(Z)-3-Allyl-5-(3-meth­oxy­benzyl­idene)-2-sulfanyl­idene-1,3-thia­zolidin-4-one

El Ajlaoui, R.; Rakib, E.M.; Mojahidi, S.; Saadi, M.; El Ammari, L.

doi:10.1107/S2414314616000523

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 1| January 2016| x160052

doi:10.1107/S2414314616000523

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(Z)-3-Allyl-5-(3-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one

Rahhal El Ajlaoui,^a ^* El Mostapha Rakib,^a Souad Mojahidi,^a Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V de Rabat, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: r_elajlaoui@yahoo.fr

Edited by H. Ishida, Okayama University, Japan (Received 24 December 2015; accepted 11 January 2016; online 16 January 2016)

In the title compound, C₁₄H₁₃NO₂S₂, the rhodanine ring and the 3-methoxybenzylidene ring are nearly coplanar, as indicated by the dihedral angle of 1.77 (6)° between their planes. The allyl group is nearly perpendicular to the rhodanine ring, with a dihedral angle of 83.64 (19)°. An intramolecular C—H⋯S interaction forms an S(6) ring motif. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds into inversion dimers.

Keywords: crystal structure; rhodanine-based molecule; hydrogen bonds.

CCDC reference: 1446566

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Chemical scheme

Structure description

Compounds containing 2-thioxothiazolidin-4-one (rhodanine) and its derivatives have been reported to exhibit a broad spectrum of biological activities, acting as antidiabetic, anticancer, antitubercular, anti-HIV and antiparasitic agents (Murugan et al., 2009 ; Chandrappa et al., 2009 ; Mallikarjuna et al., 2009 ; Murugesan et al., 2011 ; Zhang et al., 2009 ). The unusual biological activity displayed by many rhodanine-based molecules has made them attractive synthetic targets.

The molecule of the title compound is build up from a rhodanine ring (S1/N1/C8–C10) linked to an allyl group (C11–C13) at the nitrogen atom and to a 3-methoxybenzylidene ring (C1–C6) as shown in Fig. 1. In the crystal, molecules are linked by pairs of C—H⋯O hydrogen bonds (Table 1), forming an inversion dimer as shown in Fig. 2.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯S1	0.93	2.55	3.2497 (17)	133
C13—H13A⋯O2ⁱ	0.93	2.57	3.441 (2)	157
Symmetry code: (i) -x+1, -y+2, -z+1.

Figure 1
The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

Figure 2
A crystal packing diagram of the title compound, showing the hydrogen bonds as dashed lines.

Synthesis and crystallization

To a solution of 3-allylrhodanine (1.15 mmol, 0.2 g) in 10 ml of THF, (3-methoxybenzylidene)-4-methyl-5-oxopyrazolidin-2-ium-1-ide (1.38 mmol) was added. The mixture was refluxed for 8 h until the reaction was completed (TLC) and a yellow spot (TLC R_f = 0.3, using hexane/ethyl acetate 1:9) was generated cleanly. The solvent was evaporated in vacuo. The crude product was purified on silica gel using hexane/ethyl acetate (1:9) as eluent. The title compound was recrystallized from ethanol (yield 78%, m.p. 364 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The reflection (0 0 1) was affected by the beam-stop and was removed during refinement.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂S₂
M_r	291.37
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	6.9841 (14), 8.3241 (18), 13.116 (3)
α, β, γ (°)	89.276 (9), 75.614 (9), 72.095 (10)
V (Å³)	701.2 (3)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.38
Crystal size (mm)	0.31 × 0.27 × 0.21

Data collection
Diffractometer	Bruker X8 APEX diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009 )
T_min, T_max	0.479, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	28065, 4522, 3618
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.729

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.02
No. of reflections	4522
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS2014 (Sheldrick, 2008 ), SHELXL2014 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 1446566

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616000523/is4001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616000523/is4001Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616000523/is4001Isup3.cml

checkCIF report

Comment top

Compounds containing 2-thioxothiazolidin-4-one (rhodanine) and its derivatives have been reported to exhibit a broad spectrum of biological activities, such as antidiabetic, anticancer, antitubercular, anti-HIV and antiparasitic agents (Murugan et al., 2009; Chandrappa et al., 2009; Mallikarjuna et al., 2009; Murugesan et al., 2011; Zhang et al., 2009). The unusual biological activity displayed by many rhodanine-based molecules has made them attractive synthetic targets.

The molecule of the title compound is build up from a rhodanine ring (S1/N1/C8–C10) linked to an allyl group (C11–C13) at the nitrogen atom and to a 3-methoxybenzylidene ring (C1–C6) as shown in Fig. 1. In the crystal, molecules are linked by a pair of C—H···O hydrogen bonds (Table 2), forming an inversion dimer as shown in Fig. 2.

Experimental top

To a solution of 3-allylrhodanine (1.15 mmol, 0.2 g) in 10 ml of THF, (3-methoxybenzylidene)-4-methyl-5-oxopyrazolidin-2-ium-1-ide (1.38 mmol) was added. The mixture was refluxed for 8 h, monitored by TLC, the reaction completed and a yellow spot (TLC R_f = 0.3, using hexane/ethyl acetate 1:9) was generated cleanly. The solvent was evaporated in vacuo. The crude product was purified on silica gel using hexane/ethyl acetate (1:9) as eluent. The title compound was recrystallized from ethanol (yield 78%, m.p. 364 K).

Structure description top

Compounds containing 2-thioxothiazolidin-4-one (rhodanine) and its derivatives have been reported to exhibit a broad spectrum of biological activities, acting as antidiabetic, anticancer, antitubercular, anti-HIV and antiparasitic agents (Murugan et al., 2009; Chandrappa et al., 2009; Mallikarjuna et al., 2009; Murugesan et al., 2011; Zhang et al., 2009). The unusual biological activity displayed by many rhodanine-based molecules has made them attractive synthetic targets.

The molecule of the title compound is build up from a rhodanine ring (S1/N1/C8–C10) linked to an allyl group (C11–C13) at the nitrogen atom and to a 3-methoxybenzylidene ring (C1–C6) as shown in Fig. 1. In the crystal, molecules are linked by pairs of C—H···O hydrogen bonds (Table 1), forming an inversion dimer as shown in Fig. 2.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.
	Fig. 2. A crystal packing diagram of the title compound, showing the hydrogen bonds as dashed lines.

(Z)-3-Allyl-5-(3-methoxybenzylidene)-2-sulfanylidene-1,3-thiazolidin-4-one top

Crystal data top

C₁₄H₁₃NO₂S₂	F(000) = 304
M_r = 291.37	D_x = 1.380 Mg m⁻³
Triclinic, P1	Melting point: 364 K
a = 6.9841 (14) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.3241 (18) Å	Cell parameters from 4522 reflections
c = 13.116 (3) Å	θ = 2.6–31.2°
α = 89.276 (9)°	µ = 0.38 mm⁻¹
β = 75.614 (9)°	T = 296 K
γ = 72.095 (10)°	Block, colourless
V = 701.2 (3) Å³	0.31 × 0.27 × 0.21 mm
Z = 2

Data collection top

Bruker X8 APEX diffractometer	4522 independent reflections
Radiation source: fine-focus sealed tube	3618 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
φ and ω scans	θ_max = 31.2°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→10
T_min = 0.479, T_max = 0.746	k = −12→12
28065 measured reflections	l = −19→19

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H-atom parameters constrained
wR(F²) = 0.117	w = 1/[σ²(F_o²) + (0.0624P)² + 0.1273P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
4522 reflections	Δρ_max = 0.30 e Å⁻³
172 parameters	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₄H₁₃NO₂S₂	γ = 72.095 (10)°
M_r = 291.37	V = 701.2 (3) Å³
Triclinic, P1	Z = 2
a = 6.9841 (14) Å	Mo Kα radiation
b = 8.3241 (18) Å	µ = 0.38 mm⁻¹
c = 13.116 (3) Å	T = 296 K
α = 89.276 (9)°	0.31 × 0.27 × 0.21 mm
β = 75.614 (9)°

Data collection top

Bruker X8 APEX diffractometer	4522 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	3618 reflections with I > 2σ(I)
T_min = 0.479, T_max = 0.746	R_int = 0.029
28065 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
4522 reflections	Δρ_min = −0.26 e Å⁻³
172 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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

	x	y	z	U_iso*/U_eq
C1	0.6784 (2)	0.92899 (16)	0.26792 (11)	0.0453 (3)
C2	0.8814 (2)	0.88347 (19)	0.27837 (12)	0.0528 (3)
H2	0.9846	0.9093	0.2274	0.063*
C3	0.9283 (2)	0.8002 (2)	0.36440 (12)	0.0555 (3)
H3	1.0641	0.7700	0.3711	0.067*
C4	0.7776 (2)	0.76011 (19)	0.44141 (11)	0.0512 (3)
H4	0.8122	0.7042	0.4993	0.061*
C5	0.57287 (19)	0.80427 (16)	0.43169 (10)	0.0410 (2)
C6	0.52494 (19)	0.88990 (16)	0.34378 (10)	0.0418 (3)
H6	0.3895	0.9205	0.3365	0.050*
C7	0.40267 (19)	0.76903 (16)	0.50824 (10)	0.0431 (3)
H7	0.2737	0.8106	0.4932	0.052*
C8	0.40122 (19)	0.68638 (16)	0.59698 (10)	0.0408 (2)
C9	0.2049 (2)	0.66565 (17)	0.66206 (10)	0.0450 (3)
C10	0.4403 (2)	0.52824 (16)	0.76057 (10)	0.0434 (3)
C11	0.0714 (2)	0.53236 (19)	0.82335 (12)	0.0520 (3)
H11A	0.1286	0.4223	0.8486	0.062*
H11B	−0.0273	0.5227	0.7851	0.062*
C12	−0.0422 (2)	0.65574 (19)	0.91596 (12)	0.0533 (3)
H12	−0.1612	0.6390	0.9590	0.064*
C13	0.0068 (3)	0.7842 (2)	0.94329 (14)	0.0677 (4)
H13A	0.1244	0.8067	0.9030	0.081*
H13B	−0.0757	0.8538	1.0031	0.081*
C14	0.4469 (3)	1.0541 (2)	0.16012 (13)	0.0616 (4)
H14A	0.4481	1.1117	0.0962	0.092*
H14B	0.4124	0.9525	0.1529	0.092*
H14C	0.3452	1.1265	0.2178	0.092*
N1	0.24062 (17)	0.57615 (14)	0.75017 (9)	0.0435 (2)
O1	0.03559 (17)	0.71622 (17)	0.64424 (9)	0.0660 (3)
O2	0.64706 (17)	1.01213 (16)	0.18002 (9)	0.0643 (3)
S1	0.60384 (5)	0.59150 (4)	0.65517 (3)	0.04671 (11)
S2	0.52699 (7)	0.42768 (6)	0.85588 (3)	0.06213 (13)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0380 (6)	0.0469 (6)	0.0453 (6)	−0.0068 (5)	−0.0083 (5)	−0.0009 (5)
C2	0.0346 (6)	0.0607 (8)	0.0560 (8)	−0.0105 (5)	−0.0042 (5)	−0.0015 (6)
C3	0.0317 (6)	0.0695 (9)	0.0612 (9)	−0.0085 (6)	−0.0135 (6)	−0.0020 (7)
C4	0.0391 (6)	0.0636 (8)	0.0488 (7)	−0.0090 (6)	−0.0162 (5)	0.0004 (6)
C5	0.0352 (5)	0.0458 (6)	0.0395 (6)	−0.0076 (4)	−0.0110 (4)	−0.0062 (5)
C6	0.0332 (5)	0.0470 (6)	0.0422 (6)	−0.0077 (4)	−0.0100 (4)	−0.0035 (5)
C7	0.0354 (5)	0.0534 (7)	0.0409 (6)	−0.0113 (5)	−0.0135 (5)	−0.0028 (5)
C8	0.0349 (5)	0.0488 (6)	0.0392 (6)	−0.0105 (5)	−0.0132 (4)	−0.0048 (5)
C9	0.0406 (6)	0.0549 (7)	0.0441 (6)	−0.0171 (5)	−0.0166 (5)	0.0017 (5)
C10	0.0416 (6)	0.0445 (6)	0.0449 (6)	−0.0107 (5)	−0.0161 (5)	−0.0023 (5)
C11	0.0508 (7)	0.0571 (8)	0.0593 (8)	−0.0288 (6)	−0.0195 (6)	0.0116 (6)
C12	0.0428 (7)	0.0607 (8)	0.0539 (8)	−0.0159 (6)	−0.0095 (6)	0.0197 (6)
C13	0.0682 (10)	0.0646 (9)	0.0590 (9)	−0.0200 (8)	0.0030 (8)	−0.0032 (7)
C14	0.0578 (9)	0.0692 (9)	0.0569 (9)	−0.0132 (7)	−0.0219 (7)	0.0129 (7)
N1	0.0412 (5)	0.0495 (6)	0.0440 (5)	−0.0169 (4)	−0.0150 (4)	0.0016 (4)
O1	0.0423 (5)	0.0990 (9)	0.0671 (7)	−0.0278 (5)	−0.0264 (5)	0.0233 (6)
O2	0.0462 (6)	0.0820 (8)	0.0585 (6)	−0.0147 (5)	−0.0103 (5)	0.0227 (6)
S1	0.03460 (15)	0.0597 (2)	0.04389 (18)	−0.00911 (13)	−0.01372 (12)	0.00062 (13)
S2	0.0570 (2)	0.0726 (3)	0.0594 (2)	−0.01587 (19)	−0.02600 (18)	0.01825 (18)

Geometric parameters (Å, º) top

C1—O2	1.3668 (17)	C9—N1	1.4001 (17)
C1—C6	1.3860 (18)	C10—N1	1.3685 (17)
C1—C2	1.3920 (19)	C10—S2	1.6335 (14)
C2—C3	1.373 (2)	C10—S1	1.7494 (14)
C2—H2	0.9300	C11—N1	1.4639 (17)
C3—C4	1.385 (2)	C11—C12	1.487 (2)
C3—H3	0.9300	C11—H11A	0.9700
C4—C5	1.4008 (18)	C11—H11B	0.9700
C4—H4	0.9300	C12—C13	1.298 (2)
C5—C6	1.4050 (18)	C12—H12	0.9300
C5—C7	1.4564 (18)	C13—H13A	0.9300
C6—H6	0.9300	C13—H13B	0.9300
C7—C8	1.3441 (19)	C14—O2	1.422 (2)
C7—H7	0.9300	C14—H14A	0.9600
C8—C9	1.4827 (18)	C14—H14B	0.9600
C8—S1	1.7445 (13)	C14—H14C	0.9600
C9—O1	1.2079 (16)

O2—C1—C6	124.67 (12)	N1—C10—S2	127.52 (11)
O2—C1—C2	115.21 (13)	N1—C10—S1	110.74 (10)
C6—C1—C2	120.12 (13)	S2—C10—S1	121.74 (8)
C3—C2—C1	119.57 (13)	N1—C11—C12	114.59 (11)
C3—C2—H2	120.2	N1—C11—H11A	108.6
C1—C2—H2	120.2	C12—C11—H11A	108.6
C2—C3—C4	121.39 (13)	N1—C11—H11B	108.6
C2—C3—H3	119.3	C12—C11—H11B	108.6
C4—C3—H3	119.3	H11A—C11—H11B	107.6
C3—C4—C5	119.69 (14)	C13—C12—C11	127.06 (14)
C3—C4—H4	120.2	C13—C12—H12	116.5
C5—C4—H4	120.2	C11—C12—H12	116.5
C4—C5—C6	118.87 (12)	C12—C13—H13A	120.0
C4—C5—C7	124.13 (12)	C12—C13—H13B	120.0
C6—C5—C7	117.00 (11)	H13A—C13—H13B	120.0
C1—C6—C5	120.35 (12)	O2—C14—H14A	109.5
C1—C6—H6	119.8	O2—C14—H14B	109.5
C5—C6—H6	119.8	H14A—C14—H14B	109.5
C8—C7—C5	130.67 (12)	O2—C14—H14C	109.5
C8—C7—H7	114.7	H14A—C14—H14C	109.5
C5—C7—H7	114.7	H14B—C14—H14C	109.5
C7—C8—C9	120.39 (11)	C10—N1—C9	116.48 (11)
C7—C8—S1	130.08 (10)	C10—N1—C11	123.16 (12)
C9—C8—S1	109.53 (9)	C9—N1—C11	120.32 (11)
O1—C9—N1	123.01 (13)	C1—O2—C14	118.75 (12)
O1—C9—C8	126.62 (13)	C8—S1—C10	92.87 (6)
N1—C9—C8	110.37 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···S1	0.93	2.55	3.2497 (17)	133
C13—H13A···O2ⁱ	0.93	2.57	3.441 (2)	157

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
C4—H4···S1	0.93	2.55	3.2497 (17)	133
C13—H13A···O2ⁱ	0.93	2.57	3.441 (2)	157

Symmetry code: (i) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃NO₂S₂
M_r	291.37
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	6.9841 (14), 8.3241 (18), 13.116 (3)
α, β, γ (°)	89.276 (9), 75.614 (9), 72.095 (10)
V (Å³)	701.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.38
Crystal size (mm)	0.31 × 0.27 × 0.21

Data collection
Diffractometer	Bruker X8 APEX
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.479, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	28065, 4522, 3618
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.729

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.117, 1.02
No. of reflections	4522
No. of parameters	172
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.26

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS2014 (Sheldrick, 2008), SHELXL2014 (Sheldrick, 2015), ORTEP-3 for Windows (Farrugia, 2012), publCIF (Westrip, 2010).

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements and the University Sultan Moulay Slimane, Beni-Mellal, Morocco, for financial support.

References

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