research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages 264-267
doi:10.1107/S2056989015001954

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

CROSSMARK_Color_square_no_text.svg
Hemant P. Yennawar,a John Tierney,b Patrick D. Hullihenc and Lee J. Silverbergc*

aDepartment of Chemistry, Pennsylvania State University, University Park, PA 16802, USA, bPennsylvania State University, Brandywine Campus, 312 M Main Building, 25, Yearsley Mill Rd, Media, PA 19063, USA, and cPennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA
*Correspondence e-mail: ljs43@psu.edu

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 13 January 2015; accepted 29 January 2015; online 11 February 2015)

In the crystal structures of the title compounds, C15H11Cl2NOS, (1), and C15H11Cl2NO2S, (2), wherein (2) is the oxidized form of (1), the thia­zolidine ring is attached to two chloro­phenyl rings. The chloro­phenyl ring on the 2-carbon atom position points in the same direction as that of the S atom in (1), while in (2), the S atom points in the opposite direction. The O atom on the chiral S atom in (2) is trans to the chloro­phenyl ring on the 2-carbon. The chloro­phenyl ring planes in each structure are close to orthogonal, making dihedral angles of 78.61 (6) and 87.46 (8)° in (1) and (2), respectively. The thia­zolidine ring has a twisted conformation on the S—Cmethine bond in (1), and an envelope conformation with the S atom 0.715 (3) Å out of the plane of other four atoms in (2). In the crystal of (1), mol­ecules are linked by C—H⋯O hydrogen bonds, as well as by slipped parallel π–π inter­actions [inter-centroid distance = 3.840 (3) Å] between inversion-related phenyl rings, forming sheets parallel to (001). In the crystal of (2), mol­ecules are linked via C—H⋯O and C—H⋯Cl hydrogen bonds, forming slabs parallel to (001).

CCDC references: 1046346; 1046345

1. 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[Jain, A. K., Vaidya, A., Ravichandran, V., Kashaw, S. K. & Agrawal, R. A. (2012). Bioorg. Med. Chem. 20, 3378-3395.]; Abhinit et al., 2009[Abhinit, M., Ghodke, M. & Pratima, N. A. (2009). Int. J. Pharm. Pharm. Sci. 1, 47-64.]; Hamama et al., 2008[Hamama, W. S., Ismail, M. A., Shaaban, S. & Zoorob, H. H. (2008). J. Heterocycl. Chem. 45, 939-956.]; Singh et al., 1981[Singh, S. P., Parmar, S. S., Raman, R. & Stenberg, V. I. (1981). Chem. Rev. 81, 175-203.]; Brown, 1961[Brown, F. C. (1961). Chem. Rev. 61, 463-521.]; Tripathi et al., 2014[Tripathi, A. C., Gupta, S. J., Fatima, G. N., Sonar, P. K., Verma, A. & Saraf, S. K. (2014). Eur. J. Med. Chem. 72, 52-77.]; Prabhakar et al., 2006[Prabhakar, Y. S., Solomon, V. R., Gupta, M. K. & Katti, S. B. (2006). Top. Heterocycl. Chem. 4, 161-249.]). 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[Gududuru, V., Hurh, E., Dalton, J. T. & Miller, D. D. (2004). Bioorg. Med. Chem. Lett. 14, 5289-5293.]). 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 atom attached to the S atom and the substituent at the 2-position (Rozwadowska et al., 2002[Rozwadowska, M. D., Sulima, A. & Gzella, A. (2002). Tetrahedron Asymmetry, 13, 2329-2333.]; Colombo et al., 2008[Colombo, A., Fernàndez, J. C., Fernández-Forner, D., de la Figuera, N., Albericio, F. & Forns, P. (2008). Tetrahedron Lett. 49, 1569-1572.]). The stereocenters may however be configurationally unstable in solution or even in the solid state (Rozwadowska et al., 2002[Rozwadowska, M. D., Sulima, A. & Gzella, A. (2002). Tetrahedron Asymmetry, 13, 2329-2333.]). 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[Tierney, J., Sheridan, D., Mascavage, L., Gorbecheva, D., Ripp, M. & Son, S. (2005). Heterocycl. Commun. 11, 215-222.]). 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[Trost, B. M. & Curran, D. P. (1981). Tetrahedron Lett. 22, 1287-1290.]; Yu et al., 2012[Yu, B., Liu, A.-H., He, L.-N., Li, B., Diao, Z.-F. & Li, Y.-N. (2012). Green Chem. 14, 957-962.]; Webb, 1994[Webb, K. S. (1994). Tetrahedron Lett. 35, 3457-3460.]), which gave compound (2), and on their crystal structures.

[Scheme 1]

2. Structural commentary

The mol­ecular structures of compounds (1) and (2), Figs. 1[link] and 2[link], 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 atom on the S atom and the aromatic ring on C1 is favoured due to steric hindrance which would occur in the cis isomer. The chloro­phenyl rings are almost orthogonal to each other, making a dihedral angle of 78.61 (6)° in (1) and 87.46 (8)° in (2).

[Figure 1]
Figure 1
A view of the mol­ecular structure of compound (1), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2]
Figure 2
A view of the mol­ecular structure of compound (2), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

Comparison of the two structures shows that the oxygen–sulfur bond in (2) formed on the less hindered side of compound (1), away from the aryl group on C1, leading to a trans stereoisomer. Steric strain was further relieved by twisting so that both the aryl ring on C1 and the oxygen on S1 became pseudo-axial.

3. Supra­molecular features

In the crystal of (1), mol­ecules are linked via C—H⋯O hydrogen bonds, forming chains along [100]; see Table 1[link] and Fig. 3[link]. 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].

Table 1
Hydrogen-bond geometry (Å, °) for (1)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C3—H3⋯O1i 0.93 2.48 3.326 (3) 151
C15—H15B⋯O1ii 0.97 2.46 3.221 (3) 135
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x, -y+1, -z+2.
[Figure 3]
Figure 3
Crystal packing of compound (1) viewed along the a axis, showing the hydrogen bonds as dashed lines (see Table 1[link] for details; H atoms not involved in these inter­actions have been omitted for clarity).

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[link] and Fig. 4[link].

Table 2
Hydrogen-bond geometry (Å, °) for (2)[link]

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C1—H1⋯O1i 0.98 2.19 3.154 (3) 167
C6—H6⋯Cl2ii 0.93 2.83 3.676 (3) 152
Symmetry codes: (i) [x+{\script{1\over 2}}, y, -z+{\script{3\over 2}}]; (ii) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z].
[Figure 4]
Figure 4
Crystal packing of compound (2) viewed along the b axis, showing the hydrogen bonds as dashed lines (see Table 2[link] for details; H atoms not involved in these inter­actions have been omitted for clarity).

4. Database survey

Compound (1) differs from the previously reported 2,3-diphenyl-1, 3-thia­zolidin-4-one (Yennawar et al., 2014[Yennawar, H. P., Tierney, J. & Silverberg, L. J. (2014). Acta Cryst. E70, o847.]) only in the presence of p-chlorine atoms on both 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[Wang, Q., Xu, Z. & Sun, Y. (2010). Acta Cryst. E66, o1422.]), (1b, 2a, 5a)-3, 5-dimethyl-1-oxo-2-phenyl-4-thia­zolidinone (Johnson et al., 1983[Johnson, M. R., Fazio, M. J., Ward, D. L. & Sousa, L. R. (1983). J. Org. Chem. 48, 494-499.]), 2-(2, 6-di­chloro­phen­yl)-3-(4, 5, 6-tri­methyl­pyrimidin-2-yl)-1, 3-thia­zolidin-4-one 1-oxide (Chen et al., 2011[Chen, H., Zai-Hong, G., Qing-Mei, Y. & Xiao-Liu, L. (2011). Chin. J. Org. Chem. 31, 249-255.]) and trans-3-benzyl-2-(4-meth­oxy­phen­yl)thia­zolidin-4-one 1-oxide (Colombo et al., 2008[Colombo, A., Fernàndez, J. C., Fernández-Forner, D., de la Figuera, N., Albericio, F. & Forns, P. (2008). Tetrahedron Lett. 49, 1569-1572.]). All five compounds have a trans relationship between the O atom attached to the S atom and the 2-aryl ring.

5. Synthesis and crystallization

Compound (1): prepared as previously reported (Tierney et al., 2005[Tierney, J., Sheridan, D., Mascavage, L., Gorbecheva, D., Ripp, M. & Son, S. (2005). Heterocycl. Commun. 11, 215-222.]). 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.

6. Refinement details

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

Table 3
Experimental details

  (1) (2)
Crystal data
Chemical formula C15H11Cl2NOS C15H11Cl2NO2S
Mr 324.21 340.21
Crystal system, space group Triclinic, P[\overline{1}] Orthorhombic, Pbca
Temperature (K) 298 298
a, b, c (Å) 8.019 (6), 9.562 (8), 9.984 (8) 7.1094 (17), 20.940 (5), 20.940
α, β, γ (°) 88.937 (13), 76.254 (12), 71.586 (13) 90, 90, 90
V (Å3) 704.3 (10) 3117.4 (11)
Z 2 8
Radiation type Mo Kα Mo Kα
μ (mm−1) 0.60 0.55
Crystal size (mm) 0.22 × 0.20 × 0.16 0.19 × 0.17 × 0.05
 
Data collection
Diffractometer Bruker SMART CCD area detector Bruker SMART CCD area detector
Absorption correction Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Multi-scan (SADABS; Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.879, 0.910 0.902, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections 6575, 3406, 3070 26788, 3862, 2543
Rint 0.016 0.038
(sin θ/λ)max (Å−1) 0.666 0.666
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.099, 1.05 0.051, 0.138, 1.07
No. of reflections 3406 3862
No. of parameters 181 190
H-atom treatment H-atom parameters constrained H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.24, −0.42 0.33, −0.31
Computer programs: SMART and SAINT (Bruker, 2001[Bruker (2001). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information

CCDC references: 1046346; 1046345

Crystal structure: contains datablocks 1, 2, global. DOI: 10.1107/S2056989015001954/su5062sup1.cif

Structure factors: contains datablock 1. DOI: 10.1107/S2056989015001954/su50621sup2.hkl

Structure factors: contains datablock 2. DOI: 10.1107/S2056989015001954/su50622sup3.hkl

Supporting information file. DOI: 10.1107/S2056989015001954/su50621sup4.cml

Supporting information file. DOI: 10.1107/S2056989015001954/su50622sup5.cml

checkCIF report


Chemical context top

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.

Structural commentary top

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).

Supra­molecular features top

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.

Database survey top

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.

Synthesis and crystallization top

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.

Refinement details top

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 Uiso(H) = 1.2Ueq(C).

Related literature top

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 top

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 top
[Figure 1] Fig. 1. A view of the molecular structure of compound (1), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. A view of the molecular structure of compound (2), with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 3] 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).
[Figure 4] 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 top
Crystal data top
C15H11Cl2NOSZ = 2
Mr = 324.21F(000) = 332
Triclinic, P1Dx = 1.529 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.019 (6) ÅCell parameters from 4305 reflections
b = 9.562 (8) Åθ = 2.3–28.2°
c = 9.984 (8) ŵ = 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) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		3406 independent reflections
Radiation source: fine-focus sealed tube3070 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 8.34 pixels mm-1θmax = 28.3°, θmin = 2.1°
phi and ω scansh = −10→10
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		k = −12→12
Tmin = 0.879, Tmax = 0.910l = −13→13
6575 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.036Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0523P)2 + 0.2029P]
where P = (Fo2 + 2Fc2)/3
3406 reflections(Δ/σ)max = 0.001
181 parametersΔρmax = 0.24 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
C15H11Cl2NOSγ = 71.586 (13)°
Mr = 324.21V = 704.3 (10) Å3
Triclinic, P1Z = 2
a = 8.019 (6) ÅMo Kα radiation
b = 9.562 (8) ŵ = 0.60 mm−1
c = 9.984 (8) ÅT = 298 K
α = 88.937 (13)°0.22 × 0.20 × 0.16 mm
β = 76.254 (12)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3406 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		3070 reflections with I > 2σ(I)
Tmin = 0.879, Tmax = 0.910Rint = 0.016
6575 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.099H-atom parameters constrained
S = 1.05Δρmax = 0.24 e Å−3
3406 reflectionsΔρmin = −0.42 e Å−3
181 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.48888 (17)0.30999 (15)0.71043 (13)0.0330 (3)
H10.44910.23000.68380.040*
C20.68202 (17)0.28648 (14)0.63246 (13)0.0310 (3)
C30.78163 (19)0.36815 (16)0.66932 (14)0.0356 (3)
H30.73060.43550.74550.043*
C40.95613 (19)0.34994 (16)0.59348 (14)0.0375 (3)
H41.02330.40400.61840.045*
C51.02943 (19)0.24998 (16)0.47982 (15)0.0391 (3)
C60.9333 (2)0.16883 (17)0.44035 (15)0.0418 (3)
H60.98410.10290.36310.050*
C70.7584 (2)0.18715 (16)0.51810 (14)0.0377 (3)
H70.69200.13230.49320.045*
C80.56811 (17)0.21103 (15)0.93089 (13)0.0317 (3)
C90.64973 (19)0.06770 (15)0.87310 (14)0.0366 (3)
H90.63640.04410.78720.044*
C100.7510 (2)−0.04056 (17)0.94240 (16)0.0422 (3)
H100.8060−0.13660.90340.051*
C110.7694 (2)−0.00403 (18)1.07003 (17)0.0434 (3)
C120.6911 (2)0.13821 (19)1.12805 (16)0.0457 (3)
H120.70530.16141.21390.055*
C130.5915 (2)0.24636 (17)1.05824 (15)0.0395 (3)
H130.54010.34291.09640.047*
C140.29560 (18)0.41916 (16)0.93219 (15)0.0364 (3)
C150.19141 (19)0.51206 (17)0.83648 (16)0.0429 (3)
H15A0.14730.61530.86890.051*
H15B0.08840.48110.83290.051*
Cl11.25015 (6)0.22688 (6)0.38612 (5)0.06617 (16)
Cl20.89079 (7)−0.14012 (6)1.16121 (6)0.06647 (16)
N10.45860 (15)0.32152 (13)0.86178 (11)0.0322 (2)
O10.23825 (15)0.42928 (15)1.05662 (11)0.0510 (3)
S10.34401 (5)0.48672 (5)0.66875 (4)0.04576 (12)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0324 (6)0.0375 (7)0.0286 (6)−0.0104 (5)−0.0075 (5)0.0019 (5)
C20.0327 (6)0.0329 (6)0.0252 (5)−0.0080 (5)−0.0064 (5)0.0040 (5)
C30.0379 (7)0.0386 (7)0.0279 (6)−0.0109 (5)−0.0051 (5)−0.0032 (5)
C40.0380 (7)0.0413 (7)0.0344 (7)−0.0147 (6)−0.0084 (5)0.0018 (6)
C50.0354 (7)0.0393 (7)0.0352 (7)−0.0084 (6)0.0004 (5)0.0025 (6)
C60.0465 (8)0.0391 (7)0.0328 (7)−0.0108 (6)0.0004 (6)−0.0052 (6)
C70.0439 (7)0.0372 (7)0.0322 (6)−0.0145 (6)−0.0072 (6)−0.0016 (5)
C80.0288 (6)0.0361 (6)0.0297 (6)−0.0121 (5)−0.0044 (5)0.0056 (5)
C90.0371 (7)0.0375 (7)0.0333 (6)−0.0120 (6)−0.0053 (5)0.0035 (5)
C100.0378 (7)0.0370 (7)0.0476 (8)−0.0105 (6)−0.0053 (6)0.0093 (6)
C110.0367 (7)0.0487 (8)0.0499 (8)−0.0184 (6)−0.0153 (6)0.0224 (7)
C120.0485 (8)0.0583 (9)0.0392 (7)−0.0240 (7)−0.0185 (6)0.0127 (7)
C130.0413 (7)0.0427 (7)0.0368 (7)−0.0155 (6)−0.0110 (6)0.0022 (6)
C140.0303 (6)0.0402 (7)0.0372 (7)−0.0107 (5)−0.0056 (5)−0.0027 (5)
C150.0308 (6)0.0451 (8)0.0473 (8)−0.0053 (6)−0.0085 (6)0.0014 (6)
Cl10.0465 (2)0.0702 (3)0.0689 (3)−0.0232 (2)0.0179 (2)−0.0170 (2)
Cl20.0627 (3)0.0667 (3)0.0827 (3)−0.0258 (2)−0.0377 (3)0.0424 (3)
N10.0307 (5)0.0357 (5)0.0269 (5)−0.0076 (4)−0.0050 (4)0.0013 (4)
O10.0377 (5)0.0675 (8)0.0360 (5)−0.0062 (5)−0.0002 (4)−0.0081 (5)
S10.0374 (2)0.0520 (2)0.0426 (2)−0.00607 (16)−0.01206 (16)0.01364 (17)
Geometric parameters (Å, º) top
C1—N11.473 (2)C8—N11.4277 (18)
C1—C21.506 (2)C9—C101.386 (2)
C1—S11.8282 (17)C9—H90.9300
C1—H10.9800C10—C111.380 (3)
C2—C71.386 (2)C10—H100.9300
C2—C31.388 (2)C11—C121.377 (3)
C3—C41.382 (2)C11—Cl21.7455 (17)
C3—H30.9300C12—C131.382 (2)
C4—C51.384 (2)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.373 (2)C14—O11.212 (2)
C5—Cl11.7408 (19)C14—N11.3751 (19)
C6—C71.390 (2)C14—C151.510 (2)
C6—H60.9300C15—S11.7930 (19)
C7—H70.9300C15—H15A0.9700
C8—C91.387 (2)C15—H15B0.9700
C8—C131.391 (2)
N1—C1—C2114.30 (11)C10—C9—H9119.8
N1—C1—S1104.57 (9)C8—C9—H9119.8
C2—C1—S1109.22 (10)C11—C10—C9119.14 (15)
N1—C1—H1109.5C11—C10—H10120.4
C2—C1—H1109.5C9—C10—H10120.4
S1—C1—H1109.5C12—C11—C10121.07 (14)
C7—C2—C3119.49 (13)C12—C11—Cl2119.13 (13)
C7—C2—C1119.49 (12)C10—C11—Cl2119.80 (13)
C3—C2—C1120.94 (12)C11—C12—C13119.72 (15)
C4—C3—C2120.40 (13)C11—C12—H12120.1
C4—C3—H3119.8C13—C12—H12120.1
C2—C3—H3119.8C12—C13—C8120.07 (15)
C3—C4—C5119.01 (13)C12—C13—H13120.0
C3—C4—H4120.5C8—C13—H13120.0
C5—C4—H4120.5O1—C14—N1124.72 (14)
C6—C5—C4121.77 (14)O1—C14—C15122.94 (13)
C6—C5—Cl1119.69 (12)N1—C14—C15112.33 (13)
C4—C5—Cl1118.54 (12)C14—C15—S1107.22 (11)
C5—C6—C7118.72 (14)C14—C15—H15A110.3
C5—C6—H6120.6S1—C15—H15A110.3
C7—C6—H6120.6C14—C15—H15B110.3
C2—C7—C6120.60 (13)S1—C15—H15B110.3
C2—C7—H7119.7H15A—C15—H15B108.5
C6—C7—H7119.7C14—N1—C8121.42 (12)
C9—C8—C13119.47 (13)C14—N1—C1115.85 (11)
C9—C8—N1120.56 (13)C8—N1—C1120.65 (11)
C13—C8—N1119.96 (13)C15—S1—C191.77 (7)
C10—C9—C8120.50 (14)
N1—C1—C2—C7138.56 (13)C11—C12—C13—C81.0 (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—C12177.27 (13)
S1—C1—C2—C372.06 (15)O1—C14—C15—S1168.76 (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—C86.5 (2)
C2—C3—C4—C50.5 (2)C15—C14—N1—C8−172.19 (12)
C3—C4—C5—C60.1 (2)O1—C14—N1—C1170.20 (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—C14136.45 (14)
Cl1—C5—C6—C7178.88 (12)C13—C8—N1—C14−42.65 (18)
C3—C2—C7—C60.0 (2)C9—C8—N1—C1−26.44 (18)
C1—C2—C7—C6176.81 (13)C13—C8—N1—C1154.46 (13)
C5—C6—C7—C20.6 (2)C2—C1—N1—C14144.10 (13)
C13—C8—C9—C101.3 (2)S1—C1—N1—C1424.72 (14)
N1—C8—C9—C10−177.86 (12)C2—C1—N1—C8−52.09 (16)
C8—C9—C10—C110.2 (2)S1—C1—N1—C8−171.47 (9)
C9—C10—C11—C12−1.0 (2)C14—C15—S1—C122.62 (11)
C9—C10—C11—Cl2178.08 (11)N1—C1—S1—C15−26.42 (10)
C10—C11—C12—C130.4 (2)C2—C1—S1—C15−149.16 (10)
Cl2—C11—C12—C13−178.68 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.483.326 (3)151
C15—H15B···O1ii0.972.463.221 (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 top
Crystal data top
C15H11Cl2NO2SF(000) = 1392
Mr = 340.21Dx = 1.450 Mg m−3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ab 2acCell parameters from 5771 reflections
a = 7.1094 (17) Åθ = 2.2–28.2°
b = 20.940 (5) ŵ = 0.55 mm−1
c = 20.940 ÅT = 298 K
V = 3117.4 (11) Å3Plate, colourless
Z = 80.19 × 0.17 × 0.05 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3862 independent reflections
Radiation source: fine-focus sealed tube2543 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
Detector resolution: 8.34 pixels mm-1θmax = 28.3°, θmin = 2.0°
phi and ω scansh = −9→9
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		k = −27→27
Tmin = 0.902, Tmax = 0.973l = −27→27
26788 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0581P)2 + 1.0427P]
where P = (Fo2 + 2Fc2)/3
3862 reflections(Δ/σ)max = 0.003
190 parametersΔρmax = 0.33 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Crystal data top
C15H11Cl2NO2SV = 3117.4 (11) Å3
Mr = 340.21Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 7.1094 (17) ŵ = 0.55 mm−1
b = 20.940 (5) ÅT = 298 K
c = 20.940 Å0.19 × 0.17 × 0.05 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer		3862 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)		2543 reflections with I > 2σ(I)
Tmin = 0.902, Tmax = 0.973Rint = 0.038
26788 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.138H-atom parameters constrained
S = 1.07Δρmax = 0.33 e Å−3
3862 reflectionsΔρmin = −0.31 e Å−3
190 parameters
Special details top

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 (Å2) top
xyzUiso*/Ueq
C10.1427 (3)0.56601 (10)0.84451 (10)0.0447 (5)
H10.18170.56150.79990.054*
C20.2832 (3)0.60780 (10)0.87867 (10)0.0446 (5)
C30.3302 (3)0.59815 (12)0.94158 (11)0.0508 (6)
H30.27830.56400.96380.061*
C40.4542 (4)0.63897 (14)0.97198 (12)0.0627 (7)
H40.48430.63261.01470.075*
C50.5322 (4)0.68858 (14)0.93908 (15)0.0710 (8)
C60.4887 (4)0.69891 (13)0.87616 (16)0.0745 (8)
H60.54330.73270.85410.089*
C70.3629 (4)0.65874 (12)0.84583 (12)0.0594 (6)
H70.33160.66580.80330.071*
C80.2445 (3)0.45232 (11)0.85694 (9)0.0455 (5)
C90.4140 (3)0.46695 (12)0.82790 (12)0.0563 (6)
H90.44470.50940.81990.068*
C100.5379 (4)0.41909 (14)0.81076 (13)0.0684 (7)
H100.65110.42930.79100.082*
C110.4939 (5)0.35700 (14)0.82285 (13)0.0716 (8)
C120.3310 (5)0.34158 (14)0.85240 (14)0.0808 (9)
H120.30380.29900.86120.097*
C130.2046 (4)0.38873 (13)0.86954 (13)0.0677 (7)
H130.09250.37780.88960.081*
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−0.09520.58390.95490.071*
H15B−0.27110.55230.92190.071*
Cl10.68956 (15)0.73930 (6)0.97629 (6)0.1258 (4)
Cl20.64436 (17)0.29545 (5)0.79888 (5)0.1196 (4)
N10.1163 (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 (Å2) top
U11U22U33U12U13U23
C10.0457 (12)0.0505 (13)0.0378 (10)−0.0016 (10)0.0072 (9)0.0010 (9)
C20.0398 (11)0.0484 (12)0.0456 (11)0.0011 (10)0.0086 (9)−0.0022 (9)
C30.0454 (13)0.0594 (15)0.0475 (12)−0.0024 (11)0.0063 (10)−0.0046 (10)
C40.0507 (14)0.0793 (19)0.0580 (14)−0.0008 (13)0.0003 (12)−0.0162 (13)
C50.0479 (15)0.077 (2)0.089 (2)−0.0116 (14)0.0071 (14)−0.0282 (16)
C60.0671 (18)0.0580 (17)0.099 (2)−0.0187 (14)0.0212 (16)−0.0015 (15)
C70.0607 (15)0.0567 (15)0.0607 (14)−0.0082 (12)0.0083 (12)0.0027 (12)
C80.0469 (12)0.0508 (13)0.0387 (11)−0.0038 (10)0.0008 (9)−0.0001 (9)
C90.0518 (14)0.0577 (15)0.0593 (14)−0.0008 (11)0.0120 (11)0.0030 (11)
C100.0566 (16)0.079 (2)0.0700 (17)0.0129 (14)0.0092 (13)0.0026 (14)
C110.080 (2)0.0716 (19)0.0636 (16)0.0273 (16)0.0024 (15)0.0056 (14)
C120.110 (3)0.0470 (15)0.085 (2)0.0075 (16)0.0129 (19)0.0078 (14)
C130.0747 (19)0.0548 (16)0.0735 (17)−0.0092 (14)0.0156 (14)0.0053 (13)
C140.0445 (12)0.0728 (16)0.0352 (10)−0.0074 (11)0.0039 (9)0.0008 (11)
C150.0434 (13)0.0903 (19)0.0442 (12)0.0087 (13)0.0042 (10)−0.0051 (12)
Cl10.0974 (7)0.1391 (9)0.1409 (9)−0.0599 (7)−0.0018 (6)−0.0500 (7)
Cl20.1392 (9)0.1012 (7)0.1184 (8)0.0708 (7)0.0144 (7)0.0076 (6)
N10.0405 (9)0.0512 (10)0.0387 (8)−0.0037 (8)0.0068 (7)0.0014 (8)
O10.0607 (12)0.1197 (16)0.0534 (10)−0.0018 (11)−0.0179 (9)−0.0016 (10)
O20.0764 (13)0.0803 (13)0.0579 (10)−0.0134 (10)0.0236 (9)0.0120 (9)
S10.0494 (4)0.0702 (4)0.0484 (3)0.0080 (3)−0.0057 (3)0.0022 (3)
Geometric parameters (Å, º) top
C1—N11.460 (3)C8—N11.425 (3)
C1—C21.508 (3)C9—C101.382 (4)
C1—S11.846 (2)C9—H90.9300
C1—H10.9800C10—C111.361 (4)
C2—C31.374 (3)C10—H100.9300
C2—C71.390 (3)C11—C121.352 (4)
C3—C41.383 (3)C11—Cl21.749 (3)
C3—H30.9300C12—C131.382 (4)
C4—C51.365 (4)C12—H120.9300
C4—H40.9300C13—H130.9300
C5—C61.371 (4)C14—O21.213 (3)
C5—Cl11.728 (3)C14—N11.372 (3)
C6—C71.382 (4)C14—C151.506 (4)
C6—H60.9300C15—S11.784 (2)
C7—H70.9300C15—H15A0.9700
C8—C91.384 (3)C15—H15B0.9700
C8—C131.387 (3)O1—S11.4742 (19)
N1—C1—C2115.38 (18)C8—C9—H9119.7
N1—C1—S1105.78 (14)C11—C10—C9119.9 (3)
C2—C1—S1109.30 (15)C11—C10—H10120.1
N1—C1—H1108.7C9—C10—H10120.1
C2—C1—H1108.7C12—C11—C10120.7 (3)
S1—C1—H1108.7C12—C11—Cl2118.6 (2)
C3—C2—C7119.2 (2)C10—C11—Cl2120.7 (2)
C3—C2—C1122.0 (2)C11—C12—C13120.3 (3)
C7—C2—C1118.7 (2)C11—C12—H12119.8
C2—C3—C4120.4 (2)C13—C12—H12119.8
C2—C3—H3119.8C12—C13—C8120.2 (3)
C4—C3—H3119.8C12—C13—H13119.9
C5—C4—C3119.8 (2)C8—C13—H13119.9
C5—C4—H4120.1O2—C14—N1125.1 (2)
C3—C4—H4120.1O2—C14—C15123.8 (2)
C4—C5—C6120.9 (3)N1—C14—C15111.1 (2)
C4—C5—Cl1120.2 (2)C14—C15—S1107.83 (15)
C6—C5—Cl1118.9 (2)C14—C15—H15A110.1
C5—C6—C7119.5 (3)S1—C15—H15A110.1
C5—C6—H6120.3C14—C15—H15B110.1
C7—C6—H6120.3S1—C15—H15B110.1
C6—C7—C2120.2 (3)H15A—C15—H15B108.5
C6—C7—H7119.9C14—N1—C8125.37 (19)
C2—C7—H7119.9C14—N1—C1114.26 (19)
C9—C8—C13118.3 (2)C8—N1—C1120.31 (17)
C9—C8—N1119.3 (2)O1—S1—C15105.16 (13)
C13—C8—N1122.4 (2)O1—S1—C1107.35 (11)
C10—C9—C8120.6 (2)C15—S1—C187.74 (10)
C10—C9—H9119.7
N1—C1—C2—C3−23.1 (3)C9—C8—C13—C12−1.0 (4)
S1—C1—C2—C396.0 (2)N1—C8—C13—C12177.9 (2)
N1—C1—C2—C7158.9 (2)O2—C14—C15—S1−158.4 (2)
S1—C1—C2—C7−82.1 (2)N1—C14—C15—S123.1 (2)
C7—C2—C3—C40.5 (3)O2—C14—N1—C81.0 (4)
C1—C2—C3—C4−177.5 (2)C15—C14—N1—C8179.50 (19)
C2—C3—C4—C5−0.9 (4)O2—C14—N1—C1−176.0 (2)
C3—C4—C5—C60.4 (4)C15—C14—N1—C12.4 (3)
C3—C4—C5—Cl1−179.2 (2)C9—C8—N1—C14−163.5 (2)
C4—C5—C6—C70.5 (4)C13—C8—N1—C1417.7 (3)
Cl1—C5—C6—C7−179.9 (2)C9—C8—N1—C113.4 (3)
C5—C6—C7—C2−0.8 (4)C13—C8—N1—C1−165.4 (2)
C3—C2—C7—C60.3 (4)C2—C1—N1—C1495.3 (2)
C1—C2—C7—C6178.4 (2)S1—C1—N1—C14−25.7 (2)
C13—C8—C9—C101.4 (4)C2—C1—N1—C8−82.0 (2)
N1—C8—C9—C10−177.5 (2)S1—C1—N1—C8157.09 (15)
C8—C9—C10—C11−0.4 (4)C14—C15—S1—O176.00 (19)
C9—C10—C11—C12−1.0 (5)C14—C15—S1—C1−31.37 (17)
C9—C10—C11—Cl2177.6 (2)N1—C1—S1—O1−72.87 (16)
C10—C11—C12—C131.4 (5)C2—C1—S1—O1162.31 (15)
Cl2—C11—C12—C13−177.2 (2)N1—C1—S1—C1532.31 (16)
C11—C12—C13—C8−0.4 (5)C2—C1—S1—C15−92.52 (16)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.982.193.154 (3)167
C6—H6···Cl2ii0.932.833.676 (3)152
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+3/2, y+1/2, z.
Hydrogen-bond geometry (Å, º) for (1) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O1i0.932.483.326 (3)151
C15—H15B···O1ii0.972.463.221 (3)135
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x, −y+1, −z+2.
Hydrogen-bond geometry (Å, º) for (2) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O1i0.982.193.154 (3)167
C6—H6···Cl2ii0.932.833.676 (3)152
Symmetry codes: (i) x+1/2, y, −z+3/2; (ii) −x+3/2, y+1/2, z.

Experimental details

(1)(2)
Crystal data
Chemical formulaC15H11Cl2NOSC15H11Cl2NO2S
Mr324.21340.21
Crystal system, space groupTriclinic, P1Orthorhombic, Pbca
Temperature (K)298298
a, b, c (Å)8.019 (6), 9.562 (8), 9.984 (8)7.1094 (17), 20.940 (5), 20.940
α, β, γ (°)88.937 (13), 76.254 (12), 71.586 (13)90, 90, 90
V (Å3)704.3 (10)3117.4 (11)
Z28
Radiation typeMo KαMo Kα
µ (mm−1)0.600.55
Crystal size (mm)0.22 × 0.20 × 0.160.19 × 0.17 × 0.05
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer		Bruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2001)		Multi-scan
(SADABS; Bruker, 2001)
Tmin, Tmax0.879, 0.9100.902, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections		6575, 3406, 3070 26788, 3862, 2543
Rint0.0160.038
(sin θ/λ)max (Å−1)0.6660.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.036, 0.099, 1.05 0.051, 0.138, 1.07
No. of reflections34063862
No. of parameters181190
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.24, −0.420.33, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

 

Acknowledgements

We acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer.

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ISSN: 2056-9890
Volume 71| Part 3| March 2015| Pages 264-267
doi:10.1107/S2056989015001954
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