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

Abstract

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,

• a = 12.1591 (4) Å

• b = 13.0708 (4) Å

• c = 18.5125 (7) Å

• V = 2942.18 (17) ų

• 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[F ² > 2σ(F ²)] = 0.044

• wR(F ²) = 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 ▶).

Supplementary Material

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

supplementary crystallographic information

Comment

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)°.

Experimental

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.

Refinement

H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.95 (aromatic), 0.99 (methylene), 1.00 (methylidyne) and 0.98 Å(methyl), and with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(C_methyl).

Figures

Fig. 1.

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

Crystal data

C16H14ClNOS	F(000) = 1264
Mr = 303.79	Dx = 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

Bruker APEXII area-detector diffractometer	3377 independent reflections
Radiation source: fine-focus sealed tube	2205 reflections with I > 2˘I)
graphite	Rint = 0.058
Detector resolution: 0 pixels mm-1	θmax = 27.5°, θmin = 2.2°
w\ scans	h = −14→15
Absorption correction: multi-scan (SADABS; Bruker, 2000)	k = −16→16
Tmin = 0.85, Tmax = 0.92	l = −24→24
16959 measured reflections

Refinement

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(Fo2) + (0.0467P)2 + 0.6312P] where P = (Fo2 + 2Fc2)/3
3377 reflections	(Δ/σ)max = 0.002
182 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.34 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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)