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The mol­ecules of the title compound, C17H21N3OS, are characterized by a wide C-C-C angle at the methine C atom linking the aryl and thia­zolidine rings, associated with a short repulsive intra­molecular S...H contact between atoms in these two rings. A single piperidine-arene C-H...[pi] hydrogen bond links pairs of mol­ecules into centrosymmetric dimers.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270112047956/yf3021sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270112047956/yf3021Isup2.hkl
Contains datablock I

CCDC reference: 925266

Comment top

We report here the molecular structure and the supramolecular aggregation of (Z)-5-[4-(dimethylamino)benzylidene]-2-(piperidin-1-yl)-1,3-thiazolidin-4(5H)-one, (I) (Fig. 1), which we compare briefly with those of the analogues (II) (Low et al., 2007) and (III) (Insuasty et al., 2012) (see Scheme 1). Compound (I) was prepared by reaction of piperidine with the intermediate (Z)-5-[4-(dimethylamino)benzylidene]-1,3-thiazolidin-4-one (A) (see Scheme 2), which was itself prepared using a base-catalysed condensation reaction between rhodanine (2-sulfanylidene-1,3-thiazolidin-4-one) and 4-(dimethylamino)benzaldehyde. The structures of a number of substituted (Z)-benzylidene-2-sulfanylidene-1,3-thiazolidin-4-ones have been reported recently (Delgado et al., 2005, 2006); these compounds are of interest, both as potential intermediates for the synthesis of novel fused heterocyclic systems and as potential antifungal agents (Sortino et al., 2007).

As generally found for (Z)-5-benzylidene-1,3-thiazolidin-4-ones (Delgado et al., 2005, 2006; Low et al., 2007), the aryl and thiazolidine rings in compound (I) are only modestly displaced from coplanarity, as indicated by the relevant torsion angles (Table 1). The dihedral angle between these two ring planes is only 28.1 (2)° and the piperidine substituent adopts an almost perfect chair conformation with the N21—C2 bond occupying an equatorial site.

Perhaps the most striking feature of the molecular structure of (I) is the very wide C—C—C angle of 130.2 (2)° at the bridging C57 atom. Associated with this wide angle is a rather short intramolecular contact distance of 2.62 Å between atoms S1 and H56 (Fig. 1); this distance is significantly shorter than the sum (2.89 Å) of the van der Waals radii for S and H (Bondi, 1964; Rowland & Taylor, 1996), and it may be compared with the corresponding value of 2.50 Å in compound (II) (Low et al., 2007) and 2.75 and 2.77 Å for the two independent molecules of compound (III) (Insuasty et al., 2012). In addition, the exocyclic angles S1—C5—C57 and C56—C51—C57 are both significantly larger than the corresponding angles C4—C5—C57 and C52—C51—C57, respectively (Table 1). These observations, taken together, indicate that the nonbonded intramolecular contact S1···H56 is strongly repulsive. It appears that distortion of the bond angles at atoms C5, C51 and C57 is an energetically more favourable route for accommodating the repulsive S···H contact than that provided by a significant rotation of the aryl ring around the C51—C57 bond. On the other hand, although the aryl-ring C52—C53 and C55—C56 bond lengths of 1.379 (4) and 1.389 (3) Å, respectively, are slightly shorter than the remaining C—C distances in this ring [range 1.397 (3)–1.412 (3) Å; mean 1.405 Å], none of the other bond lengths in (I) (Table 1) provides any evidence for the development of a polarized (zwitterionic) electronic structure of type (Ia) which might lead to restricted rotation about the C51—C57 bond.

The supramolecular aggregation in compound (I) is very simple as the crystal structure contains neither conventional hydrogen bonds nor aromatic ππ stacking interactions. Instead the molecules are linked in pairs by a single C—H···π(arene) hydrogen bond (Table 2) to form centrosymmetric dimers, with the reference dimer centred across (1/2, 1/2, 1/2) (Fig. 2). There are two such dimers per unit cell, but there are no direction-specific interactions between adjacent dimers. The only other potentially significant intermolecular contact is of C—H···S type between the molecules at (x, y, z) and (-x+1, -y, -z+1) (Table 2). However, not only is the H···S distance greater than the sum (2.89 Å) of the van der Waals radii for H and H (Bondi, 1964; Rowland & Taylor, 1996), but two-connected sulfur has been shown (Allen et al., 1997) to be an extremely poor acceptor in hydrogen bonds, even from O—H and N—H as donors; accordingly, this contact cannot be regarded as structurally significant.

It is of interest to compare briefly the supramolecular aggregation reported here for compound (I) with that in compounds (II) and (III). In compound (II) (Low et al., 2007), symmetry-related pairs of molecules are again linked into cyclic dimers, but here the component molecules are related by a twofold rotation axis, rather than by inversion as in compound (I) and hydrogen bond concerned in (II) is of the C—H···O type rather than of the C—H···π(arene) type found in (I), Compound (III) (Insuasty et al., 2012) crystallizes in the space group P1 with Z' = 2, and in one of the two independent molecules the chair-form morpholine ring is conformationally disordered over two sets of sites, with the two disorder forms exhibiting different orientation of the ring, while the other molecule is fully ordered. An extensive series of C—H···O hydrogen bonds link the molecules of (III) into a complex two-dimensional structure; it is notable that, despite the molecular constitution, intermolecular hydrogen bonds of the C—H···N type are absent from the structure of compound (III).

Related literature top

For related literature, see: Allen et al. (1997); Bondi (1964); Delgado et al. (2005, 2006); Insuasty et al. (2012); Low et al. (2007); Rowland & Taylor (1996); Sortino et al. (2007).

Experimental top

To a mixture of 4-(dimethylamino)benzaldehyde (1.1 mmol) and rhodanine (1.0 mmol) in dry ethanol (10 ml) was added one drop of piperidine. This mixture was then heated under reflux for 6 h. After cooling the mixture to ambient temperature, the resulting solid precipitate was collected by filtration and washed with cold ethanol to provide intermediate (A). A mixture of (A) (1.0 mmol) and piperidine (2.0 mmol) in dry tetrahydrofuran (10 ml) as then heated under reflux for 20 h. After warming to ambient temperature, this mixture was poured onto an excess of crushed ice. The resulting solid product was collected by filtration and washed successively with water and hexane, and then crystallized from ethanol (yield 42%, m.p. 490–492 K). MS (EI, 70 eV) m/z (%): 315 (M+, 45), 179 (6), 178 (15), 177 (100), 176 (27), 162 (5), 161 (7).

Refinement top

All H atoms were located in difference maps and thereafter treated as riding atoms in geometrically idealized positions, with C—H = 0.95 (aromatic and methane), 0.98 (CH3) or 0.99 Å (CH2) and Uiso(H) = kUeq(C), where k = 1.5 for the methyl groups, which were permitted to rotate but not to tilt, and k = 1.2 for all other H atoms.

Computing details top

Data collection: COLLECT (Hooft, 1999); cell refinement: DIRAX/LSQ (Duisenberg et al., 2000); data reduction: EVALCCD (Duisenberg et al., 2003); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
Fig. 1. The molecular structure of compound (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.

Fig. 2. Part of the crystal structure of compound (I), showing the formation of a hydrogen-bonded dimer centred at (1/2, 1/2, 1/2). For the sake of clarity, H atoms not involved in the motif shown have been omitted. The atom marked with an asterisk (*) is at the symmetry position (-x+1, -y+1, -z+1).
(Z)-5-[4-(Dimethylamino)benzylidene]-2-(piperidin-1-yl)- 1,3-thiazolidin-4(5H)-one top
Crystal data top
C17H21N3OSF(000) = 672
Mr = 315.44Dx = 1.328 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3627 reflections
a = 12.7125 (14) Åθ = 2.9–27.5°
b = 7.8246 (4) ŵ = 0.21 mm1
c = 16.579 (2) ÅT = 120 K
β = 106.904 (9)°Block, colourless
V = 1577.9 (3) Å30.44 × 0.25 × 0.16 mm
Z = 4
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3627 independent reflections
Radiation source: Bruker–Nonius FR591 rotating anode2147 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.098
Detector resolution: 9.091 pixels mm-1θmax = 27.5°, θmin = 2.9°
ϕ and ω scansh = 1616
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
k = 1010
Tmin = 0.913, Tmax = 0.967l = 2121
27613 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.140H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0597P)2 + 0.6166P]
where P = (Fo2 + 2Fc2)/3
3627 reflections(Δ/σ)max = 0.001
201 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = 0.36 e Å3
Crystal data top
C17H21N3OSV = 1577.9 (3) Å3
Mr = 315.44Z = 4
Monoclinic, P21/nMo Kα radiation
a = 12.7125 (14) ŵ = 0.21 mm1
b = 7.8246 (4) ÅT = 120 K
c = 16.579 (2) Å0.44 × 0.25 × 0.16 mm
β = 106.904 (9)°
Data collection top
Bruker–Nonius KappaCCD
diffractometer
3627 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2003)
2147 reflections with I > 2σ(I)
Tmin = 0.913, Tmax = 0.967Rint = 0.098
27613 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.140H-atom parameters constrained
S = 1.05Δρmax = 0.34 e Å3
3627 reflectionsΔρmin = 0.36 e Å3
201 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.57880 (5)0.35790 (8)0.60139 (4)0.0247 (2)
C20.7183 (2)0.3012 (3)0.61626 (15)0.0227 (6)
N30.79382 (17)0.4167 (3)0.64922 (13)0.0250 (5)
C40.7471 (2)0.5646 (3)0.66841 (16)0.0246 (6)
O40.80069 (15)0.6917 (2)0.69924 (12)0.0310 (5)
C50.6244 (2)0.5547 (3)0.64865 (15)0.0224 (6)
N210.74172 (17)0.1446 (3)0.59428 (14)0.0261 (5)
C220.6587 (2)0.0147 (3)0.55802 (18)0.0329 (7)
H22A0.58450.06600.54530.039*
H22B0.66370.07850.59940.039*
C230.6756 (2)0.0578 (4)0.47794 (18)0.0344 (7)
H23A0.66240.03280.43450.041*
H23B0.62180.15070.45630.041*
C240.7922 (2)0.1276 (4)0.49418 (18)0.0330 (7)
H24A0.80240.22770.53220.040*
H24B0.80350.16540.44030.040*
C250.8761 (2)0.0094 (4)0.53403 (17)0.0308 (7)
H25A0.87260.10180.49260.037*
H25B0.95080.04080.54890.037*
C260.8557 (2)0.0845 (4)0.61281 (17)0.0293 (6)
H26A0.87010.00340.65760.035*
H26B0.90670.18110.63350.035*
C570.5648 (2)0.6763 (3)0.67246 (16)0.0235 (6)
H570.60560.77300.69900.028*
C510.4478 (2)0.6830 (3)0.66400 (16)0.0220 (6)
C520.4111 (2)0.7902 (3)0.71806 (16)0.0250 (6)
H520.46270.86280.75560.030*
C530.3030 (2)0.7941 (3)0.71881 (16)0.0249 (6)
H530.28210.86630.75760.030*
C540.2231 (2)0.6920 (3)0.66267 (16)0.0224 (6)
C550.2576 (2)0.5921 (3)0.60410 (15)0.0235 (6)
H550.20500.52820.56270.028*
C560.3677 (2)0.5865 (3)0.60647 (16)0.0224 (6)
H560.38910.51480.56780.027*
N540.11585 (17)0.6904 (3)0.66440 (13)0.0267 (5)
C580.0840 (2)0.7813 (4)0.73049 (17)0.0298 (6)
H58A0.13210.74690.78570.045*
H58B0.00760.75350.72690.045*
H58C0.09080.90470.72320.045*
C590.0342 (2)0.5876 (3)0.60426 (16)0.0276 (6)
H59A0.02460.63120.54720.041*
H59B0.03600.59390.61750.041*
H59C0.05900.46850.60760.041*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0176 (3)0.0263 (4)0.0309 (4)0.0001 (3)0.0079 (3)0.0016 (3)
C20.0212 (14)0.0272 (15)0.0206 (14)0.0006 (11)0.0073 (11)0.0024 (11)
N30.0194 (12)0.0280 (13)0.0278 (12)0.0018 (10)0.0073 (10)0.0002 (10)
C40.0231 (15)0.0285 (15)0.0251 (15)0.0018 (12)0.0117 (12)0.0026 (12)
O40.0227 (10)0.0319 (11)0.0388 (12)0.0057 (9)0.0097 (9)0.0063 (9)
C50.0220 (14)0.0260 (14)0.0193 (14)0.0027 (11)0.0065 (11)0.0025 (11)
N210.0184 (11)0.0252 (12)0.0349 (13)0.0017 (10)0.0081 (10)0.0027 (10)
C220.0211 (15)0.0263 (15)0.0510 (19)0.0003 (12)0.0100 (13)0.0021 (14)
C230.0305 (17)0.0293 (16)0.0397 (18)0.0023 (13)0.0044 (13)0.0045 (13)
C240.0332 (17)0.0341 (16)0.0317 (16)0.0067 (14)0.0094 (13)0.0048 (13)
C250.0281 (16)0.0320 (16)0.0352 (16)0.0063 (13)0.0136 (13)0.0035 (13)
C260.0185 (14)0.0311 (15)0.0389 (17)0.0047 (12)0.0090 (12)0.0011 (13)
C570.0219 (14)0.0256 (15)0.0242 (14)0.0022 (11)0.0086 (11)0.0016 (11)
C510.0197 (13)0.0226 (14)0.0244 (14)0.0012 (11)0.0078 (11)0.0046 (11)
C520.0239 (15)0.0238 (14)0.0270 (15)0.0009 (11)0.0067 (12)0.0038 (12)
C530.0249 (15)0.0246 (14)0.0263 (15)0.0027 (12)0.0091 (12)0.0016 (12)
C540.0199 (14)0.0235 (14)0.0246 (14)0.0008 (11)0.0076 (11)0.0023 (11)
C550.0217 (14)0.0267 (14)0.0210 (14)0.0010 (11)0.0044 (11)0.0013 (11)
C560.0247 (14)0.0224 (14)0.0214 (14)0.0013 (11)0.0087 (11)0.0001 (11)
N540.0193 (12)0.0330 (13)0.0284 (12)0.0022 (10)0.0080 (10)0.0059 (10)
C580.0218 (14)0.0394 (16)0.0308 (15)0.0045 (13)0.0116 (12)0.0038 (13)
C590.0205 (14)0.0324 (15)0.0282 (15)0.0006 (12)0.0044 (11)0.0004 (12)
Geometric parameters (Å, º) top
S1—C21.775 (3)C26—H26B0.9900
C2—N31.316 (3)C57—C511.454 (3)
C2—N211.336 (3)C57—H570.9500
N3—C41.379 (3)C51—C521.402 (3)
C4—C51.500 (4)C52—C531.379 (4)
C5—S11.748 (3)C52—H520.9500
C4—O41.230 (3)C53—C541.409 (4)
C5—C571.345 (3)C53—H530.9500
N21—C221.463 (3)C54—C551.412 (3)
N21—C261.468 (3)C55—C561.389 (3)
C22—C231.515 (4)C55—H550.9500
C22—H22A0.9900C56—H560.9500
C22—H22B0.9900C56—C511.397 (3)
C23—C241.529 (4)C54—N541.372 (3)
C23—H23A0.9900N54—C591.455 (3)
C23—H23B0.9900N54—C581.459 (3)
C24—C251.521 (4)C58—H58A0.9800
C24—H24A0.9900C58—H58B0.9800
C24—H24B0.9900C58—H58C0.9800
C25—C261.522 (4)C59—H59A0.9800
C25—H25A0.9900C59—H59B0.9800
C25—H25B0.9900C59—H59C0.9800
C26—H26A0.9900
C5—S1—C288.30 (12)N21—C26—H26A109.6
N3—C2—N21123.3 (2)C25—C26—H26A109.6
N3—C2—S1117.69 (19)N21—C26—H26B109.6
N21—C2—S1118.96 (19)C25—C26—H26B109.6
C2—N3—C4111.2 (2)H26A—C26—H26B108.1
O4—C4—N3123.4 (2)C5—C57—H57114.9
O4—C4—C5123.2 (2)C51—C57—H57114.9
N3—C4—C5113.4 (2)C56—C51—C52116.6 (2)
C5—C57—C51130.2 (2)C52—C51—C57118.7 (2)
C4—C5—C57122.6 (2)C56—C51—C57124.6 (2)
S1—C5—C57127.8 (2)C53—C52—C51122.4 (2)
C4—C5—S1109.35 (18)C53—C52—H52118.8
C2—N21—C22123.9 (2)C51—C52—H52118.8
C2—N21—C26121.4 (2)C52—C53—C54120.7 (2)
C22—N21—C26114.4 (2)C52—C53—H53119.7
N21—C22—C23110.6 (2)C54—C53—H53119.7
N21—C22—H22A109.5N54—C54—C53121.4 (2)
C23—C22—H22A109.5N54—C54—C55121.2 (2)
N21—C22—H22B109.5C53—C54—C55117.4 (2)
C23—C22—H22B109.5C56—C55—C54120.7 (2)
H22A—C22—H22B108.1C56—C55—H55119.7
C22—C23—C24110.9 (2)C54—C55—H55119.7
C22—C23—H23A109.5C55—C56—C51122.0 (2)
C24—C23—H23A109.5C55—C56—H56119.0
C22—C23—H23B109.5C51—C56—H56119.0
C24—C23—H23B109.5C54—N54—C59120.4 (2)
H23A—C23—H23B108.1C54—N54—C58120.4 (2)
C25—C24—C23110.3 (2)C59—N54—C58119.0 (2)
C25—C24—H24A109.6N54—C58—H58A109.5
C23—C24—H24A109.6N54—C58—H58B109.5
C25—C24—H24B109.6H58A—C58—H58B109.5
C23—C24—H24B109.6N54—C58—H58C109.5
H24A—C24—H24B108.1H58A—C58—H58C109.5
C24—C25—C26111.9 (2)H58B—C58—H58C109.5
C24—C25—H25A109.2N54—C59—H59A109.5
C26—C25—H25A109.2N54—C59—H59B109.5
C24—C25—H25B109.2H59A—C59—H59B109.5
C26—C25—H25B109.2N54—C59—H59C109.5
H25A—C25—H25B107.9H59A—C59—H59C109.5
N21—C26—C25110.4 (2)H59B—C59—H59C109.5
C5—S1—C2—N32.9 (2)C2—N21—C26—C25130.0 (2)
C5—S1—C2—N21176.6 (2)C22—N21—C26—C2555.5 (3)
N21—C2—N3—C4178.0 (2)C24—C25—C26—N2153.3 (3)
S1—C2—N3—C41.5 (3)C4—C5—C57—C51175.5 (2)
C2—N3—C4—O4179.4 (2)S1—C5—C57—C512.1 (4)
C2—N3—C4—C51.1 (3)C5—C57—C51—C5620.6 (4)
O4—C4—C5—C578.3 (4)C5—C57—C51—C52157.9 (3)
N3—C4—C5—C57171.3 (2)C56—C51—C52—C533.8 (4)
O4—C4—C5—S1177.3 (2)C57—C51—C52—C53174.7 (2)
N3—C4—C5—S13.2 (3)C51—C52—C53—C541.8 (4)
C2—S1—C5—C57170.9 (2)C52—C53—C54—N54177.9 (2)
C2—S1—C5—C43.15 (17)C52—C53—C54—C552.5 (4)
N3—C2—N21—C22179.7 (2)N54—C54—C55—C56175.9 (2)
S1—C2—N21—C220.1 (3)C53—C54—C55—C564.5 (4)
N3—C2—N21—C265.7 (4)C54—C55—C56—C512.5 (4)
S1—C2—N21—C26173.81 (18)C52—C51—C56—C551.7 (4)
C2—N21—C22—C23128.7 (3)C57—C51—C56—C55176.8 (2)
C26—N21—C22—C2357.0 (3)C55—C54—N54—C591.3 (4)
N21—C22—C23—C2455.4 (3)C53—C54—N54—C586.4 (4)
C22—C23—C24—C2554.6 (3)C55—C54—N54—C58174.0 (2)
C23—C24—C25—C2653.8 (3)C53—C54—N54—C59178.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···Cgi0.992.713.680 (3)168
C23—H23B···S1ii0.992.943.902 (3)165
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.

Experimental details

Crystal data
Chemical formulaC17H21N3OS
Mr315.44
Crystal system, space groupMonoclinic, P21/n
Temperature (K)120
a, b, c (Å)12.7125 (14), 7.8246 (4), 16.579 (2)
β (°) 106.904 (9)
V3)1577.9 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.21
Crystal size (mm)0.44 × 0.25 × 0.16
Data collection
DiffractometerBruker–Nonius KappaCCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2003)
Tmin, Tmax0.913, 0.967
No. of measured, independent and
observed [I > 2σ(I)] reflections
27613, 3627, 2147
Rint0.098
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.140, 1.05
No. of reflections3627
No. of parameters201
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.36

Computer programs: COLLECT (Hooft, 1999), DIRAX/LSQ (Duisenberg et al., 2000), EVALCCD (Duisenberg et al., 2003), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top
S1—C21.775 (3)C51—C521.402 (3)
C2—N31.316 (3)C52—C531.379 (4)
N3—C41.379 (3)C53—C541.409 (4)
C4—C51.500 (4)C54—C551.412 (3)
C5—S11.748 (3)C55—C561.389 (3)
C4—O41.230 (3)C56—C511.397 (3)
C5—C571.345 (3)C54—N541.372 (3)
C57—C511.454 (3)
C5—C57—C51130.2 (2)C52—C51—C57118.7 (2)
C4—C5—C57122.6 (2)C56—C51—C57124.6 (2)
S1—C5—C57127.8 (2)
S1—C5—C57—C512.1 (4)C53—C54—N54—C586.4 (4)
C5—C57—C51—C52157.9 (3)C53—C54—N54—C59178.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C23—H23A···Cgi0.992.713.680 (3)168
C23—H23B···S1ii0.992.943.902 (3)165
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z+1.
 

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