organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296

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

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[Brugarolas, A. & Gosálvez, M. (1982). Recent Results Cancer Res. 80, 346-350.]). 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, D. E., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1998). Aust. J. Chem. 51, 587-592.]; Lynch, Cooper et al., 1999[Lynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695-703.]; Lynch, Nicholls et al., 1999[Lynch, D. E., Nicholls, L. J., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1999). Acta Cryst. B55, 758-766.]). 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[Lynch, D. E., Barfield, J., Frost, J., Antrobus, R. & Simmons, J. (2004). Cryst. Eng. 6, 109-122.]). Although the structure of 2-aminothia­zole was published by Caranoni & Reboul (1982[Caranoni, P. C. & Reboul, J. P. (1982). Acta Cryst. B38, 1255-1259.]), the structure of 2-amino-2-thia­zoline has not been reported; the structure of this compound, (I[link]), 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[The Merck Index (2001). 13th ed. Whitehouse Station: Merck and Co. Inc.]). 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[Lynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695-703.]) and should thus have comparable structural properties. Furthermore, the Cambridge Structural Database (Allen, 2002[Allen, F. H. (2002). Acta Cryst. B58, 380-388.]) contains only four previously reported crystal structures containing the compound, of which two are the parent structure (Howie et al., 2001[Howie, R. A., Skakle, J. M. S. & Wardell, S. M. S. V. (2001). Acta Cryst. E57, o72-o74.]), thus more structures containing 2-­naphthoxy­acetic acid are required. For these reasons, the structure of the 1:1 organic salt of (I[link]) with 2-naphthoxy­acetic acid is also reported here, viz. (II[link]).

[Scheme 1]

Compound (I[link]) packs with two unique thia­zoline mol­ecules associated in a hydrogen-bonded [R_2^2](8) graph-set dimer (Etter, 1990[Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.]) via N—H⋯N interactions (Fig. 1[link]). 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[link]. Together, these interactions create a convoluted hydrogen-bonded ribbon that runs in the direction of the ac axis diagonal (Fig. 2[link]). 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[Lynch, D. E., McClenaghan, I., Light, M. E. & Coles, S. J. (2002). Cryst. Eng. 5, 123-136.]). In (I[link]), 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[link]) 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[link]) adopts an anticlinical (or hooked) arrangement, as classified for phenoxy­acetic acids (Smith & Kennard, 1979[Smith, G. & Kennard, C. H. L. (1979). J. Agric. Food Chem. 27, 779-787.]) and defined by the C2B—O11B—C12B—C13B torsion angle [92.8 (2)°; Fig. 3[link]]. 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[Lynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695-703.]). The components of (II[link]), 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[link]). 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[link] indicate that the structure of (I[link]) 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[Lynch, D. E., Daly, D. & Parsons, S. (2000). Acta Cryst. C56, 1478-1479.]). 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[Lynch, D. E., Nicholls, L. J., Smith, G., Byriel, K. A. & Kennard, C. H. L. (1999). Acta Cryst. B55, 758-766.]), although the additional interaction with atom O11B is not common amongst complexes of 2-amino­thiazole derivatives and phenoxy­acetic acids (Lynch, Cooper et al., 1999[Lynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695-703.]).

The structure of (II[link]) is actually the eighth known complex of a carboxylic acid with (I[link]), with three others currently unpublished (Lynch et al., 2004[Lynch, D. E., Barfield, J., Frost, J., Antrobus, R. & Simmons, J. (2004). Cryst. Eng. 6, 109-122.]). Elucidation of the structure of (I[link]) 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[link]), 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[link]), values of 124.8 (3) and 125.8 (3)° with that of 124.53 (17)° in (II[link]) [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]
Figure 1
A view of the asymmetric unit and atom-numbering scheme of (I[link]). Displacement ellipsoids are drawn at the 50% probability level. Broken lines indicate intramolecular hydrogen bonds.
[Figure 2]
Figure 2
A packing diagram for (I[link]). [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]
Figure 3
A view of the asymmetric unit and atom-numbering scheme of (II[link]). Displacement ellipsoids are drawn at the 50% probability level. Broken lines indicate intramolecular hydrogen bonds.
[Figure 4]
Figure 4
A packing diagram for (II[link]). [Symmetry code: (iii) x, y − 1, z.]

Experimental

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

Compound (I)[link]

Crystal data
  • C3H6N2S

  • Mr = 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

  • Dx = 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[Blessing, R. H. (1995). Acta Cryst. A51, 33-37.]) Tmin = 0.826, Tmax = 0.948

  • 10 396 measured reflections

  • 2101 independent reflections

  • 1149 reflections with I > 2σ(I)

  • Rint = 0.112

  • θmax = 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(Fo2) + (0.0802P)2] where P = (Fo2 + 2Fc2c2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.49 e Å−3

  • Δρmin = −0.41 e Å−3

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

D—H⋯A D—H H⋯A DA 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)[link]

Crystal data
  • C3H7N2S+·C12H9O3

  • Mr = 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

  • Dx = 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[Blessing, R. H. (1995). Acta Cryst. A51, 33-37.]) Tmin = 0.710, Tmax = 0.990

  • 15 534 measured reflections

  • 3183 independent reflections

  • 2546 reflections with I > 2σ(I)

  • Rint = 0.091

  • θmax = 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(Fo2) + (0.0503P)2 + 0.8055P] where P = (Fo2 + 2Fc2)/3

  • (Δ/σ)max < 0.001

  • Δρmax = 0.25 e Å−3

  • Δρmin = −0.34 e Å−3

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

D—H⋯A D—H H⋯A DA 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[link]), 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 Uiso(H) values were set at 1.25Ueq 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 Rint value for (I[link]) was the result of weak high-angle data.

For both compounds, data collection: DENZO (Otwinowski & Minor, 1997[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.]) and COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and COLLECT; data reduction: DENZO, SCALEPACK (Otwin­owski & Minor, 1997[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.]) and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]); molecular graphics: PLUTON94 (Spek, 1994[Spek, A. L. (1994). PLUTON94. University of Utrecht, The Netherlands.]) and PLATON97 (Spek, 1997[Spek, A. L. (1997). PLATON97. University of Utrecht, The Netherlands.]); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997[Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.]).

Supporting information


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.

Refinement top

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 isotropic displacement parameters were set to 1.25Ueq of the carrier atom. The H atom on the N+ ion was located in a difference synthesis and both the positional and the displacement parameters were refined. A high Rint value for (I) was the result of weak high-angle data.

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
[Figure 1] Fig. 1. The molecular configuration and atom-numbering scheme for (I). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] 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.]
[Figure 3] Fig. 3. The molecular configuration and atom-numbering scheme for (II). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 4] Fig. 4. A packing diagram for (II). [Symmetry code: (i) x, y − 1, z.]
(I) 2-Amino-2-thiazoline top
Crystal data top
C3H6N2SF(000) = 432
Mr = 102.17Dx = 1.481 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 8580 reflections
a = 5.8980 (5) Åθ = 2.9–27.5°
b = 14.8324 (12) ŵ = 0.53 mm1
c = 10.7092 (8) ÅT = 120 K
β = 101.974 (4)°Prism, yellow
V = 916.47 (13) Å30.20 × 0.20 × 0.10 mm
Z = 8
Data collection top
Nonius KappaCCD area-detector
diffractometer
2101 independent reflections
Radiation source: Nonius FR591 rotating anode1149 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.112
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 3.4°
ϕ and ω scansh = 77
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 1919
Tmin = 0.826, Tmax = 0.948l = 1313
10396 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.160H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0802P)2]
where P = (Fo2 + 2Fc2)/3
2101 reflections(Δ/σ)max < 0.001
109 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.41 e Å3
Crystal data top
C3H6N2SV = 916.47 (13) Å3
Mr = 102.17Z = 8
Monoclinic, P21/nMo Kα radiation
a = 5.8980 (5) ŵ = 0.53 mm1
b = 14.8324 (12) ÅT = 120 K
c = 10.7092 (8) Å0.20 × 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)
Tmin = 0.826, Tmax = 0.948Rint = 0.112
10396 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0610 restraints
wR(F2) = 0.160H-atom parameters constrained
S = 1.02Δρmax = 0.49 e Å3
2101 reflectionsΔρmin = 0.41 e Å3
109 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.02730 (17)0.06496 (7)0.20321 (9)0.0269 (3)
C2A0.1754 (6)0.1438 (2)0.1644 (4)0.0219 (8)
N21A0.3725 (6)0.1576 (2)0.2517 (3)0.0295 (8)
H21A0.47880.19460.23480.037*
H22A0.39490.12960.32570.037*
N3A0.1270 (5)0.1808 (2)0.0554 (3)0.0263 (8)
C4A0.0968 (7)0.1525 (3)0.0198 (4)0.0271 (9)
H41A0.19590.20620.04340.034*
H42A0.07320.12380.09960.034*
C5A0.2206 (7)0.0864 (3)0.0520 (4)0.0309 (10)
H51A0.36790.11270.06550.039*
H52A0.25540.02970.00310.039*
S1B0.77862 (17)0.43581 (7)0.04456 (9)0.0246 (3)
C2B0.5938 (6)0.3476 (2)0.0781 (4)0.0228 (8)
N21B0.4037 (5)0.3289 (2)0.0124 (3)0.0289 (8)
H21B0.30880.28560.00020.036*
H22B0.37470.35990.08400.036*
N3B0.6540 (5)0.3076 (2)0.1853 (3)0.0260 (8)
C4B0.8603 (6)0.3461 (3)0.2639 (4)0.0270 (9)
H41B0.96210.29720.30620.034*
H42B0.81630.38410.33110.034*
C5B0.9918 (7)0.4032 (3)0.1840 (4)0.0306 (10)
H51B1.11780.36780.15920.038*
H52B1.05990.45710.23220.038*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0240 (6)0.0311 (6)0.0266 (6)0.0060 (4)0.0077 (4)0.0016 (4)
C2A0.020 (2)0.0226 (19)0.024 (2)0.0013 (15)0.0066 (17)0.0004 (16)
N21A0.0234 (18)0.0421 (19)0.0225 (18)0.0074 (16)0.0039 (14)0.0078 (15)
N3A0.0228 (18)0.0346 (18)0.0217 (18)0.0079 (14)0.0049 (14)0.0011 (15)
C4A0.024 (2)0.031 (2)0.026 (2)0.0034 (17)0.0041 (17)0.0014 (18)
C5A0.020 (2)0.043 (3)0.030 (2)0.0073 (18)0.0067 (19)0.0003 (19)
S1B0.0229 (6)0.0269 (5)0.0253 (6)0.0042 (4)0.0079 (4)0.0014 (4)
C2B0.019 (2)0.0241 (19)0.028 (2)0.0016 (16)0.0109 (17)0.0035 (17)
N21B0.0272 (19)0.0346 (18)0.0232 (18)0.0097 (14)0.0014 (15)0.0031 (15)
N3B0.0213 (18)0.0331 (18)0.0229 (18)0.0037 (14)0.0034 (15)0.0018 (14)
C4B0.020 (2)0.032 (2)0.028 (2)0.0064 (17)0.0043 (17)0.0013 (18)
C5B0.024 (2)0.040 (2)0.027 (2)0.0027 (18)0.0037 (18)0.0074 (19)
Geometric parameters (Å, º) top
S1A—C2A1.782 (4)S1B—C2B1.786 (4)
S1A—C5A1.805 (4)S1B—C5B1.807 (4)
C2A—N3A1.267 (5)C2B—N3B1.276 (5)
C2A—N21A1.348 (5)C2B—N21B1.351 (5)
N21A—H21A0.88N21B—H21B0.88
N21A—H22A0.88N21B—H22B0.88
N3A—C4A1.458 (5)N3B—C4B1.446 (5)
C4A—C5A1.522 (5)C4B—C5B1.525 (5)
C4A—H41A0.99C4B—H41B0.99
C4A—H42A0.99C4B—H42B0.99
C5A—H51A0.99C5B—H51B0.99
C5A—H52A0.99C5B—H52B0.99
C2A—S1A—C5A90.24 (18)C2B—S1B—C5B89.24 (18)
N3A—C2A—N21A124.8 (3)N3B—C2B—N21B125.8 (3)
N3A—C2A—S1A117.7 (3)N3B—C2B—S1B117.1 (3)
N21A—C2A—S1A117.5 (3)N21B—C2B—S1B117.2 (3)
C2A—N21A—H21A120.0C2B—N21B—H21B120.0
C2A—N21A—H22A120.0C2B—N21B—H22B120.0
H21A—N21A—H22A120.0H21B—N21B—H22B120.0
C2A—N3A—C4A112.9 (3)C2B—N3B—C4B112.5 (3)
N3A—C4A—C5A112.4 (3)N3B—C4B—C5B110.9 (3)
N3A—C4A—H41A109.1N3B—C4B—H41B109.5
C5A—C4A—H41A109.1C5B—C4B—H41B109.5
N3A—C4A—H42A109.1N3B—C4B—H42B109.5
C5A—C4A—H42A109.1C5B—C4B—H42B109.5
H41A—C4A—H42A107.9H41B—C4B—H42B108.0
C4A—C5A—S1A106.7 (3)C4B—C5B—S1B105.3 (3)
C4A—C5A—H51A110.4C4B—C5B—H51B110.7
S1A—C5A—H51A110.4S1B—C5B—H51B110.7
C4A—C5A—H52A110.4C4B—C5B—H52B110.7
S1A—C5A—H52A110.4S1B—C5B—H52B110.7
H51A—C5A—H52A108.6H51B—C5B—H52B108.8
C5A—S1A—C2A—N3A2.7 (3)C5B—S1B—C2B—N3B9.6 (3)
C5A—S1A—C2A—N21A179.3 (3)C5B—S1B—C2B—N21B170.0 (3)
N21A—C2A—N3A—C4A179.2 (4)N21B—C2B—N3B—C4B177.2 (4)
S1A—C2A—N3A—C4A1.4 (4)S1B—C2B—N3B—C4B3.3 (4)
C2A—N3A—C4A—C5A1.0 (5)C2B—N3B—C4B—C5B17.9 (5)
N3A—C4A—C5A—S1A2.8 (4)N3B—C4B—C5B—S1B23.4 (4)
C2A—S1A—C5A—C4A2.9 (3)C2B—S1B—C5B—C4B17.7 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21A—H21A···N3B0.882.092.950 (5)164
N21A—H22A···S1Bi0.882.753.575 (3)156
N21B—H21B···N3A0.882.042.916 (5)171
N21B—H22B···S1Aii0.882.703.526 (3)156
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2.
(II) 2-Amino-2-thiazolium 2-naphthoxyacetate top
Crystal data top
C3H7N2S+·C12H9O3F(000) = 640
Mr = 304.36Dx = 1.441 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4067 reflections
a = 8.3669 (2) Åθ = 2.9–27.5°
b = 6.3707 (1) ŵ = 0.24 mm1
c = 26.3457 (6) ÅT = 120 K
β = 92.1992 (9)°Plate, colourless
V = 1403.27 (5) Å30.32 × 0.10 × 0.04 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
3183 independent reflections
Radiation source: Nonius FR591 rotating anode2546 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.091
Detector resolution: 9.091 pixels mm-1θmax = 27.4°, θmin = 3.1°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SORTAV; Blessing, 1995)
k = 78
Tmin = 0.710, Tmax = 0.990l = 3434
15534 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0503P)2 + 0.8055P]
where P = (Fo2 + 2Fc2)/3
3183 reflections(Δ/σ)max < 0.001
194 parametersΔρmax = 0.25 e Å3
0 restraintsΔρmin = 0.34 e Å3
Crystal data top
C3H7N2S+·C12H9O3V = 1403.27 (5) Å3
Mr = 304.36Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.3669 (2) ŵ = 0.24 mm1
b = 6.3707 (1) ÅT = 120 K
c = 26.3457 (6) Å0.32 × 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)
Tmin = 0.710, Tmax = 0.990Rint = 0.091
15534 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.25 e Å3
3183 reflectionsΔρmin = 0.34 e Å3
194 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.19892 (6)0.56175 (8)0.06199 (19)0.02416 (16)
C2A0.0340 (2)0.3943 (3)0.06063 (7)0.0173 (4)
N21A0.11091 (18)0.4589 (3)0.07144 (6)0.0198 (4)
H21A0.19130.36980.07120.025*
H22A0.12850.59170.07900.025*
N3A0.07266 (19)0.1983 (3)0.04883 (6)0.0188 (3)
H3A0.005 (3)0.097 (4)0.0543 (8)0.023 (6)*
C4A0.2446 (2)0.1539 (3)0.04747 (7)0.0218 (4)
H41A0.27150.04410.02200.027*
H42A0.27810.10500.08110.027*
C5A0.3271 (2)0.3597 (3)0.03314 (8)0.0228 (4)
H51A0.33560.37680.00420.029*
H52A0.43560.36550.04680.029*
C1B0.2758 (2)0.3025 (3)0.19187 (7)0.0194 (4)
H1B0.24420.16660.18050.024*
C2B0.3684 (2)0.4257 (3)0.16244 (7)0.0177 (4)
C3B0.4200 (2)0.6263 (3)0.17909 (7)0.0206 (4)
H3B0.48660.70820.15840.026*
C4B0.3745 (2)0.7029 (3)0.22471 (7)0.0215 (4)
H4B0.40950.83810.23550.027*
C5B0.2202 (2)0.6600 (3)0.30307 (7)0.0241 (4)
H5B0.25360.79480.31470.030*
C6B0.1201 (2)0.5432 (3)0.33145 (7)0.0258 (5)
H6B0.08180.59850.36220.032*
C7B0.0730 (2)0.3398 (3)0.31514 (7)0.0274 (5)
H7B0.00420.25880.33530.034*
C8B0.1256 (2)0.2589 (3)0.27081 (7)0.0234 (4)
H8B0.09450.12130.26070.029*
C9B0.2266 (2)0.3787 (3)0.23966 (7)0.0201 (4)
C10B0.2751 (2)0.5823 (3)0.25623 (7)0.0199 (4)
O11B0.41670 (15)0.3708 (2)0.11458 (5)0.0190 (3)
C12B0.4426 (2)0.1542 (3)0.10439 (8)0.0209 (4)
H12B0.47650.08520.13670.026*
H13B0.53290.14330.08130.026*
C13B0.3018 (2)0.0295 (3)0.08086 (7)0.0177 (4)
O14B0.16423 (15)0.1099 (2)0.07750 (5)0.0199 (3)
O15B0.34007 (16)0.15009 (2)0.06632 (5)0.0239 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0187 (3)0.0224 (3)0.0313 (3)0.00326 (18)0.00004 (19)0.0037 (2)
C2A0.0178 (9)0.0186 (10)0.0157 (8)0.0009 (7)0.0024 (7)0.0017 (7)
N21A0.0162 (8)0.0173 (9)0.0259 (8)0.0007 (6)0.0005 (6)0.0011 (6)
N3A0.0152 (8)0.0182 (9)0.0229 (8)0.0009 (7)0.0005 (6)0.0009 (7)
C4A0.0170 (9)0.0251 (11)0.0231 (10)0.0058 (8)0.0003 (7)0.0008 (8)
C5A0.0165 (9)0.0267 (11)0.0253 (10)0.0024 (8)0.0003 (7)0.0004 (8)
C1B0.0177 (9)0.0178 (10)0.0225 (10)0.0003 (7)0.0019 (7)0.0003 (7)
C2B0.0149 (9)0.0197 (10)0.0185 (9)0.0031 (7)0.0014 (7)0.0001 (7)
C3B0.0183 (9)0.0208 (10)0.0226 (10)0.0012 (7)0.0001 (7)0.0036 (8)
C4B0.0213 (9)0.0187 (10)0.0241 (10)0.0010 (8)0.0026 (7)0.0015 (8)
C5B0.0213 (10)0.0300 (12)0.0207 (10)0.0030 (8)0.0047 (8)0.0022 (8)
C6B0.0224 (10)0.0369 (13)0.0179 (10)0.0050 (8)0.0019 (8)0.0009 (8)
C7B0.0214 (10)0.0394 (13)0.0213 (10)0.0020 (9)0.0005 (8)0.0064 (9)
C8B0.0218 (10)0.0263 (11)0.0218 (10)0.0042 (8)0.0034 (7)0.0044 (8)
C9B0.0150 (9)0.0241 (10)0.0208 (9)0.0002 (7)0.0040 (7)0.0028 (8)
C10B0.0163 (9)0.0216 (10)0.0214 (9)0.0031 (7)0.0039 (7)0.0008 (8)
O11B0.0194 (7)0.0172 (7)0.0206 (7)0.0004 (5)0.0032 (5)0.0014 (5)
C12B0.0163 (9)0.0188 (10)0.0277 (10)0.0017 (7)0.0019 (7)0.0023 (8)
C13B0.0175 (9)0.0190 (10)0.0167 (9)0.0012 (7)0.0042 (7)0.0029 (7)
O14B0.0152 (6)0.0200 (7)0.0245 (7)0.0006 (5)0.0001 (5)0.0008 (5)
O15B0.0221 (7)0.0189 (8)0.0309 (8)0.0016 (5)0.0018 (6)0.0038 (6)
Geometric parameters (Å, º) top
S1A—C2A1.7455 (19)C3B—H3B0.95
S1A—C5A1.823 (2)C4B—C10B1.423 (3)
C2A—N21A1.302 (2)C4B—H4B0.95
C2A—N3A1.324 (2)C5B—C6B1.365 (3)
N21A—H21A0.88C5B—C10B1.422 (3)
N21A—H22A0.88C5B—H5B0.95
N3A—C4A1.465 (2)C6B—C7B1.417 (3)
N3A—H3A0.87 (2)C6B—H6B0.95
C4A—C5A1.523 (3)C7B—C8B1.365 (3)
C4A—H41A0.99C7B—H7B0.95
C4A—H42A0.99C8B—C9B1.422 (3)
C5A—H51A0.99C8B—H8B0.95
C5A—H52A0.99C9B—C10B1.423 (3)
C1B—C2B1.365 (3)O11B—C12B1.424 (2)
C1B—C9B1.425 (3)C12B—C13B1.532 (3)
C1B—H1B0.95C12B—H12B0.99
C2B—O11B1.384 (2)C12B—H13B0.99
C2B—C3B1.413 (3)C13B—O15B1.252 (2)
C3B—C4B1.365 (3)C13B—O14B1.260 (2)
C2A—S1A—C5A90.73 (9)C3B—C4B—C10B120.65 (18)
N21A—C2A—N3A124.53 (17)C3B—C4B—H4B119.7
N21A—C2A—S1A122.19 (15)C10B—C4B—H4B119.7
N3A—C2A—S1A113.27 (14)C6B—C5B—C10B120.7 (2)
C2A—N21A—H21A120.0C6B—C5B—H5B119.6
C2A—N21A—H22A120.0C10B—C5B—H5B119.6
H21A—N21A—H22A120.0C5B—C6B—C7B120.13 (19)
C2A—N3A—C4A114.77 (16)C5B—C6B—H6B119.9
C2A—N3A—H3A120.5 (15)C7B—C6B—H6B119.9
C4A—N3A—H3A120.0 (15)C8B—C7B—C6B120.66 (19)
N3A—C4A—C5A105.96 (15)C8B—C7B—H7B119.7
N3A—C4A—H41A110.5C6B—C7B—H7B119.7
C5A—C4A—H41A110.5C7B—C8B—C9B120.64 (19)
N3A—C4A—H42A110.5C7B—C8B—H8B119.7
C5A—C4A—H42A110.5C9B—C8B—H8B119.7
H41A—C4A—H42A108.7C8B—C9B—C10B118.74 (18)
C4A—C5A—S1A104.53 (12)C8B—C9B—C1B121.69 (18)
C4A—C5A—H51A110.8C10B—C9B—C1B119.54 (17)
S1A—C5A—H51A110.8C5B—C10B—C9B119.08 (18)
C4A—C5A—H52A110.8C5B—C10B—C4B122.26 (18)
S1A—C5A—H52A110.8C9B—C10B—C4B118.65 (17)
H51A—C5A—H52A108.9C2B—O11B—C12B117.93 (14)
C2B—C1B—C9B119.71 (18)O11B—C12B—C13B117.32 (15)
C2B—C1B—H1B120.1O11B—C12B—H12B108.0
C9B—C1B—H1B120.1C13B—C12B—H12B108.0
C1B—C2B—O11B124.35 (17)O11B—C12B—H13B108.0
C1B—C2B—C3B121.10 (17)C13B—C12B—H13B108.0
O11B—C2B—C3B114.53 (16)H12B—C12B—H13B107.2
C4B—C3B—C2B120.32 (18)O15B—C13B—O14B126.43 (17)
C4B—C3B—H3B119.8O15B—C13B—C12B113.33 (15)
C2B—C3B—H3B119.8O14B—C13B—C12B120.24 (16)
C5A—S1A—C2A—N21A171.09 (16)C7B—C8B—C9B—C1B176.41 (17)
C5A—S1A—C2A—N3A10.36 (15)C2B—C1B—C9B—C8B177.84 (17)
N21A—C2A—N3A—C4A169.07 (17)C2B—C1B—C9B—C10B0.2 (3)
S1A—C2A—N3A—C4A9.4 (2)C6B—C5B—C10B—C9B1.2 (3)
C2A—N3A—C4A—C5A28.8 (2)C6B—C5B—C10B—C4B177.48 (17)
N3A—C4A—C5A—S1A33.38 (17)C8B—C9B—C10B—C5B0.5 (3)
C2A—S1A—C5A—C4A25.22 (14)C1B—C9B—C10B—C5B177.55 (16)
C9B—C1B—C2B—O11B177.00 (16)C8B—C9B—C10B—C4B179.21 (17)
C9B—C1B—C2B—C3B1.5 (3)C1B—C9B—C10B—C4B1.1 (3)
C1B—C2B—C3B—C4B1.5 (3)C3B—C4B—C10B—C5B177.51 (17)
O11B—C2B—C3B—C4B177.12 (16)C3B—C4B—C10B—C9B1.1 (3)
C2B—C3B—C4B—C10B0.2 (3)C1B—C2B—O11B—C12B31.7 (2)
C10B—C5B—C6B—C7B1.8 (3)C3B—C2B—O11B—C12B149.67 (16)
C5B—C6B—C7B—C8B0.6 (3)C2B—O11B—C12B—C13B92.8 (2)
C6B—C7B—C8B—C9B1.1 (3)O11B—C12B—C13B—O15B170.22 (16)
C7B—C8B—C9B—C10B1.6 (3)O11B—C12B—C13B—O14B9.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N21A—H21A···O15B0.881.882.754 (2)171
N21A—H22A···O14Bi0.881.932.787 (2)166
N21A—H22A···O11Bi0.882.562.965 (2)109
N3A—H3A···O14B0.87 (2)2.01 (2)2.871 (2)170 (2)
Symmetry code: (i) x, y1, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC3H6N2SC3H7N2S+·C12H9O3
Mr102.17304.36
Crystal system, space groupMonoclinic, P21/nMonoclinic, P21/c
Temperature (K)120120
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)
V3)916.47 (13)1403.27 (5)
Z84
Radiation typeMo KαMo Kα
µ (mm1)0.530.24
Crystal size (mm)0.20 × 0.20 × 0.100.32 × 0.10 × 0.04
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correctionMulti-scan
(SORTAV; Blessing, 1995)
Multi-scan
(SORTAV; Blessing, 1995)
Tmin, Tmax0.826, 0.9480.710, 0.990
No. of measured, independent and
observed [I > 2σ(I)] reflections
10396, 2101, 1149 15534, 3183, 2546
Rint0.1120.091
(sin θ/λ)max1)0.6500.648
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.160, 1.02 0.046, 0.121, 1.02
No. of reflections21013183
No. of parameters109194
H-atom treatmentH-atom parameters constrainedH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.49, 0.410.25, 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···AD—HH···AD···AD—H···A
N21A—H21A···N3B0.882.092.950 (5)164
N21A—H22A···S1Bi0.882.753.575 (3)156
N21B—H21B···N3A0.882.042.916 (5)171
N21B—H22B···S1Aii0.882.703.526 (3)156
Symmetry codes: (i) x1/2, y+1/2, z+1/2; (ii) x+1/2, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N21A—H21A···O15B0.881.882.754 (2)171
N21A—H22A···O14Bi0.881.932.787 (2)166
N21A—H22A···O11Bi0.882.562.965 (2)109
N3A—H3A···O14B0.87 (2)2.01 (2)2.871 (2)170 (2)
Symmetry code: (i) x, y1, z.
 

Acknowledgements

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

References

First citationAllen, F. H. (2002). Acta Cryst. B58, 380–388.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBlessing, R. H. (1995). Acta Cryst. A51, 33–37.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationBrugarolas, A. & Gosálvez, M. (1982). Recent Results Cancer Res. 80, 346–350.  CrossRef CAS PubMed Google Scholar
First citationCaranoni, P. C. & Reboul, J. P. (1982). Acta Cryst. B38, 1255–1259.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationEtter, M. C. (1990). Acc. Chem. Res. 23, 120–126.  CrossRef CAS Web of Science Google Scholar
First citationHooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands.  Google Scholar
First citationHowie, 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
First citationLynch, D. E., Barfield, J., Frost, J., Antrobus, R. & Simmons, J. (2004). Cryst. Eng. 6, 109–122.  Web of Science CSD CrossRef Google Scholar
First citationLynch, D. E., Cooper, C. J., Chauhan, V., Smith, G., Healy, P. & Parsons, S. (1999). Aust. J. Chem. 52, 695–703.  CAS Google Scholar
First citationLynch, D. E., Daly, D. & Parsons, S. (2000). Acta Cryst. C56, 1478–1479.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationLynch, D. E., McClenaghan, I., Light, M. E. & Coles, S. J. (2002). Cryst. Eng. 5, 123–136.  Web of Science CSD CrossRef CAS Google Scholar
First citationLynch, 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
First citationLynch, 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
First citationOtwinowski, 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
First citationSheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.  Google Scholar
First citationSmith, G. & Kennard, C. H. L. (1979). J. Agric. Food Chem. 27, 779–787.  CrossRef CAS Web of Science Google Scholar
First citationSpek, A. L. (1994). PLUTON94. University of Utrecht, The Netherlands.  Google Scholar
First citationSpek, A. L. (1997). PLATON97. University of Utrecht, The Netherlands.  Google Scholar
First citationThe Merck Index (2001). 13th ed. Whitehouse Station: Merck and Co. Inc.  Google Scholar

© International Union of Crystallography. Prior permission is not required to reproduce short quotations, tables and figures from this article, provided the original authors and source are cited. For more information, click here.

Journal logoSTRUCTURAL
CHEMISTRY
ISSN: 2053-2296
Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds