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1.  2-[6-(4-Bromo­phen­yl)imidazo[2,1-b][1,3]thia­zol-3-yl]-N-[8-(4-hy­droxy­phen­yl)-2-methyl-3-oxo-1-thia-4-aza­spiro­[4.5]decan-4-yl]acetamide ethanol disolvate 
In the title compound, C28H27BrN4O3S2·2C2H6O, the cyclo­hexane ring adopts a chair conformation. The imidazo[2,1-b][1,3]thia­zole ring system is essentially planar with a dihedral angle of 1.1 (2)° between the thia­zole and imidazole rings. The mean plane of this ring system makes dihedral angles of 8.11 (16) and 79.43 (17)°, respectively, with the bromo- and hy­droxy-substituted benzene rings. In the 5-methyl-1,3-thia­zolidin-4-one group, the S atom, the methyl group and the ring C atoms bonded to them are disordered over two sets of sites with refined occupancies of 0.610 (19) and 0.390 (19). The crystal structure features N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds and C—H⋯π inter­actions. Furthermore, two weak π–π stacking inter­actions [centroid–centroid distances = 3.967 (3) and 3.892 (2) Å] are also observed.
PMCID: PMC3344614  PMID: 22590376
2.  1-(5-Bromo-4-phenyl-1,3-thia­zol-2-yl)pyrrolidin-2-one 
The asymmetric unit of the title compound, C13H11BrN2OS, consists of two crystallographically independent mol­ecules (A and B). In each mol­ecule, the pyrrolidine ring adopts an envelope conformation with a methyl­ene C atom as the flap atom. In mol­ecule A, the central thia­zole ring makes a dihedral angle of 36.69 (11)° with the adjacent phenyl ring, whereas the corresponding angle is 36.85 (12)° in mol­ecule B. The pyrrolidine ring is slightly twisted from the thia­zole ring, with C—N—C—N torsion angles of 4.8 (3) and 3.0 (4)° in mol­ecules A and B, respectively. In the crystal, C—H⋯π and π–π [centroid-to-centroid distance = 3.7539 (14) Å] inter­actions are observed. The crystal studied was a pseudo-merohedral twin with twin law (-100 0-10 101) and a refined component ratio of 0.7188 (5):0.2812 (5).
PMCID: PMC3379326  PMID: 22719524
3.  4-{2-[5-(4-Chloro­phen­yl)-1-(4-fluoro­phen­yl)-1H-pyrazol-3-yl]thia­zol-4-yl}benzonitrile 
The asymmetric unit of the title compound, C25H14ClFN4S, contains two independent mol­ecules (A and B). Each mol­ecule consists of five rings, namely chloro­phenyl, fluoro­phenyl, 1H-pyrazole, thia­zole and benzonitrile. In mol­ecule A, the 1H-pyrazole ring makes dihedral angles of 52.54 (8), 35.96 (8) and 15.43 (8)° with respect to the attached chloro­phenyl, fluoro­phenyl and thia­zole rings. The corresponding values in mol­ecule B are 51.65 (8), 37.26 (8) and 8.32 (8)°. In the crystal, mol­ecules are linked into dimers by C—H⋯N hydrogen bonds, generating R 2 2(10) ring motifs. These dimers are further linked into two-dimensional arrays parallel to the ab plane via inter­molecular weak C—H⋯N and C—H⋯F hydrogen bonds. The crystal structure is further stabilized by weak π-π inter­actions [with centroid–centroid distances of 3.4303 (9) and 3.6826 (9) Å] and weak C—H⋯π inter­actions.
PMCID: PMC3007991  PMID: 21588640
4.  (1S,3′S,3a′R,6′S)-6′-(2-Chloro­phen­yl)-3′-[(2R,3S)-1-(4-meth­oxy­phen­yl)-4-oxo-3-phenyl­azetidin-2-yl]-2-oxo-3′,3′a,4′,6′-tetra­hydro-2H,2′H-spiro­[ace­naphthyl­ene-1,1′-pyrrolo­[1,2-c][1,3]thia­zole]-2′,2′-dicarbo­nitrile 
The mol­ecular conformation of the title compound, C41H29ClN4O3S, is stabilized by intra­molecular C—H⋯O and C—H⋯Cl hydrogen bonds. The thia­zole ring adopts an envelope conformation with the N atom as the flap, while the pyrrolidine ring has a twisted conformation on the N—C bond involving the spiro C atom. The β la­ctam ring makes dihedral angles of 39.74 (15) and 16.21 (16)° with the mean planes of the thia­zole and pyrrolidine rings, respectively. The thia­zole ring mean plane makes dihedral angles of 23.79 (13) and 70.88 (13) ° with the pyrrolidine and cyclo­pentane rings, respectively, while the pyrrolidine ring makes a dihedral angle of 85.63 (13)° with the cyclo­pentane ring. The O atom attached to the β la­ctam ring deviates from its mean plane by 0.040 (2) Å, while the O atom attached to the cyclo­pentane ring deviates from its mean plane by 0.132 (2) Å. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds, forming chains along [010], and C—H⋯π and π-π inter­actions [centroid-centroid distance = 3.6928 (17) Å].
PMCID: PMC3648279  PMID: 23723899
5.  N-[(E)-Thio­phen-2-yl­methyl­idene]-1,3-benzothia­zol-2-amine 
In the title thio­phene-derived Schiff base compound, C12H8N2S2, the thio­phene ring is slighty rotated from the benzothia­zole group mean plane, giving a dihedral angle of 12.87 (6)°. The largest displacement of an atom in the mol­ecule from the nine-atom mean plane defined by the non-H atoms of the benzothia­zole ring system is 0.572 (1) Å, exhibited by the C atom at the 3-position of the thio­phene ring. In the crystal, weak C—H⋯S hydrogen bonds involving the thio­phene group S atom and the 4-position thio­phene C—H group of a symmetry-related mol­ecule lead to an infinite one-dimensional chain colinear with the c axis. The structure is further stabilized by π–π inter­actions; the distance between the thia­zole ring centroid and the centroid of an adjacent benzene ring is 3.686 (1) Å. The crystal studied was an inversion twin with the ratio of components 0.73 (3):0.27 (3).
PMCID: PMC3414944  PMID: 22904931
6.  2-[5-(4-Fluoro­phen­yl)-3-(4-methyl­phen­yl)-4,5-dihydro-1H-pyrazol-1-yl]-4-phenyl-1,3-thia­zole 
In the title compound, C25H20FN3S, two independent mol­ecules comprise the asymmetric unit, which differ in the relative orientation of the fluoro­benzene ring with respect to the pyrazole ring to which it is attached [dihedral angles = 89.39 (17) and 75.23 (16)° in the two mol­ecules]. Each pyrazole ring adopts an envelope conformation with the methine C atom being the flap atom. There are additional twists in the mol­ecules, e.g. between the five-membered rings [dihedral angles = 18.23 (16) and 17.84 (16)°] and between the thia­zole and attached phenyl ring [10.26 (16) and 20.87 (15)°]. Overall, each mol­ecule has a T-shape. In the crystal, mol­ecules are connected into a three-dimensional architecture by weak C—H⋯π inter­actions.
PMCID: PMC3588500  PMID: 23476577
7.  Crystal structures of N-[(4-phenyl­thia­zol-2-yl)carbamo­thio­yl]benzamide and N-{[4-(4-bromo­phen­yl)thia­zol-2-yl]carbamo­thio­yl}benzamide from synchrotron X-ray diffraction 
The crystal structures of two new thio­urea derivatives – potential active pharmaceutical ingredients (APIs) – were studied by synchrotron X-ray diffraction.
The title compounds, C17H13N3OS2, (I), and C17H12BrN3OS2, (II), are potential active pharmaceutical ingredients. Compound (I) comprises two almost planar fragments. The first is the central (carbamo­thio­yl)amide (r.m.s. deviation = 0.038 Å), and the second consists of the thia­zole and two phenyl rings (r.m.s. deviation = 0.053 Å). The dihedral angle between these planes is 15.17 (5)°. Unlike (I), compound (II) comprises three almost planar fragments. The first is the central N-(thia­zol-2-ylcarbamo­thio­yl)amide (r.m.s. deviation = 0.084 Å), and the two others comprise the bromo­phenyl and phenyl substituents, respectively. The dihedral angles between the central and two terminal planar fragments are 21.58 (7) and 17.90 (9)°, respectively. Both (I) and (II) feature an intra­molecular N—H⋯O hydrogen bond, which closes an S(6) ring. In the crystal of (I), mol­ecules form hydrogen-bonded layers parallel to (100) mediated by N—H⋯S and C—H⋯O hydrogen bonds. In the crystal of (II), mol­ecules form a three-dimensional framework mediated by N—H⋯Br and C—H⋯O hydrogen bonds, as well as secondary S⋯Br [3.3507 (11) Å] and S⋯S [3.4343 (14) Å] inter­actions.
PMCID: PMC5120721  PMID: 27920931
crystal structure; thio­urea; thia­zoles; synchrotron; hydrogen bonds
8.  5-(4-Chloro­phen­yl)-3-(2,4-dimethyl­thiazol-5-yl)-1,2,4-triazolo[3,4-a]isoquinoline 
In the title mol­ecule, C21H15ClN4S, the triazoloisoquinoline ring system is approximately planar, with an r.m.s. deviation of 0.054 (2) Å and a maximum deviation of 0.098 (2) Å from the mean plane for the triazole ring C atom that is bonded to the thia­zole ring. The thia­zole and benzene rings are twisted by 66.36 (7) and 56.32 (7)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, mol­ecules are linked by inter­molecular C—H⋯N inter­actions along the a axis. The mol­ecular conformation is stabilized by a weak intra­molecular π–π inter­action involving the thia­zole and benzene rings, with a centroid–centroid distance of 3.6546 (11) Å. In addition, two other intermolecular π–π stacking inter­actions are observed, between the triazole and benzene rings and between the dihydro­pyridine and benzene rings [centroid–centroid distances = 3.6489 (11) and 3.5967 (10) Å, respectively].
PMCID: PMC2979146  PMID: 21579114
9.  N-[4-(4-Bromo­phen­yl)thia­zol-2-yl]-4-(piperidin-1-yl)butanamide 
In the title compound, C18H22BrN3OS, the piperidine ring adopts a chair conformation. The mean plane of the thia­zole ring forms dihedral angles of 23.97 (10) and 75.82 (10)° with the mean planes of its adjacent benzene and piperidine rings, respectively. An intra­molecular N—H⋯N hydrogen bond generates an S(7) ring motif in the mol­ecule. In the crystal, no significant inter­moelcular hydrogen bonds are observed, but a weak π–π inter­action with a centroid–centroid distance of 3.8855 (13) Å occurs.
PMCID: PMC3379262  PMID: 22719460
10.  {2-[(1,3-Benzo­thia­zol-2-yl)meth­oxy]-5-fluoro­phen­yl}(4-chloro­phen­yl)methanone 
The asymmetric unit of the title compound, C21H13ClFNO2S, contains two independent mol­ecules with similar conformations. In the mol­ecules, the thia­zole ring is essentially planar [maximum atomic deviations = 0.014 (4) and 0.023 (5) Å] and is oriented with respect to the fluoro­phenyl ring and chloro­phenyl rings at 9.96 (18) and 70.39 (18)° in one mol­ecule and at 7.50 (18) and 68.43 (18)° in the other; the dihedral angles between the fluoro­phenyl and chloro­phenyl rings are 64.9 (2) and 64.6 (2)°, respectively. Inter­molecular C—H⋯O and C—H⋯F hydrogen bonds stabilize the three-dimensional supra­molecular architecture. Weak C—H⋯π and π–π inter­actions [centroid–centroid distance = 3.877 (3) Å] lead to a criss-cross mol­ecular packing along the c axis.
PMCID: PMC3772451  PMID: 24046594
11.  4-Methyl-N-(4-methyl­phenyl­sulfon­yl)-N-[4-(4-methyl­phen­yl)-1,3-thia­zol-2-yl]benzene­sulfonamide 
There are two independent mol­ecules in the asymmetric unit of the title compound, C24H22N2O4S3. In each, the sulfonamide N atoms reveal nearly a trigonal-planar geometry with two S atoms of the O=S=O groups and one C atom of the thia­zole ring; the angles around the N atoms are between 117.00 (13) and 123.86 (9)°. The methyl­phenyl­sulfonyl groups are in anti conformations, forming dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)° with the trigonal S—N—S planes in the two mol­ecules. The thia­zole groups are rotated around the C—N bonds and are almost perpendicular to the S—N—S plane [dihedral angles of 78.00 (7)/72.53 (5) and 77.09 (6)/71.50 (7)°]. In the crystal, pairs of C—H⋯O inter­actions, with the O atoms of the sulfonamide groups as acceptors, link each of the independent mol­ecules into inversion dimers.
PMCID: PMC3914048  PMID: 24526999
12.  2-[N-(4-Meth­oxy­phen­yl)acetamido]-1,3-thia­zol-4-yl acetate 
The structural analysis of the title compound, C14H14N2O4S, particularly the presence of an acetyl group at the exocyclic N atom and the C(H)—C(O2CMe)—N acet­oxy group in the thia­zole ring, may indicate that one of the starting materials, i.e. 2-(4-meth­oxy­anilino)-1,3-thia­zol-4(5H)-one, exists in the reaction mixture, at least partially, as a tautomer with an exocyclic amine N atom and an enol group. The acet­oxy and acetyl groups deviate from the thia­zole plane by 69.17 (6) and 7.25 (19)°, respectively. The thia­zole and benzene rings form a dihedral angle of 73.50 (4)°. In the crystal, centrosymmetrically related mol­ecules are connected into dimeric aggregates via C—H⋯O inter­actions.
PMCID: PMC3588441  PMID: 23476576
13.  (E)-Methyl 1,3-thia­zol-2-yl ketone 2,4-dinitro­phenyl­hydrazone 
Crystals of the title compound, C11H9N5O4S, were obtained from a condensation reaction of 2,4-dinitro­phenyl­hydrazine and methyl 1,3-thia­zol-2-yl ketone. Excluding two methyl H atoms, the mol­ecule displays a planar structure, the dihedral angle between the terminal thia­zole and benzene rings being 1.82 (8)°. The imino group links with adjacent nitro and thia­zole groups by intra­molecular bifurcated hydrogen bonding. The centroid–centroid separation of 3.7273 (11) Å between nearly parallel benzene and thia­zole rings of adjacent mol­ecules indicates the existence of π–π stacking in the crystal structure. Weak inter­molecular C—H⋯O hydrogen bonding is also observed.
PMCID: PMC2961542  PMID: 21202664
14.  (Z)-3-(2-{2-[1-(4-Hy­droxy­phen­yl)ethyl­idene]hydrazin-1-yl}-1,3-thia­zol-4-yl)-2H-chromen-2-one 
In the title compound, C20H15N3O3S, an intra­molecular C—H⋯O hydrogen bond generates an S(6) ring motif. The chromene ring system is inclined at dihedral angles of 14.21 (9) and 9.91 (10)°, respectively, with respect to the thia­zole and benzene rings. The thia­zole ring makes a dihedral angle of 24.06 (11)° with the benzene ring. In the crystal structure, O—H⋯O hydrogen bonds link the mol­ecules into a zigzag chain along [20]. Weak N—H⋯O and C—H⋯O inter­actions connect the chains into a three-dimensional network. π–π stacking inter­actions with a centroid–centroid distance of 3.4209 (14) Å are also observed between the chains.
PMCID: PMC3006946  PMID: 21587863
15.  3-(2-Bromo­phen­yl)thia­zolo[3,2-a]benzimidazole 
The title compound, C15H9BrN2S, was prepared by the reaction of 1-bromo-2-(2,2-dibromo­vin­yl)benzene with 1H-benzo[d]imidazole-2(3H)-thione. The thia­zolo[3,2-a]benz­imidazole fused-ring system is nearly planar, the maximum atomic deviation being 0.049 (4) Å. This mean plane is oriented at a dihedral angle of 71.55 (17)° with respect ot the bromo­phenyl ring. π–π stacking is observed in the crystal structure, the centroid–centroid distance between the thia­zole and imidazole rings of adjacent mol­ecules being 3.582 (2) Å.
PMCID: PMC3200872  PMID: 22065022
16.  (E)-3-(2-{2-[1-(3-Hy­droxy­phen­yl)ethyl­idene]hydrazin­yl}-1,3-thia­zol-4-yl)-2H-chromen-2-one 
In the title compound, C20H15N3O3S, the thia­zole ring is approximately planar, with a maximum deviation of 0.003 (1) Å, and makes dihedral angles of 7.44 (6) and 1.88 (6)° with the hy­droxy-substituted phenyl ring and the pyran ring, respectively. The hydroxyl group is disordered over two sets of sites, with an occupancy ratio of 0.567 (3):0.433 (3). In the crystal, the major disorder component mol­ecules are connected via bifurcated (three-centre) O—H⋯O and C—H⋯O hydrogen bonds, generating R 1 2(6) motifs and resulting in supra­molecular chains along the a axis. In the minor occupancy component, however, mol­ecules are connected via C—H⋯O hydrogen bonds, forming supra­molecular chains along the b axis. Furthermore, the crystal structure is stabilized by π–π inter­actions between the thia­zole rings [centroid–centroid distance = 3.5476 (7) Å].
PMCID: PMC3089171  PMID: 21754396
17.  Crystal structure of (2Z,5Z)-3-(4-meth­oxy­phen­yl)-2-[(4-meth­oxy­phenyl)­imino]-5-[(E)-3-(2-nitro­phen­yl)allyl­idene]-1,3-thia­zolidin-4-one 
The thia­zole ring of the title compound is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°.
In the title compound, C26H21N3O5S, the thia­zole ring is nearly planar with a maximum deviation of 0.017 (2) Å, and is twisted with respect to the three benzene rings, making dihedral angles of 25.52 (12), 85.77 (12) and 81.85 (13)°. In the crystal, weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions link the mol­ecules into a three-dimensional supra­molecular architecture. Aromatic π–π stacking is also observed between the parallel nitro­benzene rings of neighbouring mol­ecules, the centroid-to-centroid distance being 3.5872 (15) Å.
PMCID: PMC4770957  PMID: 26958377
crystal structure; thia­zolidinone; hydrogen bonding; π–π stacking
18.  N-(2,4-Dichloro­phen­yl)-1,3-thia­zol-2-amine 
In the title mol­ecule, C9H6Cl2N2S, the mean planes of the benzene and thia­zole rings make a dihedral angle of 54.18 (8)°. In the crystal, mol­ecules are joined into dimers with an R 2 2(8) ring motif by pairs of N—H⋯N hydrogen bonds. These dimers are linked by C—H⋯Cl inter­actions into layers parallel to (011). The thia­zole rings form columns along the c-axis direction, with a centroid–centroid separation of 3.8581 (9) Å, indicating π–π inter­actions. An intra­molecular C—H⋯S contact also occurs.
PMCID: PMC3435722  PMID: 22969593
19.  2-((1E)-1-{2-[(2Z)-4-(4-Bromo­phen­yl)-3-phenyl-2,3-di­hydro-1,3-thia­zol-2-yl­idene]hydrazin-1-yl­idene}eth­yl)pyridin-1-ium bromide monohydrate 
In the title hydrated molecular salt, C22H18BrN4S+·Br−·H2O, the aromatic rings make dihedral angles of 14.20 (12), 34.29 (10) and 68.75 (11)° with the thia­zole ring. In the crystal, mol­ecules are linked into chains running parallel to the a axis by association of the bromide ions and the water mol­ecules of crystallization with the cations via N—H⋯O, O—H⋯Br, C—H⋯N and C—H⋯Br hydrogen-bonding inter­actions. C—H⋯π and C—Br⋯π [3.7426 (11) Å, 161.73 (7)°] inter­actions are also observed, forming infinite chains extending along the b-axis direction.
PMCID: PMC3998394  PMID: 24765025
20.  N-(1,3-Thia­zol-2-yl)-N′-[(thio­phen-2-yl)carbon­yl]thio­urea hemihydrate 
The title compound, C9H7N3OS3·0.5H2O, crystallizes with two independent but similar mol­ecules in the asymmetric unit, both of which are linked by a water mol­ecule through O—H⋯N hydrogen bonds. In addition the water O atom is further linked by N—H⋯O hydrogen bonds to two additional main mol­ecules, forming a tetra­meric unit. These tetra­meric units then form infinite ribbons parallel to the ac plane.The dihedral angle between the thio­phenoyl and thia­zolyl rings is 12.15 (10) and 21.69 (11)° in mol­ecules A and B, respectively. The central thio­urea core makes dihedral angles of 5.77 (11) and 8.61 (9)°, respectively, with the thio­­phen­oyl and thia­zolyl rings in mol­ecule A and 8.41 (10) and 13.43 (12)° in mol­ecule B. Each mol­ecule adopts a trans–cis geometry with respect to the position of thio­phenoyl and thia­zole groups relative to the S atom across the thio­urea C—N bonds. This geometry is stabilized by intra­molecular N—H⋯O hydrogen bonds.
PMCID: PMC3588839  PMID: 23468804
21.  2-(2-Methyl­phen­yl)-N-(1,3-thia­zol-2-yl)acetamide 
In the title compound, C12H12N2OS, the dihedral angle between the benzene and thia­zole rings is 83.5 (7)°. The acetamide group is almost coplanar with the thia­zole ring, being twisted from it by 4.2 (9)°. In the crystal, pairs of N—H⋯N hydrogen bonds link mol­ecules into inversion dimers, generating R 2 2[8] loops; the dimers are stacked along [001].
PMCID: PMC4051114  PMID: 24940286
22.  (Z)-N-[3-(2-Methoxy­phen­yl)-4-phenyl-2,3-dihydro­thia­zol-2-yl­idene]-2-methyl­benzamide 
In the title mol­ecule, C24H20N2O2S, the thia­zole and amide groups are essentially coplanar. The thia­zole ring forms dihedral angles of 61.62 (4) and 26.75 (5)° with the benzene rings of the methoxy­phenyl and methyl­phenyl groups, respectively, and 33.69 (6)° with the phenyl ring. The crystal packing is stabilized by inter­molecular C—H⋯O hydrogen bonds, forming a three-dimensional network.
PMCID: PMC2915024  PMID: 21200943
23.  Crystal structures of two substituted thia­zolidine derivatives 
In both compounds, namely 2′-ferrocenyl-6′-methyl-6a’-nitro-6′,6a’,6b’,7′,9′,11a’-hexa­hydro-2H-spiro­[ace­naphthyl­ene-1,11′-chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zol]-2-one, (I), and 6′-(4-meth­oxy­phen­yl)-6a’-nitro-6′,6a’,6b’,7′,9′,11a’-hexa­hydro-2H-spiro­[ace­naphthyl­ene-1,11′-chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zol]-2-one, (II), an intra­molecular C—H⋯O hydrogen bond forms an S(7) ring motif. In (I), mol­ecules are linked via two different C—H⋯O hydrogen bonds, forming chains along [001] and [100]. In (II), they are linked through C—H⋯O hydrogen bonds, forming dimers with an (10) ring motif while C—H⋯π inter­actions link the mol­ecules in a head-to-tail fashion, forming chains along the a-axis direction.
In the first of the compounds reported herein, namely 6′-ferrocenyl-6a′-nitro-6′,6a′,6b′,7′,9′,11a′-hexa­hydro-2H-spiro­[ace­naphthyl­ene-1,11′-chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zol]-2-one, [Fe(C5H5)(C29H21N2O4S)], (I), the thia­zolidine ring adopts a twist conformation on the methine N—C atoms. In the second compound, viz. 6′-(4-methoxy­phen­yl)-6a′-nitro-6′,6a′,6b′,7′,9′,11a′-hexa­hydro-2H-spiro­[ace­naphthyl­ene-1,11′-chromeno[3′,4′:3,4]pyrrolo­[1,2-c]thia­zol]-2-one, [Fe(C5H5)(C26H19N2O5S)], (II), the thia­zolidine ring adopts an envelope conformation with a methine C atom as the flap. In both compounds, the pyrrolidine ring adopts a twist conformation on the thia­zolidine and tetra­hydro­pyran C atoms. The mean planes of the thia­zolidine and pyrrolidine rings subtend angles of 67.30 (1) and 62.95 (7)° in (I) and (II), respectively, while the mean plane of the pyrrolidine ring makes dihedral angles of 76.53 (1) and 87.74 (7)° with the ace­naphthyl­ene ring system in (I) and (II), respectively. In both compounds, an intra­molecular C—H⋯O hydrogen bond forms an S(7) ring motif. In the crystal of (I), mol­ecules are linked via two different C—H⋯O hydrogen bonds, forming chains along [001] and [100]. In (II), they are linked through C—H⋯O hydrogen bonds, forming dimers with an R 2 2(10) ring motif while C—H⋯π inter­actions link the mol­ecules in a head-to-tail fashion, forming chains along the a-axis direction.
PMCID: PMC4971855  PMID: 27536396
crystal structure; thia­zolidine deriv­ative; ferrocen­yl; ace­naphthyl­ene; chromane; hydrogen bonding; C—H⋯π inter­actions
24.  1-{[(E)-(4-{[(2Z)-2,3-Di­hydro-1,3-thia­zol-2-yl­idene]sulfamo­yl}phen­yl)iminium­yl]meth­yl}naphthalen-2-olate 
In the title zwitterionic compound, C20H15N3O3S2, the 2-hy­droxy­naphthalene-1-carbaldehyde group A, the anilinic unit B and the 1,3-thia­zol-2(3H)-imine group C are each approximately planar with r.m.s. deviation of 0.0721, 0.0412 and 0.0125 Å, respectively. The dihedral angles between A/B, A/C and B/C are 24.70 (10), 79.97 (7) and 83.14 (6)°, respectively. There is an intra­molecular S(6) motif involving the imine N—H and the naphtho­late O atom. In the crystal, inversion-related mol­ecules form dimers as a result of N—H⋯N and N—H⋯O hydrogen bonds with R 2 2(8) and R 1 2(4) motifs, respectively. Weak π–π inter­actions between the benzene and naphthyl rings of inversion-related mol­ecules have ring centroid–centroid distances of 3.638 (2) and 4.041 (2) Å. A C—H⋯π inter­action occurs between the thia­zol ring and the benzene ring of an adjacent mol­ecule.
PMCID: PMC4459363  PMID: 26090203
crystal structure; zwitterionic compound; sulfa­thia­zole; hydrogen bonding; C—H⋯π inter­actions; π–π inter­actions
25.  2-[3-Cyano-4-(2-methyl­prop­oxy)phen­yl]-4-methyl­thia­zole-5-carboxylic acid pyridine solvate 
In the title compound, C16H16N2O3S·C5H5N, the benzene and thia­zole rings of the Febuxostat [2-(3-cyano-4-isobut­yloxy)phenyl-4-methyl-5-thia­zolecarboxylic acid] mol­ecule are almost coplanar [dihedral angle = 2.4 (1)°]. The carboxyl group is coplanar with the thia­zole ring [O—C—C—C and O—C—C—S torsion angles of −0.7 (4) and 0.6 (3)°, respectively]. The pyridine mol­ecule of crystallization is linked to the Febuxostat mol­ecule through an O—H⋯N hydrogen bond. A weak π–π stacking inter­action is observed between the benzene ring of the Febuxostat mol­ecule and pyridine mol­ecule, with a centroid–centroid distance of 3.7530 (18) Å.
PMCID: PMC2971045  PMID: 21578222

Results 1-25 (136871)