Dimethyl (2Z)-2-[4-((1Z)-1-{2-[(2Z,5Z)-5-(2-meth­oxy-2-oxo­ethyl­idene)-4-oxo-3-phenyl-1,3-thia­zolidin-2-yl­idene]hydra­zin-1-yl­idene}eth­yl)anilino]but-2-ene­dio­ate

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

doi:10.1107/S1600536813032042

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 12| December 2013| Pages o1844-o1845

doi:10.1107/S1600536813032042

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Dimethyl (2Z)-2-[4-((1Z)-1-{2-[(2Z,5Z)-5-(2-methoxy-2-oxoethylidene)-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]hydrazin-1-ylidene}ethyl)anilino]but-2-enedioate

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

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and ^eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 22 November 2013; accepted 24 November 2013; online 30 November 2013)

The molecule of the title compound, C₂₆H₂₄N₄O₇S, adopts a trans conformation about the central N—N bond, presumably to minimize steric between the substituents on these two atoms. An intramolecular N—H⋯O hydrogen bond occurs. The phenyl ring is disordered over two sets of sites, with an occupancy ratio of 0.624 (8):0.376 (8). The azolidine ring is essentially planar [maximum deviation = 0.008 (5) Å] and makes a dihedral angle of 4.3 (2)° with the benzene ring and dihedral angles of 74.1 (3) and 69.1 (5)°, respectively, with the mean planes of the major and minor components of the disordered phenyl ring. The packing in the crystal is aided by the formation of several weak C—H⋯O and C—H⋯N interactions.

CCDC reference: 973423

Related literature

For the biological activity of thiazolidinene-containing compounds, see: Chaudhari et al. (1975 ); Chaudhary et al. (1976 ); Babaoglu et al. (2003 ); Dwivedi et al. (1972 ); Parmar et al. (1972 ); Bondock et al. (2007 ); Vicini et al. (2008 ); Gududuru et al. (2004 ); Ottanà et al. (2005 ); Agrawal et al. (2000 ); Diurno et al. (1999 ); Omar et al. (2010 ); Vigorita et al. (2003 ); Rawal et al. (2005 ); Suzuki et al. (1999 ).

Experimental

Crystal data

C₂₆H₂₄N₄O₇S
M_r = 536.56
Monoclinic, P 2₁ /n
a = 15.7027 (6) Å
b = 4.8543 (2) Å
c = 33.5974 (13) Å
β = 92.539 (3)°
V = 2558.47 (17) Å³
Z = 4
Cu Kα radiation
μ = 1.59 mm⁻¹
T = 100 K
0.16 × 0.03 × 0.03 mm

Data collection

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.83, T_max = 0.95
11600 measured reflections
3655 independent reflections
2351 reflections with I > 2σ(I)
R_int = 0.106
θ_max = 59.1°

Refinement

R[F² > 2σ(F²)] = 0.070
wR(F²) = 0.156
S = 1.03
3655 reflections
339 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4⋯O6	0.88	2.01	2.705 (5)	135
C1—H1B⋯O4ⁱ	0.98	2.54	3.402 (8)	147
C3—H3⋯O3ⁱⁱ	0.95	2.37	3.191 (6)	145
C8B—H8B⋯N2ⁱⁱⁱ	0.95	2.58	3.461 (8)	155
C12B—H12B⋯O3^iv	0.95	2.31	3.216 (7)	159
C14—H14A⋯O6^v	0.98	2.50	3.375 (6)	148
Symmetry codes: (i) -x+1, -y+2, -z; (ii) -x+2, -y+3, -z; (iii) x, y+1, z; (iv) x, y-1, z; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT; program(s) used to solve structure: SHELXT (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: 973423

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813032042/sj5373sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813032042/sj5373Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813032042/sj5373Isup3.cml

checkCIF report

Comment top

The 4-thiazolidinone ring system is a core structure in various synthetic compounds and an important scaffold known to be associated with several biological activities such as hypnotic activity (Chaudhari et al., 1975; Chaudhary et al., 1976), anti-tubercular (Babaoglu et al., 2003), anti-convulsant (Dwivedi et al., 1972; Parmar et al., 1972), anti-bacterial (Bondock et al., 2007; Vicini et al., 2008), anti-cancer (Gududuru et al., 2004; Ottanà et al., 2005), anti-histaminic (Agrawal et al., 2000; Diurno et al., 1999), anti-fungal (Omar et al., 2010), anti-inflammatory (Vigorita et al., 2003), anti-viral (Rawal et al., 2005) properties and cardiovascular effects (Suzuki et al., 1999). Based on such findings and further to our studies on synthesis of a series of thiazolidinones, we report herein the synthesis and crystal structure of the title compound.

The title molecule (I), (Fig. 1), adopts a trans conformation about the central N2—N3 bond, presumably to minimize contact between the substituents on these two atoms. The conformation about the N4—C21 bond is determined by the presence of an intramolecular N4—H1···O6 hydrogen bond (Fig. 1 and Table 1). The azolidine ring (S1/N1/C4–C6) is essentially planar [maximum deviation = 0.008 (5) Å for C5] and makes a dihedral angle of 4.3 (2)° with the benzene ring (C15–C20) and dihedral angles of 74.1 (3) and 69.1 (5)°, respectively, with the mean planes of the major and minor components (C7B–C12B and C7A–C12A) of the disordered phenyl ring.

In the crystal, the molecular packing is stabilized by the several weak C—H···O and C—H···N intermolecular interactions (Fig. 2 and Table 1).

Related literature top

For the biological activity of thiazolidinene-containing compounds, see: Chaudhari et al. (1975); Chaudhary et al. (1976); Babaoglu et al. (2003); Dwivedi et al. (1972); Parmar et al. (1972); Bondock et al. (2007); Vicini et al. (2008); Gududuru et al. (2004); Ottanà et al. (2005); Agrawal et al. (2000); Diurno et al. (1999); Omar et al. (2010); Vigorita et al. (2003); Rawal et al. (2005); Suzuki et al. (1999).

Experimental top

A mixture of 283 mg (1 mmol) (2E)-2-[1-(4-aminophenyl)ethylidene]-N-phenylhydrazinecarbothioamide and 284 mg (2 mmol) dimethyl but-2-ynedioate in 50 ml of ethanol was refluxed and monitored by TLC until completion of the reaction. The excess solvent was evaporated under vacuum and the solid obtained was recrystallized from ethanol to afford clear yellow crystals (M.p. 443–445 K) of X-ray quality.

IR: 3420 (NH), 1742, 1717, 1665 (CO), 1599(Ar—C=C). ¹H-NMR (CDCl₃) δ=2.24 (s,3H,CH₃), 3.76(s,3H,OCH₃), 3.78(s,3H,OCH₃), 3.89(s,3H,OCH₃), 6.86 (s,1H,vinyl-CH), 6.88(s,1H,vinyl-CH), 7.43–7.48 (m, 4H,Ar—H), 7.52–7.57 (m,3H,Ar—H), 7.83–7.87 (m,2H,Ar—H), 9.75 (br,1H,NH). ¹³C-NMR (CDCl₃) δ=14.84 (CH₃), 51.36, 52.52, 53.03 (OCH₃), 116.02 (vinyl-CH), 119.61 (vinyl-CH), 127.44, 128.02, 128.91, 129.09, 129.93 (Ar—CH), 132.73, 141.97 (Ar—C), 142.15 (=C—NH), 146.88 (acyclic C=N), 158.27 (thiazole-C2), 164.03 (cyclic C=O), 164.61, 166.62, 169.66 (ester C=O).

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (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 molecule showing the intramolecular hydrogen bond (dashed line). Displacement ellipsoids are drawn at the 50% probability level. For clarity only the major disorder component of the disordered phenyl ring is shown.
	Fig. 2. Packing of the title molecule view down b showing the intermolecular hydrogen bonds as dashed lines.

Dimethyl (2Z)-2-{4-[(1Z)-1-{2-[(2Z,5Z)-5-(2-methoxy-2-oxoethylidene)-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]hydrazin-1-ylidene}ethyl]anilino}but-2-enedioate top

Crystal data top

C₂₆H₂₄N₄O₇S	F(000) = 1120
M_r = 536.56	D_x = 1.393 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2yn	Cell parameters from 9855 reflections
a = 15.7027 (6) Å	θ = 3.1–61.2°
b = 4.8543 (2) Å	µ = 1.59 mm⁻¹
c = 33.5974 (13) Å	T = 100 K
β = 92.539 (3)°	Column, yellow
V = 2558.47 (17) Å³	0.16 × 0.03 × 0.03 mm
Z = 4

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3655 independent reflections
Radiation source: INCOATEC IµS micro–focus source	2351 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.106
Detector resolution: 10.4167 pixels mm^-1	θ_max = 59.1°, θ_min = 2.6°
ω scans	h = −17→17
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −5→5
T_min = 0.83, T_max = 0.95	l = −37→31
11600 measured reflections

Refinement top

Refinement on F²	6 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.070	H-atom parameters constrained
wR(F²) = 0.156	W = 1/[Σ²(F_o²) + (0.0309P)² + 6.4905P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3655 reflections	Δρ_max = 0.30 e Å⁻³
339 parameters	Δρ_min = −0.28 e Å⁻³

Crystal data top

C₂₆H₂₄N₄O₇S	V = 2558.47 (17) Å³
M_r = 536.56	Z = 4
Monoclinic, P2₁/n	Cu Kα radiation
a = 15.7027 (6) Å	µ = 1.59 mm⁻¹
b = 4.8543 (2) Å	T = 100 K
c = 33.5974 (13) Å	0.16 × 0.03 × 0.03 mm
β = 92.539 (3)°

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	3655 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2351 reflections with I > 2σ(I)
T_min = 0.83, T_max = 0.95	R_int = 0.106
11600 measured reflections	θ_max = 59.1°

Refinement top

R[F² > 2σ(F²)] = 0.070	6 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
3655 reflections	Δρ_min = −0.28 e Å⁻³
339 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	Occ. (<1)
S1	0.82910 (8)	0.9838 (3)	0.07318 (4)	0.0352 (4)
O1	0.7365 (2)	1.5472 (9)	−0.02761 (10)	0.0509 (14)
O2	0.7018 (2)	1.2215 (9)	0.01654 (11)	0.0503 (14)
O3	1.0163 (2)	1.4497 (8)	0.04611 (11)	0.0500 (14)
O4	0.4439 (2)	−0.0248 (8)	0.10592 (10)	0.0485 (14)
O5	0.5638 (2)	−0.2773 (7)	0.10342 (10)	0.0383 (12)
O6	0.4864 (2)	−0.5316 (7)	0.24001 (10)	0.0420 (12)
O7	0.3549 (2)	−0.6713 (8)	0.22011 (10)	0.0474 (14)
N1	0.9907 (2)	1.0985 (9)	0.08935 (12)	0.0346 (14)
N2	0.9367 (3)	0.7543 (9)	0.12948 (12)	0.0370 (16)
N3	0.8626 (3)	0.5940 (8)	0.13394 (13)	0.0353 (14)
N4	0.5687 (2)	−0.2105 (8)	0.18830 (12)	0.0331 (14)
C1	0.6494 (4)	1.5545 (15)	−0.04284 (18)	0.066 (3)
C2	0.7544 (3)	1.3729 (12)	0.00233 (15)	0.0383 (17)
C3	0.8436 (3)	1.3888 (11)	0.01578 (15)	0.0372 (17)
C4	0.8772 (3)	1.2395 (11)	0.04549 (15)	0.0338 (17)
C5	0.9686 (3)	1.2793 (12)	0.05910 (15)	0.0382 (17)
C6	0.9255 (3)	0.9273 (11)	0.10114 (15)	0.0366 (17)
C7B	1.0773 (3)	1.0893 (13)	0.1080 (2)	0.0320 (17)	0.624 (8)
C8B	1.1061 (4)	1.2977 (13)	0.1336 (2)	0.044 (3)	0.624 (8)
C9B	1.1888 (4)	1.2897 (13)	0.1501 (2)	0.046 (3)	0.624 (8)
C10B	1.2426 (3)	1.0733 (14)	0.1411 (2)	0.045 (2)	0.624 (8)
C11B	1.2137 (4)	0.8649 (12)	0.1155 (2)	0.051 (3)	0.624 (8)
C12B	1.1311 (4)	0.8729 (12)	0.0990 (2)	0.045 (3)	0.624 (8)
C13	0.8620 (3)	0.4521 (10)	0.16606 (14)	0.0300 (17)
C14	0.9306 (3)	0.4598 (11)	0.19870 (15)	0.0426 (17)
C15	0.7858 (3)	0.2779 (10)	0.17131 (13)	0.0287 (17)
C16	0.7861 (3)	0.0648 (10)	0.19881 (14)	0.0312 (17)
C17	0.7147 (3)	−0.0942 (10)	0.20385 (14)	0.0327 (17)
C18	0.6403 (3)	−0.0423 (10)	0.18172 (14)	0.0300 (17)
C19	0.6384 (3)	0.1794 (10)	0.15518 (14)	0.0336 (17)
C20	0.7097 (3)	0.3316 (10)	0.14958 (14)	0.0317 (17)
C21	0.4985 (3)	−0.2571 (10)	0.16418 (14)	0.0324 (17)
C22	0.4970 (3)	−0.1693 (11)	0.12144 (15)	0.0354 (17)
C23	0.5758 (4)	−0.1888 (14)	0.06307 (15)	0.055 (2)
C24	0.4309 (3)	−0.4101 (10)	0.17585 (15)	0.0345 (17)
C25	0.4288 (3)	−0.5354 (11)	0.21454 (16)	0.0364 (17)
C26	0.3515 (4)	−0.8178 (14)	0.25707 (17)	0.058 (2)
C12A	1.0914 (6)	1.165 (3)	0.1430 (3)	0.045 (3)	0.376 (8)
C9A	1.2206 (5)	0.972 (3)	0.0964 (3)	0.046 (3)	0.376 (8)
C7A	1.0723 (5)	1.075 (2)	0.1044 (3)	0.0320 (17)	0.376 (8)
C8A	1.1370 (6)	0.978 (3)	0.0811 (3)	0.044 (3)	0.376 (8)
C10A	1.2397 (5)	1.063 (3)	0.1350 (3)	0.045 (2)	0.376 (8)
C11A	1.1750 (7)	1.159 (3)	0.1583 (3)	0.051 (3)	0.376 (8)
H1B	0.64500	1.67420	−0.06630	0.0980*
H1A	0.63100	1.36790	−0.05030	0.0980*
H11B	1.25050	0.71690	0.10940	0.0610*	0.624 (8)
H1C	0.61300	1.62650	−0.02230	0.0980*
H3	0.87960	1.51280	0.00250	0.0450*
H4	0.56980	−0.29720	0.21130	0.0400*
H8B	1.06940	1.44570	0.13970	0.0530*	0.624 (8)
H9B	1.20860	1.43210	0.16760	0.0550*	0.624 (8)
H10B	1.29910	1.06780	0.15240	0.0540*	0.624 (8)
H19	0.58670	0.22460	0.14090	0.0400*
H20	0.70770	0.47660	0.13060	0.0380*
H23A	0.52380	−0.22530	0.04670	0.0830*
H23B	0.62350	−0.29000	0.05220	0.0830*
H23C	0.58810	0.00910	0.06280	0.0830*
H24	0.38350	−0.43460	0.15770	0.0410*
H26A	0.39650	−0.95760	0.25860	0.0870*
H26B	0.29580	−0.90740	0.25860	0.0870*
H26C	0.35980	−0.68840	0.27930	0.0870*
H12B	1.11130	0.73040	0.08150	0.0540*	0.624 (8)
H14A	0.94080	0.27310	0.20900	0.0640*
H14B	0.91260	0.57890	0.22030	0.0640*
H14C	0.98330	0.53230	0.18810	0.0640*
H16	0.83660	0.02780	0.21450	0.0370*
H17	0.71670	−0.24050	0.22270	0.0390*
H8A	1.12400	0.91620	0.05470	0.0530*	0.376 (8)
H9A	1.26480	0.90630	0.08050	0.0550*	0.376 (8)
H10A	1.29680	1.05890	0.14550	0.0540*	0.376 (8)
H11A	1.18800	1.22130	0.18470	0.0610*	0.376 (8)
H12A	1.04720	1.23120	0.15890	0.0540*	0.376 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0316 (7)	0.0325 (7)	0.0414 (7)	−0.0036 (6)	−0.0005 (6)	0.0001 (6)
O1	0.045 (2)	0.059 (3)	0.048 (2)	0.007 (2)	−0.0057 (18)	0.011 (2)
O2	0.032 (2)	0.067 (3)	0.052 (2)	−0.008 (2)	0.0031 (18)	0.006 (2)
O3	0.042 (2)	0.058 (3)	0.050 (2)	−0.015 (2)	0.0031 (18)	0.009 (2)
O4	0.037 (2)	0.054 (3)	0.054 (2)	0.010 (2)	−0.0040 (18)	0.014 (2)
O5	0.032 (2)	0.042 (2)	0.041 (2)	0.0025 (18)	0.0033 (16)	−0.0009 (17)
O6	0.040 (2)	0.041 (2)	0.044 (2)	−0.0105 (19)	−0.0094 (18)	0.0036 (18)
O7	0.034 (2)	0.056 (3)	0.052 (2)	−0.0129 (19)	−0.0018 (18)	0.014 (2)
N1	0.025 (2)	0.039 (3)	0.040 (2)	−0.006 (2)	0.0037 (19)	0.000 (2)
N2	0.030 (2)	0.034 (3)	0.047 (3)	−0.001 (2)	0.003 (2)	−0.002 (2)
N3	0.029 (2)	0.028 (2)	0.049 (3)	−0.002 (2)	0.003 (2)	−0.001 (2)
N4	0.034 (3)	0.028 (2)	0.037 (2)	−0.004 (2)	−0.002 (2)	0.0022 (19)
C1	0.053 (4)	0.083 (5)	0.060 (4)	0.020 (4)	−0.011 (3)	0.008 (4)
C2	0.042 (3)	0.041 (3)	0.032 (3)	0.003 (3)	0.004 (3)	−0.004 (3)
C3	0.035 (3)	0.039 (3)	0.038 (3)	−0.006 (3)	0.006 (3)	0.004 (3)
C4	0.025 (3)	0.036 (3)	0.041 (3)	−0.006 (2)	0.007 (2)	−0.004 (3)
C5	0.037 (3)	0.043 (3)	0.035 (3)	−0.005 (3)	0.005 (2)	0.000 (3)
C6	0.037 (3)	0.035 (3)	0.038 (3)	−0.002 (3)	0.004 (2)	−0.002 (3)
C7B	0.021 (3)	0.033 (3)	0.042 (3)	−0.004 (2)	0.002 (2)	−0.005 (3)
C8B	0.037 (5)	0.047 (5)	0.048 (5)	0.005 (4)	0.002 (4)	−0.009 (5)
C9B	0.037 (5)	0.056 (6)	0.045 (5)	0.007 (5)	−0.003 (4)	−0.018 (5)
C10B	0.024 (3)	0.051 (4)	0.059 (4)	0.002 (3)	−0.008 (3)	−0.007 (3)
C11B	0.028 (5)	0.063 (7)	0.062 (6)	0.008 (5)	−0.002 (4)	−0.026 (5)
C12B	0.023 (5)	0.054 (6)	0.058 (6)	−0.001 (4)	−0.004 (4)	−0.015 (5)
C13	0.026 (3)	0.022 (3)	0.042 (3)	0.006 (2)	0.001 (2)	−0.002 (2)
C14	0.034 (3)	0.037 (3)	0.056 (3)	−0.001 (3)	−0.008 (3)	0.010 (3)
C15	0.027 (3)	0.025 (3)	0.034 (3)	−0.001 (2)	0.000 (2)	−0.005 (2)
C16	0.028 (3)	0.025 (3)	0.040 (3)	0.001 (2)	−0.004 (2)	−0.002 (2)
C17	0.040 (3)	0.024 (3)	0.034 (3)	0.002 (2)	−0.001 (2)	0.000 (2)
C18	0.028 (3)	0.024 (3)	0.038 (3)	−0.006 (2)	0.002 (2)	−0.006 (2)
C19	0.032 (3)	0.023 (3)	0.045 (3)	0.004 (2)	−0.007 (2)	0.000 (2)
C20	0.028 (3)	0.025 (3)	0.042 (3)	0.000 (2)	0.000 (2)	−0.004 (2)
C21	0.029 (3)	0.028 (3)	0.040 (3)	0.007 (2)	−0.002 (2)	−0.001 (2)
C22	0.029 (3)	0.031 (3)	0.046 (3)	0.000 (3)	−0.001 (3)	0.001 (3)
C23	0.049 (4)	0.075 (5)	0.042 (3)	0.009 (3)	0.009 (3)	0.006 (3)
C24	0.029 (3)	0.032 (3)	0.042 (3)	0.004 (2)	−0.004 (2)	0.002 (2)
C25	0.027 (3)	0.030 (3)	0.052 (3)	−0.002 (3)	−0.002 (3)	−0.002 (3)
C26	0.038 (4)	0.071 (4)	0.064 (4)	−0.019 (3)	0.000 (3)	0.021 (4)
C12A	0.023 (5)	0.054 (6)	0.058 (6)	−0.001 (4)	−0.004 (4)	−0.015 (5)
C9A	0.037 (5)	0.056 (6)	0.045 (5)	0.007 (5)	−0.003 (4)	−0.018 (5)
C7A	0.021 (3)	0.033 (3)	0.042 (3)	−0.004 (2)	0.002 (2)	−0.005 (3)
C8A	0.037 (5)	0.047 (5)	0.048 (5)	0.005 (4)	0.002 (4)	−0.009 (5)
C10A	0.024 (3)	0.051 (4)	0.059 (4)	0.002 (3)	−0.008 (3)	−0.007 (3)
C11A	0.028 (5)	0.063 (7)	0.062 (6)	0.008 (5)	−0.002 (4)	−0.026 (5)

Geometric parameters (Å, º) top

S1—C4	1.743 (5)	C13—C14	1.503 (7)
S1—C6	1.767 (5)	C15—C20	1.397 (7)
O1—C1	1.439 (7)	C15—C16	1.387 (7)
O1—C2	1.335 (7)	C16—C17	1.378 (7)
O2—C2	1.219 (6)	C17—C18	1.380 (7)
O3—C5	1.210 (6)	C18—C19	1.397 (7)
O4—C22	1.192 (6)	C19—C20	1.361 (7)
O5—C22	1.341 (6)	C21—C22	1.497 (7)
O5—C23	1.442 (6)	C21—C24	1.367 (7)
O6—C25	1.217 (6)	C24—C25	1.437 (7)
O7—C25	1.355 (6)	C1—H1A	0.9800
O7—C26	1.434 (7)	C1—H1B	0.9800
N1—C5	1.376 (7)	C1—H1C	0.9800
N1—C6	1.390 (6)	C3—H3	0.9500
N1—C7B	1.473 (6)	C8A—H8A	0.9500
N1—C7A	1.361 (9)	C8B—H8B	0.9500
N2—N3	1.413 (6)	C9A—H9A	0.9500
N2—C6	1.276 (7)	C9B—H9B	0.9500
N3—C13	1.281 (6)	C10A—H10A	0.9500
N4—C18	1.415 (6)	C10B—H10B	0.9500
N4—C21	1.358 (6)	C11A—H11A	0.9500
N4—H4	0.8800	C11B—H11B	0.9500
C2—C3	1.455 (7)	C12A—H12A	0.9500
C3—C4	1.324 (7)	C12B—H12B	0.9500
C4—C5	1.499 (7)	C14—H14A	0.9800
C7A—C12A	1.389 (15)	C14—H14B	0.9800
C7A—C8A	1.392 (14)	C14—H14C	0.9800
C7B—C8B	1.390 (9)	C16—H16	0.9500
C7B—C12B	1.390 (8)	C17—H17	0.9500
C8A—C9A	1.389 (13)	C19—H19	0.9500
C8B—C9B	1.390 (9)	C20—H20	0.9500
C9A—C10A	1.390 (15)	C23—H23B	0.9800
C9B—C10B	1.390 (9)	C23—H23C	0.9800
C10A—C11A	1.390 (15)	C23—H23A	0.9800
C10B—C11B	1.391 (9)	C24—H24	0.9500
C11A—C12A	1.389 (14)	C26—H26B	0.9800
C11B—C12B	1.388 (9)	C26—H26C	0.9800
C13—C15	1.482 (7)	C26—H26A	0.9800

C4—S1—C6	90.8 (2)	O4—C22—O5	125.4 (5)
C1—O1—C2	116.7 (4)	C21—C24—C25	122.6 (4)
C22—O5—C23	116.4 (4)	O6—C25—O7	121.6 (5)
C25—O7—C26	115.2 (4)	O6—C25—C24	125.7 (5)
C5—N1—C6	115.3 (4)	O7—C25—C24	112.7 (4)
C5—N1—C7B	122.1 (4)	O1—C1—H1A	109.00
C5—N1—C7A	122.0 (5)	O1—C1—H1B	109.00
C6—N1—C7B	122.6 (4)	O1—C1—H1C	109.00
C6—N1—C7A	122.5 (5)	H1A—C1—H1B	109.00
N3—N2—C6	110.8 (4)	H1A—C1—H1C	110.00
N2—N3—C13	115.0 (4)	H1B—C1—H1C	109.00
C18—N4—C21	129.2 (4)	C2—C3—H3	118.00
C21—N4—H4	115.00	C4—C3—H3	118.00
C18—N4—H4	115.00	C7A—C8A—H8A	120.00
O1—C2—C3	111.6 (4)	C9A—C8A—H8A	120.00
O2—C2—C3	124.8 (5)	C9B—C8B—H8B	120.00
O1—C2—O2	123.6 (4)	C7B—C8B—H8B	120.00
C2—C3—C4	123.5 (5)	C10A—C9A—H9A	120.00
S1—C4—C5	111.1 (4)	C8A—C9A—H9A	120.00
S1—C4—C3	128.6 (4)	C8B—C9B—H9B	120.00
C3—C4—C5	120.2 (5)	C10B—C9B—H9B	120.00
N1—C5—C4	110.5 (4)	C11A—C10A—H10A	120.00
O3—C5—C4	125.3 (5)	C9A—C10A—H10A	120.00
O3—C5—N1	124.2 (4)	C11B—C10B—H10B	120.00
S1—C6—N1	112.3 (4)	C9B—C10B—H10B	120.00
S1—C6—N2	125.8 (4)	C10A—C11A—H11A	120.00
N1—C6—N2	121.8 (4)	C12A—C11A—H11A	120.00
N1—C7A—C8A	121.2 (8)	C10B—C11B—H11B	120.00
C8A—C7A—C12A	119.9 (8)	C12B—C11B—H11B	120.00
N1—C7A—C12A	118.8 (8)	C7A—C12A—H12A	120.00
N1—C7B—C12B	119.3 (5)	C11A—C12A—H12A	120.00
C8B—C7B—C12B	120.0 (5)	C11B—C12B—H12B	120.00
N1—C7B—C8B	120.7 (5)	C7B—C12B—H12B	120.00
C7A—C8A—C9A	120.0 (10)	C13—C14—H14A	110.00
C7B—C8B—C9B	119.9 (6)	C13—C14—H14C	109.00
C8A—C9A—C10A	120.0 (9)	H14A—C14—H14B	109.00
C8B—C9B—C10B	120.0 (6)	C13—C14—H14B	110.00
C9A—C10A—C11A	119.9 (8)	H14B—C14—H14C	109.00
C9B—C10B—C11B	120.0 (5)	H14A—C14—H14C	109.00
C10A—C11A—C12A	120.1 (10)	C15—C16—H16	119.00
C10B—C11B—C12B	120.0 (5)	C17—C16—H16	119.00
C7A—C12A—C11A	120.0 (9)	C18—C17—H17	120.00
C7B—C12B—C11B	120.0 (6)	C16—C17—H17	120.00
N3—C13—C15	116.3 (4)	C18—C19—H19	120.00
C14—C13—C15	118.9 (4)	C20—C19—H19	120.00
N3—C13—C14	124.7 (4)	C15—C20—H20	119.00
C13—C15—C20	120.5 (4)	C19—C20—H20	119.00
C13—C15—C16	121.7 (4)	O5—C23—H23B	110.00
C16—C15—C20	117.7 (4)	O5—C23—H23C	110.00
C15—C16—C17	121.4 (4)	H23A—C23—H23C	109.00
C16—C17—C18	120.4 (4)	H23B—C23—H23C	110.00
C17—C18—C19	118.6 (4)	H23A—C23—H23B	109.00
N4—C18—C17	118.0 (4)	O5—C23—H23A	109.00
N4—C18—C19	123.3 (4)	C25—C24—H24	119.00
C18—C19—C20	120.8 (4)	C21—C24—H24	119.00
C15—C20—C19	121.1 (4)	O7—C26—H26C	109.00
N4—C21—C24	122.7 (4)	O7—C26—H26B	109.00
N4—C21—C22	120.2 (4)	H26B—C26—H26C	109.00
C22—C21—C24	116.8 (4)	H26A—C26—H26B	109.00
O5—C22—C21	110.0 (4)	H26A—C26—H26C	109.00
O4—C22—C21	124.6 (4)	O7—C26—H26A	110.00

C6—S1—C4—C3	178.8 (5)	S1—C4—C5—O3	−177.2 (5)
C6—S1—C4—C5	−0.7 (4)	C3—C4—C5—N1	−178.3 (5)
C4—S1—C6—N1	0.0 (4)	C3—C4—C5—O3	3.2 (8)
C4—S1—C6—N2	179.2 (5)	S1—C4—C5—N1	1.3 (5)
C1—O1—C2—C3	−178.6 (5)	N1—C7B—C12B—C11B	178.3 (5)
C1—O1—C2—O2	1.0 (8)	N1—C7B—C8B—C9B	−178.3 (6)
C23—O5—C22—C21	−174.0 (4)	C8B—C7B—C12B—C11B	−0.1 (10)
C23—O5—C22—O4	6.1 (7)	C12B—C7B—C8B—C9B	0.2 (10)
C26—O7—C25—C24	175.6 (5)	C7B—C8B—C9B—C10B	−0.2 (10)
C26—O7—C25—O6	−2.6 (7)	C8B—C9B—C10B—C11B	0.1 (10)
C5—N1—C6—N2	−178.4 (5)	C9B—C10B—C11B—C12B	−0.1 (10)
C7B—N1—C5—C4	179.1 (5)	C10B—C11B—C12B—C7B	0.1 (10)
C5—N1—C7B—C12B	−105.5 (7)	N3—C13—C15—C16	163.1 (5)
C6—N1—C5—O3	177.2 (5)	C14—C13—C15—C16	−19.2 (7)
C7B—N1—C5—O3	−2.4 (8)	C14—C13—C15—C20	158.1 (4)
C6—N1—C5—C4	−1.4 (6)	N3—C13—C15—C20	−19.5 (7)
C5—N1—C6—S1	0.8 (6)	C13—C15—C16—C17	179.2 (4)
C5—N1—C7B—C8B	72.9 (7)	C20—C15—C16—C17	1.8 (7)
C6—N1—C7B—C8B	−106.6 (7)	C16—C15—C20—C19	−0.1 (7)
C7B—N1—C6—N2	1.2 (8)	C13—C15—C20—C19	−177.6 (4)
C7B—N1—C6—S1	−179.6 (4)	C15—C16—C17—C18	−0.7 (7)
C6—N1—C7B—C12B	74.9 (7)	C16—C17—C18—C19	−2.0 (7)
N3—N2—C6—N1	−176.3 (4)	C16—C17—C18—N4	−179.5 (4)
N3—N2—C6—S1	4.6 (6)	C17—C18—C19—C20	3.7 (7)
C6—N2—N3—C13	−167.4 (5)	N4—C18—C19—C20	−179.0 (4)
N2—N3—C13—C15	−179.0 (4)	C18—C19—C20—C15	−2.6 (7)
N2—N3—C13—C14	3.5 (7)	C24—C21—C22—O4	61.8 (7)
C18—N4—C21—C24	−175.0 (5)	N4—C21—C22—O5	54.8 (6)
C21—N4—C18—C19	23.3 (8)	C22—C21—C24—C25	172.4 (5)
C18—N4—C21—C22	12.5 (7)	N4—C21—C22—O4	−125.3 (5)
C21—N4—C18—C17	−159.3 (5)	N4—C21—C24—C25	−0.3 (8)
O2—C2—C3—C4	−0.5 (9)	C24—C21—C22—O5	−118.2 (5)
O1—C2—C3—C4	179.1 (5)	C21—C24—C25—O7	178.4 (5)
C2—C3—C4—C5	−176.5 (5)	C21—C24—C25—O6	−3.5 (8)
C2—C3—C4—S1	4.0 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O6	0.88	2.01	2.705 (5)	135
C1—H1B···O4ⁱ	0.98	2.54	3.402 (8)	147
C3—H3···O3ⁱⁱ	0.95	2.37	3.191 (6)	145
C8B—H8B···N2ⁱⁱⁱ	0.95	2.58	3.461 (8)	155
C12B—H12B···O3^iv	0.95	2.31	3.216 (7)	159
C14—H14A···O6^v	0.98	2.50	3.375 (6)	148
C14—H14C···N2	0.98	2.33	2.735 (7)	104

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+3, −z; (iii) x, y+1, z; (iv) x, y−1, z; (v) −x+3/2, y+1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O6	0.88	2.01	2.705 (5)	135
C1—H1B···O4ⁱ	0.98	2.54	3.402 (8)	147
C3—H3···O3ⁱⁱ	0.95	2.37	3.191 (6)	145
C8B—H8B···N2ⁱⁱⁱ	0.95	2.58	3.461 (8)	155
C12B—H12B···O3^iv	0.95	2.31	3.216 (7)	159
C14—H14A···O6^v	0.98	2.50	3.375 (6)	148

Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x+2, −y+3, −z; (iii) x, y+1, z; (iv) x, y−1, z; (v) −x+3/2, y+1/2, −z+1/2.

Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.

References

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Volume 69| Part 12| December 2013| Pages o1844-o1845

doi:10.1107/S1600536813032042

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

Di­methyl (2Z)-2-[4-((1Z)-1-{2-[(2Z,5Z)-5-(2-meth­­oxy-2-oxo­ethyl­­idene)-4-oxo-3-phenyl-1,3-thia­zolidin-2-yl­­idene]hydra­zin-1-yl­­idene}eth­yl)anilino]but-2-ene­dio­ate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Dimethyl (2Z)-2-[4-((1Z)-1-{2-[(2Z,5Z)-5-(2-methoxy-2-oxoethylidene)-4-oxo-3-phenyl-1,3-thiazolidin-2-ylidene]hydrazin-1-ylidene}ethyl)anilino]but-2-enedioate