2-Amino-2-thia­zoline and its 1:1 organic salt with 2-naphthoxy­acetic acid

Lynch, D.E.

doi:10.1107/S0108270104015604

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 9| September 2004| Pages o677-o679

doi:10.1107/S0108270104015604

2-Amino-2-thiazoline and its 1:1 organic salt with 2-naphthoxyacetic acid

Daniel E. Lynch ^a ^*

^aSchool of Science and the Environment, Coventry University, Coventry CV1 5FB, England
^*Correspondence e-mail: apx106@coventry.ac.uk

(Received 15 June 2004; accepted 25 June 2004; online 21 August 2004)

The crystal structures of 2-amino-2-thiazoline, C₃H₆N₂S, and 2-amino-2-thiazolinium 2-naphthoxyacetate, C₃H₇N₂S⁺·C₁₂H₉O₃⁻, are reported. The structure of 2-amino-2-thiazoline consists of two unique molecules that construct a convoluted hydrogen-bonded ribbon involving [R_2^2] (8) graph-set association via both N—H⋯N and N—H⋯S interactions. The organic salt structure consists of the two molecules associated via an [R_2^2] (8) graph-set dimer through N—H⋯O interactions, with the hydrogen-bonding network propagated via additional N—H⋯O three-centre interactions from the second 2-amine H atom.

Comment

2-Amino-2-thiazoline has been reported as a potential inducer of the reverse transformation of tumour cells, with the mechanism for anticancer action depending on strong metal–ligand binding via the N atoms (Brugarolas & Gosálvez, 1982 ). Alternatively, the placement of the N atoms in this molecule also makes it suitable for association with carboxylic acids, and four subsequent crystal structures have been reported (Lynch et al., 1998 ; Lynch, Cooper et al., 1999 ; Lynch, Nicholls et al., 1999 ). Such structures are part of a broader study of complexes of carboxylic acids with 2-aminothiazole derivatives that has thus far resulted in the characterization of 19 published crystal structures, with three others published recently (Lynch et al., 2004 ). Although the structure of 2-aminothiazole was published by Caranoni & Reboul (1982 ), the structure of 2-amino-2-thiazoline has not been reported; the structure of this compound, (I), is reported here. 2-Naphthoxyacetic acid is used as a plant hormone to promote growth of roots on clippings and to prevent fruit from falling prematurely, although stunted growth results if it is used in excess (The Merck Index, 2001 ). 2-Naphthoxyacetic acid is related in structure to phenoxyacetic acid, whose chloro derivatives have been used extensively by the author for complexing with carboxylic acids (Lynch, Cooper et al., 1999) and should thus have comparable structural properties. Furthermore, the Cambridge Structural Database (Allen, 2002 ) contains only four previously reported crystal structures containing the compound, of which two are the parent structure (Howie et al., 2001 ), thus more structures containing 2-naphthoxyacetic acid are required. For these reasons, the structure of the 1:1 organic salt of (I) with 2-naphthoxyacetic acid is also reported here, viz. (II).

Compound (I) packs with two unique thiazoline molecules associated in a hydrogen-bonded [R_2^2] (8) graph-set dimer (Etter, 1990 ) via N—H⋯N interactions (Fig. 1). The hydrogen-bonding network is then extended by N—H⋯S interactions, resulting in further [R_2^2] (8) graph-set arrangements. Hydrogen-bonding associations for this compound are listed in Table 1. Together, these interactions create a convoluted hydrogen-bonded ribbon that runs in the direction of the ac axis diagonal (Fig. 2). The incorporation of the S atoms into the hydrogen-bonding network is not observed in the structure of 2-aminothiazole but is seen in the structure of a related 2-aminothiazole derivative, viz. 2-amino-4-(4-bisphenyl)-1,3-thiazole (Lynch et al., 2002 ). In (I), there is a single S⋯S close contact [3.520 (5) Å] between atom S1B and the symmetry-equivalent atom at (2 − x, 1 − y, −z).

The structure of (II) comprises the organic salt of a non-planar acetate molecule and a protonated thiazoline molecule arranged in a packing mode commonly observed for these types of molecules. In contrast to its planar parent structure, the acetate chain of the naphthoxyacetate molecule in (II) adopts an anticlinical (or hooked) arrangement, as classified for phenoxyacetic acids (Smith & Kennard, 1979 ) and defined by the C2B—O11B—C12B—C13B torsion angle [92.8 (2)°; Fig. 3]. Packing with the thiazoline molecule has an associated effect on (2,4,5-trichlorophenoxy)acetic acid, whose structure is planar in the parent compound but hooked in the salt complex (Lynch, Cooper et al., 1999). The components of (II), like those of the vast majority of adducts/organic salts comprising a 2-amino-heterocycle and a carboxylic acid molecule, associate via an unsymmetrical [R_2^2] (8) graph-set dimer between the N=C—NH₂ site and the carboxylate group (Fig. 4). In general, this association is unsymmetrical in that the N3A⋯O14B distance, or equivalent, is (apart from a very few cases) shorter than the N21A⋯O15B distance, although the values listed in Table 2 indicate that the structure of (I) is one of the very few exceptions where the opposite has occurred. Another common feature of this association is the inconsistency of the C2A—N21A [1.302 (2) Å] and C2A—N3A [1.324 (2) Å] bond lengths, as previously highlighted (Lynch et al., 2000 ). The propagation of the hydrogen-bonding network via the N21A—H22A⋯O14B(x, y − 1, z) interaction has also been observed previously for these types of systems (Lynch, Nicholls et al., 1999), although the additional interaction with atom O11B is not common amongst complexes of 2-aminothiazole derivatives and phenoxyacetic acids (Lynch, Cooper et al., 1999).

The structure of (II) is actually the eighth known complex of a carboxylic acid with (I), with three others currently unpublished (Lynch et al., 2004). Elucidation of the structure of (I) is important because, as highlighted above, when collecting data on the inconsistencies in the bond distances across the N=C—NH₂ site for any type of complexed 2-amino-heterocyclic compound, it is important to compare bond distances against those of the parent structure. For example, compare the C2A—N21A and C2A—N3A distances listed above with those for (I), viz. 1.348 (5)/1.267 (5) and 1.351 (5)/1.276 (5) Å for molecules A and B, respectively. The mean respective distances for the seven complex structures are 1.305 (5) and 1.314 (5) Å. Also of interest is the N3—C2—N21 (or equivalent) angle, which decreases upon association with a carboxylic acid. Compare, for (I), values of 124.8 (3) and 125.8 (3)° with that of 124.53 (17)° in (II) [the mean angle over the eight structures is 124.0 (5)°]. In one or two instances where N1A is a quaternary N atom, it might be suitable to suggest that the N1A—C2A double bond has moved to C2A—N21A, but this simple `pushing of the double bond around' does not fit a significant portion of the available data. It is the intention of the author to publish such findings in a dedicated paper, but not without each of the parent structures and a supportive list of different complexes, which the structures in this paper add to.

Figure 1
A view of the asymmetric unit and atom-numbering scheme of (I

). Displacement ellipsoids are drawn at the 50% probability level. Broken lines indicate intramolecular hydrogen bonds.

Figure 2
A packing diagram for (I

). [Symmetry codes: (i) x − $[{1\over 2}]$ , −y + $[1\over 2]$ , z + $[1\over 2]$ ; (ii) x + $[1\over 2]$ , −y + $[1\over 2]$ , z − $[1\over2]$ .]

Figure 3
A view of the asymmetric unit and atom-numbering scheme of (II

). Displacement ellipsoids are drawn at the 50% probability level. Broken lines indicate intramolecular hydrogen bonds.

Figure 4
A packing diagram for (II

). [Symmetry code: (iii) x, y − 1, z.]

Experimental

Crystals of (I) were grown from an ethanol solution. For (II), equimolar amounts of (I) and 2-naphthoxyacetic acid were refluxed in ethanol for 20 min. Crystals of (II) were grown by slow evaporation of the reaction solution.

Compound (I)

Crystal data

C₃H₆N₂S
M_r = 102.17
Monoclinic, P2₁/n
a = 5.8980 (5) Å
b = 14.8324 (12) Å
c = 10.7092 (8) Å
β = 101.974 (4)°
V = 916.47 (13) Å³
Z = 8
D_x = 1.481 Mg m⁻³
Mo Kα radiation
Cell parameters from 8580 reflections
θ = 2.9–27.5°
μ = 0.53 mm⁻¹
T = 120 (2) K
Prism, yellow
0.20 × 0.20 × 0.10 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995 ) T_min = 0.826, T_max = 0.948
10 396 measured reflections
2101 independent reflections
1149 reflections with I > 2σ(I)
R_int = 0.112
θ_max = 27.5°
h = −7 → 7
k = −19 → 19
l = −13 → 13

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.160
S = 1.02
2101 reflections
109 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0802P)²] where P = (F_o² + 2F_c²_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.49 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bonding geometry (Å, °) for (I)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21A—H21A⋯N3B	0.88	2.09	2.950 (5)	164
N21A—H22A⋯S1Bⁱ	0.88	2.75	3.575 (3)	156
N21B—H21B⋯N3A	0.88	2.04	2.916 (5)	171
N21B—H22B⋯S1Aⁱⁱ	0.88	2.70	3.526 (3)	156
Symmetry codes: (i) $[x-{\script{1\over 2}},-y+{\script{1\over 2}},z+{\script{1\over 2}}]$ ; (ii) $[x+ {\script{1\over 2}},-y+{\script{1\over 2}},z-{\script{1\over 2}}]$ .

Compound (II)

Crystal data

C₃H₇N₂S⁺·C₁₂H₉O₃⁻
M_r = 304.36
Monoclinic, P2₁/c
a = 8.3669 (2) Å
b = 6.3707 (1) Å
c = 26.3457 (6) Å
β = 92.1992 (9)°
V = 1403.27 (5) Å³
Z = 4
D_x = 1.441 Mg m⁻³
Mo Kα radiation
Cell parameters from 4067 reflections
θ = 2.9–27.5°
μ = 0.24 mm⁻¹
T = 120 (2) K
Plate, colourless
0.32 × 0.10 × 0.04 mm

Data collection

Nonius KappaCCD area-detector diffractometer
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995) T_min = 0.710, T_max = 0.990
15 534 measured reflections
3183 independent reflections
2546 reflections with I > 2σ(I)
R_int = 0.091
θ_max = 27.4°
h = −10 → 10
k = −7 → 8
l = −34 → 34

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.121
S = 1.02
3183 reflections
194 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.0503P)² + 0.8055P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 2
Hydrogen-bonding geometry (Å, °) for (II)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N21A—H21A⋯O15B	0.88	1.88	2.754 (2)	171
N21A—H22A⋯O14Bⁱⁱⁱ	0.88	1.93	2.787 (2)	166
N21A—H22A⋯O11Bⁱⁱⁱ	0.88	2.56	2.965 (2)	109
N3A—H3A⋯O14B	0.87 (2)	2.01 (2)	2.871 (2)	170 (2)
Symmetry code: (iii) x,y-1,z.

All H atoms, except for the H atom on the N⁺ ion in (II), were included in the refinement at calculated positions in the riding-model approximation, with N—H distances of 0.88 Å, and C—H distances of 0.95 (aromatic H atoms) and 0.99 Å (CH₂ H atoms). The U_iso(H) values were set at 1.25U_eq of the carrier atom. The H atom on the N⁺ ion was located in a difference synthesis and both the positional and displacement parameters were refined. A high R_int value for (I) was the result of weak high-angle data.

For both compounds, data collection: DENZO (Otwinowski & Minor, 1997 ) and COLLECT (Hooft, 1998 ); cell refinement: DENZO and COLLECT; data reduction: DENZO, SCALEPACK (Otwinowski & Minor, 1997) and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994 ) and PLATON97 (Spek, 1997 ); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Supporting information

Crystal structure: contains datablocks I, II, global. DOI: 10.1107/S0108270104015604/sk1737sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104015604/sk1737Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270104015604/sk1737IIsup3.hkl

Comment top

2-Amino-2-thiazoline has been reported as a potential inducer of the reverse transformation of tumour cells, with the mechanism for anticancer action depending on strong metal–ligand binding via the N atoms (Brugarolas & Gosálvez, 1982). Alternatively, the placement of the N atoms in this molecule also makes it suitable for association with carboxylic acids, and four subsequent crystal structures have been reported (Lynch et al., 1998; Lynch et al., 1999a; Lynch et al., 1999b). Such structures are part of a broader study of complexes of carboxylic acids with 2-aminothiazole derivatives that has thus far resulted in the characterization of 19 published crystal structures, with another four currently awaiting publication (Lynch et al., 2004). Although the structure of 2-aminothiazole was published by Caranoni & Reboul (1982), the structure of 2-amino-2-thiazoline has not been reported; the structure of this compound, C₃H₆N₂S, (I), is reported here. 2-Naphthoxyacetic acid is used as a plant hormone, to promote growth of roots on clippings and to prevent fruit from falling prematurely, although stunted growth results if it is used in excess (The Merck Index, 2001). 2-Naphthoxyacetic acid is related in structure to phenoxyacetic acid, whose chloro-derivatives have been used extensively by the author for complexing with carboxylic acids (Lynch et al., 1999a), and should thus have comparable structural properties. Furthermore, the Cambridge Crystallographic Database (Allen, 2002) reveals that there are only four previously reported crystal structures containing the compound, of which two are both the parent structure (Howie et al., 2001), thus more structures containing 2-naphthoxyacetic acid are required. For these reasons the 1:1 organic salt structure of (I) with 2-naphthoxyacetic acid, (C₃H₈N₂S)⁺(C₁₂H₈O₃)⁻, (II), is also reported here.

Compound (I) packs with two unique thiazoline molecules associated in a hydrogen-bonded R₂²(8) graph-set dimer (Etter, 1990) via N—H···N interactions (Fig. 1). The hydrogen-bonding network is then extended by N—H···S interactions, resulting in further R₂²(8) graph-set arrangements. Hydrogen-bonding associations for this compound are listed in Table 1. Together, these interactions create a convoluted hydrogen-bonded ribbon that runs in the direction of the ac axis diagonal. The incorporation of the S atoms into the hydrogen-bonding network to form a hydrogen-bonded ribbon is not observed in the structure of 2-aminothiazole but is seen in the structure of another related 2-aminothiazole derivative, 2-amino-4-(4-bisphenyl)-1,3-thiazole (Lynch et al., 2002). In (I), there is a single S···S close contact of 3.520 (5) Å between atom S1B and a symmetry-equivalent atom (2 − x, 1 − y, −z).

The structure of (II) comprises the organic salt of a non-planar acetate molecule and a protonated thiazoline molecule arranged in a packing mode commonly observed for these types of molecules. In contrast to its planar parent structure, the acetate chain of the naphthoxyacetate molecule in (II) adopts an anticlinical (or hooked) arrangement, as classified for phenoxyacetic acids (Smith & Kennard, 1979) and defined by the equivalent C2B—O11B—C12B—C13B torsion angle [92.8 (2)°; Fig. 3]. Packing with the thiazoline molecule had an associated effect on (2,4,5-trichlorophenoxy)acetic acid, whose parent structure is planar but is hooked in the salt complex (Lynch et al., 1999a). Like the vast majority of adducts/organic salts comprising a 2-aminoheterocyclic and a carboxylic acid, the components of (II) associate via an unsymmetrical R₂²(8) graph-set dimer between the N=C—NH₂ site and the carboxylate group (Fig. 4). In general, this association is unsymmetrical in that the N3A···O14B distance, or equivalent, is (apart from very few cases) shorter than the N21A···O15B distance, although the values listed in Table 2 indicate that this structure is one of the very few exceptions where the opposite has occurred. Another common feature of this association includes the inconsistency of the C2A—N21A [1.302 (2) Å] and C2A—N3A [1.324 (2) Å] bond lengths, as previously highlighted (Lynch et al., 2000). The propagation of the hydrogen-bonding network via the N21A—H22A···O14B interaction has also been previously observed for these types of systems (Lynch et al., 1999b), although the additional interaction with atom O11B is not common amongst complexes of 2-aminothaizole derivatives and phenoxyacetic acids (Lynch et al., 1999a).

The structure of (II) is actually the eighth known complex of a carboxylic acid with (I), with three others currently unpublished (Lynch et al., 2004). Elucidation of the structure of (I) is important because in each case where the author has been collecting data on the inconsistencies in the bond distances across the N=C—NH₂ site, as highlighted above, for any type of complexed 2-aminoheterocyclic compound, it is important to compare bond distances against those of the parent structure. For example, compare the C2A—N21A and C2A—N3A distances listed above against those for (I), viz. 1.348 (5) and 1.267 (5) Å, and 1.351 (5) and 1.276 (5) Å, for molecules A and B, respectively. The mean respective distances for the seven complex structures are 1.305 (5) and 1.314 (5) Å. Also of interest is the N3—C2—N21 (or equivalent) angle that decreases upon association with a carboxylic acid. Compare, for (I), 124.8 (3) and 125.8 (3)° against 124.53 (17)° in (II) (mean angle over the eight structures = 124.0 (5)°]. In one or two instances where N1A is a quaternary N atom it might be suitable to suggest that the N1A—C2A double bond has moved to C2A—N21A, but this simple `pushing of the double bond around' does not fit a significant portion of the available data. It is the author's full intention to publish such findings in a dedicated paper, but not without each of the parent structures and a supportive list of different complexes, which the structures in this paper add to.

Experimental top

Crystals of (I) were grown from ethanol solution. For (II), equimolar amounts of (I) and 2-naphthoxyacetic acid were refluxed in ethanol for 20 min. Crystals of (II) were grown from the slow evaporation of the reaction solution.

Computing details top

For both compounds, data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO, SCALEPACK (Otwinowski & Minor, 1997) and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

	Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A packing diagram for (I). [Symmetry codes: (i) x − 1/2, −y + 1/2, z + 1/2; (ii) x + 1/2, −y + 1/2, z − 1/2.]
	Fig. 3. The molecular configuration and atom-numbering scheme for (II). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 4. A packing diagram for (II). [Symmetry code: (i) x, y − 1, z.]

(I) 2-Amino-2-thiazoline top

Crystal data top

C₃H₆N₂S	F(000) = 432
M_r = 102.17	D_x = 1.481 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 8580 reflections
a = 5.8980 (5) Å	θ = 2.9–27.5°
b = 14.8324 (12) Å	µ = 0.53 mm⁻¹
c = 10.7092 (8) Å	T = 120 K
β = 101.974 (4)°	Prism, yellow
V = 916.47 (13) Å³	0.20 × 0.20 × 0.10 mm
Z = 8

Data collection top

Nonius KappaCCD area-detector diffractometer	2101 independent reflections
Radiation source: Nonius FR591 rotating anode	1149 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.112
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.4°
ϕ and ω scans	h = −7→7
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −19→19
T_min = 0.826, T_max = 0.948	l = −13→13
10396 measured reflections

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.160	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0802P)²] where P = (F_o² + 2F_c²)/3
2101 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.49 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₃H₆N₂S	V = 916.47 (13) Å³
M_r = 102.17	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.8980 (5) Å	µ = 0.53 mm⁻¹
b = 14.8324 (12) Å	T = 120 K
c = 10.7092 (8) Å	0.20 × 0.20 × 0.10 mm
β = 101.974 (4)°

Data collection top

Nonius KappaCCD area-detector diffractometer	2101 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1149 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.948	R_int = 0.112
10396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.160	H-atom parameters constrained
S = 1.02	Δρ_max = 0.49 e Å⁻³
2101 reflections	Δρ_min = −0.41 e Å⁻³
109 parameters

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

	x	y	z	U_iso*/U_eq
S1A	−0.02730 (17)	0.06496 (7)	0.20321 (9)	0.0269 (3)
C2A	0.1754 (6)	0.1438 (2)	0.1644 (4)	0.0219 (8)
N21A	0.3725 (6)	0.1576 (2)	0.2517 (3)	0.0295 (8)
H21A	0.4788	0.1946	0.2348	0.037*
H22A	0.3949	0.1296	0.3257	0.037*
N3A	0.1270 (5)	0.1808 (2)	0.0554 (3)	0.0263 (8)
C4A	−0.0968 (7)	0.1525 (3)	−0.0198 (4)	0.0271 (9)
H41A	−0.1959	0.2062	−0.0434	0.034*
H42A	−0.0732	0.1238	−0.0996	0.034*
C5A	−0.2206 (7)	0.0864 (3)	0.0520 (4)	0.0309 (10)
H51A	−0.3679	0.1127	0.0655	0.039*
H52A	−0.2554	0.0297	0.0031	0.039*
S1B	0.77862 (17)	0.43581 (7)	0.04456 (9)	0.0246 (3)
C2B	0.5938 (6)	0.3476 (2)	0.0781 (4)	0.0228 (8)
N21B	0.4037 (5)	0.3289 (2)	−0.0124 (3)	0.0289 (8)
H21B	0.3088	0.2856	0.0002	0.036*
H22B	0.3747	0.3599	−0.0840	0.036*
N3B	0.6540 (5)	0.3076 (2)	0.1853 (3)	0.0260 (8)
C4B	0.8603 (6)	0.3461 (3)	0.2639 (4)	0.0270 (9)
H41B	0.9621	0.2972	0.3062	0.034*
H42B	0.8163	0.3841	0.3311	0.034*
C5B	0.9918 (7)	0.4032 (3)	0.1840 (4)	0.0306 (10)
H51B	1.1178	0.3678	0.1592	0.038*
H52B	1.0599	0.4571	0.2322	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0240 (6)	0.0311 (6)	0.0266 (6)	−0.0060 (4)	0.0077 (4)	0.0016 (4)
C2A	0.020 (2)	0.0226 (19)	0.024 (2)	−0.0013 (15)	0.0066 (17)	−0.0004 (16)
N21A	0.0234 (18)	0.0421 (19)	0.0225 (18)	−0.0074 (16)	0.0039 (14)	0.0078 (15)
N3A	0.0228 (18)	0.0346 (18)	0.0217 (18)	−0.0079 (14)	0.0049 (14)	0.0011 (15)
C4A	0.024 (2)	0.031 (2)	0.026 (2)	−0.0034 (17)	0.0041 (17)	0.0014 (18)
C5A	0.020 (2)	0.043 (3)	0.030 (2)	−0.0073 (18)	0.0067 (19)	0.0003 (19)
S1B	0.0229 (6)	0.0269 (5)	0.0253 (6)	0.0042 (4)	0.0079 (4)	−0.0014 (4)
C2B	0.019 (2)	0.0241 (19)	0.028 (2)	0.0016 (16)	0.0109 (17)	0.0035 (17)
N21B	0.0272 (19)	0.0346 (18)	0.0232 (18)	0.0097 (14)	0.0014 (15)	−0.0031 (15)
N3B	0.0213 (18)	0.0331 (18)	0.0229 (18)	0.0037 (14)	0.0034 (15)	−0.0018 (14)
C4B	0.020 (2)	0.032 (2)	0.028 (2)	0.0064 (17)	0.0043 (17)	−0.0013 (18)
C5B	0.024 (2)	0.040 (2)	0.027 (2)	0.0027 (18)	0.0037 (18)	−0.0074 (19)

Geometric parameters (Å, º) top

S1A—C2A	1.782 (4)	S1B—C2B	1.786 (4)
S1A—C5A	1.805 (4)	S1B—C5B	1.807 (4)
C2A—N3A	1.267 (5)	C2B—N3B	1.276 (5)
C2A—N21A	1.348 (5)	C2B—N21B	1.351 (5)
N21A—H21A	0.88	N21B—H21B	0.88
N21A—H22A	0.88	N21B—H22B	0.88
N3A—C4A	1.458 (5)	N3B—C4B	1.446 (5)
C4A—C5A	1.522 (5)	C4B—C5B	1.525 (5)
C4A—H41A	0.99	C4B—H41B	0.99
C4A—H42A	0.99	C4B—H42B	0.99
C5A—H51A	0.99	C5B—H51B	0.99
C5A—H52A	0.99	C5B—H52B	0.99

C2A—S1A—C5A	90.24 (18)	C2B—S1B—C5B	89.24 (18)
N3A—C2A—N21A	124.8 (3)	N3B—C2B—N21B	125.8 (3)
N3A—C2A—S1A	117.7 (3)	N3B—C2B—S1B	117.1 (3)
N21A—C2A—S1A	117.5 (3)	N21B—C2B—S1B	117.2 (3)
C2A—N21A—H21A	120.0	C2B—N21B—H21B	120.0
C2A—N21A—H22A	120.0	C2B—N21B—H22B	120.0
H21A—N21A—H22A	120.0	H21B—N21B—H22B	120.0
C2A—N3A—C4A	112.9 (3)	C2B—N3B—C4B	112.5 (3)
N3A—C4A—C5A	112.4 (3)	N3B—C4B—C5B	110.9 (3)
N3A—C4A—H41A	109.1	N3B—C4B—H41B	109.5
C5A—C4A—H41A	109.1	C5B—C4B—H41B	109.5
N3A—C4A—H42A	109.1	N3B—C4B—H42B	109.5
C5A—C4A—H42A	109.1	C5B—C4B—H42B	109.5
H41A—C4A—H42A	107.9	H41B—C4B—H42B	108.0
C4A—C5A—S1A	106.7 (3)	C4B—C5B—S1B	105.3 (3)
C4A—C5A—H51A	110.4	C4B—C5B—H51B	110.7
S1A—C5A—H51A	110.4	S1B—C5B—H51B	110.7
C4A—C5A—H52A	110.4	C4B—C5B—H52B	110.7
S1A—C5A—H52A	110.4	S1B—C5B—H52B	110.7
H51A—C5A—H52A	108.6	H51B—C5B—H52B	108.8

C5A—S1A—C2A—N3A	−2.7 (3)	C5B—S1B—C2B—N3B	9.6 (3)
C5A—S1A—C2A—N21A	179.3 (3)	C5B—S1B—C2B—N21B	−170.0 (3)
N21A—C2A—N3A—C4A	179.2 (4)	N21B—C2B—N3B—C4B	−177.2 (4)
S1A—C2A—N3A—C4A	1.4 (4)	S1B—C2B—N3B—C4B	3.3 (4)
C2A—N3A—C4A—C5A	1.0 (5)	C2B—N3B—C4B—C5B	−17.9 (5)
N3A—C4A—C5A—S1A	−2.8 (4)	N3B—C4B—C5B—S1B	23.4 (4)
C2A—S1A—C5A—C4A	2.9 (3)	C2B—S1B—C5B—C4B	−17.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N3B	0.88	2.09	2.950 (5)	164
N21A—H22A···S1Bⁱ	0.88	2.75	3.575 (3)	156
N21B—H21B···N3A	0.88	2.04	2.916 (5)	171
N21B—H22B···S1Aⁱⁱ	0.88	2.70	3.526 (3)	156

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

(II) 2-Amino-2-thiazolium 2-naphthoxyacetate top

Crystal data top

C₃H₇N₂S⁺·C₁₂H₉O₃⁻	F(000) = 640
M_r = 304.36	D_x = 1.441 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4067 reflections
a = 8.3669 (2) Å	θ = 2.9–27.5°
b = 6.3707 (1) Å	µ = 0.24 mm⁻¹
c = 26.3457 (6) Å	T = 120 K
β = 92.1992 (9)°	Plate, colourless
V = 1403.27 (5) Å³	0.32 × 0.10 × 0.04 mm
Z = 4

Data collection top

Nonius KappaCCD area-detector diffractometer	3183 independent reflections
Radiation source: Nonius FR591 rotating anode	2546 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.091
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.4°, θ_min = 3.1°
ϕ and ω scans	h = −10→10
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −7→8
T_min = 0.710, T_max = 0.990	l = −34→34
15534 measured reflections

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0503P)² + 0.8055P] where P = (F_o² + 2F_c²)/3
3183 reflections	(Δ/σ)_max < 0.001
194 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₃H₇N₂S⁺·C₁₂H₉O₃⁻	V = 1403.27 (5) Å³
M_r = 304.36	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.3669 (2) Å	µ = 0.24 mm⁻¹
b = 6.3707 (1) Å	T = 120 K
c = 26.3457 (6) Å	0.32 × 0.10 × 0.04 mm
β = 92.1992 (9)°

Data collection top

Nonius KappaCCD area-detector diffractometer	3183 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	2546 reflections with I > 2σ(I)
T_min = 0.710, T_max = 0.990	R_int = 0.091
15534 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.121	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.25 e Å⁻³
3183 reflections	Δρ_min = −0.34 e Å⁻³
194 parameters

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

	x	y	z	U_iso*/U_eq
S1A	−0.19892 (6)	−0.56175 (8)	0.06199 (19)	0.02416 (16)
C2A	−0.0340 (2)	−0.3943 (3)	0.06063 (7)	0.0173 (4)
N21A	0.11091 (18)	−0.4589 (3)	0.07144 (6)	0.0198 (4)
H21A	0.1913	−0.3698	0.0712	0.025*
H22A	0.1285	−0.5917	0.0790	0.025*
N3A	−0.07266 (19)	−0.1983 (3)	0.04883 (6)	0.0188 (3)
H3A	−0.005 (3)	−0.097 (4)	0.0543 (8)	0.023 (6)*
C4A	−0.2446 (2)	−0.1539 (3)	0.04747 (7)	0.0218 (4)
H41A	−0.2715	−0.0441	0.0220	0.027*
H42A	−0.2781	−0.1050	0.0811	0.027*
C5A	−0.3271 (2)	−0.3597 (3)	0.03314 (8)	0.0228 (4)
H51A	−0.3356	−0.3768	−0.0042	0.029*
H52A	−0.4356	−0.3655	0.0468	0.029*
C1B	0.2758 (2)	0.3025 (3)	0.19187 (7)	0.0194 (4)
H1B	0.2442	0.1666	0.1805	0.024*
C2B	0.3684 (2)	0.4257 (3)	0.16244 (7)	0.0177 (4)
C3B	0.4200 (2)	0.6263 (3)	0.17909 (7)	0.0206 (4)
H3B	0.4866	0.7082	0.1584	0.026*
C4B	0.3745 (2)	0.7029 (3)	0.22471 (7)	0.0215 (4)
H4B	0.4095	0.8381	0.2355	0.027*
C5B	0.2202 (2)	0.6600 (3)	0.30307 (7)	0.0241 (4)
H5B	0.2536	0.7948	0.3147	0.030*
C6B	0.1201 (2)	0.5432 (3)	0.33145 (7)	0.0258 (5)
H6B	0.0818	0.5985	0.3622	0.032*
C7B	0.0730 (2)	0.3398 (3)	0.31514 (7)	0.0274 (5)
H7B	0.0042	0.2588	0.3353	0.034*
C8B	0.1256 (2)	0.2589 (3)	0.27081 (7)	0.0234 (4)
H8B	0.0945	0.1213	0.2607	0.029*
C9B	0.2266 (2)	0.3787 (3)	0.23966 (7)	0.0201 (4)
C10B	0.2751 (2)	0.5823 (3)	0.25623 (7)	0.0199 (4)
O11B	0.41670 (15)	0.3708 (2)	0.11458 (5)	0.0190 (3)
C12B	0.4426 (2)	0.1542 (3)	0.10439 (8)	0.0209 (4)
H12B	0.4765	0.0852	0.1367	0.026*
H13B	0.5329	0.1433	0.0813	0.026*
C13B	0.3018 (2)	0.0295 (3)	0.08086 (7)	0.0177 (4)
O14B	0.16423 (15)	0.1099 (2)	0.07750 (5)	0.0199 (3)
O15B	0.34007 (16)	−0.15009 (2)	0.06632 (5)	0.0239 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1A	0.0187 (3)	0.0224 (3)	0.0313 (3)	0.00326 (18)	−0.00004 (19)	−0.0037 (2)
C2A	0.0178 (9)	0.0186 (10)	0.0157 (8)	0.0009 (7)	0.0024 (7)	0.0017 (7)
N21A	0.0162 (8)	0.0173 (9)	0.0259 (8)	−0.0007 (6)	−0.0005 (6)	−0.0011 (6)
N3A	0.0152 (8)	0.0182 (9)	0.0229 (8)	−0.0009 (7)	−0.0005 (6)	0.0009 (7)
C4A	0.0170 (9)	0.0251 (11)	0.0231 (10)	−0.0058 (8)	−0.0003 (7)	0.0008 (8)
C5A	0.0165 (9)	0.0267 (11)	0.0253 (10)	−0.0024 (8)	0.0003 (7)	0.0004 (8)
C1B	0.0177 (9)	0.0178 (10)	0.0225 (10)	0.0003 (7)	−0.0019 (7)	−0.0003 (7)
C2B	0.0149 (9)	0.0197 (10)	0.0185 (9)	−0.0031 (7)	−0.0014 (7)	0.0001 (7)
C3B	0.0183 (9)	0.0208 (10)	0.0226 (10)	0.0012 (7)	−0.0001 (7)	−0.0036 (8)
C4B	0.0213 (9)	0.0187 (10)	0.0241 (10)	0.0010 (8)	−0.0026 (7)	0.0015 (8)
C5B	0.0213 (10)	0.0300 (12)	0.0207 (10)	−0.0030 (8)	−0.0047 (8)	0.0022 (8)
C6B	0.0224 (10)	0.0369 (13)	0.0179 (10)	−0.0050 (8)	−0.0019 (8)	0.0009 (8)
C7B	0.0214 (10)	0.0394 (13)	0.0213 (10)	0.0020 (9)	−0.0005 (8)	−0.0064 (9)
C8B	0.0218 (10)	0.0263 (11)	0.0218 (10)	0.0042 (8)	−0.0034 (7)	−0.0044 (8)
C9B	0.0150 (9)	0.0241 (10)	0.0208 (9)	−0.0002 (7)	−0.0040 (7)	−0.0028 (8)
C10B	0.0163 (9)	0.0216 (10)	0.0214 (9)	−0.0031 (7)	−0.0039 (7)	−0.0008 (8)
O11B	0.0194 (7)	0.0172 (7)	0.0206 (7)	−0.0004 (5)	0.0032 (5)	0.0014 (5)
C12B	0.0163 (9)	0.0188 (10)	0.0277 (10)	−0.0017 (7)	0.0019 (7)	0.0023 (8)
C13B	0.0175 (9)	0.0190 (10)	0.0167 (9)	−0.0012 (7)	0.0042 (7)	−0.0029 (7)
O14B	0.0152 (6)	0.0200 (7)	0.0245 (7)	−0.0006 (5)	0.0001 (5)	0.0008 (5)
O15B	0.0221 (7)	0.0189 (8)	0.0309 (8)	−0.0016 (5)	0.0018 (6)	0.0038 (6)

Geometric parameters (Å, º) top

S1A—C2A	1.7455 (19)	C3B—H3B	0.95
S1A—C5A	1.823 (2)	C4B—C10B	1.423 (3)
C2A—N21A	1.302 (2)	C4B—H4B	0.95
C2A—N3A	1.324 (2)	C5B—C6B	1.365 (3)
N21A—H21A	0.88	C5B—C10B	1.422 (3)
N21A—H22A	0.88	C5B—H5B	0.95
N3A—C4A	1.465 (2)	C6B—C7B	1.417 (3)
N3A—H3A	0.87 (2)	C6B—H6B	0.95
C4A—C5A	1.523 (3)	C7B—C8B	1.365 (3)
C4A—H41A	0.99	C7B—H7B	0.95
C4A—H42A	0.99	C8B—C9B	1.422 (3)
C5A—H51A	0.99	C8B—H8B	0.95
C5A—H52A	0.99	C9B—C10B	1.423 (3)
C1B—C2B	1.365 (3)	O11B—C12B	1.424 (2)
C1B—C9B	1.425 (3)	C12B—C13B	1.532 (3)
C1B—H1B	0.95	C12B—H12B	0.99
C2B—O11B	1.384 (2)	C12B—H13B	0.99
C2B—C3B	1.413 (3)	C13B—O15B	1.252 (2)
C3B—C4B	1.365 (3)	C13B—O14B	1.260 (2)

C2A—S1A—C5A	90.73 (9)	C3B—C4B—C10B	120.65 (18)
N21A—C2A—N3A	124.53 (17)	C3B—C4B—H4B	119.7
N21A—C2A—S1A	122.19 (15)	C10B—C4B—H4B	119.7
N3A—C2A—S1A	113.27 (14)	C6B—C5B—C10B	120.7 (2)
C2A—N21A—H21A	120.0	C6B—C5B—H5B	119.6
C2A—N21A—H22A	120.0	C10B—C5B—H5B	119.6
H21A—N21A—H22A	120.0	C5B—C6B—C7B	120.13 (19)
C2A—N3A—C4A	114.77 (16)	C5B—C6B—H6B	119.9
C2A—N3A—H3A	120.5 (15)	C7B—C6B—H6B	119.9
C4A—N3A—H3A	120.0 (15)	C8B—C7B—C6B	120.66 (19)
N3A—C4A—C5A	105.96 (15)	C8B—C7B—H7B	119.7
N3A—C4A—H41A	110.5	C6B—C7B—H7B	119.7
C5A—C4A—H41A	110.5	C7B—C8B—C9B	120.64 (19)
N3A—C4A—H42A	110.5	C7B—C8B—H8B	119.7
C5A—C4A—H42A	110.5	C9B—C8B—H8B	119.7
H41A—C4A—H42A	108.7	C8B—C9B—C10B	118.74 (18)
C4A—C5A—S1A	104.53 (12)	C8B—C9B—C1B	121.69 (18)
C4A—C5A—H51A	110.8	C10B—C9B—C1B	119.54 (17)
S1A—C5A—H51A	110.8	C5B—C10B—C9B	119.08 (18)
C4A—C5A—H52A	110.8	C5B—C10B—C4B	122.26 (18)
S1A—C5A—H52A	110.8	C9B—C10B—C4B	118.65 (17)
H51A—C5A—H52A	108.9	C2B—O11B—C12B	117.93 (14)
C2B—C1B—C9B	119.71 (18)	O11B—C12B—C13B	117.32 (15)
C2B—C1B—H1B	120.1	O11B—C12B—H12B	108.0
C9B—C1B—H1B	120.1	C13B—C12B—H12B	108.0
C1B—C2B—O11B	124.35 (17)	O11B—C12B—H13B	108.0
C1B—C2B—C3B	121.10 (17)	C13B—C12B—H13B	108.0
O11B—C2B—C3B	114.53 (16)	H12B—C12B—H13B	107.2
C4B—C3B—C2B	120.32 (18)	O15B—C13B—O14B	126.43 (17)
C4B—C3B—H3B	119.8	O15B—C13B—C12B	113.33 (15)
C2B—C3B—H3B	119.8	O14B—C13B—C12B	120.24 (16)

C5A—S1A—C2A—N21A	−171.09 (16)	C7B—C8B—C9B—C1B	−176.41 (17)
C5A—S1A—C2A—N3A	10.36 (15)	C2B—C1B—C9B—C8B	177.84 (17)
N21A—C2A—N3A—C4A	−169.07 (17)	C2B—C1B—C9B—C10B	−0.2 (3)
S1A—C2A—N3A—C4A	9.4 (2)	C6B—C5B—C10B—C9B	−1.2 (3)
C2A—N3A—C4A—C5A	−28.8 (2)	C6B—C5B—C10B—C4B	177.48 (17)
N3A—C4A—C5A—S1A	33.38 (17)	C8B—C9B—C10B—C5B	−0.5 (3)
C2A—S1A—C5A—C4A	−25.22 (14)	C1B—C9B—C10B—C5B	177.55 (16)
C9B—C1B—C2B—O11B	−177.00 (16)	C8B—C9B—C10B—C4B	−179.21 (17)
C9B—C1B—C2B—C3B	1.5 (3)	C1B—C9B—C10B—C4B	−1.1 (3)
C1B—C2B—C3B—C4B	−1.5 (3)	C3B—C4B—C10B—C5B	−177.51 (17)
O11B—C2B—C3B—C4B	177.12 (16)	C3B—C4B—C10B—C9B	1.1 (3)
C2B—C3B—C4B—C10B	0.2 (3)	C1B—C2B—O11B—C12B	−31.7 (2)
C10B—C5B—C6B—C7B	1.8 (3)	C3B—C2B—O11B—C12B	149.67 (16)
C5B—C6B—C7B—C8B	−0.6 (3)	C2B—O11B—C12B—C13B	92.8 (2)
C6B—C7B—C8B—C9B	−1.1 (3)	O11B—C12B—C13B—O15B	170.22 (16)
C7B—C8B—C9B—C10B	1.6 (3)	O11B—C12B—C13B—O14B	−9.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O15B	0.88	1.88	2.754 (2)	171
N21A—H22A···O14Bⁱ	0.88	1.93	2.787 (2)	166
N21A—H22A···O11Bⁱ	0.88	2.56	2.965 (2)	109
N3A—H3A···O14B	0.87 (2)	2.01 (2)	2.871 (2)	170 (2)

Symmetry code: (i) x, y−1, z.

Experimental details

	(I)	(II)
Crystal data
Chemical formula	C₃H₆N₂S	C₃H₇N₂S⁺·C₁₂H₉O₃⁻
M_r	102.17	304.36
Crystal system, space group	Monoclinic, P2₁/n	Monoclinic, P2₁/c
Temperature (K)	120	120
a, b, c (Å)	5.8980 (5), 14.8324 (12), 10.7092 (8)	8.3669 (2), 6.3707 (1), 26.3457 (6)
β (°)	101.974 (4)	92.1992 (9)
V (Å³)	916.47 (13)	1403.27 (5)
Z	8	4
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.53	0.24
Crystal size (mm)	0.20 × 0.20 × 0.10	0.32 × 0.10 × 0.04

Data collection
Diffractometer	Nonius KappaCCD area-detector diffractometer	Nonius KappaCCD area-detector diffractometer
Absorption correction	Multi-scan (SORTAV; Blessing, 1995)	Multi-scan (SORTAV; Blessing, 1995)
T_min, T_max	0.826, 0.948	0.710, 0.990
No. of measured, independent and observed [I > 2σ(I)] reflections	10396, 2101, 1149	15534, 3183, 2546
R_int	0.112	0.091
(sin θ/λ)_max (Å⁻¹)	0.650	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.160, 1.02	0.046, 0.121, 1.02
No. of reflections	2101	3183
No. of parameters	109	194
H-atom treatment	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.49, −0.41	0.25, −0.34

Computer programs: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998), DENZO and COLLECT, DENZO, SCALEPACK (Otwinowski & Minor, 1997) and COLLECT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLUTON94 (Spek, 1994) and PLATON97 (Spek, 1997).

Hydrogen-bond geometry (Å, º) for (I) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···N3B	0.88	2.09	2.950 (5)	164
N21A—H22A···S1Bⁱ	0.88	2.75	3.575 (3)	156
N21B—H21B···N3A	0.88	2.04	2.916 (5)	171
N21B—H22B···S1Aⁱⁱ	0.88	2.70	3.526 (3)	156

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

Hydrogen-bond geometry (Å, º) for (II) top

D—H···A	D—H	H···A	D···A	D—H···A
N21A—H21A···O15B	0.88	1.88	2.754 (2)	171
N21A—H22A···O14Bⁱ	0.88	1.93	2.787 (2)	166
N21A—H22A···O11Bⁱ	0.88	2.56	2.965 (2)	109
N3A—H3A···O14B	0.87 (2)	2.01 (2)	2.871 (2)	170 (2)

Symmetry code: (i) x, y−1, z.

Acknowledgements

The authors thank the EPSRC National Crystallography Service (Southampton, England).

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–37. CrossRef CAS Web of Science IUCr Journals Google Scholar
Brugarolas, A. & Gosálvez, M. (1982). Recent Results Cancer Res. 80, 346–350. CrossRef CAS PubMed Google Scholar
Caranoni, P. C. & Reboul, J. P. (1982). Acta Cryst. B38, 1255–1259. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Etter, M. C. (1990). Acc. Chem. Res. 23, 120–126. CrossRef CAS Web of Science Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Howie, R. A., Skakle, J. M. S. & Wardell, S. M. S. V. (2001). Acta Cryst. E57, o72–o74. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Lynch, D. E., Barfield, J., Frost, J., Antrobus, R. & Simmons, J. (2004). Cryst. Eng. 6, 109–122. Web of Science CSD CrossRef Google Scholar
Lynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695–703. CAS Google Scholar
Lynch, D. E., Daly, D. & Parsons, S. (2000). Acta Cryst. C56, 1478–1479. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Lynch, D. E., McClenaghan, I., Light, M. E. & Coles, S. J. (2002). Cryst. Eng. 5, 123–136. Web of Science CSD CrossRef CAS Google Scholar
Lynch, D. E., Nicholls, L. J., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1999). Acta Cryst. B55, 758–766. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Lynch, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1998). Aust. J. Chem. 51, 587–592. Web of Science CSD CrossRef CAS Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Smith, G. & Kennard, C. H. L. (1979). J. Agric. Food Chem. 27, 779–787. CrossRef CAS Web of Science Google Scholar
Spek, A. L. (1994). PLUTON94. University of Utrecht, The Netherlands. Google Scholar
Spek, A. L. (1997). PLATON97. University of Utrecht, The Netherlands. Google Scholar
The Merck Index (2001). 13th ed. Whitehouse Station: Merck and Co. Inc. Google Scholar

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Volume 60| Part 9| September 2004| Pages o677-o679

doi:10.1107/S0108270104015604