research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 72| Part 3| March 2016| Pages 334-336

Crystal structure of 2-[(3aS,6R)-3,3,6-tri­methyl-3,3a,4,5,6,7-hexa­hydro-2H-indazol-2-yl]thia­zol-4(5H)-one

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aLaboratoire de Physico-Chimie Moléculaire et Synthèse Organique, Département de Chimie, Faculté des Sciences, Semlalia BP 2390, Marrakech 40001, Morocco, bInstitut de Chimie Moléculaire de Reims, CNRS UMR 7312, Bat. Europol'Agr, Moulin de la Housse, UFR Sciences, BP 1039, 51687 Reims Cédex 2, France, and cLaboratoire de Chimie de Coordination, CNRS UPR8241, 205 route de Narbonne, 31077 Toulouse Cedex 04, France
*Correspondence e-mail: a.auhmani@uca.ma

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 27 January 2016; accepted 10 February 2016; online 17 February 2016)

The title compound, C13H19N3OS, is a new thia­zolidin-4-one derivative prepared and isolated as the pure (3aS,6R)-diastereisomer from (R)-thio­semicarbazone pulegone. It crystallized with two independent mol­ecules (A and B) in the asymmetric unit. The compound is composed of a hexhydro­indazole ring system (viz. a five-membered di­hydro­pyrazole ring fused to a cyclo­hexyl ring) with a thia­zole-4-one ring system attached to one of the pyrazole N atoms (at position 2). The overall geometry of the two mol­ecules differs slightly, with the mean planes of the pyrazole and thia­zole rings being inclined to one another by 10.4 (1)° in mol­ecule A and 0.9 (1)° in mol­ecule B. In the crystal, the A and B mol­ecules are linked via C—H⋯O hydrogen bonds, forming slabs parallel to the ab plane. There are C—H⋯π inter­actions present within the layers, and between the layers, so forming a three-dimensional structure.

1. Chemical context

Thia­zolidinones constitute an important class of heterocyclic compounds containing sulfur and nitro­gen in a five-membered ring. They play a vital role due to their wide range of biological activities and industrial importance. Thia­zolidin-4-ones are particularly important because of their efficiency towards various pharmacological usages. A recent literature search reveals that thia­zolidin-4-one derivatives may exhibit anti­bacterial (Bonde & Gaikwad, 2004[Bonde, C. G. & Gaikwad, N. J. (2004). Bioorg. Med. Chem. 12, 2151-2161.]), anti­tuberculosis (Karali et al., 2007[Karalı, N., Gürsoy, A., Kandemirli, F., Shvets, N., Kaynak, F. B., Özbey, S., Kovalishyn, V. & Dimoglo, A. (2007). Bioorg. Med. Chem. 15, 5888-5904.]), anti­viral (Kaushik-Basu et al., 2008[Kaushik-Basu, N., Bopda-Waffo, A., Talele, T. T., Basu, A., Chen, Y. & Küçükgüzel, Ş. G. (2008). Front. Biosci. 13, 3857-3868.]) and anti­cancer activities (Patel et al., 2014[Patel, A. B., Chikhalia, K. H. & Kumari, P. (2014). J. Saudi Chem. Soc. 18, 646-656.]).

As a part of our endeavour toward the preparation of new heterocyclic systems, we report herein on the structure of a new optically active thia­zolidin-4-one (2) synthesized from (R)-thio­semicarbazone pulegone (1); see Scheme. The reaction involves the treatment of thio­semicarbazone (1), in

[Scheme 1]
refluxing ethanol, with ethyl bromo­acatete and an excess of sodium acetate. Crystallization from an ethano­lic solution of the resulting indazolic thia­zolidin-4-one (obtained as a diastereomeric mixture) led to the isolation of compound (2). The structure of (2) was elucidated using spectroscopic (MS and NMR) data, while its absolute structure was determined as (3aS,6R) based mainly on the synthetic pathway and confirmed by resonant scattering.

2. Structural commentary

The title compound crystallized with two independent mol­ecules (A and B) in the asymmetric unit. The compound is composed of a hexhydro­indazole ring system [viz. a five-membered di­hydro­pyrazole ring fused to a cyclo­hexyl ring] with a thia­zole-4-one ring system attached to pyrazole N atom N2 (Fig. 1[link]). Mol­ecular fitting of the two mol­ecules (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) shows that they have roughly the same conformation and the same configuration (Fig. 2[link]), even if some slight differences can be observed. The six-membered rings each display a chair conformation, with puckering parameters of θ = 12.96° and φ2 = 113.49° for mol­ecule A and θ = 9.44° and φ2 = 92.43° for mol­ecule B. The five-membered pyrazol rings are almost planar with the largest deviation being 0.081 (3) Å for atom C3 in mol­ecule A and −0.032 (1) for atom C3B in mol­ecule B. The thia­zole rings are planar, the largest deviation being −0.011 (1) Å for atom C2′ and 0.005 (1) for atom C5′B in mol­ecules A and B, respectively. In mol­ecule A, the two five-membered rings are slightly twisted with a dihedral angle of 10.4 (1)°, whereas in mol­ecule B the two rings are almost coplanar with a dihedral angle of 0.9 (1)°.

[Figure 1]
Figure 1
View of the mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
Mol­ecular fitting of independent mol­ecules A (black) and B (red).

3. Supra­molecular features

In the crystal, the two independent mol­ecules are connected via C—H⋯O hydrogen bonds forming layers, or slabs, parallel to the ab plane (Table 1[link] and Fig. 3[link]). Within the layers there are C—H⋯π inter­actions present (Fig. 4[link] and Table 1[link]). The layers are also linked by C—H⋯π inter­actions (Table 1[link]), forming a three-dimensional structure (Fig. 4[link]).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the thia­zole ring S1′/N3′/C2′/C4′/C5′.

D—H⋯A D—H H⋯A DA D—H⋯A
C5′—H5′2⋯O6′Bi 0.97 2.43 3.304 (4) 150
C9—H9B⋯O6′Bii 0.96 2.53 3.361 (3) 145
C5′B—H5′3⋯O6′iii 0.97 2.44 3.361 (3) 159
C4B—H4B2⋯Cg1 0.96 2.93 3.737 (4) 141
C7B—H7B2⋯Cg1iv 0.96 2.90 3.867 (4) 174
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z+1]; (ii) x+1, y, z; (iii) [-x+2, y-{\script{1\over 2}}, -z+1]; (iv) x, y, z+1.
[Figure 3]
Figure 3
A view along the a axis of the crystal packing of the title compound, showing the formation of layers parallel to the ab plane via C—H⋯O hydrogen bonds (see Table 1[link]). H atoms not involved in these inter­actions have been omitted for clarity.
[Figure 4]
Figure 4
A view along the a axis of the crystal packing of the title compound, showing the C—H⋯O hydrogen bonds (dashed lines), and the C—H⋯π inter­actions (represented by blue arrows) linking the A (black) and B (red) mol­ecules within and between the layers (see Table 1[link]). H atoms not involved in these inter­actions have been omitted for clarity.

4. Database survey

A search of the Cambridge Structural Database (CSD, V5.37, update November 2015; Groom & Allen, 2014[Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662-671.]) using the hexa­hydro­indazole ring system as the main skeleton, revealed the presence of 27 structures. A search for a thia­zole ring linked to an N atom of a pyrazole ring, similar to the situation in the title compound, yielded six hits. One of these structures, 2-(3-phenyl-3,3a,4,5-tetra­hydro-2H-benzo[g]indazol-2-yl)-1,3-thia­zol-4(5H)-one (refcode LUHGAY; Gautam & Chaudhary, 2015[Gautam, D. & Chaudhary, R. P. (2015). Spectrochim. Acta Part A, 135, 219-226.]), resembles the title compound with an indazole ring system linked to a thia­zole ring. The mean plane of the two five-membered rings are inclined to one another by ca 10.05°, similar to the arrangement in mol­ecule A of the title compound.

5. Synthesis and crystallization

The synthesis of the title compound is illustrated in the Scheme. A mixture of thio­semicarbazone (1) (1.5 mmol, 1 eq), ethyl 2-bromo­acetate (0.24 ml, 1.5 mmol) and anhydrous sodium acetate (0.37 g, 4.5 mmol, 3 eq) in absolute ethanol (30 ml) was heated under reflux until the completion of the reaction (1–3 h). The solvent was then evaporated under reduced pressure and the crude product was purified by chromatography on silica gel (230–400 mesh) using hexa­ne/ethyl acetate (90:10) as eluent to give pure indazolic thia­zolidin-4-one in 60% yield as a diastereomeric mixture. Slow evaporation from an ethano­lic solution gives crystals of the pure diastereoisomer of the title compound (2) suitable for crystallographic analysis.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.96–0.98 Å with Uiso(H) = 1.5Ueq(C-meth­yl) and 1.2Ueq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula C13H19N3OS
Mr 265.37
Crystal system, space group Monoclinic, P21
Temperature (K) 180
a, b, c (Å) 8.5519 (2), 18.9335 (4), 8.9165 (3)
β (°) 110.203 (3)
V3) 1354.91 (7)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.23
Crystal size (mm) 0.25 × 0.21 × 0.18
 
Data collection
Diffractometer Agilent Xcalibur Eos Gemini ultra
Absorption correction Multi-scan (CrysAlis PRO; Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Abingdon, England.])
Tmin, Tmax 0.939, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 15302, 6147, 5674
Rint 0.024
(sin θ/λ)max−1) 0.692
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.077, 1.04
No. of reflections 6147
No. of parameters 331
No. of restraints 1
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.22, −0.19
Absolute structure Flack x determined using 2349 quotients [(I+)−(I-)]/[(I+)+(I)] (Parsons et al., 2013[Parsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249-259.])
Absolute structure parameter −0.08 (3)
Computer programs: CrysAlis PRO (Agilent, 2014[Agilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Abingdon, England.]), SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]), SHELXL2013 (Sheldrick, 2015[Sheldrick, G. M. (2015). Acta Cryst. C71, 3-8.]), ORTEPIII (Burnett & Johnson, 1996[Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.]), ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Chemical context top

Thia­zolidinones constitute an important class of heterocyclic compounds containing sulfur and nitro­gen in a five-membered ring. They play a vital role due to their wide range of biological activities and industrial importance. Thia­zolidin-4-ones are particularly important because of their efficiency towards various pharmacological usages. A recent literature search reveals that thia­zolidin-4-one derivatives may exhibit anti­bacterial (Bonde & Gaikwad, 2004), anti­tuberculosis (Karali et al., 2007), anti­viral (Kaushik-Basu et al., 2008) and anti­cancer activities (Patel et al., 2014).

As a part of our endeavour toward the preparation of new heterocyclic systems, we report herein on the structure of a new optically active thia­zolidin-4-one (2) synthesized from (R)-thio­semicarbazone pulegone (1); see Scheme. The reaction involves the treatment of thio­semicarbazone (1), in refluxing ethanol, with ethyl bromo­acatete and an excess of sodium acetate. Crystallization from an ethano­lic solution of the resulting indazolic thia­zolidin-4-one (obtained as a diastereomeric mixture) led to the isolation of compound (2). The structure of (2) was elucidated using spectroscopic (MS and NMR) data, while its absolute structure was determined as (3aS,6R) based mainly on the synthetic pathway and confirmed by resonant scattering.

Structural commentary top

The title compound crystallized with two independent molecules (A and B) in the asymmetric unit. The compound is composed of a hexhydro­indazole ring system [viz. a five-membered di­hydro­pyrazole ring fused to a cyclo­hexyl ring] with a thia­zole-4-one ring system attached to pyrazole N atom N2 (Fig. 1). Molecular fitting of the two molecules (Spek, 2009) shows that they have roughly the same conformation and the same configuration (Fig. 2), even if some slight differences can be observed. The six-membered rings each display a chair conformation, with puckering parameters of θ = 12.96° and φ2 = 113.49° for molecule A and θ = 9.44° and φ2 = 92.43° for molecule B. The five-membered pyrazol rings are almost planar with the largest deviation being 0.081 (3) Å for atom C3 in molecule A and −0.032 (1) for atom C3B in molecule B. The thia­zole rings are planar, the largest deviation being −0.011 (1) Å for atom C2' and 0.005 (1) for atom C5'B in molecules A and B, respectively. In molecule A, the two five-membered rings are slightly twisted with a dihedral angle of 10.4 (1)°, whereas in molecule B the two rings are almost coplanar with a dihedral angle of 0.9 (1)°.

Supra­molecular features top

In the crystal, the two independent molecules are connected via C—H···O hydrogen bonds forming layers, or slabs, parallel to the ab plane (Table 1 and Fig. 3). Within the layers there are C—H···π inter­actions present (Fig. 4 and Table 1). The layers are also linked by C—H···π inter­actions (Table 1), forming a three-dimensional structure (Fig. 4).

Database survey top

\ A search of the Cambridge Structural Database (CSD, V5.37, update November 2015; Groom & Allen, 2014) using the hexa­hydro­indazole ring system as the main skeleton, revealed the presence of 27 structures. A search for a thia­zole ring linked to an N atom of a pyrazole ring, similar to the situation in the title compound, yielded six hits. One of these structures, 2-(3-phenyl-3,3a,4,5-tetra­hydro-2H-benzo[g]indazol-2-yl)-1,3-\ thia­zol-4(5H)-one (refcode LUHGAY; Gautam & Chaudhary, 2015), resembles the title compound with an indazole ring system linked to a thia­zole ring. The mean plane of the two five-membered rings are inclined to one another by ca 10.05°, similar to the arrangement in molecule A of the title compound.

Synthesis and crystallization top

The synthesis of the title compound is illustrated in the Scheme. A mixture of thio­semicarbazone (1) (1.5 mmol, 1 eq), ethyl 2-bromo­acetate (0.24 ml, 1.5 mmol) and anhydrous sodium acetate (0.37 g, 4.5 mmol, 3 eq) in absolute ethanol (30 ml) was heated under reflux until the completion of the reaction (1–3 h). The solvent was then evaporated under reduced pressure and the crude product was purified by chromatography on silica gel (230–400 mesh) using hexane/ethyl acetate (90:10) as eluent to give pure indazolic thia­zolidin-4-one in 60% yield as a diastereomeric mixture. Slow evaporation from an ethano­lic solution gives crystals of the pure diastereoisomer of the title compound (2) suitable for crystallographic analysis.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.96–0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.

Structure description top

Thia­zolidinones constitute an important class of heterocyclic compounds containing sulfur and nitro­gen in a five-membered ring. They play a vital role due to their wide range of biological activities and industrial importance. Thia­zolidin-4-ones are particularly important because of their efficiency towards various pharmacological usages. A recent literature search reveals that thia­zolidin-4-one derivatives may exhibit anti­bacterial (Bonde & Gaikwad, 2004), anti­tuberculosis (Karali et al., 2007), anti­viral (Kaushik-Basu et al., 2008) and anti­cancer activities (Patel et al., 2014).

As a part of our endeavour toward the preparation of new heterocyclic systems, we report herein on the structure of a new optically active thia­zolidin-4-one (2) synthesized from (R)-thio­semicarbazone pulegone (1); see Scheme. The reaction involves the treatment of thio­semicarbazone (1), in refluxing ethanol, with ethyl bromo­acatete and an excess of sodium acetate. Crystallization from an ethano­lic solution of the resulting indazolic thia­zolidin-4-one (obtained as a diastereomeric mixture) led to the isolation of compound (2). The structure of (2) was elucidated using spectroscopic (MS and NMR) data, while its absolute structure was determined as (3aS,6R) based mainly on the synthetic pathway and confirmed by resonant scattering.

The title compound crystallized with two independent molecules (A and B) in the asymmetric unit. The compound is composed of a hexhydro­indazole ring system [viz. a five-membered di­hydro­pyrazole ring fused to a cyclo­hexyl ring] with a thia­zole-4-one ring system attached to pyrazole N atom N2 (Fig. 1). Molecular fitting of the two molecules (Spek, 2009) shows that they have roughly the same conformation and the same configuration (Fig. 2), even if some slight differences can be observed. The six-membered rings each display a chair conformation, with puckering parameters of θ = 12.96° and φ2 = 113.49° for molecule A and θ = 9.44° and φ2 = 92.43° for molecule B. The five-membered pyrazol rings are almost planar with the largest deviation being 0.081 (3) Å for atom C3 in molecule A and −0.032 (1) for atom C3B in molecule B. The thia­zole rings are planar, the largest deviation being −0.011 (1) Å for atom C2' and 0.005 (1) for atom C5'B in molecules A and B, respectively. In molecule A, the two five-membered rings are slightly twisted with a dihedral angle of 10.4 (1)°, whereas in molecule B the two rings are almost coplanar with a dihedral angle of 0.9 (1)°.

In the crystal, the two independent molecules are connected via C—H···O hydrogen bonds forming layers, or slabs, parallel to the ab plane (Table 1 and Fig. 3). Within the layers there are C—H···π inter­actions present (Fig. 4 and Table 1). The layers are also linked by C—H···π inter­actions (Table 1), forming a three-dimensional structure (Fig. 4).

\ A search of the Cambridge Structural Database (CSD, V5.37, update November 2015; Groom & Allen, 2014) using the hexa­hydro­indazole ring system as the main skeleton, revealed the presence of 27 structures. A search for a thia­zole ring linked to an N atom of a pyrazole ring, similar to the situation in the title compound, yielded six hits. One of these structures, 2-(3-phenyl-3,3a,4,5-tetra­hydro-2H-benzo[g]indazol-2-yl)-1,3-\ thia­zol-4(5H)-one (refcode LUHGAY; Gautam & Chaudhary, 2015), resembles the title compound with an indazole ring system linked to a thia­zole ring. The mean plane of the two five-membered rings are inclined to one another by ca 10.05°, similar to the arrangement in molecule A of the title compound.

Synthesis and crystallization top

The synthesis of the title compound is illustrated in the Scheme. A mixture of thio­semicarbazone (1) (1.5 mmol, 1 eq), ethyl 2-bromo­acetate (0.24 ml, 1.5 mmol) and anhydrous sodium acetate (0.37 g, 4.5 mmol, 3 eq) in absolute ethanol (30 ml) was heated under reflux until the completion of the reaction (1–3 h). The solvent was then evaporated under reduced pressure and the crude product was purified by chromatography on silica gel (230–400 mesh) using hexane/ethyl acetate (90:10) as eluent to give pure indazolic thia­zolidin-4-one in 60% yield as a diastereomeric mixture. Slow evaporation from an ethano­lic solution gives crystals of the pure diastereoisomer of the title compound (2) suitable for crystallographic analysis.

Refinement details top

Crystal data, data collection and structure refinement details are summarized in Table 2. The C-bound H atoms were included in calculated positions and treated as riding atoms: C—H = 0.96–0.98 Å with Uiso(H) = 1.5Ueq(C-methyl) and 1.2Ueq(C) for other H atoms.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2014); cell refinement: CrysAlis PRO (Agilent, 2014); data reduction: CrysAlis PRO (Agilent, 2014); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

Figures top
[Figure 1] Fig. 1. View of the molecular structure of the two independent molecules (A and B) of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Molecular fitting of independent molecules A (black) and B (red).
[Figure 3] Fig. 3. A view along the a axis of the crystal packing of the title compound, showing the formation of layers parallel to the ab plane via C—H···O hydrogen bonds (see Table 1). H atoms not involved in these interactions have been omitted for clarity.
[Figure 4] Fig. 4. A view along the a axis of the crystal packing of the title compound, showing the C—H···O hydrogen bonds (dashed lines), and the C—H···π interactions (represented by blue arrows) linking the A (black) and B (red) molecules within and between the layers (see Table 1). H atoms not involved in these interactions have been omitted for clarity.
2-[(3aS,6R)-3,3,6-Trimethyl-3,3a,4,5,6,7-hexahydro-2H-indazol-2-yl]thiazol-4(5H)-one top
Crystal data top
C13H19N3OSF(000) = 568
Mr = 265.37Dx = 1.301 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.5519 (2) ÅCell parameters from 5859 reflections
b = 18.9335 (4) Åθ = 3.6–29.2°
c = 8.9165 (3) ŵ = 0.23 mm1
β = 110.203 (3)°T = 180 K
V = 1354.91 (7) Å3Prismatic, colourless
Z = 40.25 × 0.21 × 0.18 mm
Data collection top
Agilent Xcalibur Eos Gemini ultra
diffractometer
6147 independent reflections
Radiation source: Enhance (Mo) X-ray Source5674 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 16.1978 pixels mm-1θmax = 29.5°, θmin = 3.3°
ω scansh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
k = 2325
Tmin = 0.939, Tmax = 1.000l = 1211
15302 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.033 w = 1/[σ2(Fo2) + (0.0364P)2 + 0.1555P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.077(Δ/σ)max < 0.001
S = 1.04Δρmax = 0.22 e Å3
6147 reflectionsΔρmin = 0.19 e Å3
331 parametersAbsolute structure: Flack x determined using 2349 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
1 restraintAbsolute structure parameter: 0.08 (3)
Crystal data top
C13H19N3OSV = 1354.91 (7) Å3
Mr = 265.37Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.5519 (2) ŵ = 0.23 mm1
b = 18.9335 (4) ÅT = 180 K
c = 8.9165 (3) Å0.25 × 0.21 × 0.18 mm
β = 110.203 (3)°
Data collection top
Agilent Xcalibur Eos Gemini ultra
diffractometer
6147 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Agilent, 2014)
5674 reflections with I > 2σ(I)
Tmin = 0.939, Tmax = 1.000Rint = 0.024
15302 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.033H-atom parameters constrained
wR(F2) = 0.077Δρmax = 0.22 e Å3
S = 1.04Δρmin = 0.19 e Å3
6147 reflectionsAbsolute structure: Flack x determined using 2349 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
331 parametersAbsolute structure parameter: 0.08 (3)
1 restraint
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1'0.77265 (7)0.51418 (3)0.26117 (7)0.02894 (15)
O6'1.2287 (2)0.54265 (10)0.5307 (3)0.0410 (5)
N10.6528 (2)0.37534 (10)0.2176 (2)0.0258 (4)
N20.8216 (2)0.37680 (10)0.3163 (2)0.0246 (4)
N3'1.0511 (3)0.44868 (11)0.4370 (2)0.0269 (4)
C2'0.8954 (3)0.43930 (12)0.3469 (3)0.0232 (5)
C4'1.0915 (3)0.51929 (14)0.4524 (3)0.0290 (5)
C5'0.9500 (3)0.56889 (15)0.3626 (3)0.0358 (6)
H5'10.98080.59700.28620.043*
H5'20.92450.60050.43660.043*
C30.8934 (3)0.30406 (12)0.3685 (3)0.0241 (5)
C3A0.7284 (3)0.26108 (13)0.3219 (3)0.0266 (5)
H3A0.70350.25240.41970.032*
C40.7166 (3)0.19101 (16)0.2363 (3)0.0389 (6)
H4A0.78650.15640.30910.047*
H4B0.75640.19650.14740.047*
C50.5357 (4)0.16515 (15)0.1746 (4)0.0406 (7)
H5A0.53050.12000.12160.049*
H5B0.49840.15800.26450.049*
C60.4191 (3)0.21710 (15)0.0582 (3)0.0356 (6)
H60.45740.22310.03270.043*
C70.4263 (3)0.28925 (13)0.1385 (3)0.0318 (5)
H7A0.36920.32400.05830.038*
H7B0.36900.28640.21510.038*
C7A0.6020 (3)0.31236 (12)0.2218 (3)0.0257 (5)
C91.0058 (3)0.28524 (14)0.2749 (3)0.0318 (5)
H9A0.94420.28900.16250.048*
H9B1.04540.23770.29970.048*
H9C1.09880.31710.30310.048*
C80.9873 (3)0.30082 (14)0.5474 (3)0.0331 (6)
H8A1.08700.32860.57320.050*
H8B1.01610.25270.57870.050*
H8C0.91820.31910.60330.050*
C100.2398 (4)0.1906 (2)0.0055 (4)0.0551 (8)
H10A0.23580.14580.05730.083*
H10B0.17150.22400.08080.083*
H10C0.19900.18520.08160.083*
S1'B0.72290 (7)0.19227 (3)0.77175 (8)0.02873 (15)
O6'B0.2793 (2)0.16136 (10)0.4764 (3)0.0430 (5)
N1B0.8189 (2)0.33287 (10)0.8585 (2)0.0256 (4)
N2B0.6558 (2)0.32950 (10)0.7482 (2)0.0251 (4)
N3'B0.4417 (3)0.25589 (11)0.5972 (2)0.0285 (4)
C2'B0.5933 (3)0.26630 (13)0.6977 (3)0.0231 (5)
C4'B0.4099 (3)0.18550 (14)0.5654 (3)0.0297 (5)
C5'B0.5556 (3)0.13661 (14)0.6521 (3)0.0323 (6)
H5'30.58990.11010.57560.039*
H5'40.52360.10350.71940.039*
C3B0.5720 (3)0.40092 (12)0.7089 (3)0.0243 (5)
C3AB0.7198 (3)0.44937 (13)0.8040 (3)0.0272 (5)
H3AB0.68730.47630.88250.033*
C4B0.7936 (4)0.50042 (17)0.7135 (4)0.0458 (7)
H4B10.71390.53750.66510.055*
H4B20.81750.47540.62900.055*
C5B0.9540 (4)0.53296 (16)0.8284 (4)0.0483 (8)
H5B10.99780.56620.77010.058*
H5B20.92820.55900.91060.058*
C6B1.0865 (3)0.47829 (14)0.9071 (3)0.0334 (6)
H6B1.11540.45400.82310.040*
C7B1.0200 (3)0.42344 (13)0.9955 (3)0.0309 (5)
H7B11.09640.38381.02620.037*
H7B21.01170.44421.09190.037*
C7AB0.8528 (3)0.39813 (13)0.8913 (3)0.0250 (5)
C9B0.5074 (3)0.41293 (14)0.5291 (3)0.0328 (6)
H9B10.42160.37910.47880.049*
H9B20.59710.40750.48860.049*
H9B30.46250.45980.50640.049*
C8B0.4338 (3)0.40513 (15)0.7789 (3)0.0321 (6)
H8B10.38070.45050.75530.048*
H8B20.47990.39880.89260.048*
H8B30.35330.36870.73300.048*
C10B1.2448 (3)0.51173 (18)1.0226 (4)0.0468 (7)
H10D1.28620.54630.96690.070*
H10E1.32760.47581.06500.070*
H10F1.22020.53411.10850.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1'0.0251 (3)0.0232 (3)0.0350 (3)0.0039 (3)0.0059 (3)0.0028 (2)
O6'0.0283 (10)0.0288 (10)0.0563 (12)0.0043 (8)0.0025 (10)0.0012 (9)
N10.0204 (10)0.0254 (10)0.0294 (11)0.0025 (8)0.0058 (8)0.0001 (8)
N20.0189 (10)0.0229 (10)0.0299 (10)0.0017 (8)0.0059 (8)0.0029 (8)
N3'0.0226 (10)0.0242 (10)0.0311 (11)0.0008 (8)0.0057 (9)0.0023 (8)
C2'0.0254 (12)0.0218 (12)0.0237 (11)0.0035 (9)0.0103 (10)0.0022 (9)
C4'0.0276 (13)0.0272 (13)0.0320 (12)0.0002 (11)0.0100 (11)0.0012 (11)
C5'0.0315 (14)0.0259 (14)0.0447 (15)0.0006 (12)0.0065 (13)0.0030 (11)
C30.0236 (11)0.0207 (11)0.0265 (12)0.0019 (9)0.0068 (10)0.0049 (9)
C3A0.0271 (12)0.0266 (12)0.0260 (11)0.0003 (10)0.0089 (10)0.0019 (10)
C40.0365 (15)0.0238 (13)0.0521 (17)0.0023 (12)0.0098 (13)0.0040 (13)
C50.0401 (16)0.0269 (14)0.0529 (17)0.0061 (12)0.0138 (14)0.0103 (13)
C60.0362 (15)0.0388 (14)0.0319 (13)0.0079 (12)0.0121 (12)0.0107 (12)
C70.0255 (12)0.0298 (13)0.0381 (14)0.0006 (10)0.0083 (11)0.0009 (11)
C7A0.0262 (12)0.0255 (12)0.0261 (12)0.0021 (9)0.0099 (10)0.0025 (9)
C90.0302 (13)0.0313 (13)0.0353 (13)0.0074 (11)0.0130 (11)0.0061 (11)
C80.0343 (14)0.0337 (14)0.0273 (13)0.0018 (11)0.0055 (11)0.0051 (10)
C100.0411 (17)0.0507 (19)0.064 (2)0.0136 (17)0.0065 (16)0.0210 (17)
S1'B0.0231 (3)0.0223 (3)0.0364 (3)0.0027 (2)0.0046 (3)0.0057 (2)
O6'B0.0303 (11)0.0298 (10)0.0540 (12)0.0032 (9)0.0044 (10)0.0025 (9)
N1B0.0193 (9)0.0254 (11)0.0285 (10)0.0003 (8)0.0037 (8)0.0039 (8)
N2B0.0201 (10)0.0224 (10)0.0283 (10)0.0031 (8)0.0025 (8)0.0012 (8)
N3'B0.0249 (11)0.0225 (10)0.0324 (11)0.0010 (9)0.0025 (9)0.0008 (9)
C2'B0.0215 (12)0.0232 (12)0.0254 (11)0.0024 (9)0.0089 (10)0.0034 (9)
C4'B0.0268 (13)0.0262 (13)0.0335 (13)0.0005 (11)0.0072 (11)0.0009 (11)
C5'B0.0287 (14)0.0204 (13)0.0422 (15)0.0004 (11)0.0054 (12)0.0033 (11)
C3B0.0243 (12)0.0206 (11)0.0256 (12)0.0048 (9)0.0056 (10)0.0000 (9)
C3AB0.0257 (12)0.0250 (12)0.0306 (13)0.0032 (9)0.0093 (10)0.0053 (10)
C4B0.0447 (17)0.0318 (16)0.0514 (18)0.0054 (12)0.0043 (14)0.0139 (13)
C5B0.0503 (18)0.0270 (15)0.062 (2)0.0110 (13)0.0127 (16)0.0076 (13)
C6B0.0315 (14)0.0320 (14)0.0414 (15)0.0078 (11)0.0187 (12)0.0081 (11)
C7B0.0247 (12)0.0320 (13)0.0341 (13)0.0027 (10)0.0077 (10)0.0014 (11)
C7AB0.0260 (12)0.0281 (12)0.0230 (11)0.0009 (10)0.0111 (10)0.0021 (9)
C9B0.0398 (14)0.0280 (13)0.0285 (13)0.0026 (11)0.0090 (12)0.0000 (10)
C8B0.0262 (12)0.0385 (14)0.0315 (13)0.0035 (11)0.0100 (11)0.0004 (11)
C10B0.0370 (16)0.0417 (17)0.0629 (19)0.0179 (15)0.0190 (15)0.0129 (16)
Geometric parameters (Å, º) top
S1'—C2'1.772 (2)S1'B—C2'B1.767 (2)
S1'—C5'1.801 (3)S1'B—C5'B1.800 (3)
O6'—C4'1.222 (3)O6'B—C4'B1.214 (3)
N1—C7A1.274 (3)N1B—C7AB1.280 (3)
N1—N21.408 (3)N1B—N2B1.404 (3)
N2—C2'1.324 (3)N2B—C2'B1.324 (3)
N2—C31.514 (3)N2B—C3B1.513 (3)
N3'—C2'1.308 (3)N3'B—C2'B1.312 (3)
N3'—C4'1.376 (3)N3'B—C4'B1.370 (3)
C4'—C5'1.523 (4)C4'B—C5'B1.531 (3)
C5'—H5'10.9700C5'B—H5'30.9700
C5'—H5'20.9700C5'B—H5'40.9700
C3—C91.517 (3)C3B—C8B1.517 (3)
C3—C81.519 (3)C3B—C9B1.522 (3)
C3—C3A1.556 (3)C3B—C3AB1.555 (3)
C3A—C7A1.497 (3)C3AB—C7AB1.493 (3)
C3A—C41.517 (4)C3AB—C4B1.529 (4)
C3A—H3A0.9800C3AB—H3AB0.9800
C4—C51.532 (4)C4B—C5B1.529 (4)
C4—H4A0.9700C4B—H4B10.9700
C4—H4B0.9700C4B—H4B20.9700
C5—C61.524 (4)C5B—C6B1.516 (4)
C5—H5A0.9700C5B—H5B10.9700
C5—H5B0.9700C5B—H5B20.9700
C6—C101.525 (4)C6B—C10B1.527 (4)
C6—C71.534 (4)C6B—C7B1.528 (3)
C6—H60.9800C6B—H6B0.9800
C7—C7A1.493 (3)C7B—C7AB1.490 (3)
C7—H7A0.9700C7B—H7B10.9700
C7—H7B0.9700C7B—H7B20.9700
C9—H9A0.9600C9B—H9B10.9600
C9—H9B0.9600C9B—H9B20.9600
C9—H9C0.9600C9B—H9B30.9600
C8—H8A0.9600C8B—H8B10.9600
C8—H8B0.9600C8B—H8B20.9600
C8—H8C0.9600C8B—H8B30.9600
C10—H10A0.9600C10B—H10D0.9600
C10—H10B0.9600C10B—H10E0.9600
C10—H10C0.9600C10B—H10F0.9600
C2'—S1'—C5'88.45 (12)C2'B—S1'B—C5'B88.60 (12)
C7A—N1—N2106.63 (19)C7AB—N1B—N2B107.21 (19)
C2'—N2—N1117.31 (18)C2'B—N2B—N1B117.75 (19)
C2'—N2—C3129.48 (19)C2'B—N2B—C3B128.74 (19)
N1—N2—C3113.19 (17)N1B—N2B—C3B113.44 (18)
C2'—N3'—C4'111.1 (2)C2'B—N3'B—C4'B111.5 (2)
N3'—C2'—N2124.0 (2)N3'B—C2'B—N2B123.7 (2)
N3'—C2'—S1'118.80 (18)N3'B—C2'B—S1'B118.70 (18)
N2—C2'—S1'117.20 (17)N2B—C2'B—S1'B117.56 (17)
O6'—C4'—N3'124.6 (2)O6'B—C4'B—N3'B125.0 (2)
O6'—C4'—C5'120.6 (2)O6'B—C4'B—C5'B120.5 (2)
N3'—C4'—C5'114.8 (2)N3'B—C4'B—C5'B114.5 (2)
C4'—C5'—S1'106.73 (19)C4'B—C5'B—S1'B106.68 (18)
C4'—C5'—H5'1110.4C4'B—C5'B—H5'3110.4
S1'—C5'—H5'1110.4S1'B—C5'B—H5'3110.4
C4'—C5'—H5'2110.4C4'B—C5'B—H5'4110.4
S1'—C5'—H5'2110.4S1'B—C5'B—H5'4110.4
H5'1—C5'—H5'2108.6H5'3—C5'B—H5'4108.6
N2—C3—C9108.11 (18)N2B—C3B—C8B109.00 (19)
N2—C3—C8111.76 (19)N2B—C3B—C9B110.36 (19)
C9—C3—C8111.3 (2)C8B—C3B—C9B112.0 (2)
N2—C3—C3A99.17 (17)N2B—C3B—C3AB99.81 (18)
C9—C3—C3A114.7 (2)C8B—C3B—C3AB110.28 (19)
C8—C3—C3A111.2 (2)C9B—C3B—C3AB114.7 (2)
C7A—C3A—C4111.0 (2)C7AB—C3AB—C4B107.9 (2)
C7A—C3A—C3102.81 (19)C7AB—C3AB—C3B103.32 (19)
C4—C3A—C3119.2 (2)C4B—C3AB—C3B119.4 (2)
C7A—C3A—H3A107.8C7AB—C3AB—H3AB108.6
C4—C3A—H3A107.8C4B—C3AB—H3AB108.6
C3—C3A—H3A107.8C3B—C3AB—H3AB108.6
C3A—C4—C5110.1 (2)C3AB—C4B—C5B109.9 (2)
C3A—C4—H4A109.6C3AB—C4B—H4B1109.7
C5—C4—H4A109.6C5B—C4B—H4B1109.7
C3A—C4—H4B109.6C3AB—C4B—H4B2109.7
C5—C4—H4B109.6C5B—C4B—H4B2109.7
H4A—C4—H4B108.2H4B1—C4B—H4B2108.2
C6—C5—C4112.3 (2)C6B—C5B—C4B112.9 (3)
C6—C5—H5A109.1C6B—C5B—H5B1109.0
C4—C5—H5A109.1C4B—C5B—H5B1109.0
C6—C5—H5B109.1C6B—C5B—H5B2109.0
C4—C5—H5B109.1C4B—C5B—H5B2109.0
H5A—C5—H5B107.9H5B1—C5B—H5B2107.8
C5—C6—C10112.2 (3)C5B—C6B—C10B112.1 (2)
C5—C6—C7110.2 (2)C5B—C6B—C7B110.5 (2)
C10—C6—C7109.9 (2)C10B—C6B—C7B109.6 (2)
C5—C6—H6108.1C5B—C6B—H6B108.2
C10—C6—H6108.1C10B—C6B—H6B108.2
C7—C6—H6108.1C7B—C6B—H6B108.2
C7A—C7—C6111.4 (2)C7AB—C7B—C6B110.2 (2)
C7A—C7—H7A109.4C7AB—C7B—H7B1109.6
C6—C7—H7A109.4C6B—C7B—H7B1109.6
C7A—C7—H7B109.4C7AB—C7B—H7B2109.6
C6—C7—H7B109.4C6B—C7B—H7B2109.6
H7A—C7—H7B108.0H7B1—C7B—H7B2108.1
N1—C7A—C7123.6 (2)N1B—C7AB—C7B123.1 (2)
N1—C7A—C3A116.2 (2)N1B—C7AB—C3AB115.9 (2)
C7—C7A—C3A120.1 (2)C7B—C7AB—C3AB120.7 (2)
C3—C9—H9A109.5C3B—C9B—H9B1109.5
C3—C9—H9B109.5C3B—C9B—H9B2109.5
H9A—C9—H9B109.5H9B1—C9B—H9B2109.5
C3—C9—H9C109.5C3B—C9B—H9B3109.5
H9A—C9—H9C109.5H9B1—C9B—H9B3109.5
H9B—C9—H9C109.5H9B2—C9B—H9B3109.5
C3—C8—H8A109.5C3B—C8B—H8B1109.5
C3—C8—H8B109.5C3B—C8B—H8B2109.5
H8A—C8—H8B109.5H8B1—C8B—H8B2109.5
C3—C8—H8C109.5C3B—C8B—H8B3109.5
H8A—C8—H8C109.5H8B1—C8B—H8B3109.5
H8B—C8—H8C109.5H8B2—C8B—H8B3109.5
C6—C10—H10A109.5C6B—C10B—H10D109.5
C6—C10—H10B109.5C6B—C10B—H10E109.5
H10A—C10—H10B109.5H10D—C10B—H10E109.5
C6—C10—H10C109.5C6B—C10B—H10F109.5
H10A—C10—H10C109.5H10D—C10B—H10F109.5
H10B—C10—H10C109.5H10E—C10B—H10F109.5
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the thiazole ring S1'/N3'/C2'/C4'/C5'
D—H···AD—HH···AD···AD—H···A
C5—H52···O6Bi0.972.433.304 (4)150
C9—H9B···O6Bii0.962.533.361 (3)145
C5B—H53···O6iii0.972.443.361 (3)159
C4B—H4B2···Cg10.962.933.737 (4)141
C7B—H7B2···Cg1iv0.962.903.867 (4)174
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y, z; (iii) x+2, y1/2, z+1; (iv) x, y, z+1.
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the thiazole ring S1'/N3'/C2'/C4'/C5'
D—H···AD—HH···AD···AD—H···A
C5'—H5'2···O6'Bi0.972.433.304 (4)150
C9—H9B···O6'Bii0.962.533.361 (3)145
C5'B—H5'3···O6'iii0.972.443.361 (3)159
C4B—H4B2···Cg10.962.933.737 (4)141
C7B—H7B2···Cg1iv0.962.903.867 (4)174
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x+1, y, z; (iii) x+2, y1/2, z+1; (iv) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC13H19N3OS
Mr265.37
Crystal system, space groupMonoclinic, P21
Temperature (K)180
a, b, c (Å)8.5519 (2), 18.9335 (4), 8.9165 (3)
β (°) 110.203 (3)
V3)1354.91 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.23
Crystal size (mm)0.25 × 0.21 × 0.18
Data collection
DiffractometerAgilent Xcalibur Eos Gemini ultra
Absorption correctionMulti-scan
(CrysAlis PRO; Agilent, 2014)
Tmin, Tmax0.939, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
15302, 6147, 5674
Rint0.024
(sin θ/λ)max1)0.692
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.077, 1.04
No. of reflections6147
No. of parameters331
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.22, 0.19
Absolute structureFlack x determined using 2349 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
Absolute structure parameter0.08 (3)

Computer programs: CrysAlis PRO (Agilent, 2014), SIR97 (Altomare et al., 1999), SHELXL2013 (Sheldrick, 2015), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 2012) and PLATON (Spek, 2009).

 

References

First citationAgilent (2014). CrysAlis PRO. Agilent Technologies Ltd, Abingdon, England.  Google Scholar
First citationAltomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationBonde, C. G. & Gaikwad, N. J. (2004). Bioorg. Med. Chem. 12, 2151–2161.  Web of Science CrossRef PubMed CAS Google Scholar
First citationBurnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA.  Google Scholar
First citationFarrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationGautam, D. & Chaudhary, R. P. (2015). Spectrochim. Acta Part A, 135, 219–226.  Web of Science CSD CrossRef CAS Google Scholar
First citationGroom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed. 53, 662–671.  Web of Science CSD CrossRef CAS Google Scholar
First citationKaralı, N., Gürsoy, A., Kandemirli, F., Shvets, N., Kaynak, F. B., Özbey, S., Kovalishyn, V. & Dimoglo, A. (2007). Bioorg. Med. Chem. 15, 5888–5904.  Google Scholar
First citationKaushik-Basu, N., Bopda-Waffo, A., Talele, T. T., Basu, A., Chen, Y. & Küçükgüzel, Ş. G. (2008). Front. Biosci. 13, 3857–3868.  PubMed CAS Google Scholar
First citationParsons, S., Flack, H. D. & Wagner, T. (2013). Acta Cryst. B69, 249–259.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationPatel, A. B., Chikhalia, K. H. & Kumari, P. (2014). J. Saudi Chem. Soc. 18, 646–656.  CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2015). Acta Cryst. C71, 3–8.  Web of Science CrossRef IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 72| Part 3| March 2016| Pages 334-336
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