Three substituted (Z)-5-benzyl­idene-2-thioxothia­zolidin-4-ones: hydrogen-bonded dimers that can be effectively isolated or linked into chains either by aromatic π–π stacking inter­actions or by dipolar carbon­yl–carbonyl inter­actions

Delgado, P.; Quiroga, J.; Torre, J.M. de la; Cobo, J.; Low, J.N.; Glidewell, C.

doi:10.1107/S0108270106018038

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 62| Part 7| July 2006| Pages o382-o385

doi:10.1107/S0108270106018038

Three substituted (Z)-5-benzylidene-2-thioxothiazolidin-4-ones: hydrogen-bonded dimers that can be effectively isolated or linked into chains either by aromatic π–π stacking interactions or by dipolar carbonyl–carbonyl interactions

Paula Delgado,^a Jairo Quiroga,^a Jose M. de la Torre,^b Justo Cobo,^b John N. Low ^c and Christopher Glidewell ^d ^*

^aGrupo de Investigación de Compuestos Heterocíclicos, Departamento de Química, Universidad de Valle, AA 25360 Cali, Colombia, ^bDepartamento de Química Inorgánica y Orgánica, Universidad de Jaén, 23071 Jaén, Spain, ^cDepartment of Chemistry, University of Aberdeen, Meston Walk, Old Aberdeen AB24 3UE, Scotland, and ^dSchool of Chemistry, University of St Andrews, Fife KY16 9ST, Scotland
^*Correspondence e-mail: cg@st-andrews.ac.uk

(Received 15 May 2006; accepted 16 May 2006; online 15 June 2006)

In each of the isomeric compounds (Z)-5-(2-fluorobenzylidene)-2-thioxothiazolidin-4-one, C₁₀H₆FNOS₂, (I), and (Z)-5-(4-fluorobenzylidene)-2-thioxothiazolidin-4-one, C₁₀H₆FNOS₂, (II), there is a very wide C—C—C angle (ca 130°) at the methine C atom linking the two rings. In each isomer, paired N—H⋯O hydrogen bonds link the molecules into centrosymmetric R₂²(8) dimers; the hydrogen-bonded dimers are linked into chains by an aromatic π–π stacking interaction in isomer (I) and by an antiparallel dipolar carbonyl–carbonyl interaction in isomer (II). (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-thioxothiazolidin-4-one, C₁₃H₁₃NO₄S₂, (III), which crystallizes with Z′ = 2 in the space group P $[\overline{1}]$ , shows the same very wide angle at the bridging methine C atom; the two independent molecules are linked into an isolated dimer having no crystallographic symmetry.

Comment

We report here the structures of three substituted (Z)-5-benzylidene-2-thioxothiazolidin-4-ones, namely two isomers of (Z)-5-(fluorobenzylidene)-2-thioxothiazolidin-4-one, (I) and (II) (Figs. 1 and 2), and (Z)-5-(3,4,5-trimethoxybenzylidene)-2-thioxothiazolidin-4-one, (III) (Fig. 3), and we briefly compare these with the structures of the four analogues (IV)–(VII) (see scheme), which have been reported recently (Delgado et al., 2005 ). As for compounds (IV)–(VII), compounds (I)–(III) have been prepared by condensation of 2-thioxothiazolidin-4-one (rhodanine) with a substituted benzaldehyde using microwave radiation in a solvent-free system.

The molecules of compounds (I)–(III) are all effectively planar, as shown by the values of the Cx5—Cx57—Cx51—Cx52 torsion angle, where x is nil for compounds (I) and (II), and x = 1 or 2, respectively, for the two independent molecules in compound (III) (Table 1); this angle defines the rotation of the aryl ring relative to the rest of the molecule. In each isomer, the Cx5—Cx57—Cx51 angle is very large, ca 130°, and these angles, together with the exocyclic angles at Cx5 and Cx51, are consistent with the occurrence of a repulsive intramolecular interaction between atoms Sx1 and Hx56 (Table 2). This behaviour closely mimics that in the analogues (IV)–(VII). In each of the molecules in (III), the methoxy groups at Cx53 and Cx55 have their C atoms almost coplanar with the adjacent aryl rings (Table 1), but those at Cx54 have the C atoms well removed from this plane for steric reasons.

The supramolecular structures of compounds (I)–(III) are very simple. In the isomers (I) and (II), the molecules are linked by paired N—H⋯O hydrogen bonds (Table 2) into centrosymmetric R₂²(8) (Bernstein et al., 1995 ) dimers; in each isomer, the asymmetric unit was selected such that the dimer containing the reference molecule is centred at ( $[1\over2]$ , $[1\over2]$ , $[1\over2]$ ) (Figs. 4 and 5). The structures of (I) and (II) differ, however, in the manner in which the hydrogen-bonded dimers are linked into chains. In (III), the two independent molecules are again linked into a dimer but this does not exhibit even approximate centrosymmetry. There are no direction-specific interactions between the dimeric units in (III).

The hydrogen-bonded dimers in (I) are linked by an aromatic π–π stacking interaction. The aryl rings in the molecules at (x, y, z) and (2 − x, −y, 1 − z), which lie, respectively, in the R₂²(8) dimers centred at ( $[1\over2]$ , $[1\over2]$ , $[1\over2]$ ) and ( $[3\over2]$ , − $[1\over2]$ , $[1\over2]$ ), are strictly parallel, with an interplanar spacing of 3.366 (2) Å; the ring-centroid separation is 3.692 (2) Å, corresponding to an almost ideal ring offset of 1.515 (2) Å. Propagation by inversion of this interaction links the dimers into chains running parallel to the [1 $[\overline{1}]$ 0] direction (Fig. 6).

In (II), the hydrogen-bonded dimers are linked by an antiparallel carbonyl–carbonyl interaction, which is centrosymmetric. The molecules at (x, y, z) and (−x, 1 − y, 1 − z) are components of the dimers centred at ( $[1\over2]$ , $[1\over2]$ , $[1\over2]$ ) and (− $[1\over2]$ , $[1\over2]$ , $[1\over2]$ ), respectively; their carbonyl groups are antiparallel, with a C⋯Oⁱⁱ distance of 3.181 (4) Å and an O—C⋯Oⁱⁱ angle of 100.5 (2)° [symmetry code: (ii) −x, −y + 1, −z + 1], producing a slightly sheared interaction of type II (Allen et al., 1998 ), which links the dimers into chains running parallel to the [100] direction (Fig. 7).

We note very briefly the different patterns of supramolecular aggregation in the analogues (IV)–(VII) (Delgado et al., 2005). In (IV), which crystallizes with Z′ = 2 in the space group P2₁/n, the two independent molecules are linked by N—H⋯O bonds into a dimer, as in (III), but these dimers are not isolated; instead they are linked by C—H⋯π(arene) hydrogen bonds into sheets. Compound (V) is effectively isomorphous with (III) and the molecules form centrosymmetric dimers, which are linked into chains by a dipolar carbonyl–carbonyl interaction. No dimers formed by paired N—H⋯O hydrogen bonds are discernible in the structure of (VI); instead the molecules are linked into chains of rings by a combination of N—H⋯S and C—H⋯O hydrogen bonds. In (VII), the usual R₂²(8) dimers are formed and these are linked into chains of rings by C—H⋯S hydrogen bonds. Thus, within the extended series (I)–(VII), it is apparent that rather modest changes to the peripheral substituents can have a significant influence on the overall supramolecular aggregation.

Figure 1
A molecule of (I)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 2
A molecule of (II)

, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Figure 3
The two independent molecules of (III)

, showing the atom-labelling scheme and the N—H⋯O hydrogen bonds (dashed lines). Displacement ellipsoids are drawn at the 30% probability level.

Figure 4
Part of the crystal structure of (I)

, showing the formation of a centrosymmetric hydrogen-bonded dimer. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).

Figure 5
Part of the crystal structure of (II), showing the formation of a centrosymmetric hydrogen-bonded dimer. For the sake of clarity, H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).

Figure 6
A stereoview of part of the crystal structure of (I)

, showing the formation of a π-stacked [1 $[\overline{1}]$ 0] chain of hydrogen-bonded dimers. For the sake of clarity, H atoms bonded to C atoms have been omitted.

Figure 7
A stereoview of part of the crystal structure of (II)

, showing the formation of a [100] chain of hydrogen-bonded dimers linked by dipolar carbonyl–carbonyl interactions. For the sake of clarity, H atoms bonded to C atoms have been omitted.

Experimental

Equimolar quantities (1 mmol of each component) of 2-thioxothiazolidin-4-one and the appropriate substituted benzaldehyde were placed in open Pyrex glass vessels in the absence of any solvent and irradiated in a domestic microwave oven for 3 min (at 600 W); the reactions were monitored by thin-layer chromatography. The reaction mixtures were extracted with ethanol; after removal of this solvent, the products were recrystallized from dimethylformamide to give crystals suitable for single-crystal X-ray diffraction. (I): orange crystals, m.p. 438 K, yield 53%; MS (70 eV) m/z (%): 239 (4, M⁺), 152 (100), 108 (2). (II): orange crystals, m.p. 495 K, yield 88%; MS (70 eV) m/z (%): 239 (24, M⁺), 152 (100), 107 (20). (III): orange crystals, m.p. 474 K, yield 85%; MS (70 eV) m/z (%): 313 (18, M+2), 312 (11, M+1), 311(88, M⁺), 224 [100, (M – C₂HNOS)⁺], 209 (94), 181 (16), 166 (9).

Compound (I)

Crystal data

C₁₀H₆FNOS₂
M_r = 239.28
Monoclinic, P 2₁ /c
a = 11.1848 (4) Å
b = 7.7651 (4) Å
c = 12.3611 (5) Å
β = 107.417 (3)°
V = 1024.35 (8) Å³
Z = 4
D_x = 1.552 Mg m⁻³
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 298 (2) K
Plate, orange
0.36 × 0.32 × 0.04 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ) T_min = 0.869, T_max = 0.980
9920 measured reflections
2337 independent reflections
1768 reflections with I > 2σ(I)
R_int = 0.042
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.105
S = 1.04
2337 reflections
141 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0479P)² + 0.3103P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Compound (II)

Crystal data

C₁₀H₆FNOS₂
M_r = 239.28
Monoclinic, P 2₁ /c
a = 4.9173 (2) Å
b = 19.8906 (10) Å
c = 10.4976 (6) Å
β = 92.929 (3)°
V = 1025.41 (9) Å³
Z = 4
D_x = 1.550 Mg m⁻³
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 298 (2) K
Lath, orange
0.60 × 0.35 × 0.12 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.753, T_max = 0.942
7246 measured reflections
2287 independent reflections
1430 reflections with I > 2σ(I)
R_int = 0.053
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.082
wR(F²) = 0.110
S = 1.09
2287 reflections
137 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0211P)² + 1.095P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max < 0.001
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.27 e Å⁻³
Extinction correction: SHELXL97
Extinction coefficient: 0.0071 (17)

Compound (III)

Crystal data

C₁₃H₁₃NO₄S₂
M_r = 311.36
Triclinic, $[P \overline 1]$
a = 10.3432 (4) Å
b = 10.9105 (4) Å
c = 13.4621 (4) Å
α = 100.399 (2)°
β = 91.572 (2)°
γ = 110.301 (2)°
V = 1394.72 (9) Å³
Z = 4
D_x = 1.483 Mg m⁻³
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 120 (2) K
Plate, orange
0.10 × 0.08 × 0.03 mm

Data collection

Bruker–Nonius KappaCCD diffractometer
φ and ω scans
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) T_min = 0.952, T_max = 0.988
29714 measured reflections
6377 independent reflections
3786 reflections with I > 2σ(I)
R_int = 0.106
θ_max = 27.5°

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.119
S = 1.00
6377 reflections
367 parameters
H-atom parameters constrained
w = 1/[σ²(F_o²) + (0.0539P)²] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Table 1
Selected bond angles and torsion angles (°) for compounds (I)–(III)

Parameter	(I)	(II)	(III)	(III)
x	nil	nil	1	2
Cx5—Cx57—Cx51	129.25 (17)	130.6 (3)	131.3 (3)	130.6 (3)
Sx1—Cx5—Cx57	130.48 (14)	130.1 (2)	130.0 (2)	130.2 (2)
Cx4—Cx5—Cx57	120.50 (17)	121.1 (3)	120.8 (2)	120.9 (2)
Cx52—Cx51—Cx56	115.44 (16)	118.6 (3)	119.4 (2)	117.8 (2)
Cx57—Cx51—Cx56	124.47 (17)	123.6 (3)	123.0 (2)	123.0 (2)
Cx5—Cx57—Cx51—Cx52	−174.60 (19)	179.9 (3)	179.9 (3)	179.5 (3)
Cx52—Cx53—Ox53—Cx58	–	–	5.1 (4)	−15.8 (4)
Cx53—Cx54—Ox54—Cx59	–	–	−77.3 (3)	−48.1 (3)
Cx54—Cx55—Ox55—Cx50	–	–	−179.3 (2)	174.3 (2)

Table 2
Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(III)

Compound	D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
(I)	C56—H56⋯S1	0.93	2.51	3.226 (2)	134
	N3—H3⋯O4ⁱ	0.86	2.00	2.843 (2)	168

(II)	C56—H56⋯S1	0.93	2.51	3.230 (3)	135
	N3—H3⋯O4ⁱ	0.87	2.00	2.831 (3)	159

(III)	C156—H156⋯S11	0.95	2.50	3.237 (2)	134
	N13—H13⋯O24	0.88	1.95	2.814 (3)	168
	C256—H256⋯S21	0.95	2.49	3.227 (2)	134
	N23—H23⋯O14	0.88	1.96	2.807 (3)	162
Symmetry code: (i) - x+1, - y+1, - z+1.

For each of (I) and (II), the space group P2₁/c was uniquely assigned from the systematic absences. Crystals of (III) are triclinic; the space group P $[\overline{1}]$ was selected and confirmed by the subsequent structure analysis. All H atoms were located in difference maps. H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.93 Å for (I) and (II), and 0.95 (aromatic) and 0.98 Å (methyl) for (III), and with U_iso(H) values of 1.2U_eq(C) or 1.5U_eq(methyl C);H atoms bonded to N atoms were allowed to ride at the distances found from the difference maps [N—H = 0.86–0.88 Å with U_iso(H) = 1.2U_eq(N)].

For all compounds, data collection: COLLECT (Hooft, 1999 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: OSCAIL (McArdle, 2003 ) and SHELXL97 (Sheldrick, 1997 ); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I, II, III. DOI: 10.1107/S0108270106018038/sk3027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270106018038/sk3027Isup2.hkl

Structure factors: contains datablock II. DOI: 10.1107/S0108270106018038/sk3027IIsup3.hkl

Structure factors: contains datablock III. DOI: 10.1107/S0108270106018038/sk3027IIIsup4.hkl

Comment top

We report here the structures of three substituted (Z)-5-(benzylidene)-2-thioxothiazolidin-4-ones, namely two isomers of (Z)-5-(fluorobenzylidene)-2-thioxothiazolidin-4-one, (I) and (II) (Figs. 1 and 2), and (Z)-5-(3,4,5-trimethoxybenzylidene)-2-thioxothiazolidin-4-one, (III) (Fig. 3), and we briefly compare these with the structures of the four analogues (IV)–(VII) which have been reported recently (Delgado et al., 2005). As for compounds (IV)–(VII), the title compounds (I)-(III) have been prepared by condensation of 2-thioxothiazolidin-4-one (rhodanine) with a substituted benzaldehyde using microwave radiation in a solvent-free system.

The molecules of compounds (I)–(III) are both effectively planar, as shown by the values of the Cx5—Cx57—Cx51—Cx52 torsion angle, where x = nil for compounds (I) and (II), and x = 1 or 2, respectively, for the two independent molecules in compound (III) (Table 1); this angle defines the rotation of the aryl ring relative to the rest of the molecule. In each isomer the Cx5—Cx57—Cx51 angle is very large, ca 130°, and these angles, together with the exocyclic angles at Cx5 and Cx51, are consistent with the occurrence of a repulsive intramolecular interaction between Sx1 and Hx56 (Table 2). This behaviour closely mimics that in the analogues (IV)–(VII). In each of the molecules in (III), the methoxy groups at Cx53 and Cx55 have their C atoms almost coplanar with the adjacent aryl rings (Table 1), but those at Cx54 have the C atoms well removed from this plane for steric reasons.

The supramolecular structures of compounds (I)–(III) are very simple. In the isomers (I) and (II) the molecules are linked by paired N—H···O hydrogen bonds (Table 2) into centrosymmetric R₂²(8) (Bernstein et al., 1995) dimers; in each isomer the asymmetric unit was selected such that the dimer containing the reference molecule is centred at (1/2, 1/2, 1/2) (Figs. 4 and 5). The structures of (I) and (II) differ, however, in the manner in which the hydrogen-bonded dimers are linked into chains. In compound (III), the two independent molecules are again linked into a dimer but this does not exhibit even approximate centrosymmetry. There are no direction-specific interactions between the dimeric units in compound (III).

The hydrogen-bonded dimers in (I) are linked by an aromatic π–π stacking interaction. The aryl rings in the molecules at (x, y, z) and (2 − x, −y, 1 − z), which lie, respectively, in the R₂²(8) dimers centred at (1/2, 1/2, 1/2) and (3/2, −1/2, 1/2) are strictly parallel, with an interplanar spacing of 3.366 (2) Å; the ring-centroid separation is 3.692 (2) Å, corresponding to an almost ideal ring offset of 1.515 (2) Å. Propagation by inversion of this interaction links the dimers into chains running parallel to the [110] direction (Fig. 6).

In compound (II), the hydrogen-bonded dimers are linked by an antiparallel carbonyl–carbonyl interaction, which is centrosymmetric. The molecules at (x, y, z) and (−x, 1 − y, 1 − z) are components of the dimers centred at (1/2, 1/2, 1/2) and (−1/2, 1/2, 1/2), respectively; their carbonyl groups are antiparallel, with a C···Oⁱ distance of 3.181 (4) Å and an O—C···Oⁱ angle of 100.5 (2)° [symmetry code: (i) −x, 1 − y, 1 − z], producing a slightly sheared interaction of type (II) (Allen et al., 1998), which links the dimers into chains running parallel to the [100] direction (Fig. 7).

We note very briefly the different patterns of supramolecular aggregation in the analogues (IV)–(VII) (Delgado et al., 2005). In compound (IV), which crystallizes with Z' = 2 in space group P2₁/n, the two independent molecules are linked by N—H···O bonds into a dimer, as in (III), but these dimers are not isolated; instead they are linked by C—H···π(arene) hydrogen bonds into sheets. Compound (V) is effectively isomorphous with (III) and the molecules form centrosymmetric dimers, which are linked into chains by a dipolar carbonyl–carbonyl interaction. No dimers formed by paired N—H···O hydrogen bonds are discernible in the structure of (VI); instead the molecules are linked into chains of rings by a combination of N—H···S and C—H···O hydrogen bonds. In (VII), the usual R₂²(8) dimers are formed and these are linked into chains of rings by C—H···S hydrogen bonds. Thus within the extended series (I)–(VII) it is apparent that rather modest changes to the peripheral substituents can have a significant influence on the overall supramolecular aggregation.

Experimental top

Equimolar quantities (1 mmol of each component) of 2-thioxothiazolidin-4-one and the appropriate substituted benzaldehyde were placed in open Pyrex glass vessels in the absence of any solvent and irradiated in a domestic microwave oven for 3 min (at 600 W); the reactions were monitored by thin-layer chromatography. The reaction mixtures were extracted with ethanol; after removal of this solvent, the products were recrystallized from dimethylformamide to give crystals suitable for single-crystal X-ray diffraction. (I) orange crystals, m.p. 438 K, yield 53%; MS (70 eV) m/z (%) 239 (4, M⁺), 152 ?(100), 108? (2). (II) orange crystals, m.p. 495 K, yield 88%; MS (70 eV) m/z (%) 239 (24, M⁺), 152? (100), 107?(20). (III) orange crystals, m.p. 474 K, yield 85%; MS (70 eV) m/z (%) 313 (18, M+2), 312 (11, M+1), 311(88, M⁺), 224 [100, (M– C₂HNOS)⁺], 209?(94), 181 (16), 166 (9).

Computing details top

For all compounds, data collection: COLLECT (Hooft, 1999); cell refinement: DENZO (Otwinowski & Minor, 1997) and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: Sir2004 (Burla et al., 2005); program(s) used to refine structure: OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PRPKAPPA (Ferguson, 1999).

Figures top

	Fig. 1. A molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A molecule of (II), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 3. The two independent molecules of (III), showing the atom-labelling scheme and the N—H···O hydrogen bonds (dashed lines). Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 4. Part of the crystal structure of (I), showing the formation of a centrosymmetric hydrogen-bonded dimer. For the sake of clarity, H atoms bonded to C atoms have been omitted. The atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
	Fig. 5. Part of the crystal structure of II) showing the formation of a centrosymmetric hydrogen-bonded dimer. For the sake of clarity the H atoms bonded to C atoms have been omitted. Atoms marked with an asterisk (*) are at the symmetry position (1 − x, 1 − y, 1 − z).
	Fig. 6. A stereoview of part of the crystal structure of (I), showing the formation of a π-stacked [110] chain of hydrogen-bonded dimers. For the sake of clarity, H atoms bonded to C atoms have been omitted.
	Fig. 7. A stereoview of part of the crystal structure of (II), showing the formation of a [100] chain of hydrogen-bonded dimers linked by dipolar carbonyl–carbonyl interactions. For the sake of clarity, H atoms bonded to C atoms have been omitted.

(I) (Z)-5-(2-fluorobenzylidene)-2-thioxothaolidin-2-one top

Crystal data top

C₁₀H₆FNOS₂	F(000) = 488
M_r = 239.28	D_x = 1.552 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2337 reflections
a = 11.1848 (4) Å	θ = 3.1–27.5°
b = 7.7651 (4) Å	µ = 0.50 mm⁻¹
c = 12.3611 (5) Å	T = 298 K
β = 107.417 (3)°	Plate, orange
V = 1024.35 (8) Å³	0.36 × 0.32 × 0.04 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	2337 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1768 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.1°
ϕ and ω scans	h = −12→14
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −10→9
T_min = 0.869, T_max = 0.980	l = −16→12
9920 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0479P)² + 0.3103P] where P = (F_o² + 2F_c²)/3
2337 reflections	(Δ/σ)_max < 0.001
141 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₀H₆FNOS₂	V = 1024.35 (8) Å³
M_r = 239.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.1848 (4) Å	µ = 0.50 mm⁻¹
b = 7.7651 (4) Å	T = 298 K
c = 12.3611 (5) Å	0.36 × 0.32 × 0.04 mm
β = 107.417 (3)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	2337 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1768 reflections with I > 2σ(I)
T_min = 0.869, T_max = 0.980	R_int = 0.042
9920 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.04	Δρ_max = 0.22 e Å⁻³
2337 reflections	Δρ_min = −0.32 e Å⁻³
141 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.77713 (4)	0.41358 (7)	0.32725 (4)	0.04646 (17)
S2	0.55447 (5)	0.59484 (9)	0.17861 (5)	0.0631 (2)
F52	1.02797 (13)	0.09006 (18)	0.72332 (10)	0.0683 (4)
O4	0.64154 (13)	0.3975 (2)	0.57676 (12)	0.0597 (4)
N3	0.58930 (13)	0.4942 (2)	0.39335 (14)	0.0455 (4)
C2	0.62862 (16)	0.5068 (2)	0.29922 (17)	0.0441 (4)
C4	0.66675 (16)	0.4158 (2)	0.48794 (17)	0.0432 (4)
C5	0.78410 (16)	0.3595 (2)	0.46621 (16)	0.0397 (4)
C51	0.99811 (15)	0.2238 (2)	0.54620 (15)	0.0379 (4)
C52	1.07477 (18)	0.1314 (3)	0.63747 (16)	0.0449 (4)
C53	1.19345 (19)	0.0782 (3)	0.64488 (19)	0.0525 (5)
C54	1.24000 (18)	0.1142 (3)	0.5559 (2)	0.0547 (5)
C55	1.16815 (17)	0.2025 (3)	0.46334 (19)	0.0527 (5)
C56	1.04901 (16)	0.2572 (3)	0.45890 (17)	0.0460 (5)
C57	0.87484 (16)	0.2811 (2)	0.54795 (16)	0.0409 (4)
H3	0.5178	0.5350	0.3933	0.055*
H57	0.8552	0.2585	0.6151	0.041 (5)*
H53	1.2413	0.0184	0.7082	0.064 (7)*
H54	1.3202	0.0784	0.5585	0.066 (7)*
H55	1.1996	0.2264	0.4034	0.067 (7)*
H56	1.0015	0.3170	0.3955	0.055 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0347 (2)	0.0600 (3)	0.0463 (3)	0.0085 (2)	0.0146 (2)	0.0011 (2)
C2	0.0307 (8)	0.0441 (10)	0.0544 (11)	−0.0019 (8)	0.0083 (8)	−0.0051 (8)
S2	0.0413 (3)	0.0787 (4)	0.0625 (4)	0.0055 (3)	0.0050 (3)	0.0140 (3)
N3	0.0283 (7)	0.0515 (10)	0.0571 (10)	0.0055 (7)	0.0135 (7)	−0.0029 (8)
C4	0.0336 (9)	0.0458 (10)	0.0519 (11)	0.0024 (8)	0.0155 (8)	−0.0051 (8)
O4	0.0448 (7)	0.0840 (12)	0.0575 (9)	0.0167 (7)	0.0260 (7)	0.0056 (8)
C5	0.0326 (8)	0.0421 (9)	0.0469 (10)	0.0013 (8)	0.0155 (8)	−0.0053 (8)
C57	0.0377 (9)	0.0432 (10)	0.0446 (10)	0.0017 (8)	0.0163 (8)	−0.0032 (8)
C51	0.0320 (8)	0.0388 (9)	0.0414 (10)	0.0021 (7)	0.0091 (7)	−0.0043 (7)
C52	0.0452 (10)	0.0473 (10)	0.0398 (10)	0.0019 (9)	0.0092 (8)	−0.0049 (8)
F52	0.0711 (8)	0.0922 (10)	0.0428 (7)	0.0174 (7)	0.0189 (6)	0.0098 (6)
C53	0.0416 (10)	0.0504 (11)	0.0544 (12)	0.0085 (9)	−0.0027 (9)	−0.0023 (10)
C54	0.0302 (9)	0.0508 (12)	0.0794 (15)	0.0051 (8)	0.0105 (10)	−0.0066 (11)
C55	0.0367 (10)	0.0595 (13)	0.0659 (13)	0.0025 (9)	0.0212 (9)	0.0022 (10)
C56	0.0338 (9)	0.0527 (11)	0.0522 (11)	0.0063 (8)	0.0139 (8)	0.0054 (9)

Geometric parameters (Å, º) top

S1—C5	1.7471 (19)	C51—C56	1.387 (2)
S1—C2	1.7487 (18)	C51—C52	1.394 (3)
C2—N3	1.365 (2)	C52—F52	1.355 (2)
C2—S2	1.624 (2)	C52—C53	1.367 (3)
N3—C4	1.372 (3)	C53—C54	1.379 (3)
N3—H3	0.86	C53—H53	0.93
C4—O4	1.221 (2)	C54—C55	1.369 (3)
C4—C5	1.482 (2)	C54—H54	0.93
C5—C57	1.345 (3)	C55—C56	1.384 (2)
C57—C51	1.455 (2)	C55—H55	0.93
C57—H57	0.93	C56—H56	0.93

C5—S1—C2	93.12 (9)	C56—C51—C57	124.47 (17)
N3—C2—S2	127.32 (14)	C52—C51—C57	120.08 (16)
N3—C2—S1	109.32 (14)	F52—C52—C53	118.11 (18)
S2—C2—S1	123.36 (12)	F52—C52—C51	117.88 (16)
C2—N3—C4	118.43 (15)	C53—C52—C51	124.01 (19)
C2—N3—H3	120.6	C52—C53—C54	118.44 (19)
C4—N3—H3	120.9	C52—C53—H53	120.7
O4—C4—N3	124.16 (16)	C54—C53—H53	120.9
O4—C4—C5	125.73 (18)	C55—C54—C53	120.05 (18)
N3—C4—C5	110.11 (16)	C55—C54—H54	119.8
C57—C5—C4	120.50 (17)	C53—C54—H54	120.1
C57—C5—S1	130.48 (14)	C54—C55—C56	120.3 (2)
C4—C5—S1	109.02 (13)	C54—C55—H55	119.9
C5—C57—C51	129.25 (17)	C56—C55—H55	119.8
C5—C57—H57	115.2	C55—C56—C51	121.76 (18)
C51—C57—H57	115.5	C55—C56—H56	119.1
C56—C51—C52	115.44 (16)	C51—C56—H56	119.1

C5—S1—C2—N3	−0.19 (15)	C5—C57—C51—C56	6.7 (3)
C5—S1—C2—S2	179.10 (13)	C5—C57—C51—C52	−174.60 (19)
S2—C2—N3—C4	−179.38 (15)	C56—C51—C52—F52	−177.76 (17)
S1—C2—N3—C4	−0.1 (2)	C57—C51—C52—F52	3.4 (3)
C2—N3—C4—O4	179.91 (18)	C56—C51—C52—C53	1.4 (3)
C2—N3—C4—C5	0.4 (2)	C57—C51—C52—C53	−177.47 (19)
O4—C4—C5—C57	−0.2 (3)	F52—C52—C53—C54	177.62 (18)
N3—C4—C5—C57	179.22 (17)	C51—C52—C53—C54	−1.5 (3)
O4—C4—C5—S1	179.99 (17)	C52—C53—C54—C55	0.5 (3)
N3—C4—C5—S1	−0.55 (19)	C53—C54—C55—C56	0.5 (3)
C2—S1—C5—C57	−179.32 (19)	C54—C55—C56—C51	−0.6 (3)
C2—S1—C5—C4	0.42 (14)	C52—C51—C56—C55	−0.3 (3)
C4—C5—C57—C51	−176.72 (18)	C57—C51—C56—C55	178.51 (19)
S1—C5—C57—C51	3.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O4ⁱ	0.86	2.00	2.843 (2)	168
C56—H56···S1	0.93	2.51	3.226 (2)	134

Symmetry code: (i) −x+1, −y+1, −z+1.

(II) (Z)-5-(4-fluorobenzylidene)-2-thioxothaolidin-2-one top

Crystal data top

C₁₀H₆FNOS₂	F(000) = 488
M_r = 239.28	D_x = 1.550 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2287 reflections
a = 4.9173 (2) Å	θ = 3.6–27.5°
b = 19.8906 (10) Å	µ = 0.50 mm⁻¹
c = 10.4976 (6) Å	T = 298 K
β = 92.929 (3)°	Lath, orange
V = 1025.41 (9) Å³	0.60 × 0.35 × 0.12 mm
Z = 4

Data collection top

Bruker–Nonius KappaCCD diffractometer	2287 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	1430 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.053
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 3.6°
ϕ and ω scans	h = −5→6
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −25→25
T_min = 0.753, T_max = 0.942	l = −10→13
7246 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.082	H-atom parameters constrained
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0211P)² + 1.095P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max < 0.001
2287 reflections	Δρ_max = 0.31 e Å⁻³
137 parameters	Δρ_min = −0.27 e Å⁻³
0 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0071 (17)

Crystal data top

C₁₀H₆FNOS₂	V = 1025.41 (9) Å³
M_r = 239.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.9173 (2) Å	µ = 0.50 mm⁻¹
b = 19.8906 (10) Å	T = 298 K
c = 10.4976 (6) Å	0.60 × 0.35 × 0.12 mm
β = 92.929 (3)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	2287 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1430 reflections with I > 2σ(I)
T_min = 0.753, T_max = 0.942	R_int = 0.053
7246 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.082	0 restraints
wR(F²) = 0.110	H-atom parameters constrained
S = 1.09	Δρ_max = 0.31 e Å⁻³
2287 reflections	Δρ_min = −0.27 e Å⁻³
137 parameters

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

	x	y	z	U_iso*/U_eq
S1	−0.09085 (14)	0.50772 (4)	0.18496 (8)	0.0407 (3)
S2	0.27590 (19)	0.38918 (5)	0.17203 (11)	0.0585 (3)
F54	−1.0271 (4)	0.75575 (11)	0.0713 (2)	0.0693 (7)
O4	0.2516 (4)	0.56639 (11)	0.5020 (2)	0.0420 (6)
N3	0.2897 (4)	0.48323 (13)	0.3535 (2)	0.0354 (6)
C2	0.1782 (5)	0.45690 (16)	0.2424 (3)	0.0364 (8)
C4	0.1741 (5)	0.54003 (16)	0.4010 (3)	0.0326 (7)
C5	−0.0537 (5)	0.56341 (15)	0.3145 (3)	0.0313 (7)
C51	−0.4126 (5)	0.65280 (15)	0.2672 (3)	0.0331 (7)
C52	−0.5213 (6)	0.71123 (17)	0.3166 (3)	0.0488 (9)
C53	−0.7278 (7)	0.74614 (18)	0.2514 (4)	0.0552 (10)
C54	−0.8236 (6)	0.72169 (18)	0.1359 (3)	0.0452 (9)
C55	−0.7269 (6)	0.66447 (18)	0.0836 (3)	0.0469 (9)
C56	−0.5198 (6)	0.63011 (17)	0.1496 (3)	0.0422 (8)
C57	−0.1918 (5)	0.61927 (15)	0.3396 (3)	0.0338 (7)
H3	0.4394	0.4631	0.3794	0.043*
H57	−0.1380	0.6402	0.4160	0.041*
H52	−0.4536	0.7272	0.3952	0.059*
H53	−0.7995	0.7852	0.2851	0.066*
H55	−0.7983	0.6489	0.0053	0.056*
H56	−0.4507	0.5911	0.1147	0.051*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0365 (4)	0.0431 (5)	0.0412 (5)	0.0036 (3)	−0.0109 (3)	−0.0059 (4)
C2	0.0318 (14)	0.0370 (19)	0.0400 (19)	−0.0028 (13)	−0.0012 (13)	0.0007 (15)
S2	0.0548 (5)	0.0492 (6)	0.0700 (7)	0.0099 (4)	−0.0105 (5)	−0.0200 (5)
N3	0.0286 (11)	0.0401 (16)	0.0368 (15)	0.0057 (11)	−0.0052 (10)	−0.0014 (13)
C4	0.0270 (13)	0.0377 (19)	0.0330 (18)	−0.0010 (13)	0.0003 (12)	0.0048 (15)
O4	0.0393 (11)	0.0500 (15)	0.0356 (13)	0.0088 (10)	−0.0098 (10)	−0.0048 (11)
C5	0.0279 (13)	0.0361 (18)	0.0296 (17)	−0.0019 (12)	−0.0031 (12)	0.0017 (14)
C57	0.0324 (14)	0.0378 (19)	0.0307 (17)	−0.0018 (13)	−0.0032 (12)	0.0003 (15)
F54	0.0589 (12)	0.0675 (15)	0.0787 (17)	0.0202 (11)	−0.0233 (11)	0.0161 (13)
C51	0.0284 (13)	0.0332 (18)	0.0372 (18)	−0.0015 (12)	−0.0027 (12)	0.0035 (14)
C54	0.0344 (15)	0.047 (2)	0.054 (2)	0.0034 (15)	−0.0074 (15)	0.0155 (18)
C52	0.0445 (17)	0.046 (2)	0.054 (2)	0.0059 (16)	−0.0145 (16)	−0.0095 (18)
C53	0.0512 (19)	0.042 (2)	0.071 (3)	0.0125 (17)	−0.0120 (18)	−0.007 (2)
C55	0.0451 (17)	0.056 (2)	0.038 (2)	0.0045 (17)	−0.0107 (15)	0.0038 (18)
C56	0.0417 (16)	0.046 (2)	0.038 (2)	0.0068 (15)	−0.0034 (14)	0.0003 (16)

Geometric parameters (Å, º) top

S1—C2	1.748 (3)	F54—C54	1.360 (3)
S1—C5	1.756 (3)	C51—C52	1.391 (4)
C2—N3	1.367 (4)	C51—C56	1.393 (4)
C2—S2	1.621 (3)	C54—C55	1.360 (5)
N3—C4	1.370 (4)	C54—C53	1.367 (5)
N3—H3	0.87	C52—C53	1.382 (4)
C4—O4	1.226 (3)	C52—H52	0.93
C4—C5	1.481 (4)	C53—H53	0.93
C5—C57	1.336 (4)	C55—C56	1.383 (4)
C57—C51	1.455 (4)	C55—H55	0.93
C57—H57	0.93	C56—H56	0.93

C2—S1—C5	92.91 (14)	C52—C51—C57	118.6 (3)
N3—C2—S2	126.3 (2)	C56—C51—C57	123.6 (3)
N3—C2—S1	109.7 (2)	C55—C54—F54	118.6 (3)
S2—C2—S1	124.05 (18)	C55—C54—C53	123.0 (3)
C2—N3—C4	118.1 (2)	F54—C54—C53	118.4 (3)
C2—N3—H3	112.8	C53—C52—C51	121.4 (3)
C4—N3—H3	128.8	C53—C52—H52	119.3
O4—C4—N3	123.4 (2)	C51—C52—H52	119.3
O4—C4—C5	126.1 (3)	C54—C53—C52	118.1 (3)
N3—C4—C5	110.5 (2)	C54—C53—H53	120.9
C57—C5—C4	121.1 (3)	C52—C53—H53	120.9
C57—C5—S1	130.1 (2)	C54—C55—C56	118.3 (3)
C4—C5—S1	108.8 (2)	C54—C55—H55	120.8
C5—C57—C51	130.6 (3)	C56—C55—H55	120.8
C5—C57—H57	114.7	C55—C56—C51	121.3 (3)
C51—C57—H57	114.7	C55—C56—H56	119.3
C52—C51—C56	117.8 (3)	C51—C56—H56	119.3

C5—S1—C2—N3	−1.2 (2)	S1—C5—C57—C51	−1.5 (5)
C5—S1—C2—S2	179.0 (2)	C5—C57—C51—C52	179.9 (3)
S2—C2—N3—C4	−178.0 (2)	C5—C57—C51—C56	−1.0 (5)
S1—C2—N3—C4	2.2 (3)	C56—C51—C52—C53	−0.4 (5)
C2—N3—C4—O4	177.3 (3)	C57—C51—C52—C53	178.8 (3)
C2—N3—C4—C5	−2.2 (4)	C55—C54—C53—C52	0.7 (6)
O4—C4—C5—C57	2.5 (5)	F54—C54—C53—C52	179.9 (3)
N3—C4—C5—C57	−178.0 (3)	C51—C52—C53—C54	−0.1 (6)
O4—C4—C5—S1	−178.4 (3)	F54—C54—C55—C56	179.9 (3)
N3—C4—C5—S1	1.1 (3)	C53—C54—C55—C56	−0.9 (6)
C2—S1—C5—C57	179.0 (3)	C54—C55—C56—C51	0.4 (5)
C2—S1—C5—C4	0.1 (2)	C52—C51—C56—C55	0.2 (5)
C4—C5—C57—C51	177.4 (3)	C57—C51—C56—C55	−178.9 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C56—H56···S1	0.93	2.51	3.230 (3)	135
N3—H3···O4ⁱ	0.87	2.00	2.831 (3)	159

Symmetry code: (i) −x+1, −y+1, −z+1.

(III) (Z)-5-(3,4,5-Trimethoxybenzylidene)-2-thioxothaolidin-2-one top

Crystal data top

C₁₃H₁₃NO₄S₂	Z = 4
M_r = 311.36	F(000) = 648
Triclinic, P1	D_x = 1.483 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.3432 (4) Å	Cell parameters from 6377 reflections
b = 10.9105 (4) Å	θ = 2.7–27.5°
c = 13.4621 (4) Å	µ = 0.39 mm⁻¹
α = 100.399 (2)°	T = 120 K
β = 91.572 (2)°	Plate, orange
γ = 110.301 (2)°	0.10 × 0.08 × 0.03 mm
V = 1394.72 (9) Å³

Data collection top

Bruker–Nonius KappaCCD diffractometer	6377 independent reflections
Radiation source: Bruker-Nonius FR591 rotating anode	3786 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.106
Detector resolution: 9.091 pixels mm^-1	θ_max = 27.5°, θ_min = 2.7°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	k = −14→14
T_min = 0.952, T_max = 0.988	l = −17→17
29714 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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0539P)²] where P = (F_o² + 2F_c²)/3
6377 reflections	(Δ/σ)_max = 0.001
367 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.42 e Å⁻³

Crystal data top

C₁₃H₁₃NO₄S₂	γ = 110.301 (2)°
M_r = 311.36	V = 1394.72 (9) Å³
Triclinic, P1	Z = 4
a = 10.3432 (4) Å	Mo Kα radiation
b = 10.9105 (4) Å	µ = 0.39 mm⁻¹
c = 13.4621 (4) Å	T = 120 K
α = 100.399 (2)°	0.10 × 0.08 × 0.03 mm
β = 91.572 (2)°

Data collection top

Bruker–Nonius KappaCCD diffractometer	6377 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	3786 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.988	R_int = 0.106
29714 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.00	Δρ_max = 0.33 e Å⁻³
6377 reflections	Δρ_min = −0.42 e Å⁻³
367 parameters

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

	x	y	z	U_iso*/U_eq
S11	0.88927 (7)	1.14205 (7)	0.93278 (5)	0.02349 (18)
S12	0.88234 (8)	1.14023 (7)	0.71059 (5)	0.02956 (19)
O14	0.71179 (19)	0.76133 (18)	0.88920 (12)	0.0254 (4)
N13	0.7868 (2)	0.9277 (2)	0.79756 (14)	0.0208 (5)
C12	0.8492 (3)	1.0620 (3)	0.80518 (18)	0.0225 (6)
C14	0.7672 (3)	0.8801 (3)	0.88691 (18)	0.0205 (6)
C15	0.8220 (3)	0.9912 (3)	0.97520 (18)	0.0197 (6)
C157	0.8165 (3)	0.9684 (3)	1.07014 (18)	0.0201 (6)
C151	0.8672 (3)	1.0580 (3)	1.16742 (18)	0.0185 (6)
C152	0.8448 (3)	1.0027 (3)	1.25423 (18)	0.0206 (6)
C153	0.8926 (3)	1.0830 (3)	1.34957 (18)	0.0211 (6)
O153	0.87569 (19)	1.03880 (18)	1.43900 (12)	0.0271 (5)
C158	0.8139 (3)	0.8987 (3)	1.4343 (2)	0.0302 (7)
C154	0.9635 (3)	1.2197 (3)	1.36037 (18)	0.0204 (6)
O154	1.01952 (17)	1.29983 (17)	1.45341 (12)	0.0231 (4)
C155	0.9863 (3)	1.2757 (3)	1.27333 (18)	0.0189 (6)
C159	0.9202 (3)	1.3319 (3)	1.51525 (19)	0.0272 (7)
O155	1.05683 (18)	1.41070 (17)	1.29121 (12)	0.0242 (4)
C150	1.0806 (3)	1.4715 (3)	1.20455 (19)	0.0270 (7)
C156	0.9384 (3)	1.1951 (3)	1.17770 (18)	0.0205 (6)
S21	0.57903 (7)	0.34519 (7)	0.58269 (5)	0.02293 (18)
C22	0.5770 (3)	0.4278 (3)	0.70628 (18)	0.0200 (6)
S22	0.52094 (8)	0.35185 (7)	0.79946 (5)	0.0296 (2)
N23	0.6282 (2)	0.5620 (2)	0.71191 (15)	0.0198 (5)
C24	0.6698 (2)	0.6082 (3)	0.62460 (18)	0.0185 (6)
O24	0.71258 (18)	0.72673 (17)	0.62060 (12)	0.0223 (4)
C25	0.6511 (3)	0.4955 (2)	0.53957 (18)	0.0177 (6)
C257	0.6865 (2)	0.5166 (3)	0.44703 (18)	0.0190 (6)
C251	0.6724 (3)	0.4227 (3)	0.35233 (17)	0.0177 (6)
C252	0.7184 (3)	0.4747 (3)	0.26660 (18)	0.0208 (6)
C253	0.7018 (3)	0.3897 (3)	0.17292 (18)	0.0212 (6)
O253	0.75011 (19)	0.43225 (18)	0.08640 (12)	0.0284 (5)
C258	0.7887 (3)	0.5719 (3)	0.0867 (2)	0.0370 (8)
C254	0.6374 (3)	0.2523 (3)	0.16284 (18)	0.0208 (6)
O254	0.61905 (19)	0.16169 (18)	0.07461 (12)	0.0278 (5)
C259	0.5633 (3)	0.1858 (3)	−0.01633 (19)	0.0287 (7)
C255	0.5947 (3)	0.2002 (3)	0.24972 (18)	0.0195 (6)
O255	0.53508 (19)	0.06435 (17)	0.23400 (12)	0.0257 (4)
C250	0.5024 (3)	0.0074 (3)	0.32222 (19)	0.0304 (7)
C256	0.6117 (3)	0.2846 (3)	0.34292 (18)	0.0206 (6)
H13	0.7599	0.8731	0.7380	0.025*
H157	0.7716	0.8775	1.0740	0.024*
H152	0.7966	0.9096	1.2478	0.025*
H18A	0.7188	0.8661	1.4021	0.045*
H18B	0.8128	0.8810	1.5032	0.045*
H18C	0.8677	0.8528	1.3945	0.045*
H19A	0.8769	1.3824	1.4816	0.041*
H19B	0.9669	1.3858	1.5813	0.041*
H19C	0.8488	1.2493	1.5251	0.041*
H10A	1.1406	1.4365	1.1622	0.040*
H10B	1.1256	1.5683	1.2269	0.040*
H10C	0.9920	1.4511	1.1652	0.040*
H156	0.9540	1.2332	1.1190	0.025*
H23	0.6347	0.6178	0.7695	0.024*
H257	0.7274	0.6079	0.4429	0.023*
H252	0.7610	0.5684	0.2724	0.025*
H28A	0.7130	0.6017	0.1086	0.055*
H28B	0.8073	0.5874	0.0181	0.055*
H28C	0.8722	0.6222	0.1335	0.055*
H29A	0.5023	0.2362	0.0017	0.043*
H29B	0.5103	0.1003	−0.0614	0.043*
H29C	0.6393	0.2371	−0.0511	0.043*
H20A	0.5867	0.0343	0.3684	0.046*
H20B	0.4639	−0.0902	0.3019	0.046*
H20C	0.4342	0.0390	0.3567	0.046*
H256	0.5818	0.2484	0.4010	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S11	0.0321 (4)	0.0175 (4)	0.0181 (3)	0.0061 (3)	0.0020 (3)	0.0025 (3)
C12	0.0272 (16)	0.0233 (17)	0.0187 (14)	0.0122 (14)	0.0021 (11)	0.0027 (12)
S12	0.0422 (5)	0.0256 (4)	0.0210 (4)	0.0101 (4)	0.0051 (3)	0.0085 (3)
N13	0.0297 (13)	0.0178 (13)	0.0121 (11)	0.0063 (11)	0.0011 (9)	0.0007 (9)
C14	0.0210 (15)	0.0207 (16)	0.0204 (14)	0.0082 (13)	0.0047 (11)	0.0036 (12)
O14	0.0358 (12)	0.0189 (12)	0.0172 (9)	0.0054 (10)	0.0045 (8)	0.0014 (8)
C15	0.0209 (15)	0.0151 (15)	0.0210 (14)	0.0051 (12)	0.0022 (11)	0.0012 (11)
C157	0.0212 (15)	0.0170 (15)	0.0207 (14)	0.0050 (12)	0.0034 (11)	0.0038 (11)
C151	0.0188 (14)	0.0191 (16)	0.0165 (13)	0.0061 (12)	0.0027 (11)	0.0024 (11)
C152	0.0235 (15)	0.0151 (15)	0.0200 (14)	0.0031 (12)	−0.0008 (11)	0.0032 (11)
C153	0.0238 (15)	0.0239 (16)	0.0161 (13)	0.0087 (13)	0.0017 (11)	0.0054 (11)
O153	0.0377 (12)	0.0229 (11)	0.0154 (9)	0.0033 (9)	0.0010 (8)	0.0059 (8)
C158	0.0348 (18)	0.0301 (19)	0.0241 (15)	0.0057 (15)	0.0053 (13)	0.0132 (13)
C154	0.0188 (15)	0.0224 (16)	0.0169 (13)	0.0059 (13)	0.0009 (11)	−0.0010 (11)
O154	0.0225 (10)	0.0268 (11)	0.0146 (9)	0.0059 (9)	−0.0005 (8)	−0.0027 (8)
C155	0.0193 (14)	0.0153 (15)	0.0204 (14)	0.0044 (12)	0.0023 (11)	0.0032 (11)
C159	0.0343 (17)	0.0270 (17)	0.0203 (14)	0.0139 (14)	0.0003 (12)	−0.0010 (12)
O155	0.0302 (11)	0.0179 (11)	0.0208 (10)	0.0043 (9)	0.0034 (8)	0.0028 (8)
C150	0.0321 (17)	0.0169 (16)	0.0278 (15)	0.0027 (14)	0.0006 (13)	0.0070 (12)
C156	0.0253 (15)	0.0211 (16)	0.0160 (13)	0.0090 (13)	0.0007 (11)	0.0047 (11)
S21	0.0317 (4)	0.0167 (4)	0.0185 (3)	0.0065 (3)	0.0042 (3)	0.0031 (3)
C22	0.0239 (15)	0.0218 (16)	0.0153 (13)	0.0098 (13)	0.0008 (11)	0.0031 (11)
S22	0.0444 (5)	0.0247 (4)	0.0219 (4)	0.0120 (4)	0.0096 (3)	0.0102 (3)
N23	0.0276 (13)	0.0165 (13)	0.0139 (11)	0.0078 (11)	0.0020 (9)	0.0002 (9)
C24	0.0165 (14)	0.0227 (17)	0.0166 (13)	0.0073 (13)	0.0013 (11)	0.0045 (12)
O24	0.0294 (11)	0.0160 (11)	0.0188 (9)	0.0052 (9)	0.0033 (8)	0.0025 (8)
C25	0.0175 (14)	0.0135 (14)	0.0193 (13)	0.0032 (12)	−0.0011 (11)	0.0019 (11)
C257	0.0162 (14)	0.0165 (15)	0.0227 (14)	0.0039 (12)	0.0002 (11)	0.0041 (11)
C251	0.0183 (14)	0.0178 (15)	0.0157 (13)	0.0056 (12)	−0.0007 (10)	0.0022 (11)
C252	0.0219 (15)	0.0174 (15)	0.0218 (14)	0.0053 (12)	0.0018 (11)	0.0044 (11)
C253	0.0240 (15)	0.0283 (17)	0.0133 (13)	0.0112 (13)	0.0042 (11)	0.0049 (12)
O253	0.0376 (12)	0.0249 (12)	0.0179 (10)	0.0048 (10)	0.0072 (8)	0.0047 (8)
C258	0.051 (2)	0.032 (2)	0.0282 (16)	0.0102 (16)	0.0138 (14)	0.0138 (14)
C254	0.0238 (15)	0.0210 (16)	0.0163 (13)	0.0087 (13)	−0.0005 (11)	−0.0001 (11)
O254	0.0444 (13)	0.0261 (11)	0.0144 (9)	0.0170 (10)	−0.0004 (8)	−0.0002 (8)
C259	0.0346 (18)	0.0318 (18)	0.0190 (14)	0.0136 (15)	−0.0030 (12)	0.0010 (12)
C255	0.0203 (14)	0.0160 (16)	0.0190 (14)	0.0047 (12)	−0.0033 (11)	0.0003 (11)
O255	0.0359 (12)	0.0177 (11)	0.0193 (10)	0.0058 (9)	0.0006 (8)	0.0010 (8)
C250	0.0412 (19)	0.0187 (16)	0.0278 (15)	0.0065 (14)	0.0032 (14)	0.0048 (13)
C256	0.0240 (15)	0.0253 (17)	0.0151 (13)	0.0109 (13)	0.0033 (11)	0.0066 (11)

Geometric parameters (Å, º) top

S11—C12	1.747 (3)	S21—C22	1.748 (2)
S11—C15	1.757 (3)	S21—C25	1.761 (3)
C12—N13	1.364 (3)	C22—N23	1.359 (3)
C12—S12	1.637 (3)	C22—S22	1.637 (2)
N13—C14	1.387 (3)	N23—C24	1.383 (3)
N13—H13	0.88	N23—H23	0.88
C14—O14	1.228 (3)	C24—O24	1.225 (3)
C14—C15	1.473 (4)	C24—C25	1.475 (3)
C15—C157	1.345 (3)	C25—C257	1.345 (3)
C157—C151	1.446 (3)	C257—C251	1.453 (3)
C157—H157	0.95	C257—H257	0.95
C151—C156	1.398 (4)	C251—C256	1.397 (4)
C151—C152	1.398 (3)	C251—C252	1.399 (3)
C152—C153	1.385 (3)	C252—C253	1.391 (3)
C152—H152	0.95	C252—H252	0.95
C153—O153	1.370 (3)	C253—O253	1.374 (3)
C153—C154	1.392 (4)	C253—C254	1.392 (4)
O153—C158	1.426 (3)	O253—C258	1.435 (3)
C158—H18A	0.98	C258—H28A	0.98
C158—H18B	0.98	C258—H28B	0.98
C158—H18C	0.98	C258—H28C	0.98
C154—O154	1.372 (3)	C254—O254	1.363 (3)
C154—C155	1.406 (3)	C254—C255	1.407 (3)
O154—C159	1.436 (3)	O254—C259	1.443 (3)
C155—O155	1.369 (3)	C259—H29A	0.98
C155—C156	1.390 (3)	C259—H29B	0.98
C159—H19A	0.98	C259—H29C	0.98
C159—H19B	0.98	C255—O255	1.367 (3)
C159—H19C	0.98	C255—C256	1.383 (3)
O155—C150	1.429 (3)	O255—C250	1.433 (3)
C150—H10A	0.98	C250—H20A	0.98
C150—H10B	0.98	C250—H20B	0.98
C150—H10C	0.98	C250—H20C	0.98
C156—H156	0.95	C256—H256	0.95

C12—S11—C15	92.79 (12)	C22—S21—C25	92.91 (12)
N13—C12—S12	126.18 (19)	N23—C22—S22	126.26 (19)
N13—C12—S11	110.00 (18)	N23—C22—S21	109.76 (17)
S12—C12—S11	123.82 (17)	S22—C22—S21	123.98 (16)
C12—N13—C14	117.7 (2)	C22—N23—C24	118.1 (2)
C12—N13—H13	121.2	C22—N23—H23	120.9
C14—N13—H13	121.2	C24—N23—H23	120.9
O14—C14—N13	123.3 (2)	O24—C24—N23	123.3 (2)
O14—C14—C15	126.4 (2)	O24—C24—C25	126.3 (2)
N13—C14—C15	110.3 (2)	N23—C24—C25	110.4 (2)
C157—C15—C14	120.8 (2)	C257—C25—C24	120.9 (2)
C157—C15—S11	130.0 (2)	C257—C25—S21	130.2 (2)
C14—C15—S11	109.22 (18)	C24—C25—S21	108.83 (17)
C15—C157—C151	131.3 (3)	C25—C257—C251	130.6 (3)
C15—C157—H157	114.4	C25—C257—H257	114.7
C151—C157—H157	114.4	C251—C257—H257	114.7
C156—C151—C152	119.4 (2)	C256—C251—C252	119.2 (2)
C156—C151—C157	123.0 (2)	C256—C251—C257	123.0 (2)
C152—C151—C157	117.6 (2)	C252—C251—C257	117.8 (2)
C153—C152—C151	120.3 (2)	C253—C252—C251	120.3 (2)
C153—C152—H152	119.8	C253—C252—H252	119.8
C151—C152—H152	119.8	C251—C252—H252	119.8
O153—C153—C152	124.8 (2)	O253—C253—C252	123.8 (2)
O153—C153—C154	114.6 (2)	O253—C253—C254	115.6 (2)
C152—C153—C154	120.6 (2)	C252—C253—C254	120.5 (2)
C153—O153—C158	118.2 (2)	C253—O253—C258	117.4 (2)
O153—C158—H18A	109.5	O253—C258—H28A	109.5
O153—C158—H18B	109.5	O253—C258—H28B	109.5
H18A—C158—H18B	109.5	H28A—C258—H28B	109.5
O153—C158—H18C	109.5	O253—C258—H28C	109.5
H18A—C158—H18C	109.5	H28A—C258—H28C	109.5
H18B—C158—H18C	109.5	H28B—C258—H28C	109.5
O154—C154—C153	121.6 (2)	O254—C254—C253	124.5 (2)
O154—C154—C155	118.9 (2)	O254—C254—C255	116.4 (2)
C153—C154—C155	119.3 (2)	C253—C254—C255	119.0 (2)
C154—O154—C159	114.13 (19)	C254—O254—C259	118.4 (2)
O155—C155—C156	124.7 (2)	O254—C259—H29A	109.5
O155—C155—C154	115.3 (2)	O254—C259—H29B	109.5
C156—C155—C154	120.0 (2)	H29A—C259—H29B	109.5
O154—C159—H19A	109.5	O254—C259—H29C	109.5
O154—C159—H19B	109.5	H29A—C259—H29C	109.5
H19A—C159—H19B	109.5	H29B—C259—H29C	109.5
O154—C159—H19C	109.5	O255—C255—C256	124.1 (2)
H19A—C159—H19C	109.5	O255—C255—C254	115.5 (2)
H19B—C159—H19C	109.5	C256—C255—C254	120.4 (2)
C155—O155—C150	116.85 (19)	C255—O255—C250	116.83 (19)
O155—C150—H10A	109.5	O255—C250—H20A	109.5
O155—C150—H10B	109.5	O255—C250—H20B	109.5
H10A—C150—H10B	109.5	H20A—C250—H20B	109.5
O155—C150—H10C	109.5	O255—C250—H20C	109.5
H10A—C150—H10C	109.5	H20A—C250—H20C	109.5
H10B—C150—H10C	109.5	H20B—C250—H20C	109.5
C155—C156—C151	120.3 (2)	C255—C256—C251	120.5 (2)
C155—C156—H156	119.8	C255—C256—H256	119.8
C151—C156—H156	119.8	C251—C256—H256	119.8

C15—S11—C12—N13	0.51 (19)	C25—S21—C22—N23	0.25 (19)
C15—S11—C12—S12	−179.82 (17)	C25—S21—C22—S22	−179.75 (17)
S12—C12—N13—C14	−179.79 (18)	S22—C22—N23—C24	−179.51 (18)
S11—C12—N13—C14	−0.1 (3)	S21—C22—N23—C24	0.5 (3)
C12—N13—C14—O14	179.8 (2)	C22—N23—C24—O24	177.2 (2)
C12—N13—C14—C15	−0.4 (3)	C22—N23—C24—C25	−1.2 (3)
O14—C14—C15—C157	1.0 (4)	O24—C24—C25—C257	2.6 (4)
N13—C14—C15—C157	−178.8 (2)	N23—C24—C25—C257	−179.1 (2)
O14—C14—C15—S11	−179.4 (2)	O24—C24—C25—S21	−177.1 (2)
N13—C14—C15—S11	0.8 (2)	N23—C24—C25—S21	1.2 (2)
C12—S11—C15—C157	178.8 (2)	C22—S21—C25—C257	179.5 (2)
C12—S11—C15—C14	−0.74 (19)	C22—S21—C25—C24	−0.84 (18)
C14—C15—C157—C151	177.2 (2)	C24—C25—C257—C251	−177.2 (2)
S11—C15—C157—C151	−2.2 (4)	S21—C25—C257—C251	2.4 (4)
C15—C157—C151—C156	−1.2 (4)	C25—C257—C251—C256	1.6 (4)
C15—C157—C151—C152	179.9 (3)	C25—C257—C251—C252	179.5 (2)
C156—C151—C152—C153	0.1 (4)	C256—C251—C252—C253	0.9 (4)
C157—C151—C152—C153	179.1 (2)	C257—C251—C252—C253	−177.1 (2)
C151—C152—C153—O153	179.8 (2)	C251—C252—C253—O253	−176.6 (2)
C151—C152—C153—C154	0.0 (4)	C251—C252—C253—C254	1.1 (4)
C152—C153—O153—C158	5.1 (4)	C252—C253—O253—C258	−15.8 (4)
C154—C153—O153—C158	−175.1 (2)	C254—C253—O253—C258	166.4 (2)
O153—C153—C154—O154	4.4 (3)	O253—C253—C254—O254	−0.9 (4)
C152—C153—C154—O154	−175.7 (2)	C252—C253—C254—O254	−178.7 (2)
O153—C153—C154—C155	−179.9 (2)	O253—C253—C254—C255	175.1 (2)
C152—C153—C154—C155	0.0 (4)	C252—C253—C254—C255	−2.7 (4)
C153—C154—O154—C159	−77.3 (3)	C253—C254—O254—C259	−48.1 (3)
C155—C154—O154—C159	107.0 (3)	C255—C254—O254—C259	135.8 (2)
O154—C154—C155—O155	−4.2 (3)	O254—C254—C255—O255	−2.3 (3)
C153—C154—C155—O155	180.0 (2)	C253—C254—C255—O255	−178.6 (2)
O154—C154—C155—C156	175.8 (2)	O254—C254—C255—C256	178.8 (2)
C153—C154—C155—C156	0.0 (4)	C253—C254—C255—C256	2.5 (4)
C156—C155—O155—C150	0.6 (3)	C256—C255—O255—C250	−6.9 (3)
C154—C155—O155—C150	−179.3 (2)	C254—C255—O255—C250	174.3 (2)
O155—C155—C156—C151	−179.9 (2)	O255—C255—C256—C251	−179.3 (2)
C154—C155—C156—C151	0.0 (4)	C254—C255—C256—C251	−0.6 (4)
C152—C151—C156—C155	−0.1 (4)	C252—C251—C256—C255	−1.2 (4)
C157—C151—C156—C155	−179.0 (2)	C257—C251—C256—C255	176.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C156—H156···S11	0.95	2.50	3.237 (2)	134
C256—H256···S21	0.95	2.49	3.227 (2)	134
N13—H13···O24	0.88	1.95	2.814 (3)	168
N23—H23···O14	0.88	1.96	2.807 (3)	162

Experimental details

	(I)	(II)	(III)
Crystal data
Chemical formula	C₁₀H₆FNOS₂	C₁₀H₆FNOS₂	C₁₃H₁₃NO₄S₂
M_r	239.28	239.28	311.36
Crystal system, space group	Monoclinic, P2₁/c	Monoclinic, P2₁/c	Triclinic, P1
Temperature (K)	298	298	120
a, b, c (Å)	11.1848 (4), 7.7651 (4), 12.3611 (5)	4.9173 (2), 19.8906 (10), 10.4976 (6)	10.3432 (4), 10.9105 (4), 13.4621 (4)
α, β, γ (°)	90, 107.417 (3), 90	90, 92.929 (3), 90	100.399 (2), 91.572 (2), 110.301 (2)
V (Å³)	1024.35 (8)	1025.41 (9)	1394.72 (9)
Z	4	4	4
Radiation type	Mo Kα	Mo Kα	Mo Kα
µ (mm⁻¹)	0.50	0.50	0.39
Crystal size (mm)	0.36 × 0.32 × 0.04	0.60 × 0.35 × 0.12	0.10 × 0.08 × 0.03

Data collection
Diffractometer	Bruker–Nonius KappaCCD diffractometer	Bruker–Nonius KappaCCD diffractometer	Bruker–Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.869, 0.980	0.753, 0.942	0.952, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	9920, 2337, 1768	7246, 2287, 1430	29714, 6377, 3786
R_int	0.042	0.053	0.106
(sin θ/λ)_max (Å⁻¹)	0.649	0.649	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.105, 1.04	0.082, 0.110, 1.09	0.063, 0.119, 1.00
No. of reflections	2337	2287	6377
No. of parameters	141	137	367
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.32	0.31, −0.27	0.33, −0.42

Computer programs: COLLECT (Hooft, 1999), DENZO (Otwinowski & Minor, 1997) and COLLECT, DENZO and COLLECT, Sir2004 (Burla et al., 2005), OSCAIL (McArdle, 2003) and SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97 and PRPKAPPA (Ferguson, 1999).

Selected bond angles and torsion angles (°) for compounds (I)–(III) top

Parameter	(I)	(II)	(III)	(III)
x	nil	nil	1	2
Cx5—Cx57—Cx51	129.25 (17)	130.6 (3)	131.3 (3)	130.6 (3)
Sx1—Cx5—Cx57	130.48 (14)	130.1 (2)	130.0 (2)	130.2 (2)
Cx4—Cx5—Cx57	120.50 (17)	121.1 (3)	120.8 (2)	120.9 (2)
Cx52—Cx51—Cx56	115.44 (16)	118.6 (3)	119.4 (2)	117.8 (2)
Cx57—Cx51—Cx56	124.47 (17)	123.6 (3)	123.0 (2)	123.0 (2)
Cx5—Cx57—Cx51—Cx52	-174.60 (19)	179.9 (3)	179.9 (3)	179.5 (3)
Cx52—Cx53—Ox53—Cx58			5.1 (4)	-15.8 (4)
Cx53—Cx54—Ox54—Cx59			-77.3 (3)	-48.1 (3)
Cx54—Cx55—Ox55—Cx50			-179.3 (2)	174.3 (2)

Hydrogen bonds and short intramolecular contacts (Å, °) for compounds (I)–(III) top

Compound	D-H···A	D-H	H···A	D···A	D-H···A
(I)	C56—H56···S1	0.93	2.51	3.226 (2)	134
	N3—H3···O4ⁱ	0.86	2.00	2.843 (2)	168
(II)	C56—H56···S1	0.93	2.51	3.230 (3)	135
	N3—H3···O4ⁱ	0.87	2.00	2.831 (3)	159
(III)	C156—H156···S11	0.95	2.50	3.237 (2)	134
	N13—H13···O24	0.88	1.95	2.814 (3)	168
	C256—H256···S21	0.95	2.49	3.227 (2)	134
	N23—H23···O14	0.88	1.96	2.807 (3)	162

Symmetry code: (i) 1 − x, 1 − y, 1 − z.

Acknowledgements

X-ray data were collected at the EPSRC X-ray Crystallographic Service, University of Southampton, England. JC and JT thank the Consejería de Innovación, Ciencia y Empresa (Junta de Andalucía, Spain) and the Universidad de Jaén for financial support. JT also thanks the Universidad de Jaén for a research scholarship supporting a short stay at the EPSRC X-ray Crystallographic Service, University of Southampton, England. JP thanks COLCIENCIAS and UNIVALLE (Universidad del Valle, Colombia) for financial support.

References

Allen, F. H., Baalham, C. A., Lommerse, J. P. M. & Raithby, P. R. (1998). Acta Cryst. B54, 320–329. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Delgado, P., Quiroga, J., Cobo, J., Low, J. N. & Glidewell, C. (2005). Acta Cryst. C61, o477–o482. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Ferguson, G. (1999). PRPKAPPA. University of Guelph, Canada. Google Scholar
Hooft, R. W. W. (1999). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
McArdle, P. (2003). OSCAIL for Windows. Version 10. Crystallography Centre, Chemistry Department, NUI Galway, Ireland. 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). SHELXL97. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2003). SADABS. Version 2.10. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2053-2296

Volume 62| Part 7| July 2006| Pages o382-o385

doi:10.1107/S0108270106018038

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

Three substituted (Z)-5-benzyl­­idene-2-thioxo­thia­zolidin-4-ones: hydrogen-bonded dimers that can be effectively isolated or linked into chains either by aromatic π–π stacking inter­actions or by dipolar carbon­yl–carbonyl inter­actions

Comment

Experimental

Compound (I)

Crystal data

Data collection

Refinement

Compound (II)

Crystal data

Data collection

Refinement

Compound (III)

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Three substituted (Z)-5-benzylidene-2-thioxothiazolidin-4-ones: hydrogen-bonded dimers that can be effectively isolated or linked into chains either by aromatic π–π stacking interactions or by dipolar carbonyl–carbonyl interactions