Crystal structures of 2,3-bis­(4-chloro­phen­yl)-1,3-thia­zolidin-4-one and trans-2,3-bis­(4-chloro­phen­yl)-1,3-thia­zolidin-4-one 1-oxide

In the related title compounds, (1) and (2), the 3-thia­zolidine ring pucker is twisted on the S—C_methine bond in (1), while in (2), the ring has an envelope conformation with the S atom as the flap. In the crystal of (1), mol­ecules are linked by C—H...O hydrogen bonds forming chains along [100], while in the crystal of (2), mol­ecules are linked by C—H...O and C—H...Cl hydrogen bonds forming slabs parallel to (001).

Key indicators

Structure: 1

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.036
• wR factor = 0.099
• Data-to-parameter ratio = 18.8

Structure: 2

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.051
• wR factor = 0.138
• Data-to-parameter ratio = 20.3

checkCIF/PLATON results

No syntax errors found



Datablock: 1


Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......      0.975 Note
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         19 Report

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600         70 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   3 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check




Datablock: 2


Alert level C
PLAT127_ALERT_1_C Implicit Hall Symbol  Inconsistent with Explicit    -P 2ab 2ac
PLAT143_ALERT_4_C su on c - Axis Small or Missing ................    0.00000 Ang.
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....         C5 Check
PLAT242_ALERT_2_C Low       Ueq as Compared to Neighbors for .....        C11 Check
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......      6.085 Check

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details  in the CIF     Please Do !
PLAT066_ALERT_1_G Predicted and Reported Tmin&Tmax Range Identical          ? Check
PLAT793_ALERT_4_G The Model has Chirality at C1      (Centro SPGR)          S Verify
PLAT899_ALERT_4_G SHELXL97   is Deprecated and Succeeded by SHELXL       2014 Note
PLAT912_ALERT_4_G Missing # of FCF Reflections Above STh/L=  0.600          6 Note

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
   5 ALERT level G = General information/check it is not something unexpected

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Chemical context

1,3-Thia­zolidin-4-ones, also known as 4-thia­zolidinones, are known to have a wide range of biological activities (Jain et al., 2012; Abhinit et al., 2009; Hamama et al., 2008; Singh et al., 1981; Brown, 1961; Tripathi et al., 2014; Prabhakar et al., 2006). The S-oxides have been observed to show enhanced activity, for example, it was shown that on converting a 4-thia­zolidinone to its sulfoxide and sulfone, the oxide showed greater activity against some cancer cell lines than the sulfide (Gududuru et al., 2004). Oxidation from sulfide to sulfoxide makes the sulfur a chiral center, and produces cis and trans diastereomers with regard to the relationship of the oxygen on the sulfur atom and the substituent at the 2-position (Rozwadowska et al., 2002; Colombo et al., 2008). The stereocenters may however be configurationally unstable in solution or even in the solid state (Rozwadowska et al., 2002). We have previously reported on the preparation and NMR studies of a series of 2,3-di­aryl-1,3-thia­zolidin-4-ones in which the two aryl groups had the same substitution pattern (Tierney et al., 2005). In this study, we report on the S-oxidation of one of these compounds, 2,3-bis­(4-chloro­phenyl)-1, 3-thia­zolidin-4-one (1), with oxone (Trost & Curran, 1981; Yu et al., 2012; Webb, 1994), which gave compound (2), and on their crystal structures.

S2. Structural commentary

The molecular structures of compounds (1) and (2), Figs. 1 and 2, respectively, show a slight dissimilarity in the thia­zine ring conformation. In (1), the ring pucker is twisted on the S1—C1 bond, while in (2) the ring has an envelope conformation with atom S1 as the flap. The structures also differ in the disposition of the chloro­phenyl ring at atom C1. In (1), this ring points in the same direction as the S atom with respect to the thia­zolidine ring plane, while in (2), the S atom points in the opposite direction. The trans relationship between the oxygen on the S atom and the aromatic ring on C1 is favoured due to steric hindrance which would occur in the cis isomer. The two chloro­phenyl rings are almost orthogonal to each other, making a dihedral angle of 78.61 (6)° in (1) and 87.46 (8)° in (2).

Comparison of the two structures shows that the oxygen–sulfur bond formed on the less hindered side of compound (1), away from the aryl group on C1, leads to a trans stereoisomer. Steric strain was further relieved by the sulfur atom moving from being on the same side as the aryl ring to being on the opposite side of the central ring, and by the aryl ring moving from a pseudo-equatorial position in (1) to a pseudo-axial position in (2).

S3. Supra­molecular features

In the crystal of (1), molecules are linked via C—H···O hydrogen bonds, forming chains along [100]; see Table 1 and Fig. 3. The chains are linked via slipped parallel π–π inter­actions involving inversion-related chloro­phenyl rings, leading to the formation of sheets parallel to (001) [Cg3···Cg3ⁱ = 3.840 (3) Å; Cg3 is the centroid of the C8–C13 ring; inter-planar distance = 3.3364 (7) Å; slippage = 1.901 Å; symmetry code: (i) -x + 2, -y, -z + 2].

In the crystal of (2), molecules are linked via by C—H···O and C—H···Cl hydrogen bonds, forming slabs parallel to (001); see Table 2 and Fig. 4.

S4. Database survey

Compound (1) differs from the previously reported 2,3-di­phenyl-1, 3-thia­zolidin-4-one (Yennawar et al., 2014) only in the presence of p-chlorines on the two phenyl rings, and the compound does not have a twist in the thia­zine ring. Compound (2) is related to 2-aryl-1,3-thia­zolidin-4-one 1-oxides, viz. 3-butyl-2-phenyl-1,3-thia­zolidine-1,4-dione (Wang et al., 2010), (1b, 2a, 5a)-3, 5-di­methyl-1-oxo-2-phenyl-4-thia­zolidinone (Johnson et al., 1983), 2-(2, 6-di­chloro­phenyl)-3-(4, 5, 6-tri­methyl­pyrimidin-2-yl)-1, 3-thia­zolidin-4-one 1-oxide (Chen et al., 2011) and trans-3-benzyl-2-(4-meth­oxy­phenyl)­thia­zolidin-4-one 1-oxide (Colombo et al., 2008). All five compounds have a trans relationship between the oxygen on sulfur and the 2-aryl ring.

S5. Synthesis and crystallization

Compound (1): prepared as previously reported (Tierney et al., 2005). Colourless block-like crystals were obtained by slow evaporation of a solution in ethanol.

Compound (2): 2,3-bis (4-chloro­phenyl)-1,3-thia­zolidin-4-one (1) (0.326 g, 1 mmol) was added to a 25 ml round-bottom flask. Methanol (4 ml) was added and the mixture was stirred at room temperature before cooling to 273–278 K. A solution of oxone (0.456 g, 3.0 mmol calculated as KHSO₅, 152.2 g mol^-1) in distilled water (4 ml) was prepared. This solution (2.67 ml, 2 equivalents) was slowly added to the reaction mixture with stirring at 273–278 K. The reaction was followed by TLC. An additional aliquot of oxone solution (0.67 ml) was added to convert the remaining starting material to sulfoxide. The mixture was extracted three times with methyl­ene chloride. The organic layers were combined and washed with water and saturated NaCl, then dried over sodium sulfate. The solution was concentrated under vacuum to give compound (2) as a crude solid. The solid was recrystallized from a mixture of methyl­ene chloride and hexane, and then dried (yield: 0.2413 g; 70.5%; m.p.: 406–409 K). Colourless plate-like crystals were obtained by slow evaporation of a solution in ethanol.

S6. Refinement details

Crystal data, data collection and structure refinement details for structures (1) and (2) are summarized in Table 3. H atoms were positioned geometrically with C—H = 0.93–0.97 Å, and refined as riding with U_iso(H) = 1.2U_eq(C).

Related literature

For related literature, see: Abhinit et al. (2009); Brown (1961); Chen et al. (2011); Colombo et al. (2008); Gududuru et al. (2004); Hamama et al. (2008); Jain et al. (2012); Johnson et al. (1983); Prabhakar et al. (2006); Rozwadowska et al. (2002); Singh et al. (1981); Tierney et al. (2005); Tripathi et al. (2014); Trost & Curran (1981); Wang et al. (2010); Webb (1994); Yennawar et al. (2014); Yu et al. (2012).

Computing details

For both compounds, data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures

	Fig. 1. A view of the molecular structure of compound (1), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A view of the molecular structure of compound (2), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 3. Crystal packing of compound (1) viewed along the a axis, showing the hydrogen bonds as dashed lines (see Table 1 for details; H atoms not involved in these interactions have been omitted for clarity).
	Fig. 4. Crystal packing of compound (2) viewed along the b axis, showing the hydrogen bonds as dashed lines (see Table 2 for details; H atoms not involved in these interactions have been omitted for clarity).

(1) 2,3-Bis(4-chlorophenyl)-1,3-thiazolidin-4-one

Crystal data

C15H11Cl2NOS	Z = 2
Mr = 324.21	F(000) = 332
Triclinic, P1	Dx = 1.529 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.019 (6) Å	Cell parameters from 4305 reflections
b = 9.562 (8) Å	θ = 2.3–28.2°
c = 9.984 (8) Å	µ = 0.60 mm^−1
α = 88.937 (13)°	T = 298 K
β = 76.254 (12)°	Block, colourless
γ = 71.586 (13)°	0.22 × 0.20 × 0.16 mm
V = 704.3 (10) Å^3

Data collection

Bruker SMART CCD area-detector diffractometer	3406 independent reflections
Radiation source: fine-focus sealed tube	3070 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.016
Detector resolution: 8.34 pixels mm^-1	θmax = 28.3°, θmin = 2.1°
phi and ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −12→12
Tmin = 0.879, Tmax = 0.910	l = −13→13
6575 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.099	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0523P)^2 + 0.2029P] where P = (Fo^2 + 2Fc^2)/3
3406 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.24 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different ϕ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

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	0.48888 (17)	0.30999 (15)	0.71043 (13)	0.0330 (3)
H1	0.4491	0.2300	0.6838	0.040*
C2	0.68202 (17)	0.28648 (14)	0.63246 (13)	0.0310 (3)
C3	0.78163 (19)	0.36815 (16)	0.66932 (14)	0.0356 (3)
H3	0.7306	0.4355	0.7455	0.043*
C4	0.95613 (19)	0.34994 (16)	0.59348 (14)	0.0375 (3)
H4	1.0233	0.4040	0.6184	0.045*
C5	1.02943 (19)	0.24998 (16)	0.47982 (15)	0.0391 (3)
C6	0.9333 (2)	0.16883 (17)	0.44035 (15)	0.0418 (3)
H6	0.9841	0.1029	0.3631	0.050*
C7	0.7584 (2)	0.18715 (16)	0.51810 (14)	0.0377 (3)
H7	0.6920	0.1323	0.4932	0.045*
C8	0.56811 (17)	0.21103 (15)	0.93089 (13)	0.0317 (3)
C9	0.64973 (19)	0.06770 (15)	0.87310 (14)	0.0366 (3)
H9	0.6364	0.0441	0.7872	0.044*
C10	0.7510 (2)	−0.04056 (17)	0.94240 (16)	0.0422 (3)
H10	0.8060	−0.1366	0.9034	0.051*
C11	0.7694 (2)	−0.00403 (18)	1.07003 (17)	0.0434 (3)
C12	0.6911 (2)	0.13821 (19)	1.12805 (16)	0.0457 (3)
H12	0.7053	0.1614	1.2139	0.055*
C13	0.5915 (2)	0.24636 (17)	1.05824 (15)	0.0395 (3)
H13	0.5401	0.3429	1.0964	0.047*
C14	0.29560 (18)	0.41916 (16)	0.93219 (15)	0.0364 (3)
C15	0.19141 (19)	0.51206 (17)	0.83648 (16)	0.0429 (3)
H15A	0.1473	0.6153	0.8689	0.051*
H15B	0.0884	0.4811	0.8329	0.051*
Cl1	1.25015 (6)	0.22688 (6)	0.38612 (5)	0.06617 (16)
Cl2	0.89079 (7)	−0.14012 (6)	1.16121 (6)	0.06647 (16)
N1	0.45860 (15)	0.32152 (13)	0.86178 (11)	0.0322 (2)
O1	0.23825 (15)	0.42928 (15)	1.05662 (11)	0.0510 (3)
S1	0.34401 (5)	0.48672 (5)	0.66875 (4)	0.04576 (12)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0324 (6)	0.0375 (7)	0.0286 (6)	−0.0104 (5)	−0.0075 (5)	0.0019 (5)
C2	0.0327 (6)	0.0329 (6)	0.0252 (5)	−0.0080 (5)	−0.0064 (5)	0.0040 (5)
C3	0.0379 (7)	0.0386 (7)	0.0279 (6)	−0.0109 (5)	−0.0051 (5)	−0.0032 (5)
C4	0.0380 (7)	0.0413 (7)	0.0344 (7)	−0.0147 (6)	−0.0084 (5)	0.0018 (6)
C5	0.0354 (7)	0.0393 (7)	0.0352 (7)	−0.0084 (6)	0.0004 (5)	0.0025 (6)
C6	0.0465 (8)	0.0391 (7)	0.0328 (7)	−0.0108 (6)	0.0004 (6)	−0.0052 (6)
C7	0.0439 (7)	0.0372 (7)	0.0322 (6)	−0.0145 (6)	−0.0072 (6)	−0.0016 (5)
C8	0.0288 (6)	0.0361 (6)	0.0297 (6)	−0.0121 (5)	−0.0044 (5)	0.0056 (5)
C9	0.0371 (7)	0.0375 (7)	0.0333 (6)	−0.0120 (6)	−0.0053 (5)	0.0035 (5)
C10	0.0378 (7)	0.0370 (7)	0.0476 (8)	−0.0105 (6)	−0.0053 (6)	0.0093 (6)
C11	0.0367 (7)	0.0487 (8)	0.0499 (8)	−0.0184 (6)	−0.0153 (6)	0.0224 (7)
C12	0.0485 (8)	0.0583 (9)	0.0392 (7)	−0.0240 (7)	−0.0185 (6)	0.0127 (7)
C13	0.0413 (7)	0.0427 (7)	0.0368 (7)	−0.0155 (6)	−0.0110 (6)	0.0022 (6)
C14	0.0303 (6)	0.0402 (7)	0.0372 (7)	−0.0107 (5)	−0.0056 (5)	−0.0027 (5)
C15	0.0308 (6)	0.0451 (8)	0.0473 (8)	−0.0053 (6)	−0.0085 (6)	0.0014 (6)
Cl1	0.0465 (2)	0.0702 (3)	0.0689 (3)	−0.0232 (2)	0.0179 (2)	−0.0170 (2)
Cl2	0.0627 (3)	0.0667 (3)	0.0827 (3)	−0.0258 (2)	−0.0377 (3)	0.0424 (3)
N1	0.0307 (5)	0.0357 (5)	0.0269 (5)	−0.0076 (4)	−0.0050 (4)	0.0013 (4)
O1	0.0377 (5)	0.0675 (8)	0.0360 (5)	−0.0062 (5)	−0.0002 (4)	−0.0081 (5)
S1	0.0374 (2)	0.0520 (2)	0.0426 (2)	−0.00607 (16)	−0.01206 (16)	0.01364 (17)

Geometric parameters (Å, º)

C1—N1	1.473 (2)	C8—N1	1.4277 (18)
C1—C2	1.506 (2)	C9—C10	1.386 (2)
C1—S1	1.8282 (17)	C9—H9	0.9300
C1—H1	0.9800	C10—C11	1.380 (3)
C2—C7	1.386 (2)	C10—H10	0.9300
C2—C3	1.388 (2)	C11—C12	1.377 (3)
C3—C4	1.382 (2)	C11—Cl2	1.7455 (17)
C3—H3	0.9300	C12—C13	1.382 (2)
C4—C5	1.384 (2)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.373 (2)	C14—O1	1.212 (2)
C5—Cl1	1.7408 (19)	C14—N1	1.3751 (19)
C6—C7	1.390 (2)	C14—C15	1.510 (2)
C6—H6	0.9300	C15—S1	1.7930 (19)
C7—H7	0.9300	C15—H15A	0.9700
C8—C9	1.387 (2)	C15—H15B	0.9700
C8—C13	1.391 (2)
N1—C1—C2	114.30 (11)	C10—C9—H9	119.8
N1—C1—S1	104.57 (9)	C8—C9—H9	119.8
C2—C1—S1	109.22 (10)	C11—C10—C9	119.14 (15)
N1—C1—H1	109.5	C11—C10—H10	120.4
C2—C1—H1	109.5	C9—C10—H10	120.4
S1—C1—H1	109.5	C12—C11—C10	121.07 (14)
C7—C2—C3	119.49 (13)	C12—C11—Cl2	119.13 (13)
C7—C2—C1	119.49 (12)	C10—C11—Cl2	119.80 (13)
C3—C2—C1	120.94 (12)	C11—C12—C13	119.72 (15)
C4—C3—C2	120.40 (13)	C11—C12—H12	120.1
C4—C3—H3	119.8	C13—C12—H12	120.1
C2—C3—H3	119.8	C12—C13—C8	120.07 (15)
C3—C4—C5	119.01 (13)	C12—C13—H13	120.0
C3—C4—H4	120.5	C8—C13—H13	120.0
C5—C4—H4	120.5	O1—C14—N1	124.72 (14)
C6—C5—C4	121.77 (14)	O1—C14—C15	122.94 (13)
C6—C5—Cl1	119.69 (12)	N1—C14—C15	112.33 (13)
C4—C5—Cl1	118.54 (12)	C14—C15—S1	107.22 (11)
C5—C6—C7	118.72 (14)	C14—C15—H15A	110.3
C5—C6—H6	120.6	S1—C15—H15A	110.3
C7—C6—H6	120.6	C14—C15—H15B	110.3
C2—C7—C6	120.60 (13)	S1—C15—H15B	110.3
C2—C7—H7	119.7	H15A—C15—H15B	108.5
C6—C7—H7	119.7	C14—N1—C8	121.42 (12)
C9—C8—C13	119.47 (13)	C14—N1—C1	115.85 (11)
C9—C8—N1	120.56 (13)	C8—N1—C1	120.65 (11)
C13—C8—N1	119.96 (13)	C15—S1—C1	91.77 (7)
C10—C9—C8	120.50 (14)
N1—C1—C2—C7	138.56 (13)	C11—C12—C13—C8	1.0 (2)
S1—C1—C2—C7	−104.71 (14)	C9—C8—C13—C12	−1.8 (2)
N1—C1—C2—C3	−44.66 (17)	N1—C8—C13—C12	177.27 (13)
S1—C1—C2—C3	72.06 (15)	O1—C14—C15—S1	168.76 (13)
C7—C2—C3—C4	−0.5 (2)	N1—C14—C15—S1	−12.48 (15)
C1—C2—C3—C4	−177.31 (13)	O1—C14—N1—C8	6.5 (2)
C2—C3—C4—C5	0.5 (2)	C15—C14—N1—C8	−172.19 (12)
C3—C4—C5—C6	0.1 (2)	O1—C14—N1—C1	170.20 (14)
C3—C4—C5—Cl1	−179.42 (11)	C15—C14—N1—C1	−8.53 (17)
C4—C5—C6—C7	−0.7 (2)	C9—C8—N1—C14	136.45 (14)
Cl1—C5—C6—C7	178.88 (12)	C13—C8—N1—C14	−42.65 (18)
C3—C2—C7—C6	0.0 (2)	C9—C8—N1—C1	−26.44 (18)
C1—C2—C7—C6	176.81 (13)	C13—C8—N1—C1	154.46 (13)
C5—C6—C7—C2	0.6 (2)	C2—C1—N1—C14	144.10 (13)
C13—C8—C9—C10	1.3 (2)	S1—C1—N1—C14	24.72 (14)
N1—C8—C9—C10	−177.86 (12)	C2—C1—N1—C8	−52.09 (16)
C8—C9—C10—C11	0.2 (2)	S1—C1—N1—C8	−171.47 (9)
C9—C10—C11—C12	−1.0 (2)	C14—C15—S1—C1	22.62 (11)
C9—C10—C11—Cl2	178.08 (11)	N1—C1—S1—C15	−26.42 (10)
C10—C11—C12—C13	0.4 (2)	C2—C1—S1—C15	−149.16 (10)
Cl2—C11—C12—C13	−178.68 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O1^i	0.93	2.48	3.326 (3)	151
C15—H15B···O1^ii	0.97	2.46	3.221 (3)	135

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

(2) 2,3-Bis(4-chlorophenyl)-1,3-thiazolidin-4-one 1-oxide

Crystal data

C15H11Cl2NO2S	F(000) = 1392
Mr = 340.21	Dx = 1.450 Mg m^−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2ac	Cell parameters from 5771 reflections
a = 7.1094 (17) Å	θ = 2.2–28.2°
b = 20.940 (5) Å	µ = 0.55 mm^−1
c = 20.940 Å	T = 298 K
V = 3117.4 (11) Å^3	Plate, colourless
Z = 8	0.19 × 0.17 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer	3862 independent reflections
Radiation source: fine-focus sealed tube	2543 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 8.34 pixels mm^-1	θmax = 28.3°, θmin = 2.0°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2001)	k = −27→27
Tmin = 0.902, Tmax = 0.973	l = −27→27
26788 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.138	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0581P)^2 + 1.0427P] where P = (Fo^2 + 2Fc^2)/3
3862 reflections	(Δ/σ)max = 0.003
190 parameters	Δρmax = 0.33 e Å^−3
0 restraints	Δρmin = −0.31 e Å^−3

Special details

Experimental. The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of ω scans each set at different ϕ and/or 2θ angles and each scan (10 s exposure) covering -0.300° degrees in ω. The crystal to detector distance was 5.82 cm.

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	0.1427 (3)	0.56601 (10)	0.84451 (10)	0.0447 (5)
H1	0.1817	0.5615	0.7999	0.054*
C2	0.2832 (3)	0.60780 (10)	0.87867 (10)	0.0446 (5)
C3	0.3302 (3)	0.59815 (12)	0.94158 (11)	0.0508 (6)
H3	0.2783	0.5640	0.9638	0.061*
C4	0.4542 (4)	0.63897 (14)	0.97198 (12)	0.0627 (7)
H4	0.4843	0.6326	1.0147	0.075*
C5	0.5322 (4)	0.68858 (14)	0.93908 (15)	0.0710 (8)
C6	0.4887 (4)	0.69891 (13)	0.87616 (16)	0.0745 (8)
H6	0.5433	0.7327	0.8541	0.089*
C7	0.3629 (4)	0.65874 (12)	0.84583 (12)	0.0594 (6)
H7	0.3316	0.6658	0.8033	0.071*
C8	0.2445 (3)	0.45232 (11)	0.85694 (9)	0.0455 (5)
C9	0.4140 (3)	0.46695 (12)	0.82790 (12)	0.0563 (6)
H9	0.4447	0.5094	0.8199	0.068*
C10	0.5379 (4)	0.41909 (14)	0.81076 (13)	0.0684 (7)
H10	0.6511	0.4293	0.7910	0.082*
C11	0.4939 (5)	0.35700 (14)	0.82285 (13)	0.0716 (8)
C12	0.3310 (5)	0.34158 (14)	0.85240 (14)	0.0808 (9)
H12	0.3038	0.2990	0.8612	0.097*
C13	0.2046 (4)	0.38873 (13)	0.86954 (13)	0.0677 (7)
H13	0.0925	0.3778	0.8896	0.081*
C14	−0.0326 (3)	0.49782 (12)	0.91318 (10)	0.0508 (6)
C15	−0.1372 (3)	0.56016 (13)	0.91777 (10)	0.0593 (7)
H15A	−0.0952	0.5839	0.9549	0.071*
H15B	−0.2711	0.5523	0.9219	0.071*
Cl1	0.68956 (15)	0.73930 (6)	0.97629 (6)	0.1258 (4)
Cl2	0.64436 (17)	0.29545 (5)	0.79888 (5)	0.1196 (4)
N1	0.1163 (2)	0.50246 (9)	0.87174 (8)	0.0434 (4)
O1	−0.2071 (3)	0.57407 (11)	0.79699 (8)	0.0779 (6)
O2	−0.0736 (3)	0.45046 (9)	0.94350 (8)	0.0715 (5)
S1	−0.09086 (9)	0.60445 (3)	0.84674 (3)	0.0560 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0457 (12)	0.0505 (13)	0.0378 (10)	−0.0016 (10)	0.0072 (9)	0.0010 (9)
C2	0.0398 (11)	0.0484 (12)	0.0456 (11)	0.0011 (10)	0.0086 (9)	−0.0022 (9)
C3	0.0454 (13)	0.0594 (15)	0.0475 (12)	−0.0024 (11)	0.0063 (10)	−0.0046 (10)
C4	0.0507 (14)	0.0793 (19)	0.0580 (14)	−0.0008 (13)	0.0003 (12)	−0.0162 (13)
C5	0.0479 (15)	0.077 (2)	0.089 (2)	−0.0116 (14)	0.0071 (14)	−0.0282 (16)
C6	0.0671 (18)	0.0580 (17)	0.099 (2)	−0.0187 (14)	0.0212 (16)	−0.0015 (15)
C7	0.0607 (15)	0.0567 (15)	0.0607 (14)	−0.0082 (12)	0.0083 (12)	0.0027 (12)
C8	0.0469 (12)	0.0508 (13)	0.0387 (11)	−0.0038 (10)	0.0008 (9)	−0.0001 (9)
C9	0.0518 (14)	0.0577 (15)	0.0593 (14)	−0.0008 (11)	0.0120 (11)	0.0030 (11)
C10	0.0566 (16)	0.079 (2)	0.0700 (17)	0.0129 (14)	0.0092 (13)	0.0026 (14)
C11	0.080 (2)	0.0716 (19)	0.0636 (16)	0.0273 (16)	0.0024 (15)	0.0056 (14)
C12	0.110 (3)	0.0470 (15)	0.085 (2)	0.0075 (16)	0.0129 (19)	0.0078 (14)
C13	0.0747 (19)	0.0548 (16)	0.0735 (17)	−0.0092 (14)	0.0156 (14)	0.0053 (13)
C14	0.0445 (12)	0.0728 (16)	0.0352 (10)	−0.0074 (11)	0.0039 (9)	0.0008 (11)
C15	0.0434 (13)	0.0903 (19)	0.0442 (12)	0.0087 (13)	0.0042 (10)	−0.0051 (12)
Cl1	0.0974 (7)	0.1391 (9)	0.1409 (9)	−0.0599 (7)	−0.0018 (6)	−0.0500 (7)
Cl2	0.1392 (9)	0.1012 (7)	0.1184 (8)	0.0708 (7)	0.0144 (7)	0.0076 (6)
N1	0.0405 (9)	0.0512 (10)	0.0387 (8)	−0.0037 (8)	0.0068 (7)	0.0014 (8)
O1	0.0607 (12)	0.1197 (16)	0.0534 (10)	−0.0018 (11)	−0.0179 (9)	−0.0016 (10)
O2	0.0764 (13)	0.0803 (13)	0.0579 (10)	−0.0134 (10)	0.0236 (9)	0.0120 (9)
S1	0.0494 (4)	0.0702 (4)	0.0484 (3)	0.0080 (3)	−0.0057 (3)	0.0022 (3)

Geometric parameters (Å, º)

C1—N1	1.460 (3)	C8—N1	1.425 (3)
C1—C2	1.508 (3)	C9—C10	1.382 (4)
C1—S1	1.846 (2)	C9—H9	0.9300
C1—H1	0.9800	C10—C11	1.361 (4)
C2—C3	1.374 (3)	C10—H10	0.9300
C2—C7	1.390 (3)	C11—C12	1.352 (4)
C3—C4	1.383 (3)	C11—Cl2	1.749 (3)
C3—H3	0.9300	C12—C13	1.382 (4)
C4—C5	1.365 (4)	C12—H12	0.9300
C4—H4	0.9300	C13—H13	0.9300
C5—C6	1.371 (4)	C14—O2	1.213 (3)
C5—Cl1	1.728 (3)	C14—N1	1.372 (3)
C6—C7	1.382 (4)	C14—C15	1.506 (4)
C6—H6	0.9300	C15—S1	1.784 (2)
C7—H7	0.9300	C15—H15A	0.9700
C8—C9	1.384 (3)	C15—H15B	0.9700
C8—C13	1.387 (3)	O1—S1	1.4742 (19)
N1—C1—C2	115.38 (18)	C8—C9—H9	119.7
N1—C1—S1	105.78 (14)	C11—C10—C9	119.9 (3)
C2—C1—S1	109.30 (15)	C11—C10—H10	120.1
N1—C1—H1	108.7	C9—C10—H10	120.1
C2—C1—H1	108.7	C12—C11—C10	120.7 (3)
S1—C1—H1	108.7	C12—C11—Cl2	118.6 (2)
C3—C2—C7	119.2 (2)	C10—C11—Cl2	120.7 (2)
C3—C2—C1	122.0 (2)	C11—C12—C13	120.3 (3)
C7—C2—C1	118.7 (2)	C11—C12—H12	119.8
C2—C3—C4	120.4 (2)	C13—C12—H12	119.8
C2—C3—H3	119.8	C12—C13—C8	120.2 (3)
C4—C3—H3	119.8	C12—C13—H13	119.9
C5—C4—C3	119.8 (2)	C8—C13—H13	119.9
C5—C4—H4	120.1	O2—C14—N1	125.1 (2)
C3—C4—H4	120.1	O2—C14—C15	123.8 (2)
C4—C5—C6	120.9 (3)	N1—C14—C15	111.1 (2)
C4—C5—Cl1	120.2 (2)	C14—C15—S1	107.83 (15)
C6—C5—Cl1	118.9 (2)	C14—C15—H15A	110.1
C5—C6—C7	119.5 (3)	S1—C15—H15A	110.1
C5—C6—H6	120.3	C14—C15—H15B	110.1
C7—C6—H6	120.3	S1—C15—H15B	110.1
C6—C7—C2	120.2 (3)	H15A—C15—H15B	108.5
C6—C7—H7	119.9	C14—N1—C8	125.37 (19)
C2—C7—H7	119.9	C14—N1—C1	114.26 (19)
C9—C8—C13	118.3 (2)	C8—N1—C1	120.31 (17)
C9—C8—N1	119.3 (2)	O1—S1—C15	105.16 (13)
C13—C8—N1	122.4 (2)	O1—S1—C1	107.35 (11)
C10—C9—C8	120.6 (2)	C15—S1—C1	87.74 (10)
C10—C9—H9	119.7
N1—C1—C2—C3	−23.1 (3)	C9—C8—C13—C12	−1.0 (4)
S1—C1—C2—C3	96.0 (2)	N1—C8—C13—C12	177.9 (2)
N1—C1—C2—C7	158.9 (2)	O2—C14—C15—S1	−158.4 (2)
S1—C1—C2—C7	−82.1 (2)	N1—C14—C15—S1	23.1 (2)
C7—C2—C3—C4	0.5 (3)	O2—C14—N1—C8	1.0 (4)
C1—C2—C3—C4	−177.5 (2)	C15—C14—N1—C8	179.50 (19)
C2—C3—C4—C5	−0.9 (4)	O2—C14—N1—C1	−176.0 (2)
C3—C4—C5—C6	0.4 (4)	C15—C14—N1—C1	2.4 (3)
C3—C4—C5—Cl1	−179.2 (2)	C9—C8—N1—C14	−163.5 (2)
C4—C5—C6—C7	0.5 (4)	C13—C8—N1—C14	17.7 (3)
Cl1—C5—C6—C7	−179.9 (2)	C9—C8—N1—C1	13.4 (3)
C5—C6—C7—C2	−0.8 (4)	C13—C8—N1—C1	−165.4 (2)
C3—C2—C7—C6	0.3 (4)	C2—C1—N1—C14	95.3 (2)
C1—C2—C7—C6	178.4 (2)	S1—C1—N1—C14	−25.7 (2)
C13—C8—C9—C10	1.4 (4)	C2—C1—N1—C8	−82.0 (2)
N1—C8—C9—C10	−177.5 (2)	S1—C1—N1—C8	157.09 (15)
C8—C9—C10—C11	−0.4 (4)	C14—C15—S1—O1	76.00 (19)
C9—C10—C11—C12	−1.0 (5)	C14—C15—S1—C1	−31.37 (17)
C9—C10—C11—Cl2	177.6 (2)	N1—C1—S1—O1	−72.87 (16)
C10—C11—C12—C13	1.4 (5)	C2—C1—S1—O1	162.31 (15)
Cl2—C11—C12—C13	−177.2 (2)	N1—C1—S1—C15	32.31 (16)
C11—C12—C13—C8	−0.4 (5)	C2—C1—S1—C15	−92.52 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O1^i	0.98	2.19	3.154 (3)	167
C6—H6···Cl2^ii	0.93	2.83	3.676 (3)	152

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