Methyl (2Z)-2-{(2Z)-3-[(cyclo-pentyl-idene)amino]-4-oxo-2-phenyl-imino-1,3-thia-zol-idin-5-yl-idene}acetate.

In the title compound, C17H17N3O3S, the thia-zole ring is nearly planar [maximum deviation = 0.015 (1) Å for the ring N atom] and the cyclo-pentane ring has a twist conformation. The mol-ecular conformation is stabilized by a hypervalent inter-action 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 inter-actions generate chains of mol-ecules propagating along [110] and π-π stacking inter-actions [centroid-centroid distance = 3.4677 (7) Å] between the thia-zole rings organize these chains into (001) layers.

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 = 343.41

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.075

S = 1.08

2951 reflections

218 parameters

61 restraints

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.21 e Å−3

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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536814004048/gk2605sup1.cif

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

Click here for additional data file.

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

CCDC reference: 988094

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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

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) .