V (Å³)	916.85 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.34
Crystal size (mm)	0.58 × 0.42 × 0.32

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.826, 0.897
No. of measured, independent and observed [I > 2σ(I)] reflections	16689, 3691, 3442
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.787

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.077, 1.04
No. of reflections	3691
No. of parameters	167
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.45, −0.35

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+3/2, y−1/2, −z+1/2; (ii) x, y−1, z; (iii) x−1, y, z.

Footnotes

‡Permanent address: Department of Physics, Karunya University, Karunya Nagar, Coimbatore 641 114, India.

Acknowledgements

HKF and SRJ thank the Malaysian Government and Universiti Sains Malaysia for the Science Fund grant No. 305/PFIZIK/613312. SRJ thanks Universiti Sains Malaysia for a post–doctoral research fellowship. HKF also thanks Universiti Sains Malaysia for the Research University Golden Goose grant No.1001/PFIZIK/811012.

References

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