(5Z)-5-(4-Chloro­benzyl­idene)-1,3-thia­zolidine-2,4-dione

Mohamed, S.K.; Mague, J.T.; Akkurt, M.; Younes, S.H.H.; Albayati, M.R.

doi:10.1107/S2414314616009883

organic compounds

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ISSN: 2414-3146

Volume 1| Part 6| June 2016| x160988

doi:10.1107/S2414314616009883

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(5Z)-5-(4-Chlorobenzylidene)-1,3-thiazolidine-2,4-dione

Shaaban K. Mohamed,^a,^b Joel T. Mague,^c Mehmet Akkurt,^d Sabry H. H. Younes ^e and Mustafa R. Albayati ^f ^*

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, ^cDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, ^dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^eChemistry Department, Faculty of Science, Sohag University, 82524 Sohag, Egypt, and ^fKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
^*Correspondence e-mail: shaabankamel@yahoo.com

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 16 June 2016; accepted 17 June 2016; online 24 June 2016)

In the title compound, C₁₀H₆ClNO₂S, the dihedral angle between the planes of the 4-chlorophenyl and thiazolidine rings is 8.62 (9)°. In the crystal, molecules form undulating ribbons running approximately parallel to (101) through N—H⋯O hydrogen bonds.

Keywords: crystal structure; 4-chlorophenyl ring; thiazolidine ring.

CCDC reference: 1486205

Structure description

Thiazolidinedione scaffold compounds (TDZs), known as glitazones, are a class of medications used in the treatment of diabetes mellitus type 2. TZDs are an important heterocyclic ring system and have therapeutic importance when combined with other heterocyclic rings, as they can produce a wide range of biological activities, such as anti-inflammatory (Barros et al., 2008 ), antitubercular (Pattan et al., 2008 ), antimicrobial (Oya et al., 2007 ) and cytotoxic (Shankar & Kallanagouda, 2012 ). In this context, we report here the synthesis and crystal structure of the title compound (Fig. 1).

Figure 1
The title molecule, showing the atom labelling scheme and 50% probability ellipsoids.

The dihedral angle between the 4-chlorophenyl and thiazolidine rings is 8.62 (9)°. The molecules form undulating ribbons running approximately parallel to (101) through N1—H1⋯O2ⁱ hydrogen bonds (Table 1 and Fig. 2).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.91	1.87	2.782 (2)	175
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Packing viewed along the a axis, with N—H⋯O hydrogen bonds shown as dotted lines.

Synthesis and crystallization

The title compound was obtained from a three components reaction between 2 mmol (234 mg) of thiazolidin-2,4-dione, 1 mmol (147.6 mg) of 4-chlorobenzaldehyde and 1 mmol (61 mg) of 2-aminoethanol in 30 ml ethanol. The reaction mixture was refluxed and monitored by TLC until completion. The resulting solid product was collected by filtration, dried under vacuum and recrystallized from ethanol to afford suitable quality crystals for X-ray diffraction.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₀H₆ClNO₂S
M_r	239.67
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	150
a, b, c (Å)	3.9098 (1), 40.7555 (15), 6.0917 (2)
β (°)	93.748 (1)
V (Å³)	968.61 (5)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	5.33
Crystal size (mm)	0.36 × 0.13 × 0.10

Data collection
Diffractometer	Bruker D8 VENTURE PHOTON 100 CMOS
Absorption correction	Multi-scan (SADABS; Bruker, 2015 )
T_min, T_max	0.46, 0.63
No. of measured, independent and observed [I > 2σ(I)] reflections	12027, 1885, 1815
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.088, 1.14
No. of reflections	1885
No. of parameters	136
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.37
Computer programs: APEX2 and SAINT (Bruker, 2015), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ), DIAMOND (Brandenburg & Putz, 2012 ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1486205

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2414314616009883/xu4009sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616009883/xu4009Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616009883/xu4009Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2015); cell refinement: SAINT (Bruker, 2015); data reduction: SAINT (Bruker, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

(5Z)-5-(4-Chlorobenzylidene)-1,3-thiazolidine-2,4-dione top

Crystal data top

C₁₀H₆ClNO₂S	F(000) = 488
M_r = 239.67	D_x = 1.643 Mg m⁻³
Monoclinic, P2₁/n	Cu Kα radiation, λ = 1.54178 Å
a = 3.9098 (1) Å	Cell parameters from 9969 reflections
b = 40.7555 (15) Å	θ = 3.3–72.2°
c = 6.0917 (2) Å	µ = 5.33 mm⁻¹
β = 93.748 (1)°	T = 150 K
V = 968.61 (5) Å³	Column, colourless
Z = 4	0.36 × 0.13 × 0.10 mm

Data collection top

Bruker D8 VENTURE PHOTON 100 CMOS diffractometer	1885 independent reflections
Radiation source: INCOATEC IµS micro–focus source	1815 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.034
Detector resolution: 10.4167 pixels mm^-1	θ_max = 72.2°, θ_min = 2.2°
ω scans	h = −4→4
Absorption correction: multi-scan (SADABS; Bruker, 2015)	k = −50→50
T_min = 0.46, T_max = 0.63	l = −7→7
12027 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0399P)² + 0.7319P] where P = (F_o² + 2F_c²)/3
1885 reflections	(Δ/σ)_max = 0.001
136 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Special details top

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

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) 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. H-atoms attached to carbon were placed in calculated positions (C—H = 0.95 Å) while that attached to nitrogen was placed in a location derived from a difference map and its coordinates adjusted to give N—H = 0.91 Å. All were included as riding contributions with isotropic displacement parameters 1.2 times those of the attached atoms.

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

	x	y	z	U_iso*/U_eq
Cl1	0.10718 (14)	0.47151 (2)	0.79460 (8)	0.03023 (16)
S1	0.42007 (12)	0.31099 (2)	0.30938 (7)	0.02236 (15)
O1	0.8931 (4)	0.33869 (3)	−0.1933 (2)	0.0282 (3)
O2	0.4488 (4)	0.25053 (3)	0.1464 (2)	0.0336 (4)
N1	0.6783 (4)	0.29170 (4)	−0.0508 (3)	0.0234 (4)
H1	0.7546	0.2778	−0.1536	0.028*
C1	0.4756 (5)	0.39611 (4)	0.3194 (3)	0.0199 (4)
C2	0.5011 (5)	0.42973 (5)	0.2761 (3)	0.0226 (4)
H2	0.5989	0.4367	0.1453	0.027*
C3	0.3868 (5)	0.45301 (5)	0.4197 (3)	0.0240 (4)
H3	0.4029	0.4758	0.3877	0.029*
C4	0.2489 (5)	0.44247 (5)	0.6107 (3)	0.0227 (4)
C5	0.2193 (5)	0.40946 (5)	0.6594 (3)	0.0231 (4)
H5	0.1236	0.4027	0.7916	0.028*
C6	0.3308 (5)	0.38626 (5)	0.5133 (3)	0.0219 (4)
H6	0.3088	0.3636	0.5450	0.026*
C7	0.6023 (5)	0.37354 (5)	0.1576 (3)	0.0210 (4)
H7	0.7114	0.3841	0.0420	0.025*
C8	0.5946 (5)	0.34092 (4)	0.1405 (3)	0.0197 (4)
C9	0.7404 (5)	0.32495 (5)	−0.0532 (3)	0.0215 (4)
C10	0.5164 (5)	0.27923 (5)	0.1228 (3)	0.0245 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0389 (3)	0.0259 (3)	0.0262 (3)	0.00532 (19)	0.0051 (2)	−0.00617 (17)
S1	0.0309 (3)	0.0182 (2)	0.0187 (3)	−0.00121 (17)	0.00752 (18)	0.00075 (15)
O1	0.0395 (8)	0.0235 (7)	0.0229 (7)	−0.0036 (6)	0.0129 (6)	0.0011 (5)
O2	0.0540 (10)	0.0182 (7)	0.0300 (8)	−0.0052 (6)	0.0147 (7)	0.0008 (6)
N1	0.0336 (9)	0.0177 (8)	0.0198 (8)	−0.0011 (6)	0.0080 (7)	−0.0013 (6)
C1	0.0221 (9)	0.0187 (9)	0.0187 (9)	0.0003 (7)	−0.0004 (7)	0.0006 (7)
C2	0.0277 (9)	0.0212 (9)	0.0192 (9)	−0.0019 (7)	0.0031 (7)	0.0024 (7)
C3	0.0317 (10)	0.0162 (9)	0.0239 (10)	−0.0008 (7)	0.0003 (8)	0.0008 (7)
C4	0.0236 (9)	0.0231 (9)	0.0211 (9)	0.0028 (7)	0.0001 (7)	−0.0035 (7)
C5	0.0254 (9)	0.0253 (9)	0.0191 (9)	−0.0005 (7)	0.0043 (7)	0.0014 (7)
C6	0.0262 (9)	0.0187 (9)	0.0209 (9)	−0.0006 (7)	0.0020 (7)	0.0021 (7)
C7	0.0231 (9)	0.0223 (9)	0.0178 (9)	−0.0009 (7)	0.0030 (7)	0.0031 (7)
C8	0.0217 (9)	0.0217 (9)	0.0159 (9)	−0.0002 (7)	0.0027 (7)	0.0011 (7)
C9	0.0248 (9)	0.0210 (9)	0.0188 (9)	0.0006 (7)	0.0024 (7)	−0.0003 (7)
C10	0.0309 (10)	0.0225 (10)	0.0203 (9)	−0.0011 (8)	0.0039 (8)	0.0010 (7)

Geometric parameters (Å, º) top

Cl1—C4	1.7447 (19)	C2—C3	1.384 (3)
S1—C8	1.7619 (18)	C2—H2	0.9500
S1—C10	1.779 (2)	C3—C4	1.383 (3)
O1—C9	1.211 (2)	C3—H3	0.9500
O2—C10	1.210 (2)	C4—C5	1.384 (3)
N1—C10	1.365 (2)	C5—C6	1.388 (3)
N1—C9	1.377 (2)	C5—H5	0.9500
N1—H1	0.9099	C6—H6	0.9500
C1—C2	1.400 (3)	C7—C8	1.334 (3)
C1—C6	1.402 (3)	C7—H7	0.9500
C1—C7	1.458 (3)	C8—C9	1.493 (2)

C8—S1—C10	91.39 (9)	C4—C5—H5	120.3
C10—N1—C9	117.76 (16)	C6—C5—H5	120.3
C10—N1—H1	119.4	C5—C6—C1	120.44 (17)
C9—N1—H1	122.7	C5—C6—H6	119.8
C2—C1—C6	118.44 (17)	C1—C6—H6	119.8
C2—C1—C7	117.29 (17)	C8—C7—C1	132.41 (17)
C6—C1—C7	124.27 (17)	C8—C7—H7	113.8
C3—C2—C1	121.47 (18)	C1—C7—H7	113.8
C3—C2—H2	119.3	C7—C8—C9	119.25 (16)
C1—C2—H2	119.3	C7—C8—S1	130.70 (15)
C4—C3—C2	118.59 (17)	C9—C8—S1	110.01 (13)
C4—C3—H3	120.7	O1—C9—N1	123.94 (17)
C2—C3—H3	120.7	O1—C9—C8	125.93 (17)
C3—C4—C5	121.69 (17)	N1—C9—C8	110.12 (15)
C3—C4—Cl1	119.15 (15)	O2—C10—N1	124.62 (18)
C5—C4—Cl1	119.16 (15)	O2—C10—S1	124.78 (15)
C4—C5—C6	119.36 (18)	N1—C10—S1	110.60 (14)

C6—C1—C2—C3	0.0 (3)	C1—C7—C8—S1	0.7 (3)
C7—C1—C2—C3	179.82 (18)	C10—S1—C8—C7	174.7 (2)
C1—C2—C3—C4	0.8 (3)	C10—S1—C8—C9	−2.85 (15)
C2—C3—C4—C5	−0.8 (3)	C10—N1—C9—O1	177.09 (19)
C2—C3—C4—Cl1	179.45 (15)	C10—N1—C9—C8	−2.6 (2)
C3—C4—C5—C6	0.0 (3)	C7—C8—C9—O1	6.0 (3)
Cl1—C4—C5—C6	179.82 (15)	S1—C8—C9—O1	−176.14 (17)
C4—C5—C6—C1	0.7 (3)	C7—C8—C9—N1	−174.27 (17)
C2—C1—C6—C5	−0.7 (3)	S1—C8—C9—N1	3.6 (2)
C7—C1—C6—C5	179.44 (18)	C9—N1—C10—O2	−179.3 (2)
C2—C1—C7—C8	−174.5 (2)	C9—N1—C10—S1	0.5 (2)
C6—C1—C7—C8	5.3 (3)	C8—S1—C10—O2	−178.7 (2)
C1—C7—C8—C9	178.05 (19)	C8—S1—C10—N1	1.49 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.91	1.87	2.782 (2)	175

Symmetry code: (i) x+1/2, −y+1/2, z−1/2.

Acknowledgements

The support of NSF–MRI Grant No.1228232 for the purchase of the diffractometer and Tulane University for support of the Tulane Crystallography Laboratory are gratefully acknowledged.

References

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