Crystal structures of two 1,3-thia­zolidin-4-one derivatives featuring sulfide and sulfone functional groups

Yennawar, H.P.; Silverberg, L.J.; Cannon, K.; Gandla, D.; Kondaveeti, S.K.; Zdilla, M.J.; Nuriye, A.

doi:10.1107/S2056989018015098

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Volume 74| Part 12| December 2018| Pages 1695-1699

https://doi.org/10.1107/S2056989018015098

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Crystal structures of two 1,3-thiazolidin-4-one derivatives featuring sulfide and sulfone functional groups

Hemant P. Yennawar,^a Lee J. Silverberg,^b Kevin Cannon,^c Deepa Gandla,^d Sandeep K. Kondaveeti,^d Michael J. Zdilla ^d and Ahmed Nuriye ^c ^*

^aDepartment of Biochemistry and Molecular Biology, The Pennsylvania State University, University Park, Pennsylvania, 16802, USA, ^bDepartment of Chemistry, The Pennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, Pennsylvania, 17972, USA, ^cDepartment of Chemistry, The Pennsylvania State University, Abington College, 1600 Woodland Road, Abington, Pennsylvania, 19001, USA, and ^dDepartment of Chemistry, Temple University, 1901 North 13th Street, Philadelphia, Pennsylvania, 19122, USA
^*Correspondence e-mail: auy3@psu.edu

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 23 October 2018; accepted 25 October 2018; online 6 November 2018)

The crystal structures of two closely related compounds, 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one, C₁₅H₁₈N₂O₃S, (1) and 1-cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide, C₁₅H₁₈N₂O₅S, (2), are presented. These compounds are comprised of three types of rings: thiazolidinone, nitrophenyl and cyclohexyl. In both structures, the rings are close to mutually perpendicular, with interplanar dihedral angles greater than 80° in each case. The thiazolidinone rings in both structures exhibit envelope puckering with the S atom as flap and the cyclohexyl rings are in their expected chair conformations. The two structures superpose fairly well, except for the orientation of the nitro groups with respect to their host phenyl ring, with a difference of about 10° between 1 and 2. The extended structure of 1 has two kinds of weak C—H⋯O interactions, giving rise to a closed ring formation involving three symmetry-related molecules. Structure 2 has four C—H⋯O interactions, two of which are exclusively between symmetry-related thiazolidinone dioxide moieties and have a parallel `give-and-take-fashion' counterpart. In the other two interactions, the nitrophenyl ring and the cyclohexane ring each offer an H atom to the two O atoms on the sulfone group. Additionally, a C—H⋯π interaction between a C—H group of the cyclohexane ring and the nitrophenyl ring of an adjacent molecule helps to consolidate the structure.

Keywords: crystal structure; thiazolidin-4-one; thiazolidinone; envelope pucker; chair conformation.

CCDC references: 1875395; 1875394

1. Chemical context

The title compounds were synthesized as a part of our ongoing work on the synthesis of new types of 2,3-disubstituted 1,3-thiazolidin-4-ones. We have reported the crystal structures of a number of these compounds before (Nuriye et al., 2018 ; Yennawar et al., 2015 ). These compounds are synthesized by a tandem nucleophilic addition-carbonyl condensation of thioglycolic acid with the desired in situ-generated imine. The variation in substitution pattern is set during the synthesis of the imine where alkyl or aryl amines are condensed with an aldehyde (Surrey, 1947 ; von Erlenmeyer & Oberlin, 1947 ). In addition, the S atom in the thiazolidinone ring can be oxidized to the sulfoxide or the sulfone to produce structures with different properties. Thiazolidinones have well documented biological activity (Thakare et al., 2018 ; Brown, 1961 ; Abdel Rahman et al., 1990 ; Joshi et al., 2014 ; Suryawanshi et al., 2017 ; Kaushal & Kaur, 2016 ; Kumar et al., 2015 ; Tripathi et al., 2014 ; Jain et al., 2012 ; Abhinit et al. 2009 ; Hamama et al., 2008 ; Singh et al., 1981 ). The synthesis and characterization of these compounds could be valuable in investigations for the practical applications of their activities. To the best of our knowledge, only two crystal structures of thiazolidinone sulfones have been reported in the literature (Orsini et al., 1995 ; Glasl et al., 1997 ). The compounds presented in this paper both feature an ortho-nitrophenyl ring at position 2 and a cyclohexane ring at the 3-position of the thiazolidinone ring. Compound 1 is a sulfide, while compound 2 contains a fully oxidized sulfone functional group.

2. Structural commentary

Compound 2 is the dioxide version of 1, both comprising of three types of rings, a thiazolidinone (A), a nitrophenyl (B) and a cyclohexyl (C) ring. In each structure, the interplanar dihedral angles between the three pairs of rings are close to orthogonal, with values of (in ascending order) A/C = 84.04 (9), B/C = 84.98 (10) and A/B = 85.85 (9)°. The corresponding data for 2 span a slightly wider range: B/C = 80.74 (6), A/B = 83.12 (6) and A/C = 87.96 (6)° (Figs. 1 and 2). In both structures, the thiazolidinone rings exhibit an envelope pucker conformation with the sulfur atom as a flap. The cyclohexyl rings are in the most stable chair conformation in both structures. An overlay of the two structures (Fig. 3) shows that they overlap well. Fig. 3 also shows that the nitro group plane in 2 is twisted further away by ca 10° from the nitrophenyl ring plane as compared to that in 1; the dihedral angles between the nitro group plane and the host phenyl ring plane were found to be 18.3 (5)° in 1 and 28.3 (5)° in 2.

Figure 1
The molecular structure of 1 with displacement ellipsoids drawn at the 50% probability level.

Figure 2
The molecular structure of 2 with displacement ellipsoids drawn at the 50% probability level.

Figure 3
Overlay image of the two title molecules showing the difference in the orientation of the nitro group with respect to the nitrophenyl ring plane.

Looking at the thiazolidinone ring systems, the C1—N1 and C1—S1 bond lengths are 1.438 (3) and 1.839 (3) Å, respectively, for structure 1 and 1.4527 (13) and 1.8382 (12) Å for structure 2. The N—C—S bond angle is found to be 105.22 (12)° in structure 1 and 101.36 (7)° in structure 2 indicating a compression of the N—C—S bond angle going from the sulfide to the sulfone. Bond length and angle values in the thiazolidinone ring of the sulfide appear to be typical and match data that we have previously reported (Nuriye et al., 2018). Although structural data for the sulfone are scarce, the data reported by Orsini et al. (1995) matches our findings.

3. Supramolecular features

In structure 1, two weak C—H⋯O type interactions (Table 1) result in a closed-ring formation of three symmetry-related molecules (Fig. 4). One of the nitrophenyl-ring carbon atoms donates its H atom to the oxygen atom on the thiazolidinone ring of a neighboring molecule [C8⋯O1 = 3.411 (5) Å, C—H⋯O = 140°], which then interacts with a third symmetry-related molecule through a symmetry-equivalent contact. Finally, this third molecule donates one of its cyclohexane protons to the nitrophenyl oxygen atom of the first molecule [C15⋯O3 = 3.437 (5) Å, 138°], thus completing the three-molecule ring arrangement. In the extended structure, the molecules arrange themselves in distinct layers in (020) planes. Perpendicular to c, the longest axis, there is an alternating pattern of hydrophobic and hydrophilic surfaces of the molecules, as is evident in the packing diagram (Fig. 5).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1ⁱ	0.93	2.65	3.411 (5)	140
C15—H15B⋯O3ⁱⁱ	0.97	2.66	3.437 (5)	138
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) x+1, y, z.

Figure 4
Hydrogen-bond interactions between three symmetry-related molecules of 1 forming a closed-ring system.

Figure 5
View down the a axis of the packing of 1. The layering of molecules in the (020) plane as well as the alternating pattern of hydrophobic and hydrophilic regions perpendicular to c axis can be seen.

In structure 2, we observe four C—H⋯O type interactions (Table 2). Two of these involve the thiazolidinone dioxide moieties exclusively and have parallel `give-and-take' type counterparts [C⋯O = 3.4594 (16) Å, 161° and 3.3068 (16) Å, 157°], forming continuous chains propagating along the b-axis direction. The remaining two interactions are weaker and involve the carbon atoms of nitrophenyl rings and cyclohexane rings of one molecule offering protons to the oxygen pair of the dioxide group [C9⋯O1 3.5144 (16) Å, 132.6° and 3.4381 (16) Å, 129°] of a symmetry-related molecule. Similar to packing of 1, the molecules are arranged in distinct layers but this time in ( $[\overline{2}]$ 02) planes. Also seen is the alternating pattern of hydrophobic and hydrophilic surfaces perpendicular to the c-axis direction (Fig. 6).

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯O1ⁱ	0.99	2.51	3.4594 (16)	161
C3—H3B⋯O3ⁱⁱ	0.99	2.37	3.3068 (16)	157
C9—H9⋯O1ⁱⁱⁱ	0.95	2.80	3.5144 (16)	133
C10—H10⋯O2ⁱⁱⁱ	1.00	2.72	3.4381 (16)	129
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+1, -y+2, -z+2; (iii) x-1, y, z.

Figure 6
View down the b axis of the packing arrangement of 2. The layering of molecules in the ( $[\overline{2}]$ 02) plane as well as the alternating pattern of hydrophobic and hydrophilic regions perpendicular to the c axis can be seen.

4. Synthesis and crystallization

1-Cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one: Following the reported method (Cannon et al., 2015 ), 2-nitrobenzaldehyde (0.725 g, 4.80 mmol) was dissolved in CH₂Cl₂ (20 ml) and anhydrous MgSO₄ (3.0 g) and cyclohexyamine (0.5 g, 5 mmol) were added sequentially and stirred for 4 h at r.t. under nitrogen. The MgSO₄ was filtered off and the reaction was concentrated in vacuo to give 0.9826 g of an orange oil, which solidified upon sitting in a freezer and remained solid upon warming up to room temperature.

The crude imine was resuspended in toluene (25 ml) and thioglycolic acid (0.55 g, 6.0 mmol) was added and the reaction was heated at reflux for 1.5 h with a Dean–Stark trap attached. The reaction was then cooled to room temperature and washed with aqueous NaHCO₃ (2 × 35 ml). The combined organic layers were dried over anhydrous Na₂SO₄, filtered, and concentrated under reduced pressure to give an orange oil. The crude substance was purified by flash column chromatography on silica gel (15 g) using 20–60% ethyl acetate in hexanes as the eluent to yield a yellow solid (0.720 g). The solid was recrystallized from ethanol solution to give a pale-yellow solid (0.508 g, 36.4% over two steps). mp 373–383 K; IR: cm⁻¹ 1671.1 (C=O); ¹H NMR (CDCl₃): 8.08–7.46 (4H, m, aromatics), 6.25 (1H, C2), 3.94 (1H, tt, J = 12.2 Hz, and J = 3.6 Hz, NCH), 3.76 (1H, dd, C5, J = 0.7 Hz, and J = 15.7 Hz), 3.47 (1H, d, C5, J = 15.7 Hz), 1.96–0.86 (10H, m, cyclohexyls); ¹³C NMR: 172.95 (C4), 146.05, 139.12, 134.02, 129.04, 126.72, 125.68, 58.82 (C2), 55.74, 32.20(C5), 31.25, 30.29, 25.89, 25.70, 25.19; MS: (m/z) 306 (M⁺) C₁₅H₁₈O₃N₂S (306.10).

Crystals for X-ray data collection were grown by dissolving 0.101 g of the solid in hot ethanol and slow evaporation of the solvent.

1-Cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide: 1-Cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one (0.553 mmol) was dissolved in glacial acetic acid (2.4 ml), to which an aqueous solution of KMnO₄ (175 mg, 1.11 mmol, in 3.0 ml water) was added dropwise at room temperature with vigorous stirring, and stirred for an additional 5 min. Solid sodium bisulfite (NaHSO₃/Na₂S₂O₅) was then added until the solution remained colorless; 3.0 ml of water was then added and the mixture was stirred for a further 10 min. The resulting solid precipitate was filtered and rinsed with water. The resulting powder was purified by recrystallization from CH₃OH solution. Yield (64%); m.p. 471–472 K; IR: cm⁻¹ 1689.6 (C=O), 1326.9, 1308.1, 1162.7 (S=O); ¹H NMR (CDCl₃): 8.38 (1H, dd, J = 8.0, and J = 1.2 Hz, aromatic), 7.78 (1H, dddd, J = 8.0, 8.0, 1.2, 0.8 Hz, aromatic), 7.68 (1H, ddd, J = 8.0, 8.0, 1.2 Hz, aromatic), 7.54 (1H, dd, J = 7.6, 1.2 Hz, aromatic), 6.77 (1H, s, C2), 4.41 (1H, tt, J = 12.0, and J = 3.6 Hz, NCH), 3.76 (dd, J = 16.0 Hz, and J = 0.4 Hz, 1H), 3.69 (d, J = 16.4 Hz, 1 H), 1.96–0.82 (10 H, m, cyclohexyls); ¹³C NMR: 163.41 (C4), 147.80, 134.43, 131.22, 128.82, 126.92 75.77, 54.52, 50.16, 31.39, 29.67, 25.50, 25.16, 24.84; MS: (m/z) 339 ([M + H]⁺) C₁₅H₁₈O₅N₂S (338.09).

Crystals for X-ray data collection were grown by slow evaporation of a hot methanol solution of the compound.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The H atoms were placed geometrically and allowed to ride on their parent C atoms during refinement, with C—H distances of 0.93 Å (aromatic), 0.97 Å (methylene) and 0.98 Å (methyl), with U_iso(H) = 1.2U_eq(aromatic or methylene C) or 1.5U_eq(methyl C).

Table 3
Experimental details

	1	2
Crystal data
Chemical formula	C₁₅H₁₈N₂O₃S	C₁₅H₁₈N₂O₅S
M_r	306.37	338.37
Crystal system, space group	Orthorhombic, Pbca	Triclinic, P $[\overline{1}]$
Temperature (K)	298	100
a, b, c (Å)	9.582 (13), 11.444 (15), 26.69 (4)	7.114 (2), 9.401 (3), 12.038 (3)
α, β, γ (°)	90, 90, 90	94.808 (5), 92.110 (5), 107.198 (5)
V (Å³)	2927 (7)	764.8 (4)
Z	8	2
Radiation type	Mo Kα	Mo Kα
μ (mm⁻¹)	0.23	0.24
Crystal size (mm)	0.27 × 0.25 × 0.2	0.29 × 0.11 × 0.06

Data collection
Diffractometer	Bruker SMART CCD area detector	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Bruker, 2001 )	Multi-scan (SADABS; Bruker, 2013 )
T_min, T_max	0.732, 0.955	0.815, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	24930, 3685, 2924	9076, 3728, 3475
R_int	0.029	0.015
(sin θ/λ)_max (Å⁻¹)	0.673	0.663

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.135, 1.08	0.030, 0.082, 1.05
No. of reflections	3685	3728
No. of parameters	190	208
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.17	0.45, −0.34
Computer programs: SMART and SAINT (Bruker, 2001), COSMO and SAINT (Bruker, 2013), SHELXS97 (Sheldrick, 2008 ), SHELXL2014 and SHELXL2016 (Sheldrick, 2015 ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC references: 1875395; 1875394

Crystal structure: contains datablocks 1, 2. DOI: https://doi.org/10.1107/S2056989018015098/hb7781sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989018015098/hb77811sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989018015098/hb77812sup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018015098/hb77811sup4.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989018015098/hb77812sup5.cml

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2001) for (1); COSMO (Bruker, 2013) for (2). Cell refinement: SAINT (Bruker, 2001) for (1); SAINT (Bruker, 2013) for (2). Data reduction: SAINT (Bruker, 2001) for (1); SAINT (Bruker, 2013) for (2). For both structures, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015) for (1); SHELXL2014 (Sheldrick, 2015) for (2). For both structures, molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

1-Cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one (1) top

Crystal data top

C₁₅H₁₈N₂O₃S	D_x = 1.391 Mg m⁻³
M_r = 306.37	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 5287 reflections
a = 9.582 (13) Å	θ = 2.6–24.3°
b = 11.444 (15) Å	µ = 0.23 mm⁻¹
c = 26.69 (4) Å	T = 298 K
V = 2927 (7) Å³	Plate, colorless
Z = 8	0.27 × 0.25 × 0.2 mm
F(000) = 1296

Data collection top

Bruker SMART CCD area detector diffractometer	2924 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
phi and ω scans	θ_max = 28.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
T_min = 0.732, T_max = 0.955	k = −13→15
24930 measured reflections	l = −34→35
3685 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.053	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0614P)² + 0.9885P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max = 0.001
3685 reflections	Δρ_max = 0.35 e Å⁻³
190 parameters	Δρ_min = −0.17 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.

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

	x	y	z	U_iso*/U_eq
S1	0.64305 (5)	0.59741 (4)	0.55845 (2)	0.05141 (17)
O1	0.95808 (13)	0.40036 (13)	0.55305 (5)	0.0543 (4)
O2	0.43309 (16)	0.62101 (16)	0.64290 (7)	0.0743 (5)
O3	0.23757 (18)	0.55133 (18)	0.66333 (8)	0.0905 (6)
N1	0.76951 (13)	0.42423 (13)	0.60346 (5)	0.0360 (3)
N2	0.34792 (16)	0.54315 (17)	0.64206 (6)	0.0524 (4)
C1	0.63847 (16)	0.48476 (15)	0.60757 (7)	0.0374 (4)
H1	0.631265	0.521843	0.640564	0.045*
C2	0.84294 (17)	0.43948 (18)	0.56067 (7)	0.0417 (4)
C3	0.7632 (2)	0.5110 (2)	0.52278 (7)	0.0533 (5)
H3A	0.713666	0.460539	0.499625	0.064*
H3B	0.826129	0.560651	0.503872	0.064*
C4	0.51274 (17)	0.40812 (15)	0.59855 (6)	0.0371 (4)
C5	0.37756 (17)	0.43693 (18)	0.61324 (7)	0.0418 (4)
C6	0.26504 (19)	0.3690 (2)	0.60127 (8)	0.0533 (5)
H6	0.176194	0.390377	0.611901	0.064*
C7	0.2834 (2)	0.2698 (2)	0.57371 (8)	0.0603 (6)
H7	0.206700	0.224720	0.564627	0.072*
C8	0.4151 (2)	0.2367 (2)	0.55939 (8)	0.0585 (5)
H8	0.428365	0.168290	0.541158	0.070*
C9	0.5272 (2)	0.30517 (18)	0.57219 (7)	0.0470 (4)
H9	0.616167	0.281283	0.562734	0.056*
C10	0.83474 (16)	0.37054 (16)	0.64788 (6)	0.0359 (4)
H10	0.911045	0.320833	0.635901	0.043*
C11	0.73624 (19)	0.29343 (17)	0.67713 (6)	0.0438 (4)
H11A	0.701899	0.231608	0.655539	0.053*
H11B	0.656828	0.339271	0.688165	0.053*
C12	0.8082 (2)	0.2396 (2)	0.72259 (7)	0.0544 (5)
H12A	0.740381	0.195440	0.741803	0.065*
H12B	0.879757	0.185814	0.711273	0.065*
C13	0.8736 (2)	0.3306 (2)	0.75583 (7)	0.0580 (6)
H13A	0.924527	0.292580	0.782674	0.070*
H13B	0.801130	0.378481	0.770746	0.070*
C14	0.9720 (2)	0.4073 (2)	0.72616 (8)	0.0602 (6)
H14A	1.050130	0.360810	0.714471	0.072*
H14B	1.008345	0.468373	0.747720	0.072*
C15	0.89855 (19)	0.46261 (18)	0.68135 (8)	0.0498 (5)
H15A	0.825973	0.514902	0.693159	0.060*
H15B	0.965152	0.508361	0.662267	0.060*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0457 (3)	0.0450 (3)	0.0635 (3)	0.0006 (2)	−0.0051 (2)	0.0116 (2)
O1	0.0367 (7)	0.0788 (10)	0.0473 (8)	0.0056 (6)	0.0121 (5)	0.0074 (7)
O2	0.0446 (8)	0.0696 (11)	0.1087 (14)	0.0105 (8)	−0.0022 (8)	−0.0240 (10)
O3	0.0650 (10)	0.0923 (14)	0.1142 (15)	0.0137 (10)	0.0447 (11)	−0.0008 (12)
N1	0.0265 (6)	0.0465 (8)	0.0350 (7)	0.0030 (6)	0.0009 (5)	0.0024 (6)
N2	0.0391 (8)	0.0655 (11)	0.0525 (10)	0.0153 (8)	0.0033 (7)	0.0072 (8)
C1	0.0293 (7)	0.0437 (9)	0.0392 (9)	0.0029 (7)	−0.0013 (6)	0.0000 (7)
C2	0.0358 (8)	0.0510 (10)	0.0384 (9)	−0.0043 (7)	0.0015 (7)	0.0026 (8)
C3	0.0499 (10)	0.0674 (13)	0.0427 (10)	−0.0001 (10)	0.0020 (8)	0.0133 (9)
C4	0.0297 (7)	0.0488 (10)	0.0328 (8)	0.0009 (7)	−0.0028 (6)	0.0050 (7)
C5	0.0335 (8)	0.0559 (11)	0.0361 (9)	0.0031 (7)	−0.0018 (7)	0.0113 (8)
C6	0.0319 (8)	0.0767 (15)	0.0514 (11)	−0.0066 (9)	−0.0026 (8)	0.0171 (10)
C7	0.0471 (11)	0.0782 (16)	0.0557 (12)	−0.0246 (11)	−0.0119 (9)	0.0133 (12)
C8	0.0618 (13)	0.0614 (13)	0.0522 (12)	−0.0143 (11)	−0.0078 (10)	−0.0044 (10)
C9	0.0401 (9)	0.0551 (11)	0.0458 (10)	−0.0031 (8)	−0.0012 (8)	−0.0047 (9)
C10	0.0277 (7)	0.0446 (9)	0.0354 (8)	0.0052 (6)	0.0010 (6)	0.0004 (7)
C11	0.0447 (9)	0.0524 (11)	0.0341 (9)	−0.0078 (8)	−0.0021 (7)	−0.0002 (8)
C12	0.0598 (11)	0.0640 (13)	0.0395 (10)	−0.0026 (10)	−0.0014 (9)	0.0090 (9)
C13	0.0509 (11)	0.0862 (16)	0.0368 (10)	0.0024 (11)	−0.0085 (8)	−0.0009 (10)
C14	0.0443 (10)	0.0800 (16)	0.0564 (12)	−0.0056 (10)	−0.0177 (9)	−0.0020 (11)
C15	0.0384 (9)	0.0538 (12)	0.0570 (12)	−0.0061 (8)	−0.0118 (8)	−0.0006 (9)

Geometric parameters (Å, º) top

S1—C1	1.839 (3)	C8—H8	0.9300
S1—C3	1.792 (3)	C8—C9	1.373 (3)
O1—C2	1.208 (2)	C9—H9	0.9300
O2—N2	1.209 (3)	C10—H10	0.9800
O3—N2	1.204 (2)	C10—C11	1.510 (3)
N1—C1	1.438 (3)	C10—C15	1.511 (3)
N1—C2	1.353 (3)	C11—H11A	0.9700
N1—C10	1.474 (2)	C11—H11B	0.9700
N2—C5	1.466 (3)	C11—C12	1.525 (3)
C1—H1	0.9800	C12—H12A	0.9700
C1—C4	1.509 (3)	C12—H12B	0.9700
C2—C3	1.508 (3)	C12—C13	1.505 (3)
C3—H3A	0.9700	C13—H13A	0.9700
C3—H3B	0.9700	C13—H13B	0.9700
C4—C5	1.393 (3)	C13—C14	1.511 (3)
C4—C9	1.379 (3)	C14—H14A	0.9700
C5—C6	1.367 (3)	C14—H14B	0.9700
C6—H6	0.9300	C14—C15	1.525 (3)
C6—C7	1.364 (4)	C15—H15A	0.9700
C7—H7	0.9300	C15—H15B	0.9700
C7—C8	1.372 (4)

C3—S1—C1	90.40 (12)	C8—C9—C4	122.42 (19)
C1—N1—C10	120.64 (14)	C8—C9—H9	118.8
C2—N1—C1	117.15 (15)	N1—C10—H10	107.2
C2—N1—C10	120.80 (16)	N1—C10—C11	113.22 (15)
O2—N2—C5	119.36 (17)	N1—C10—C15	110.87 (17)
O3—N2—O2	121.8 (2)	C11—C10—H10	107.2
O3—N2—C5	118.8 (2)	C11—C10—C15	110.80 (17)
S1—C1—H1	109.8	C15—C10—H10	107.2
N1—C1—S1	105.22 (12)	C10—C11—H11A	109.4
N1—C1—H1	109.8	C10—C11—H11B	109.4
N1—C1—C4	113.88 (17)	C10—C11—C12	111.39 (17)
C4—C1—S1	108.22 (12)	H11A—C11—H11B	108.0
C4—C1—H1	109.8	C12—C11—H11A	109.4
O1—C2—N1	124.72 (17)	C12—C11—H11B	109.4
O1—C2—C3	123.40 (17)	C11—C12—H12A	109.2
N1—C2—C3	111.88 (17)	C11—C12—H12B	109.2
S1—C3—H3A	110.6	H12A—C12—H12B	107.9
S1—C3—H3B	110.6	C13—C12—C11	112.2 (2)
C2—C3—S1	105.59 (16)	C13—C12—H12A	109.2
C2—C3—H3A	110.6	C13—C12—H12B	109.2
C2—C3—H3B	110.6	C12—C13—H13A	109.5
H3A—C3—H3B	108.8	C12—C13—H13B	109.5
C5—C4—C1	124.04 (18)	C12—C13—C14	110.66 (19)
C9—C4—C1	119.83 (16)	H13A—C13—H13B	108.1
C9—C4—C5	116.05 (17)	C14—C13—H13A	109.5
C4—C5—N2	121.60 (17)	C14—C13—H13B	109.5
C6—C5—N2	116.18 (18)	C13—C14—H14A	109.4
C6—C5—C4	122.2 (2)	C13—C14—H14B	109.4
C5—C6—H6	120.1	C13—C14—C15	111.34 (18)
C7—C6—C5	119.84 (19)	H14A—C14—H14B	108.0
C7—C6—H6	120.1	C15—C14—H14A	109.4
C6—C7—H7	120.0	C15—C14—H14B	109.4
C6—C7—C8	119.92 (19)	C10—C15—C14	111.15 (19)
C8—C7—H7	120.0	C10—C15—H15A	109.4
C7—C8—H8	120.3	C10—C15—H15B	109.4
C7—C8—C9	119.5 (2)	C14—C15—H15A	109.4
C9—C8—H8	120.3	C14—C15—H15B	109.4
C4—C9—H9	118.8	H15A—C15—H15B	108.0

S1—C1—C4—C5	−81.4 (2)	C2—N1—C1—C4	102.13 (19)
S1—C1—C4—C9	95.38 (19)	C2—N1—C10—C11	−143.59 (18)
O1—C2—C3—S1	−155.76 (17)	C2—N1—C10—C15	91.2 (2)
O2—N2—C5—C4	18.2 (3)	C3—S1—C1—N1	25.72 (13)
O2—N2—C5—C6	−161.08 (19)	C3—S1—C1—C4	−96.37 (16)
O3—N2—C5—C4	−163.46 (19)	C4—C5—C6—C7	−0.5 (3)
O3—N2—C5—C6	17.2 (3)	C5—C4—C9—C8	2.3 (3)
N1—C1—C4—C5	162.03 (16)	C5—C6—C7—C8	2.0 (3)
N1—C1—C4—C9	−21.2 (2)	C6—C7—C8—C9	−1.3 (3)
N1—C2—C3—S1	24.8 (2)	C7—C8—C9—C4	−1.0 (3)
N1—C10—C11—C12	179.86 (15)	C9—C4—C5—N2	179.17 (16)
N1—C10—C15—C14	−177.41 (15)	C9—C4—C5—C6	−1.6 (3)
N2—C5—C6—C7	178.77 (17)	C10—N1—C1—S1	150.33 (13)
C1—S1—C3—C2	−28.32 (15)	C10—N1—C1—C4	−91.31 (19)
C1—N1—C2—O1	175.24 (18)	C10—N1—C2—O1	8.7 (3)
C1—N1—C2—C3	−5.3 (2)	C10—N1—C2—C3	−171.82 (16)
C1—N1—C10—C11	50.3 (2)	C10—C11—C12—C13	54.7 (2)
C1—N1—C10—C15	−74.9 (2)	C11—C10—C15—C14	56.0 (2)
C1—C4—C5—N2	−4.0 (3)	C11—C12—C13—C14	−54.6 (2)
C1—C4—C5—C6	175.29 (17)	C12—C13—C14—C15	55.4 (3)
C1—C4—C9—C8	−174.68 (18)	C13—C14—C15—C10	−56.6 (2)
C2—N1—C1—S1	−16.23 (18)	C15—C10—C11—C12	−54.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1ⁱ	0.93	2.65	3.411 (5)	140
C15—H15B···O3ⁱⁱ	0.97	2.66	3.437 (5)	138

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

1-Cyclohexyl-2-(2-nitrophenyl)-1,3-thiazolidin-4-one 1,1-dioxide (2) top

Crystal data top

C₁₅H₁₈N₂O₅S	Z = 2
M_r = 338.37	F(000) = 356
Triclinic, P1	D_x = 1.469 Mg m⁻³
a = 7.114 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.401 (3) Å	Cell parameters from 1021 reflections
c = 12.038 (3) Å	θ = 2.6–25.0°
α = 94.808 (5)°	µ = 0.24 mm⁻¹
β = 92.110 (5)°	T = 100 K
γ = 107.198 (5)°	Block, colorless
V = 764.8 (4) Å³	0.29 × 0.11 × 0.06 mm

Data collection top

Bruker SMART CCD area detector diffractometer	3728 independent reflections
Radiation source: fine-focus sealed tube	3475 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
phi and ω scans	θ_max = 28.1°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2013)	h = −9→9
T_min = 0.815, T_max = 0.989	k = −12→12
9076 measured reflections	l = −15→15

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.082	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0404P)² + 0.4077P] where P = (F_o² + 2F_c²)/3
3728 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.45 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq
S1	0.60965 (4)	0.67214 (3)	0.85449 (2)	0.01180 (8)
O1	0.67190 (12)	0.55058 (9)	0.89218 (7)	0.01731 (18)
O2	0.74722 (12)	0.78778 (9)	0.80246 (8)	0.01862 (18)
O3	0.27805 (12)	0.90586 (9)	0.92007 (7)	0.01539 (17)
O4	0.54722 (14)	0.41291 (10)	0.63921 (8)	0.0228 (2)
O5	0.57817 (15)	0.22722 (11)	0.72569 (10)	0.0296 (2)
N1	0.29029 (13)	0.71982 (10)	0.78749 (8)	0.01082 (18)
N2	0.49472 (15)	0.32058 (11)	0.70700 (9)	0.0170 (2)
C1	0.38198 (15)	0.60257 (11)	0.76329 (9)	0.0105 (2)
H1	0.4147	0.5983	0.6832	0.013*
C2	0.34073 (16)	0.80345 (12)	0.88860 (9)	0.0114 (2)
C3	0.49252 (16)	0.75554 (12)	0.95740 (9)	0.0136 (2)
H3A	0.4276	0.6827	1.0094	0.016*
H3B	0.5881	0.8429	1.0007	0.016*
C4	0.26158 (16)	0.44866 (12)	0.79064 (9)	0.0112 (2)
C5	0.31876 (16)	0.31896 (12)	0.76822 (9)	0.0130 (2)
C6	0.21380 (18)	0.18142 (13)	0.80081 (10)	0.0166 (2)
H6	0.2592	0.0968	0.7858	0.020*
C7	0.04245 (19)	0.16798 (14)	0.85541 (11)	0.0198 (2)
H7	−0.0318	0.0740	0.8773	0.024*
C8	−0.01917 (18)	0.29359 (14)	0.87772 (10)	0.0193 (2)
H8	−0.1375	0.2850	0.9143	0.023*
C9	0.08976 (17)	0.43194 (13)	0.84728 (10)	0.0146 (2)
H9	0.0464	0.5169	0.8654	0.018*
C10	0.18316 (16)	0.76881 (12)	0.69763 (9)	0.0117 (2)
H10	0.1191	0.8408	0.7335	0.014*
C11	0.02037 (16)	0.63935 (12)	0.63537 (9)	0.0137 (2)
H11A	−0.0743	0.5895	0.6886	0.016*
H11B	0.0783	0.5647	0.5997	0.016*
C12	−0.08705 (17)	0.69932 (13)	0.54591 (10)	0.0167 (2)
H12A	−0.1903	0.6151	0.5043	0.020*
H12B	−0.1522	0.7688	0.5824	0.020*
C13	0.05666 (19)	0.78087 (14)	0.46475 (10)	0.0190 (2)
H13A	−0.0150	0.8207	0.4090	0.023*
H13B	0.1151	0.7098	0.4244	0.023*
C14	0.22021 (18)	0.90929 (13)	0.52708 (10)	0.0188 (2)
H14A	0.1627	0.9848	0.5618	0.023*
H14B	0.3150	0.9582	0.4735	0.023*
C15	0.32904 (17)	0.85282 (13)	0.61788 (10)	0.0156 (2)
H15A	0.3984	0.7854	0.5827	0.019*
H15B	0.4287	0.9387	0.6602	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.00952 (13)	0.01062 (13)	0.01482 (14)	0.00278 (9)	−0.00059 (9)	0.00021 (9)
O1	0.0150 (4)	0.0156 (4)	0.0222 (4)	0.0069 (3)	−0.0040 (3)	0.0006 (3)
O2	0.0134 (4)	0.0156 (4)	0.0239 (4)	−0.0002 (3)	0.0037 (3)	0.0016 (3)
O3	0.0187 (4)	0.0137 (4)	0.0148 (4)	0.0072 (3)	0.0002 (3)	−0.0008 (3)
O4	0.0229 (4)	0.0203 (4)	0.0274 (5)	0.0086 (4)	0.0096 (4)	0.0034 (4)
O5	0.0233 (5)	0.0216 (5)	0.0491 (6)	0.0149 (4)	0.0014 (4)	0.0033 (4)
N1	0.0128 (4)	0.0093 (4)	0.0114 (4)	0.0050 (3)	−0.0005 (3)	0.0008 (3)
N2	0.0142 (4)	0.0121 (4)	0.0240 (5)	0.0047 (4)	−0.0021 (4)	−0.0039 (4)
C1	0.0104 (4)	0.0090 (5)	0.0123 (5)	0.0033 (4)	0.0000 (4)	0.0008 (4)
C2	0.0116 (5)	0.0102 (5)	0.0115 (5)	0.0015 (4)	0.0010 (4)	0.0024 (4)
C3	0.0154 (5)	0.0142 (5)	0.0119 (5)	0.0062 (4)	−0.0010 (4)	−0.0001 (4)
C4	0.0109 (5)	0.0104 (5)	0.0115 (5)	0.0022 (4)	−0.0022 (4)	0.0014 (4)
C5	0.0116 (5)	0.0121 (5)	0.0144 (5)	0.0031 (4)	−0.0030 (4)	0.0003 (4)
C6	0.0201 (5)	0.0104 (5)	0.0179 (5)	0.0030 (4)	−0.0065 (4)	0.0017 (4)
C7	0.0213 (6)	0.0147 (5)	0.0190 (6)	−0.0023 (4)	−0.0036 (4)	0.0065 (4)
C8	0.0160 (5)	0.0221 (6)	0.0176 (6)	0.0010 (4)	0.0028 (4)	0.0062 (5)
C9	0.0143 (5)	0.0151 (5)	0.0147 (5)	0.0047 (4)	0.0007 (4)	0.0022 (4)
C10	0.0131 (5)	0.0104 (5)	0.0122 (5)	0.0046 (4)	−0.0015 (4)	0.0015 (4)
C11	0.0130 (5)	0.0122 (5)	0.0145 (5)	0.0025 (4)	−0.0009 (4)	−0.0002 (4)
C12	0.0153 (5)	0.0189 (5)	0.0156 (5)	0.0062 (4)	−0.0030 (4)	−0.0011 (4)
C13	0.0228 (6)	0.0224 (6)	0.0130 (5)	0.0089 (5)	−0.0028 (4)	0.0022 (4)
C14	0.0224 (6)	0.0173 (5)	0.0169 (5)	0.0052 (5)	−0.0017 (4)	0.0067 (4)
C15	0.0155 (5)	0.0147 (5)	0.0160 (5)	0.0029 (4)	−0.0007 (4)	0.0047 (4)

Geometric parameters (Å, º) top

S1—O1	1.4419 (9)	C7—C8	1.3858 (18)
S1—O2	1.4360 (9)	C8—H8	0.9500
S1—C1	1.8382 (12)	C8—C9	1.3896 (16)
S1—C3	1.7729 (12)	C9—H9	0.9500
O3—C2	1.2143 (14)	C10—H10	1.0000
O4—N2	1.2281 (14)	C10—C11	1.5276 (15)
O5—N2	1.2267 (14)	C10—C15	1.5291 (16)
N1—C1	1.4527 (13)	C11—H11A	0.9900
N1—C2	1.3671 (14)	C11—H11B	0.9900
N1—C10	1.4810 (14)	C11—C12	1.5354 (16)
N2—C5	1.4726 (15)	C12—H12A	0.9900
C1—H1	1.0000	C12—H12B	0.9900
C1—C4	1.5177 (15)	C12—C13	1.5242 (17)
C2—C3	1.5294 (15)	C13—H13A	0.9900
C3—H3A	0.9900	C13—H13B	0.9900
C3—H3B	0.9900	C13—C14	1.5257 (17)
C4—C5	1.4040 (15)	C14—H14A	0.9900
C4—C9	1.3963 (16)	C14—H14B	0.9900
C5—C6	1.3853 (16)	C14—C15	1.5342 (16)
C6—H6	0.9500	C15—H15A	0.9900
C6—C7	1.3841 (18)	C15—H15B	0.9900
C7—H7	0.9500

O1—S1—C1	111.35 (5)	C9—C8—H8	119.5
O1—S1—C3	113.14 (6)	C4—C9—H9	119.3
O2—S1—O1	119.26 (6)	C8—C9—C4	121.39 (11)
O2—S1—C1	108.34 (5)	C8—C9—H9	119.3
O2—S1—C3	109.11 (6)	N1—C10—H10	107.5
C3—S1—C1	92.26 (5)	N1—C10—C11	112.55 (9)
C1—N1—C10	120.68 (9)	N1—C10—C15	109.90 (9)
C2—N1—C1	117.45 (9)	C11—C10—H10	107.5
C2—N1—C10	120.48 (9)	C11—C10—C15	111.61 (9)
O4—N2—C5	118.45 (10)	C15—C10—H10	107.5
O5—N2—O4	123.92 (11)	C10—C11—H11A	109.8
O5—N2—C5	117.62 (11)	C10—C11—H11B	109.8
S1—C1—H1	110.0	C10—C11—C12	109.49 (9)
N1—C1—S1	101.36 (7)	H11A—C11—H11B	108.2
N1—C1—H1	110.0	C12—C11—H11A	109.8
N1—C1—C4	114.61 (9)	C12—C11—H11B	109.8
C4—C1—S1	110.64 (7)	C11—C12—H12A	109.5
C4—C1—H1	110.0	C11—C12—H12B	109.5
O3—C2—N1	124.96 (10)	H12A—C12—H12B	108.1
O3—C2—C3	123.40 (10)	C13—C12—C11	110.88 (10)
N1—C2—C3	111.61 (9)	C13—C12—H12A	109.5
S1—C3—H3A	111.1	C13—C12—H12B	109.5
S1—C3—H3B	111.1	C12—C13—H13A	109.5
C2—C3—S1	103.22 (8)	C12—C13—H13B	109.5
C2—C3—H3A	111.1	C12—C13—C14	110.58 (10)
C2—C3—H3B	111.1	H13A—C13—H13B	108.1
H3A—C3—H3B	109.1	C14—C13—H13A	109.5
C5—C4—C1	123.62 (10)	C14—C13—H13B	109.5
C9—C4—C1	120.00 (10)	C13—C14—H14A	109.4
C9—C4—C5	116.27 (10)	C13—C14—H14B	109.4
C4—C5—N2	121.73 (10)	C13—C14—C15	111.06 (10)
C6—C5—N2	115.57 (10)	H14A—C14—H14B	108.0
C6—C5—C4	122.70 (11)	C15—C14—H14A	109.4
C5—C6—H6	120.2	C15—C14—H14B	109.4
C7—C6—C5	119.66 (11)	C10—C15—C14	110.26 (10)
C7—C6—H6	120.2	C10—C15—H15A	109.6
C6—C7—H7	120.5	C10—C15—H15B	109.6
C6—C7—C8	119.05 (11)	C14—C15—H15A	109.6
C8—C7—H7	120.5	C14—C15—H15B	109.6
C7—C8—H8	119.5	H15A—C15—H15B	108.1
C7—C8—C9	120.90 (12)

S1—C1—C4—C5	−69.60 (12)	C1—C4—C5—C6	175.39 (10)
S1—C1—C4—C9	106.31 (10)	C1—C4—C9—C8	−177.24 (10)
O1—S1—C1—N1	148.94 (7)	C2—N1—C1—S1	−24.61 (11)
O1—S1—C1—C4	26.96 (9)	C2—N1—C1—C4	94.57 (11)
O1—S1—C3—C2	−147.19 (7)	C2—N1—C10—C11	−138.49 (10)
O2—S1—C1—N1	−78.01 (8)	C2—N1—C10—C15	96.45 (12)
O2—S1—C1—C4	160.01 (7)	C3—S1—C1—N1	32.98 (7)
O2—S1—C3—C2	77.52 (8)	C3—S1—C1—C4	−88.99 (8)
O3—C2—C3—S1	−153.99 (9)	C4—C5—C6—C7	1.63 (17)
O4—N2—C5—C4	−28.26 (16)	C5—C4—C9—C8	−1.03 (16)
O4—N2—C5—C6	151.15 (11)	C5—C6—C7—C8	−0.87 (17)
O5—N2—C5—C4	152.98 (11)	C6—C7—C8—C9	−0.79 (18)
O5—N2—C5—C6	−27.60 (15)	C7—C8—C9—C4	1.78 (18)
N1—C1—C4—C5	176.56 (10)	C9—C4—C5—N2	178.71 (10)
N1—C1—C4—C9	−7.52 (14)	C9—C4—C5—C6	−0.67 (16)
N1—C2—C3—S1	24.31 (11)	C10—N1—C1—S1	141.97 (8)
N1—C10—C11—C12	178.54 (9)	C10—N1—C1—C4	−98.85 (11)
N1—C10—C15—C14	−177.81 (9)	C10—N1—C2—O3	12.62 (16)
N2—C5—C6—C7	−177.78 (10)	C10—N1—C2—C3	−165.64 (9)
C1—S1—C3—C2	−32.79 (8)	C10—C11—C12—C13	57.68 (12)
C1—N1—C2—O3	179.23 (10)	C11—C10—C15—C14	56.59 (12)
C1—N1—C2—C3	0.97 (13)	C11—C12—C13—C14	−57.84 (13)
C1—N1—C10—C11	55.34 (13)	C12—C13—C14—C15	56.73 (13)
C1—N1—C10—C15	−69.72 (12)	C13—C14—C15—C10	−55.78 (13)
C1—C4—C5—N2	−5.23 (16)	C15—C10—C11—C12	−57.33 (12)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···O1ⁱ	0.99	2.51	3.4594 (16)	161
C3—H3B···O3ⁱⁱ	0.99	2.37	3.3068 (16)	157
C9—H9···O1ⁱⁱⁱ	0.95	2.80	3.5144 (16)	133
C10—H10···O2ⁱⁱⁱ	1.00	2.72	3.4381 (16)	129

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

Funding information

We acknowledge NSF funding (CHEM-0131112) for the X-ray diffractometer at The Pennsylvania State University, University Park campus.

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Volume 74| Part 12| December 2018| Pages 1695-1699

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

Crystal structures of two 1,3-thia­zolidin-4-one derivatives featuring sulfide and sulfone functional groups

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Synthesis and crystallization

5. Refinement

Supporting information

Funding information

References

research communications

Crystal structures of two 1,3-thiazolidin-4-one derivatives featuring sulfide and sulfone functional groups

3. Supramolecular features