organic compounds
Methyl (2Z)-2-{(2Z)-3-[(cyclopentylidene)amino]-4-oxo-2-phenylimino-1,3-thiazolidin-5-ylidene}acetate
aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, cChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, dChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com
In the title compound, C17H17N3O3S, the thiazole ring is nearly planar [maximum deviation = 0.015 (1) Å for the ring N atom] and the cyclopentane ring has a twist conformation. The molecular conformation is stabilized by a hypervalent interaction between the S atom and the ester group carbonyl O atom, with an S⋯O distance of 2.7931 (10) Å. In the crystal, C—H⋯O interactions generate chains of molecules propagating along [110] and π–π stacking interactions [centroid–centroid distance = 3.4677 (7) Å] between the thiazole rings organize these chains into (001) layers.
CCDC reference: 988094
Related literature
For the synthesis and similar structures, see: Akkurt et al. (2009); Li et al. (2011); Mague et al. (2013); Mohamed et al. (2013a,b); Pomés Hernández et al. (1996); Sundar et al. (2003). For the general biological significance of thiazolidinone scaffold compounds, see: Pfützner et al. (2007); Schianca et al. (2012); Jain et al. (2012); Lant (1986); Rock et al. (1991).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2013); cell SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).
Supporting information
CCDC reference: 988094
10.1107/S1600536814004048/gk2605sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814004048/gk2605Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814004048/gk2605Isup3.cml
A solution of 1 mmol (233 mg) 2-cyclopentylidene-N-phenylhydrazinecarbothioamide in 15 ml ethanol was added dropwise to a solution of 1 mmol (142 mg) dimethyl but-2-ynedioate in 10 ml ethanol. The reaction mixture was stirred and refluxed at 351 K. The reaction progress was monitored by TLC until completion. On cooling a solid yellow product was precipitated, filtered off under vacuum and recrystallized from ethanol to furnish block-shaped yellow crystals (m.p. 541–543 K).
All H atoms were positioned geometrically and treated as riding atoms, with C—H = 0.95 Å (aromatic H), 0.98 Å (methyl H) and 0.99 Å (methylene H), with Uiso(H) = 1.5 Uiso(C) for methyl H atoms and Uiso(H) = 1.2 Uiso(C) for the others. The components of the displacement parameters in the direction of the bond between non-hydrogen atoms were restrained to be equal within an effective standard deviation of 0.01 (DELU instruction).
Data collection: APEX2 (Bruker, 2013); cell
SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).C17H17N3O3S | F(000) = 720 |
Mr = 343.41 | Dx = 1.406 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 9943 reflections |
a = 9.9684 (2) Å | θ = 4.4–68.3° |
b = 9.9657 (2) Å | µ = 1.96 mm−1 |
c = 16.9818 (3) Å | T = 100 K |
β = 105.9290 (6)° | Block, yellow |
V = 1622.23 (5) Å3 | 0.17 × 0.16 × 0.09 mm |
Z = 4 |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2951 independent reflections |
Radiation source: INCOATEC IµS micro-focus source | 2769 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.023 |
Detector resolution: 10.4167 pixels mm-1 | θmax = 68.2°, θmin = 4.6° |
ω scans | h = −12→12 |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | k = −11→12 |
Tmin = 0.76, Tmax = 0.84 | l = −20→20 |
17510 measured reflections |
Refinement on F2 | 61 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | H-atom parameters constrained |
wR(F2) = 0.075 | w = 1/[σ2(Fo2) + (0.038P)2 + 0.6771P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
2951 reflections | Δρmax = 0.30 e Å−3 |
218 parameters | Δρmin = −0.21 e Å−3 |
C17H17N3O3S | V = 1622.23 (5) Å3 |
Mr = 343.41 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 9.9684 (2) Å | µ = 1.96 mm−1 |
b = 9.9657 (2) Å | T = 100 K |
c = 16.9818 (3) Å | 0.17 × 0.16 × 0.09 mm |
β = 105.9290 (6)° |
Bruker D8 VENTURE PHOTON 100 CMOS diffractometer | 2951 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2013) | 2769 reflections with I > 2σ(I) |
Tmin = 0.76, Tmax = 0.84 | Rint = 0.023 |
17510 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 61 restraints |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.08 | Δρmax = 0.30 e Å−3 |
2951 reflections | Δρmin = −0.21 e Å−3 |
218 parameters |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.49073 (3) | 0.41667 (3) | 0.35998 (2) | 0.0187 (1) | |
O1 | 0.66547 (10) | 0.71951 (9) | 0.49052 (6) | 0.0244 (3) | |
O2 | 0.72709 (10) | 0.25889 (9) | 0.37200 (6) | 0.0258 (3) | |
O3 | 0.93931 (9) | 0.30447 (9) | 0.45742 (6) | 0.0238 (3) | |
N1 | 0.44614 (11) | 0.65036 (10) | 0.41830 (6) | 0.0190 (3) | |
N2 | 0.36915 (11) | 0.75447 (11) | 0.44449 (7) | 0.0214 (3) | |
N3 | 0.24379 (11) | 0.55652 (11) | 0.33548 (7) | 0.0204 (3) | |
C1 | 0.58785 (13) | 0.63691 (13) | 0.44889 (8) | 0.0193 (3) | |
C2 | 0.37387 (13) | 0.54855 (12) | 0.36801 (8) | 0.0184 (3) | |
C3 | 0.63174 (13) | 0.50466 (13) | 0.42232 (7) | 0.0186 (3) | |
C4 | 0.76427 (13) | 0.46352 (13) | 0.44650 (8) | 0.0202 (4) | |
C5 | 0.80432 (13) | 0.33216 (13) | 0.42077 (8) | 0.0207 (4) | |
C6 | 0.98665 (15) | 0.17461 (14) | 0.43752 (9) | 0.0276 (4) | |
C7 | 0.36894 (13) | 0.86381 (13) | 0.40585 (8) | 0.0202 (4) | |
C8 | 0.43371 (17) | 0.89572 (14) | 0.33790 (9) | 0.0298 (4) | |
C9 | 0.41616 (18) | 1.04928 (15) | 0.32757 (11) | 0.0364 (5) | |
C10 | 0.28241 (16) | 1.07780 (14) | 0.35110 (9) | 0.0300 (4) | |
C11 | 0.29241 (14) | 0.98521 (13) | 0.42434 (8) | 0.0241 (4) | |
C12 | 0.17495 (13) | 0.45669 (13) | 0.27910 (8) | 0.0209 (3) | |
C13 | 0.05398 (14) | 0.39885 (14) | 0.28986 (9) | 0.0249 (4) | |
C14 | −0.01893 (15) | 0.30450 (15) | 0.23424 (9) | 0.0283 (4) | |
C15 | 0.02709 (15) | 0.26783 (14) | 0.16740 (9) | 0.0291 (4) | |
C16 | 0.14570 (15) | 0.32725 (16) | 0.15559 (9) | 0.0300 (4) | |
C17 | 0.21879 (14) | 0.42310 (14) | 0.21052 (8) | 0.0252 (4) | |
H4 | 0.83320 | 0.51970 | 0.48060 | 0.0240* | |
H6A | 0.94260 | 0.10380 | 0.46180 | 0.0410* | |
H6B | 1.08820 | 0.16880 | 0.45940 | 0.0410* | |
H6C | 0.96120 | 0.16350 | 0.37790 | 0.0410* | |
H8A | 0.38460 | 0.84850 | 0.28680 | 0.0360* | |
H8B | 0.53350 | 0.87020 | 0.35310 | 0.0360* | |
H9A | 0.49630 | 1.09710 | 0.36430 | 0.0440* | |
H9B | 0.40730 | 1.07640 | 0.27030 | 0.0440* | |
H10A | 0.19940 | 1.05620 | 0.30550 | 0.0360* | |
H10B | 0.27760 | 1.17310 | 0.36660 | 0.0360* | |
H11A | 0.34520 | 1.02850 | 0.47600 | 0.0290* | |
H11B | 0.19850 | 0.96050 | 0.42870 | 0.0290* | |
H13 | 0.02130 | 0.42400 | 0.33530 | 0.0300* | |
H14 | −0.10100 | 0.26480 | 0.24210 | 0.0340* | |
H15 | −0.02240 | 0.20230 | 0.12990 | 0.0350* | |
H16 | 0.17740 | 0.30250 | 0.10970 | 0.0360* | |
H17 | 0.29840 | 0.46550 | 0.20120 | 0.0300* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0170 (2) | 0.0147 (2) | 0.0233 (2) | 0.0017 (1) | 0.0036 (1) | −0.0023 (1) |
O1 | 0.0223 (5) | 0.0191 (5) | 0.0305 (5) | −0.0023 (4) | 0.0053 (4) | −0.0060 (4) |
O2 | 0.0216 (5) | 0.0233 (5) | 0.0304 (5) | 0.0028 (4) | 0.0037 (4) | −0.0056 (4) |
O3 | 0.0179 (5) | 0.0226 (5) | 0.0294 (5) | 0.0051 (4) | 0.0040 (4) | −0.0028 (4) |
N1 | 0.0194 (5) | 0.0141 (5) | 0.0238 (5) | 0.0017 (4) | 0.0063 (4) | −0.0014 (4) |
N2 | 0.0222 (6) | 0.0160 (5) | 0.0274 (6) | 0.0036 (4) | 0.0092 (4) | −0.0026 (4) |
N3 | 0.0181 (5) | 0.0181 (5) | 0.0245 (6) | 0.0016 (4) | 0.0051 (4) | 0.0009 (4) |
C1 | 0.0200 (6) | 0.0176 (6) | 0.0211 (6) | 0.0003 (5) | 0.0072 (5) | 0.0012 (5) |
C2 | 0.0210 (6) | 0.0146 (6) | 0.0206 (6) | 0.0016 (5) | 0.0076 (5) | 0.0014 (5) |
C3 | 0.0210 (6) | 0.0161 (6) | 0.0191 (6) | −0.0013 (5) | 0.0063 (5) | 0.0000 (5) |
C4 | 0.0188 (6) | 0.0193 (7) | 0.0218 (6) | −0.0009 (5) | 0.0043 (5) | −0.0006 (5) |
C5 | 0.0178 (6) | 0.0219 (7) | 0.0223 (6) | 0.0016 (5) | 0.0054 (5) | 0.0016 (5) |
C6 | 0.0247 (7) | 0.0240 (7) | 0.0329 (7) | 0.0085 (6) | 0.0060 (6) | −0.0022 (6) |
C7 | 0.0170 (6) | 0.0182 (7) | 0.0239 (6) | −0.0004 (5) | 0.0032 (5) | −0.0041 (5) |
C8 | 0.0371 (8) | 0.0209 (7) | 0.0371 (8) | 0.0065 (6) | 0.0197 (7) | 0.0048 (6) |
C9 | 0.0487 (10) | 0.0221 (8) | 0.0451 (9) | 0.0068 (7) | 0.0243 (8) | 0.0076 (7) |
C10 | 0.0359 (8) | 0.0185 (7) | 0.0347 (8) | 0.0058 (6) | 0.0084 (6) | 0.0005 (6) |
C11 | 0.0253 (7) | 0.0172 (7) | 0.0302 (7) | 0.0034 (5) | 0.0084 (5) | −0.0032 (5) |
C12 | 0.0180 (6) | 0.0174 (6) | 0.0247 (6) | 0.0037 (5) | 0.0015 (5) | 0.0024 (5) |
C13 | 0.0220 (7) | 0.0241 (7) | 0.0281 (7) | 0.0000 (5) | 0.0062 (6) | 0.0009 (6) |
C14 | 0.0235 (7) | 0.0249 (7) | 0.0336 (8) | −0.0032 (6) | 0.0029 (6) | 0.0028 (6) |
C15 | 0.0286 (7) | 0.0230 (7) | 0.0295 (7) | −0.0002 (6) | −0.0025 (6) | −0.0017 (6) |
C16 | 0.0280 (7) | 0.0351 (8) | 0.0242 (7) | 0.0060 (6) | 0.0024 (6) | −0.0035 (6) |
C17 | 0.0200 (7) | 0.0279 (7) | 0.0262 (7) | 0.0016 (5) | 0.0038 (5) | 0.0005 (6) |
S1—C2 | 1.7861 (13) | C13—C14 | 1.388 (2) |
S1—C3 | 1.7461 (13) | C14—C15 | 1.385 (2) |
O1—C1 | 1.2148 (16) | C15—C16 | 1.385 (2) |
O2—C5 | 1.2091 (16) | C16—C17 | 1.393 (2) |
O3—C5 | 1.3471 (16) | C4—H4 | 0.9500 |
O3—C6 | 1.4489 (17) | C6—H6A | 0.9800 |
N1—N2 | 1.4320 (15) | C6—H6B | 0.9800 |
N1—C1 | 1.3713 (17) | C6—H6C | 0.9800 |
N1—C2 | 1.3929 (16) | C8—H8A | 0.9900 |
N2—C7 | 1.2717 (17) | C8—H8B | 0.9900 |
N3—C2 | 1.2648 (18) | C9—H9A | 0.9900 |
N3—C12 | 1.4201 (17) | C9—H9B | 0.9900 |
C1—C3 | 1.4968 (18) | C10—H10A | 0.9900 |
C3—C4 | 1.3358 (19) | C10—H10B | 0.9900 |
C4—C5 | 1.4696 (18) | C11—H11A | 0.9900 |
C7—C8 | 1.503 (2) | C11—H11B | 0.9900 |
C7—C11 | 1.5086 (19) | C13—H13 | 0.9500 |
C8—C9 | 1.545 (2) | C14—H14 | 0.9500 |
C9—C10 | 1.520 (2) | C15—H15 | 0.9500 |
C10—C11 | 1.530 (2) | C16—H16 | 0.9500 |
C12—C13 | 1.393 (2) | C17—H17 | 0.9500 |
C12—C17 | 1.3924 (19) | ||
C2—S1—C3 | 91.01 (6) | O3—C6—H6A | 109.00 |
C5—O3—C6 | 115.04 (10) | O3—C6—H6B | 109.00 |
N2—N1—C1 | 122.50 (10) | O3—C6—H6C | 109.00 |
N2—N1—C2 | 119.15 (11) | H6A—C6—H6B | 109.00 |
C1—N1—C2 | 117.82 (11) | H6A—C6—H6C | 110.00 |
N1—N2—C7 | 112.69 (11) | H6B—C6—H6C | 109.00 |
C2—N3—C12 | 119.89 (11) | C7—C8—H8A | 111.00 |
O1—C1—N1 | 125.42 (12) | C7—C8—H8B | 111.00 |
O1—C1—C3 | 125.44 (12) | C9—C8—H8A | 111.00 |
N1—C1—C3 | 109.14 (11) | C9—C8—H8B | 111.00 |
S1—C2—N1 | 110.15 (9) | H8A—C8—H8B | 109.00 |
S1—C2—N3 | 128.67 (10) | C8—C9—H9A | 111.00 |
N1—C2—N3 | 121.19 (12) | C8—C9—H9B | 111.00 |
S1—C3—C1 | 111.82 (9) | C10—C9—H9A | 111.00 |
S1—C3—C4 | 126.58 (10) | C10—C9—H9B | 111.00 |
C1—C3—C4 | 121.59 (12) | H9A—C9—H9B | 109.00 |
C3—C4—C5 | 120.56 (12) | C9—C10—H10A | 111.00 |
O2—C5—O3 | 124.08 (12) | C9—C10—H10B | 111.00 |
O2—C5—C4 | 124.60 (12) | C11—C10—H10A | 111.00 |
O3—C5—C4 | 111.32 (11) | C11—C10—H10B | 111.00 |
N2—C7—C8 | 129.59 (12) | H10A—C10—H10B | 109.00 |
N2—C7—C11 | 120.60 (12) | C7—C11—H11A | 111.00 |
C8—C7—C11 | 109.79 (11) | C7—C11—H11B | 111.00 |
C7—C8—C9 | 103.75 (12) | C10—C11—H11A | 111.00 |
C8—C9—C10 | 103.62 (13) | C10—C11—H11B | 111.00 |
C9—C10—C11 | 103.58 (12) | H11A—C11—H11B | 109.00 |
C7—C11—C10 | 103.79 (11) | C12—C13—H13 | 120.00 |
N3—C12—C13 | 118.49 (12) | C14—C13—H13 | 120.00 |
N3—C12—C17 | 121.86 (12) | C13—C14—H14 | 120.00 |
C13—C12—C17 | 119.47 (12) | C15—C14—H14 | 120.00 |
C12—C13—C14 | 120.09 (13) | C14—C15—H15 | 120.00 |
C13—C14—C15 | 120.46 (14) | C16—C15—H15 | 120.00 |
C14—C15—C16 | 119.58 (14) | C15—C16—H16 | 120.00 |
C15—C16—C17 | 120.43 (14) | C17—C16—H16 | 120.00 |
C12—C17—C16 | 119.90 (13) | C12—C17—H17 | 120.00 |
C3—C4—H4 | 120.00 | C16—C17—H17 | 120.00 |
C5—C4—H4 | 120.00 | ||
C3—S1—C2—N1 | −1.19 (9) | O1—C1—C3—C4 | 3.2 (2) |
C3—S1—C2—N3 | 179.13 (13) | N1—C1—C3—S1 | 1.81 (13) |
C2—S1—C3—C1 | −0.35 (10) | N1—C1—C3—C4 | −177.24 (12) |
C2—S1—C3—C4 | 178.65 (12) | S1—C3—C4—C5 | 0.00 (19) |
C6—O3—C5—O2 | −2.99 (19) | C1—C3—C4—C5 | 178.90 (12) |
C6—O3—C5—C4 | 178.11 (11) | C3—C4—C5—O2 | 6.7 (2) |
C1—N1—N2—C7 | 84.66 (15) | C3—C4—C5—O3 | −174.42 (12) |
C2—N1—N2—C7 | −103.83 (13) | N2—C7—C8—C9 | −171.37 (15) |
N2—N1—C1—O1 | −11.7 (2) | C11—C7—C8—C9 | 10.31 (16) |
N2—N1—C1—C3 | 168.71 (10) | N2—C7—C11—C10 | −164.51 (13) |
C2—N1—C1—O1 | 176.71 (13) | C8—C7—C11—C10 | 14.00 (15) |
C2—N1—C1—C3 | −2.90 (15) | C7—C8—C9—C10 | −30.79 (16) |
N2—N1—C2—S1 | −169.23 (8) | C8—C9—C10—C11 | 39.85 (15) |
N2—N1—C2—N3 | 10.49 (18) | C9—C10—C11—C7 | −33.10 (14) |
C1—N1—C2—S1 | 2.68 (14) | N3—C12—C13—C14 | 177.64 (13) |
C1—N1—C2—N3 | −177.61 (12) | C17—C12—C13—C14 | 2.6 (2) |
N1—N2—C7—C8 | 1.4 (2) | N3—C12—C17—C16 | −178.17 (13) |
N1—N2—C7—C11 | 179.58 (11) | C13—C12—C17—C16 | −3.2 (2) |
C12—N3—C2—S1 | −5.62 (19) | C12—C13—C14—C15 | −0.5 (2) |
C12—N3—C2—N1 | 174.72 (11) | C13—C14—C15—C16 | −0.9 (2) |
C2—N3—C12—C13 | 130.97 (14) | C14—C15—C16—C17 | 0.2 (2) |
C2—N3—C12—C17 | −54.06 (18) | C15—C16—C17—C12 | 1.9 (2) |
O1—C1—C3—S1 | −177.80 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O1i | 0.99 | 2.57 | 3.2889 (17) | 130 |
C11—H11A···O1i | 0.99 | 2.58 | 3.2547 (16) | 125 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10B···O1i | 0.99 | 2.57 | 3.2889 (17) | 130 |
C11—H11A···O1i | 0.99 | 2.58 | 3.2547 (16) | 125 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Acknowledgements
Manchester Metropolitan University, Tulane University and Erciyes University are gratefully acknowledged for supporting this study as is the support of NSF–MRI grant No. 1228232 for the purchase of the diffractometer.
References
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Diversity in the biological response profile of thiazolidinone and analogous scaffolds has attracted much attention to the exploration of this skeleton for a variety of therapeutic applications. Thus, the successful pharmaceutical applications of pioglitazone as a hypoglycemic agent (Pfützner et al., 2007; Schianca et al., 2012), thiazolidomycin activity against streptomyces species (Jain et al., 2012), etozoline as an antihypertensive (Lant, 1986), and ralitoline as a potent anti-convulsant (Rock et al., 1991) have established the wide spectrum potential of the thiazolidinone moiety. As part of our ongoing program of drug design and discovery, we report the synthesis and crystal structure of the title compound.
As shown in Fig. 1, the thiazole ring (S1/N1/C1–C3) of the title compound (I) is nearly planar with a maximum deviation of 0.015 (1) Å for N1. The cyclopentane ring (C7–C11) is twisted around the C9—C10 bond. The dihedral angle between the thiazole and phenyl rings is 53.84 (6)°. The C1–C3–C4–C5, C3–C4–C5–O2, C3–C4–C5–O3, C4–C5–O3–C6 and O2–C5–O3–C6 torsion angles are 178.90 (12), 6.7 (2), -174.42 (12), -178.11 (11) and 2.99 (19)°, respectively. All the bond lengths in (I) are comparable to those observed in similar structures (Akkurt et al., 2009; Li et al., 2011; Mague et al., 2013; Mohamed et al., 2013a,b; Pomés Hernández et al., 1996; Sundar et al., 2003).
Molecular conformation of (I) is stabilized by a short intramolecular (hypervalent) contact between the S1 atom and the ester group carbonyl O2 atom of 2.7931 (10) Å. In the crystal packing, the C—H···O interactions (Table 1, Fig. 2) with H···O distance of 2.57 - 2.58 Å generate chains of molecules propagating along the [110] direction. Furthermore, π-π stacking interactions [Cg1···Cg1 (1 - x, 1 - y, 1 - z) = 3.4677 (7) Å; where Cg1 is a centroid of the S1/N1/C1–C3 ring] between the thiazole rings organize these chains into the (001) layers.