Methyl (2Z)-2-{(2Z)-3-[(cyclo­pentyl­idene)amino]-4-oxo-2-phenyl­imino-1,3-thia­zol­idin-5-yl­idene}acetate

Mague, J.T.; Akkurt, M.; Mohamed, S.K.; Hassan, A.A.; Albayati, M.R.

doi:10.1107/S1600536814004048

organic compounds

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ISSN: 2056-9890

Volume 70| Part 3| March 2014| Pages o366-o367

doi:10.1107/S1600536814004048

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Methyl (2Z)-2-{(2Z)-3-[(cyclopentylidene)amino]-4-oxo-2-phenylimino-1,3-thiazolidin-5-ylidene}acetate

Joel T. Mague,^a Mehmet Akkurt,^b Shaaban K. Mohamed,^c,^d Alaa A. Hassan ^d and Mustafa R. Albayati ^e ^*

^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

(Received 19 February 2014; accepted 20 February 2014; online 26 February 2014)

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

C₁₇H₁₇N₃O₃S
M_r = 343.41
Monoclinic, P 2₁ /c
a = 9.9684 (2) Å
b = 9.9657 (2) Å
c = 16.9818 (3) Å
β = 105.9290 (6)°
V = 1622.23 (5) Å³
Z = 4
Cu Kα radiation
μ = 1.96 mm⁻¹
T = 100 K
0.17 × 0.16 × 0.09 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.76, T_max = 0.84
17510 measured reflections
2951 independent reflections
2769 reflections with I > 2σ(I)
R_int = 0.023

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.075
S = 1.08
2951 reflections
218 parameters
61 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: APEX2 (Bruker, 2013); cell refinement: 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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536814004048/gk2605sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004048/gk2605Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814004048/gk2605Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: 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).

Figures top

	Fig. 1. Perspective view of the title compound with 50% probability displacement ellipsoids.
	Fig. 2. Crystal packing of the title compound viewed down the a axis. Only hydrogen atoms involved in C-H···O interactions (dashed lines) are shown.

Methyl (2Z)-2-{(2Z)-3-[(cyclopentylidene)amino]-4-oxo-2-phenylimino-1,3-thiazolidin-5-ylidene}acetate top

Crystal data top

C₁₇H₁₇N₃O₃S	F(000) = 720
M_r = 343.41	D_x = 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

Data collection top

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	R_int = 0.023
Detector resolution: 10.4167 pixels mm^-1	θ_max = 68.2°, θ_min = 4.6°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −11→12
T_min = 0.76, T_max = 0.84	l = −20→20
17510 measured reflections

Refinement top

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(F_o²) + (0.038P)² + 0.6771P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2951 reflections	Δρ_max = 0.30 e Å⁻³
218 parameters	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₇H₁₇N₃O₃S	V = 1622.23 (5) Å³
M_r = 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)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	2951 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2769 reflections with I > 2σ(I)
T_min = 0.76, T_max = 0.84	R_int = 0.023
17510 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	61 restraints
wR(F²) = 0.075	H-atom parameters constrained
S = 1.08	Δρ_max = 0.30 e Å⁻³
2951 reflections	Δρ_min = −0.21 e Å⁻³
218 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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.

Hydrogen-bond geometry (Å, º) top

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

Akkurt, M., Karaca, S., Cihan, G., Çapan, G. & Büyükgüngör, O. (2009). Acta Cryst. E65, o1009–o1010. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Jain, A. K., Vaidya, A., Ravichandran, V., Kashaw, S. K. & Agrawal, R. K. (2012). Bioorg. Med. Chem. 20, 3378–95. Web of Science CrossRef CAS PubMed Google Scholar
Lant, A. (1986). Drugs, 31, 40–55. CrossRef CAS PubMed Google Scholar
Li, Y.-M., Li, J.-Y., Wang, Q., Hao, A.-Y. & Sun, T. (2011). Acta Cryst. E67, o3303. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mague, J. T., Akkurt, M., Mohamed, S. K., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1401–o1402. CSD CrossRef CAS IUCr Journals Google Scholar
Mohamed, S. K., Akkurt, M., Mague, J. T., Hassan, A. A. & Albayati, M. R. (2013b). Acta Cryst. E69, o1844–o1845. CSD CrossRef CAS IUCr Journals Google Scholar
Mohamed, S. K., Mague, J. T., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2013a). Acta Cryst. E69, o1553–o1554. CSD CrossRef CAS IUCr Journals Google Scholar
Pfützner, A., Weber, M. M. & Forst, T. (2007). Expert Opin. Pharmacother. 8, 1985–98. Web of Science PubMed Google Scholar
Pomés Hernández, R., Duque Rodríguez, J., Novoa de Armas, H. & Toscano, R. A. (1996). Acta Cryst. C52, 1731–1733. CSD CrossRef IUCr Journals Google Scholar
Rock, D. R., McLean, M. J., Macdonald, R. L., Catterall, W. A. & Taylor, C. P. (1991). Epilepsy Res. 8, 197–203. CrossRef PubMed CAS Web of Science Google Scholar
Schianca, G. P. C., Sola, D., Rossi, L., Fra, G. P. & Bartoli, E. (2012). ISRN Endocrinology, Article ID 601380, 1–6. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sundar, T. V., Parthasarathi, V., García-Granda, S., Jain, A. & Pardasani, R. T. (2003). Acta Cryst. E59, o1967–o1969. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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Volume 70| Part 3| March 2014| Pages o366-o367

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

Methyl (2Z)-2-{(2Z)-3-[(cyclo­pentyl­­idene)amino]-4-oxo-2-phenyl­imino-1,3-thia­zol­idin-5-yl­­idene}acetate

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Experimental

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organic compounds

Methyl (2Z)-2-{(2Z)-3-[(cyclopentylidene)amino]-4-oxo-2-phenylimino-1,3-thiazolidin-5-ylidene}acetate