2-(4-Oxo-3-phenyl-1,3-thia­zolidin-2-yl­idene)propanedi­nitrile

Akkurt, M.; El-Saghier, A.M.M.; Younes, S.H.H.; Horton, P.N.; Albayati, M.R.

doi:10.1107/S1600536813018308

organic compounds

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ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1313

doi:10.1107/S1600536813018308

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2-(4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)propanedinitrile

Mehmet Akkurt,^a Ahmed M. M. El-Saghier,^b Sabry H. H. Younes,^b Peter N. Horton ^c and Mustafa R. Albayati ^d ^*

^aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^bChemistry Department, Faculty of Science, Sohag University, 82524-Sohag, Egypt, ^cSchool of Chemistry, University of Southampton, Highfield, Southampton SO17 1BJ, England, and ^dKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

(Received 1 July 2013; accepted 2 July 2013; online 24 July 2013)

In the title compound, C₁₂H₇N₃OS, the five-membered 1,3-thiazolidine ring is nearly planar [maximum deviation = 0.032 (2) Å] and makes a dihedral angle of 84.14 (9)° with the phenyl ring. In the crystal, molecules are linked by C—H⋯N hydrogen bonds into infinite chains along [-101]. C—H⋯π interactions contribute to the arrangement of the molecules into layers parallel to (101).

Related literature

For the diverse biological applications of thiazolidinone-containing compounds, see, for example: Bouzroura et al. (2010 ); Abhinit et al. (2009 ); Naeem et al. (2009 ); Sharma et al. (2009 ); Mistry & Desai (2004 ); Ramalakshmi et al. (2009 ); Turgut et al. (2007 ). For the synthesis of similar compounds, see: Farhat et al. (2007 ). For similar structures, see: Pomés Hernández et al. (1996 ).

Experimental

Crystal data

C₁₂H₇N₃OS
M_r = 241.28
Monoclinic, C c
a = 16.979 (9) Å
b = 9.407 (5) Å
c = 7.034 (4) Å
β = 103.927 (11)°
V = 1090.5 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.28 mm⁻¹
T = 100 K
0.24 × 0.12 × 0.04 mm

Data collection

Rigaku AFC12 (Right) diffractometer
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012 ) T_min = 0.944, T_max = 1.000
3632 measured reflections
1986 independent reflections
1955 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.061
S = 1.08
1986 reflections
154 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.18 e Å⁻³
Absolute structure: Flack x parameter determined using 718 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons & Flack, 2004 )
Flack parameter: 0.03 (3)

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C7–C12 phenyl ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯N3ⁱ	0.95	2.58	3.479 (4)	157
C8—H8⋯Cg2ⁱⁱ	0.95	2.96	3.610 (3)	127
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrystalClear-SM Expert; data reduction: CrystalClear-SM Expert; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (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

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018308/hg5329sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018308/hg5329Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018308/hg5329Isup3.cml

checkCIF report

Comment top

Compounds containg thiazolidinone ring system have been found to possess a broad spectrum of biological activities (Abhinit et al., 2009). 4-Thiazolidinones is a core structure in various synthetic compounds and an important scaffold known to be associated with several biological activities such as, antitubercular (Naeem et al., 2009), anti bacterial (Sharma et al., 2009), anti-inflammatory (Turgut et al., 2007), anti-mycobacterial (Bouzroura et al., 2010), anti convulsant (Mistry & Desai, 2004), and anti cancer (Ramalakshmi et al., 2009). As such we have synthesized in our lab series of thiazolidinone derivatives and herein we report the crystal structure of the title compound (I).

In (I), (Fig. 1), the five-membered 1,3-thiazolidine ring (S1/N1/C1–C3) is nearly planar with maximum deviations of 0.031 (1) Å for S1 and -0.032 (2) Å for C3. The dihedral angle between the 1,3-thiazolidine ring and phenyl rings (S1/N1/C1–C3 and C7–C12) is 84.14 (9)°. In (I), the C4–C5–N2, C4–C6–N3 and C5–C4–C6 angles are 174.4 (2), 179.4 (2) and 115.80 (18)°, respectively. The N1–C1–C4–C5 and N1–C1–C4–C6 torsion angles are -0.5 (3) and 177.33 (18)°, respectively. The values of the geometric parameters are normal and are comparable to those observed in similar compounds (Pomés Hernández et al., 1996).

In the crystal structure, C—H···N hydrogen bonds (Table 1, Fig. 2) link the molecules to each other into infinite chains along the [-101] direction. The molecules are arranged into layers parallel to (101) through C—H···π interactions between the C(8)H8 atoms and the centroids of the phenyl rings of neighbouring molecules.

Related literature top

For the diverse biological applications of thiazolidinone-containing compounds, see, for example: Bouzroura et al. (2010); Abhinit et al. (2009); Naeem et al. (2009); Sharma et al. (2009); Mistry & Desai (2004); Ramalakshmi et al. (2009); Turgut et al. (2007). For the synthesis of similar compounds, see: Farhat et al. (2007). For similar structures, see: Pomés Hernández et al. (1996).

Experimental top

The title compound has been prepared according to the our reported method (Farhat et al., 2007). Pale brown mono-crystals suitable for X-ray diffractions were grown up by slow evaporation of an ethanol solution of the title compounds at room temperature over 48 h.

Computing details top

Data collection: CrystalClear-SM Expert (Rigaku, 2012); cell refinement: CrystalClear-SM Expert (Rigaku, 2012); data reduction: CrystalClear-SM Expert (Rigaku, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (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. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.
	Fig. 2. A view along the b axis of the packing diagram of (I) showing hydrogen bonds as dashed lines. H atoms not involved in hydrogen bonds have been omitted for clarity.

2-(4-Oxo-3-phenyl-1,3-thiazolidin-2-ylidene)propanedinitrile top

Crystal data top

C₁₂H₇N₃OS	F(000) = 496
M_r = 241.28	D_x = 1.470 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71075 Å
Hall symbol: C -2yc	Cell parameters from 1540 reflections
a = 16.979 (9) Å	θ = 2.5–29.9°
b = 9.407 (5) Å	µ = 0.28 mm⁻¹
c = 7.034 (4) Å	T = 100 K
β = 103.927 (11)°	Blade, pale brown
V = 1090.5 (10) Å³	0.24 × 0.12 × 0.04 mm
Z = 4

Data collection top

Rigaku AFC12 (Right) diffractometer	1986 independent reflections
Radiation source: Rotating Anode	1955 reflections with I > 2σ(I)
Detector resolution: 28.5714 pixels mm^-1	R_int = 0.015
profile data from ω–scans	θ_max = 27.5°, θ_min = 3.7°
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	h = −21→21
T_min = 0.944, T_max = 1.000	k = −12→11
3632 measured reflections	l = −9→9

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.022	W = 1/[Σ²(F_o²) + (0.0377P)² + 0.4177P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.061	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.19 e Å⁻³
1986 reflections	Δρ_min = −0.18 e Å⁻³
154 parameters	Absolute structure: Flack x parameter determined using 718 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
2 restraints	Absolute structure parameter: 0.03 (3)

Crystal data top

C₁₂H₇N₃OS	V = 1090.5 (10) Å³
M_r = 241.28	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 16.979 (9) Å	µ = 0.28 mm⁻¹
b = 9.407 (5) Å	T = 100 K
c = 7.034 (4) Å	0.24 × 0.12 × 0.04 mm
β = 103.927 (11)°

Data collection top

Rigaku AFC12 (Right) diffractometer	1986 independent reflections
Absorption correction: multi-scan (CrystalClear-SM Expert; Rigaku, 2012)	1955 reflections with I > 2σ(I)
T_min = 0.944, T_max = 1.000	R_int = 0.015
3632 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	H-atom parameters constrained
wR(F²) = 0.061	Δρ_max = 0.19 e Å⁻³
S = 1.08	Δρ_min = −0.18 e Å⁻³
1986 reflections	Absolute structure: Flack x parameter determined using 718 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
154 parameters	Absolute structure parameter: 0.03 (3)
2 restraints

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	0.14621 (4)	0.73643 (4)	0.22599 (6)	0.0152 (1)
O1	0.23305 (9)	0.57530 (15)	−0.1843 (2)	0.0179 (4)
N1	0.27769 (10)	0.68589 (17)	0.1115 (2)	0.0120 (4)
N2	0.45449 (12)	0.8278 (2)	0.5329 (3)	0.0210 (6)
N3	0.22781 (12)	0.91044 (19)	0.6832 (3)	0.0209 (5)
C1	0.25143 (14)	0.74325 (18)	0.2647 (3)	0.0122 (5)
C2	0.21787 (12)	0.6278 (2)	−0.0407 (3)	0.0138 (5)
C3	0.13519 (12)	0.6388 (2)	0.0001 (3)	0.0162 (6)
C4	0.29897 (12)	0.8016 (2)	0.4321 (3)	0.0135 (5)
C5	0.38554 (13)	0.8131 (2)	0.4803 (3)	0.0146 (5)
C6	0.25922 (12)	0.8615 (2)	0.5710 (3)	0.0149 (5)
C7	0.36194 (12)	0.6787 (2)	0.1046 (3)	0.0128 (5)
C8	0.40498 (13)	0.5558 (2)	0.1676 (3)	0.0157 (6)
C9	0.48583 (13)	0.5491 (2)	0.1579 (3)	0.0205 (6)
C10	0.52117 (14)	0.6634 (3)	0.0838 (3)	0.0218 (6)
C11	0.47629 (14)	0.7848 (3)	0.0200 (3)	0.0207 (6)
C12	0.39603 (13)	0.7932 (2)	0.0298 (3)	0.0159 (6)
H3A	0.11320	0.54270	0.01290	0.0190*
H3B	0.09750	0.68900	−0.10840	0.0190*
H8	0.38000	0.47790	0.21620	0.0190*
H9	0.51700	0.46640	0.20200	0.0250*
H10	0.57630	0.65810	0.07680	0.0260*
H11	0.50070	0.86240	−0.03050	0.0250*
H12	0.36490	0.87600	−0.01390	0.0190*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0091 (2)	0.0180 (2)	0.0189 (2)	0.0011 (2)	0.0041 (2)	−0.0031 (2)
O1	0.0177 (7)	0.0190 (7)	0.0177 (8)	−0.0020 (6)	0.0058 (6)	−0.0049 (6)
N1	0.0093 (8)	0.0128 (7)	0.0142 (8)	0.0004 (6)	0.0032 (6)	−0.0010 (6)
N2	0.0165 (10)	0.0269 (9)	0.0201 (10)	−0.0019 (8)	0.0055 (8)	−0.0041 (7)
N3	0.0170 (9)	0.0251 (9)	0.0210 (10)	−0.0010 (8)	0.0052 (8)	−0.0074 (8)
C1	0.0116 (9)	0.0108 (8)	0.0149 (10)	0.0013 (7)	0.0044 (8)	0.0018 (7)
C2	0.0126 (9)	0.0115 (8)	0.0166 (9)	0.0007 (7)	0.0024 (8)	0.0016 (7)
C3	0.0117 (10)	0.0203 (9)	0.0157 (10)	−0.0015 (8)	0.0018 (8)	−0.0019 (8)
C4	0.0113 (10)	0.0132 (8)	0.0161 (10)	0.0013 (7)	0.0034 (8)	−0.0010 (7)
C5	0.0159 (11)	0.0142 (8)	0.0143 (9)	−0.0007 (8)	0.0046 (8)	−0.0016 (7)
C6	0.0109 (9)	0.0150 (9)	0.0173 (10)	−0.0017 (8)	0.0002 (8)	−0.0018 (7)
C7	0.0097 (9)	0.0167 (8)	0.0126 (9)	−0.0010 (7)	0.0040 (8)	−0.0034 (7)
C8	0.0158 (10)	0.0183 (9)	0.0136 (10)	0.0013 (8)	0.0046 (8)	−0.0003 (7)
C9	0.0152 (10)	0.0284 (10)	0.0172 (10)	0.0070 (9)	0.0026 (8)	−0.0017 (8)
C10	0.0108 (9)	0.0389 (12)	0.0162 (10)	0.0003 (9)	0.0044 (8)	−0.0052 (9)
C11	0.0158 (11)	0.0299 (11)	0.0175 (11)	−0.0080 (9)	0.0064 (9)	−0.0001 (9)
C12	0.0141 (10)	0.0176 (9)	0.0145 (10)	−0.0015 (8)	0.0008 (9)	0.0005 (7)

Geometric parameters (Å, º) top

S1—C1	1.742 (3)	C7—C12	1.385 (3)
S1—C3	1.806 (2)	C8—C9	1.392 (3)
O1—C2	1.207 (3)	C9—C10	1.392 (3)
N1—C1	1.372 (3)	C10—C11	1.386 (4)
N1—C2	1.398 (3)	C11—C12	1.383 (3)
N1—C7	1.445 (3)	C3—H3A	0.9900
N2—C5	1.148 (3)	C3—H3B	0.9900
N3—C6	1.150 (3)	C8—H8	0.9500
C1—C4	1.372 (3)	C9—H9	0.9500
C2—C3	1.503 (3)	C10—H10	0.9500
C4—C5	1.431 (3)	C11—H11	0.9500
C4—C6	1.430 (3)	C12—H12	0.9500
C7—C8	1.382 (3)

C1—S1—C3	92.38 (10)	C8—C9—C10	120.15 (19)
C1—N1—C2	116.22 (18)	C9—C10—C11	120.3 (2)
C1—N1—C7	123.81 (17)	C10—C11—C12	120.2 (2)
C2—N1—C7	119.93 (16)	C7—C12—C11	118.8 (2)
S1—C1—N1	112.19 (15)	S1—C3—H3A	110.00
S1—C1—C4	121.22 (17)	S1—C3—H3B	110.00
N1—C1—C4	126.6 (2)	C2—C3—H3A	110.00
O1—C2—N1	122.62 (19)	C2—C3—H3B	110.00
O1—C2—C3	125.85 (19)	H3A—C3—H3B	109.00
N1—C2—C3	111.53 (17)	C7—C8—H8	121.00
S1—C3—C2	107.42 (14)	C9—C8—H8	121.00
C1—C4—C5	126.3 (2)	C8—C9—H9	120.00
C1—C4—C6	117.9 (2)	C10—C9—H9	120.00
C5—C4—C6	115.80 (18)	C9—C10—H10	120.00
N2—C5—C4	174.4 (2)	C11—C10—H10	120.00
N3—C6—C4	179.4 (2)	C10—C11—H11	120.00
N1—C7—C8	118.67 (18)	C12—C11—H11	120.00
N1—C7—C12	118.95 (18)	C7—C12—H12	121.00
C8—C7—C12	122.4 (2)	C11—C12—H12	121.00
C7—C8—C9	118.27 (18)

C3—S1—C1—N1	4.42 (14)	N1—C1—C4—C5	−0.5 (3)
C3—S1—C1—C4	−175.95 (16)	S1—C1—C4—C6	−2.2 (3)
C1—S1—C3—C2	−4.78 (14)	S1—C1—C4—C5	179.94 (15)
C7—N1—C1—S1	179.56 (14)	N1—C1—C4—C6	177.33 (18)
C2—N1—C1—C4	177.70 (18)	N1—C2—C3—S1	4.19 (19)
C7—N1—C1—C4	0.0 (3)	O1—C2—C3—S1	−176.30 (17)
C7—N1—C2—C3	176.70 (16)	N1—C7—C8—C9	179.13 (17)
C1—N1—C2—O1	179.35 (18)	C12—C7—C8—C9	1.1 (3)
C7—N1—C2—O1	−2.8 (3)	N1—C7—C12—C11	−178.78 (18)
C2—N1—C1—S1	−2.7 (2)	C8—C7—C12—C11	−0.8 (3)
C2—N1—C7—C12	94.9 (2)	C7—C8—C9—C10	−0.9 (3)
C1—N1—C7—C8	94.5 (2)	C8—C9—C10—C11	0.3 (3)
C1—N1—C2—C3	−1.1 (2)	C9—C10—C11—C12	0.1 (3)
C1—N1—C7—C12	−87.5 (2)	C10—C11—C12—C7	0.2 (3)
C2—N1—C7—C8	−83.2 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N3ⁱ	0.95	2.58	3.479 (4)	157
C8—H8···Cg2ⁱⁱ	0.95	2.96	3.610 (3)	127

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

Experimental details

Crystal data
Chemical formula	C₁₂H₇N₃OS
M_r	241.28
Crystal system, space group	Monoclinic, Cc
Temperature (K)	100
a, b, c (Å)	16.979 (9), 9.407 (5), 7.034 (4)
β (°)	103.927 (11)
V (Å³)	1090.5 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.28
Crystal size (mm)	0.24 × 0.12 × 0.04

Data collection
Diffractometer	Rigaku AFC12 (Right) diffractometer
Absorption correction	Multi-scan (CrystalClear-SM Expert; Rigaku, 2012)
T_min, T_max	0.944, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	3632, 1986, 1955
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.061, 1.08
No. of reflections	1986
No. of parameters	154
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18
Absolute structure	Flack x parameter determined using 718 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004)
Absolute structure parameter	0.03 (3)

Computer programs: CrystalClear-SM Expert (Rigaku, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 is the centroid of the C7–C12 phenyl ring.

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···N3ⁱ	0.95	2.58	3.479 (4)	157
C8—H8···Cg2ⁱⁱ	0.95	2.96	3.610 (3)	127

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

Acknowledgements

Manchester Metropolitan University, Erciyes University and Sohag University are gratefully acknowledged for supporting this study.

References

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Volume 69| Part 8| August 2013| Page o1313

doi:10.1107/S1600536813018308

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