2-(4-Chloro­phen­yl)-3-p-tolyl-1,3-thia­zolidin-4-one

Sun, X.-J.; Zhou, J.-F.; Zhang, Z.-C.; Wang, Y.-J.

doi:10.1107/S1600536809010307

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o874

doi:10.1107/S1600536809010307

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2-(4-Chlorophenyl)-3-p-tolyl-1,3-thiazolidin-4-one

Xiao-Jun Sun,^a ^* Jian-Feng Zhou,^a Zai-Chao Zhang ^a and Yu-Jie Wang ^a

^aDepartment of Chemistry, Huaiyin Teachers College, Huaian 223001, People's Republic of China
^*Correspondence e-mail: sunxiaojun100@126.com

(Received 19 March 2009; accepted 20 March 2009; online 25 March 2009)

The title compound, C₁₆H₁₄ClNOS, a potent antibacterial chemical, features a dihedral angle of 49.4 (1)° between the 4-tolyl and thiazolidinone rings, and a dihedral angle of 87.2 (5)° between the thiazolidinone and 4-chlorophenyl rings.

Related literature

For the synthesis, see: Srivastava et al. (2002 ).

Experimental

Crystal data

C₁₆H₁₄ClNOS
M_r = 303.79
Orthorhombic, P b c a
a = 12.1591 (4) Å
b = 13.0708 (4) Å
c = 18.5125 (7) Å
V = 2942.18 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.40 mm⁻¹
T = 296 K
0.40 × 0.35 × 0.20 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.85, T_max = 0.92
16959 measured reflections
3377 independent reflections
2205 reflections with I > 2˘I)
R_int = 0.058

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.115
S = 1.02
3377 reflections
182 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; 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, 1997 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010307/ng2565sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010307/ng2565Isup2.hkl

checkCIF report

Comment top

4-thiazolidinone ring system comprises the broad spectrum for a number of biologically active compounds.In recent years, 4-thiazolidinones are the most extensively investigated class of compounds, which exhibits various biological activities, such as anticancer, antitubercular, antibacterial and herbicidal activities. In view of these properties and in a continuation of our interest in the chemistry of 4-thiazolidinones, we have attempted to synthesize a series of 4-thiazolidinone derivatives, some of which have comparatively high antibacterial activity. The crystal structure determination of the title compound,(I), was undertaken to investigate the relationship between structure and antibacterial activity(Fig. 1). The molecular conformation is described by the dihedral angle between 4-methylbenzene ring and thiazolidinone ring of 49.4 (1)° and the dihedral angle between thiazolidinone ring and 4-chlorobenzene ring of 87.2 (5)°.

Related literature top

For the synthesis, see: Srivastava et al. (2002).

Experimental top

Compound (I) was synthesized according to the procedure of Tumul Srivastava et al. (2002). A crystal of (I) suitable for X-ray analysis was grown from an ethanol solution by slow evaporation at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of (I), showing the atom-numbering schem. Displacement ellipsoids are drawn at the 30% probability level.

2-(4-Chlorophenyl)-3-p-tolyl-1,3-thiazolidin-4-one top

Crystal data top

C₁₆H₁₄ClNOS	F(000) = 1264
M_r = 303.79	D_x = 1.372 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2211 reflections
a = 12.1591 (4) Å	θ = 2.5–25.0°
b = 13.0708 (4) Å	µ = 0.40 mm⁻¹
c = 18.5125 (7) Å	T = 296 K
V = 2942.18 (17) Å³	Plate, colorless
Z = 8	0.40 × 0.35 × 0.20 mm

Data collection top

Bruker APEXII area-detector diffractometer	3377 independent reflections
Radiation source: fine-focus sealed tube	2205 reflections with I > 2˘I)
Graphite monochromator	R_int = 0.058
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 2.2°
w\ scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −16→16
T_min = 0.85, T_max = 0.92	l = −24→24
16959 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0467P)² + 0.6312P] where P = (F_o² + 2F_c²)/3
3377 reflections	(Δ/σ)_max = 0.002
182 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₆H₁₄ClNOS	V = 2942.18 (17) Å³
M_r = 303.79	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.1591 (4) Å	µ = 0.40 mm⁻¹
b = 13.0708 (4) Å	T = 296 K
c = 18.5125 (7) Å	0.40 × 0.35 × 0.20 mm

Data collection top

Bruker APEXII area-detector diffractometer	3377 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	2205 reflections with I > 2˘I)
T_min = 0.85, T_max = 0.92	R_int = 0.058
16959 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.115	H-atom parameters constrained
S = 1.02	Δρ_max = 0.23 e Å⁻³
3377 reflections	Δρ_min = −0.34 e Å⁻³
182 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.

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 > σ(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.

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

	x	y	z	U_iso*/U_eq
C1	0.66878 (17)	0.93240 (14)	0.34463 (11)	0.0402 (5)
H1	0.6105	0.9535	0.3112	0.048*
C2	0.85314 (18)	0.96718 (14)	0.30086 (12)	0.0399 (5)
C3	0.83681 (18)	1.05986 (15)	0.34764 (13)	0.0467 (6)
H3A	0.8310	1.1207	0.3179	0.056*
H3B	0.8990	1.0681	0.3800	0.056*
C4	0.62581 (16)	0.85053 (14)	0.39467 (11)	0.0368 (5)
C5	0.69556 (17)	0.79865 (16)	0.44122 (12)	0.0434 (5)
H5	0.7708	0.8112	0.4391	0.052*
C6	0.65582 (18)	0.72901 (15)	0.49046 (12)	0.0441 (5)
H6	0.7033	0.6949	0.5217	0.053*
C7	0.54441 (18)	0.71086 (15)	0.49257 (12)	0.0429 (5)
C8	0.47397 (18)	0.75886 (19)	0.44628 (14)	0.0546 (6)
H8	0.3990	0.7448	0.4478	0.065*
C9	0.51497 (18)	0.82863 (18)	0.39704 (13)	0.0508 (6)
H9	0.4673	0.8611	0.3652	0.061*
C10	0.76107 (17)	0.81131 (14)	0.25927 (11)	0.0380 (5)
C11	0.84795 (18)	0.74324 (15)	0.25858 (13)	0.0468 (5)
H11	0.9090	0.7546	0.2877	0.056*
C12	0.8436 (2)	0.65774 (16)	0.21407 (14)	0.0552 (6)
H12	0.9030	0.6130	0.2130	0.066*
C13	0.7532 (2)	0.63756 (16)	0.17140 (12)	0.0519 (6)
C14	0.6660 (2)	0.70546 (16)	0.17427 (12)	0.0510 (6)
H14	0.6037	0.6929	0.1465	0.061*
C15	0.66950 (18)	0.79175 (15)	0.21761 (12)	0.0433 (5)
H15	0.6101	0.8365	0.2186	0.052*
C16	0.7492 (3)	0.54493 (19)	0.12222 (16)	0.0780 (9)
H16A	0.8176	0.5085	0.1252	0.117*
H16B	0.7372	0.5668	0.0733	0.117*
H16C	0.6902	0.5008	0.1370	0.117*
Cl1	0.49492 (5)	0.62309 (5)	0.55527 (4)	0.0680 (2)
N1	0.76603 (13)	0.90125 (11)	0.30369 (9)	0.0371 (4)
O1	0.93527 (13)	0.95428 (11)	0.26448 (9)	0.0529 (4)
S1	0.71335 (6)	1.04265 (4)	0.39863 (3)	0.0568 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0406 (12)	0.0425 (11)	0.0373 (12)	0.0056 (9)	0.0029 (10)	0.0017 (9)
C2	0.0395 (12)	0.0439 (11)	0.0364 (12)	0.0001 (9)	−0.0021 (10)	0.0069 (9)
C3	0.0489 (13)	0.0427 (11)	0.0484 (14)	−0.0029 (9)	−0.0055 (11)	0.0022 (10)
C4	0.0358 (11)	0.0427 (10)	0.0319 (11)	0.0016 (8)	0.0025 (9)	−0.0025 (9)
C5	0.0305 (11)	0.0568 (12)	0.0429 (13)	−0.0040 (9)	−0.0001 (10)	0.0055 (10)
C6	0.0405 (13)	0.0533 (12)	0.0385 (13)	0.0006 (9)	−0.0027 (10)	0.0038 (10)
C7	0.0431 (13)	0.0470 (11)	0.0385 (12)	−0.0054 (9)	0.0083 (10)	−0.0005 (9)
C8	0.0306 (12)	0.0760 (15)	0.0571 (16)	−0.0067 (10)	0.0021 (11)	0.0084 (13)
C9	0.0403 (13)	0.0668 (14)	0.0452 (14)	0.0062 (10)	−0.0020 (11)	0.0077 (12)
C10	0.0431 (12)	0.0387 (10)	0.0322 (11)	−0.0010 (8)	0.0073 (10)	0.0046 (8)
C11	0.0419 (13)	0.0472 (11)	0.0512 (15)	0.0024 (9)	0.0064 (11)	0.0056 (10)
C12	0.0616 (16)	0.0423 (11)	0.0616 (17)	0.0112 (10)	0.0206 (14)	0.0076 (11)
C13	0.0736 (17)	0.0411 (11)	0.0409 (13)	−0.0031 (11)	0.0150 (13)	0.0008 (10)
C14	0.0659 (16)	0.0492 (12)	0.0379 (13)	−0.0041 (11)	−0.0044 (12)	0.0001 (10)
C15	0.0489 (13)	0.0429 (11)	0.0381 (12)	0.0045 (9)	−0.0015 (10)	0.0013 (9)
C16	0.120 (2)	0.0507 (14)	0.0634 (18)	0.0008 (15)	0.0190 (18)	−0.0083 (13)
Cl1	0.0592 (4)	0.0747 (4)	0.0701 (5)	−0.0107 (3)	0.0135 (3)	0.0234 (4)
N1	0.0368 (9)	0.0405 (8)	0.0339 (9)	−0.0006 (7)	0.0038 (8)	−0.0005 (7)
O1	0.0424 (9)	0.0556 (9)	0.0606 (11)	−0.0043 (7)	0.0109 (8)	0.0000 (8)
S1	0.0723 (5)	0.0469 (3)	0.0513 (4)	−0.0062 (3)	0.0169 (3)	−0.0087 (3)

Geometric parameters (Å, º) top

C1—N1	1.462 (2)	C8—C9	1.382 (3)
C1—C4	1.509 (3)	C8—H8	0.9300
C1—S1	1.836 (2)	C9—H9	0.9300
C1—H1	0.9800	C10—C15	1.378 (3)
C2—O1	1.216 (2)	C10—C11	1.381 (3)
C2—N1	1.366 (3)	C10—N1	1.436 (2)
C2—C3	1.502 (3)	C11—C12	1.390 (3)
C3—S1	1.787 (2)	C11—H11	0.9300
C3—H3A	0.9700	C12—C13	1.378 (3)
C3—H3B	0.9700	C12—H12	0.9300
C4—C9	1.378 (3)	C13—C14	1.384 (3)
C4—C5	1.386 (3)	C13—C16	1.516 (3)
C5—C6	1.376 (3)	C14—C15	1.385 (3)
C5—H5	0.9300	C14—H14	0.9300
C6—C7	1.376 (3)	C15—H15	0.9300
C6—H6	0.9300	C16—H16A	0.9600
C7—C8	1.364 (3)	C16—H16B	0.9600
C7—Cl1	1.740 (2)	C16—H16C	0.9600

N1—C1—C4	113.63 (15)	C4—C9—H9	119.7
N1—C1—S1	105.19 (13)	C8—C9—H9	119.7
C4—C1—S1	108.94 (14)	C15—C10—C11	119.55 (19)
N1—C1—H1	109.6	C15—C10—N1	120.41 (18)
C4—C1—H1	109.6	C11—C10—N1	120.04 (19)
S1—C1—H1	109.6	C10—C11—C12	119.6 (2)
O1—C2—N1	124.76 (19)	C10—C11—H11	120.2
O1—C2—C3	122.66 (19)	C12—C11—H11	120.2
N1—C2—C3	112.58 (19)	C13—C12—C11	121.6 (2)
C2—C3—S1	108.30 (14)	C13—C12—H12	119.2
C2—C3—H3A	110.0	C11—C12—H12	119.2
S1—C3—H3A	110.0	C12—C13—C14	117.8 (2)
C2—C3—H3B	110.0	C12—C13—C16	121.6 (2)
S1—C3—H3B	110.0	C14—C13—C16	120.7 (3)
H3A—C3—H3B	108.4	C13—C14—C15	121.4 (2)
C9—C4—C5	118.47 (19)	C13—C14—H14	119.3
C9—C4—C1	120.36 (19)	C15—C14—H14	119.3
C5—C4—C1	121.12 (18)	C10—C15—C14	120.0 (2)
C6—C5—C4	121.38 (19)	C10—C15—H15	120.0
C6—C5—H5	119.3	C14—C15—H15	120.0
C4—C5—H5	119.3	C13—C16—H16A	109.5
C5—C6—C7	118.6 (2)	C13—C16—H16B	109.5
C5—C6—H6	120.7	H16A—C16—H16B	109.5
C7—C6—H6	120.7	C13—C16—H16C	109.5
C8—C7—C6	121.4 (2)	H16A—C16—H16C	109.5
C8—C7—Cl1	120.35 (17)	H16B—C16—H16C	109.5
C6—C7—Cl1	118.25 (17)	C2—N1—C10	121.80 (17)
C7—C8—C9	119.4 (2)	C2—N1—C1	118.11 (16)
C7—C8—H8	120.3	C10—N1—C1	119.39 (15)
C9—C8—H8	120.3	C3—S1—C1	93.39 (9)
C4—C9—C8	120.7 (2)

Experimental details

Crystal data
Chemical formula	C₁₆H₁₄ClNOS
M_r	303.79
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	296
a, b, c (Å)	12.1591 (4), 13.0708 (4), 18.5125 (7)
V (Å³)	2942.18 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.40
Crystal size (mm)	0.40 × 0.35 × 0.20

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.85, 0.92
No. of measured, independent and observed [I > 2˘I)] reflections	16959, 3377, 2205
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.115, 1.02
No. of reflections	3377
No. of parameters	182
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.34

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

This project was supported by Jiangsu Key Laboratory of the Chemistry of Low-Dimensional Materials.

References

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