Syntheses and structures of spontaneously resolved (2S)-2-phenyl-3-(thia­zol-2-yl)-2,3,5,6-tetra­hydro-4H-1,3-thia­zin-4-one and racemic 2-(furan-2-yl)-3-phenyl-2,3,5,6-tetra­hydro-4H-1,3-thia­zin-4-one

Yennawar, H.P.; Mal, T.K.; Olsen, M.A.; Lagalante, A.F.; Gavalis, A.D.; Frederick, I.G.; Louca, E.M.; Silverberg, L.J.

doi:10.1107/S2056989025009193

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ISSN: 2056-9890

Volume 81| Part 11| November 2025| Pages 1044-1049

https://doi.org/10.1107/S2056989025009193

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Syntheses and structures of spontaneously resolved (2S)-2-phenyl-3-(thiazol-2-yl)-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one and racemic 2-(furan-2-yl)-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one

Hemant P. Yennawar,^a Tapas K. Mal,^b Mark A. Olsen,^c Anthony F. Lagalante,^c Aloura D. Gavalis,^d Isabella G. Frederick,^d Evelyn M. Louca ^d and Lee J. Silverberg ^d ^*

^aDepartment of Biochemistry and Molecular Biology, The Pennsylvania State University, University Park, PA 16802, USA, ^bDepartment of Chemistry, The Pennsylvania State University, University Park, PA 16802, USA, ^cMendel Science Center, Villanova University, 800 Lancaster Avenue, Villanova, PA 19085, USA, and ^dPennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 10 October 2025; accepted 20 October 2025; online 24 October 2025)

The title compounds, one a thiazole derivative: (2S)-2-phenyl-3-(thiazol-2-yl)-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one, C₁₃H₁₂N₂OS₂, and the second a furan derivative: (rac)-2-(furan-2-yl)-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one, C₁₄H₁₃NO₂S, crystallize in space-groups P2₁2₁2₁ and P2₁/c, respectively, with a single molecule in their asymmetric units. The crystal of the thiazole derivative chosen for data collection was found to consist of the S enantiomer [Flack parameter 0.013 (9)]. The crystal of the furan derivative in the centrosymmetric space group is a racemic mixture. The puckering of the thiazine ring in both the structures is a half-chair. The extended structure of the thiazole derivative shows two weak C—H⋯O type interactions, but no aromatic ring interactions. In the structure of the furan derivative, an extensive and continuous network of C—H⋯O hydrogen bonds between the furan and the substituted thiazine ring, and also between symmetry-related furan rings, results in a continuous amphiphilic layer lying parallel to the (100) plane. Adjacent to this plane is the layer of hydrophobic phenyl rings. Thus, the extended structure comprises alternating layers of amphiphilic and hydrophobic regions, stacked in the a-axis direction. A C—H⋯O interaction between the phenyl ring and the thiazin-4-one moiety and the π–π stacking of the phenyl rings between pairs of symmetry-related molecules further consolidates the extended structure.

Keywords: crystal structure; spontaneous resolution; half-chair; thiazine ring pucker.

CCDC references: 2496686; 2496685

1. Chemical context

Compounds with a 2,3-diaryl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one scaffold have been shown to have a variety of bioactivities, including antiparasite (Malfara et al., 2021 ), antitumor (Chen et al., 2012 ; Dandia et al., 2013 ), antifungal (Ten Haken & Beatrice, 1983 ; Qu et al., 2013 .; Dandia et al., 2004 ; Krumkains, 1984 ), antitubercular (Dandia et al., 2004), antidiabetic (Arya et al., 2012 ), inhibition of cannabinoid receptor 1 (CB1) (Choi et al., 2008 ), inhibition of angiogenesis (possible treatment of eye disease, neoplasm, arteriosclerosis, arthritis, psoriasis, diabetes, and mellitus) (Yi et al., 2012 ), regulation of plant growth (Krumkains, 1984), antimicrobial (Mogilaiah et al., 1999 ) and antibacterial (Mahdi & Rasheed, 2023 ) effects.

We have previously used our T3P method to synthesize two series of these compounds in which the aryl rings on positions 2 and 3 had a variety of substituents on them (Silverberg et al., 2020 , 2025 ). Currently, another series in which one of the aryl rings is a heteroaryl is being synthesized. Here we report the syntheses and crystal structures of two new compounds in this series, one in which there is a thiazole ring attached to N3 (compound 1) and one in which there is a furan ring on C2 (compound 2). Thiazole and furan derivatives are each known for their biological activity (Niu et al., 2023 ; Nivrutti, 2024 ) and could have interesting effects on the activity of the 2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones.

The spontaneous resolution of a racemic solution by direct crystallization to form a conglomerate, a mechanical mixture of separate homochiral crystals, is an uncommon but well-known phenomenon, recognized first by Pasteur (Pasteur, 1848 ; Jacques et al., 1981 ; Eliel & Wilen, 1994 ; Pérez-García & Amabilino, 2007 ). It has even been used in the production of chiral active pharmaceutical ingredients (Bredikhin & Bredikhina, 2017 ). However, the reasons why this occurs with a minority of molecules are not well understood (Pérez-García & Amabilino, 2007) and have not yet yielded to attempts to predict occurrence (D'Oria et al., 2010 ; Pérez-García & Amabilino, 2007).

2. Structural commentary

Compounds 1 (Fig. 1) and 2 (Fig. 2) crystallize in the orthorhombic P2₁2₁2₁ and monoclinic P2₁/c space groups, respectively, with a single molecule in the respective asymmetric units. The chosen crystal of 1 was found to be composed of molecules with an S configuration at the stereogenic atom C1 [Flack parameter 0.013 (9)]. We had previously observed a similar spontaneous resolution in another thiazine compound (Yennawar, Bradley et al., 2018 ). The crystal of 2 belongs to a centrosymmetric space group and must be a racemic mixture of molecules.

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.

The thiazine rings of 1 and 2 both display a half-chair (pucker) conformation [Q = 0.694 (2), 0.6482 (11) Å; θ = 47.75 (17), 47.02 (10)°; φ = 347.4 (3), 349.01 (16)°, respectively] where the sulfur atom forms the back of the chair. We have observed this mode of puckering earlier (Yennawar, Yang et al., 2016 ; Yennawar, Fox et al., 2016 ; Yennawar, Bradley et al., 2018), which is different from the screw-boat (Yennawar, Bendinsky et al., 2014 ; Yennawar, Fox et al., 2017 ; Yennawar, Noble et al., 2017 ; Yennawar, Mal et al., 2023 ) conformation or the envelope pucker (Yennawar, Singh et al., 2014 ).

In the structure of 1, the C5/C6/C7/N2/S2 thiazole ring and the five non-S atoms of the thiazine ring are almost coplanar, while the dihedral angle between the thiazole and the C8–C13 phenyl ring is 81.91 (13)°. In 2, the C5–C10 phenyl and C11–C14/O1 furan rings flip positions as compared to the phenyl and thiazole rings in 1. The phenyl ring is gauche with respect to the plane of the thiazine ring's five non-S atoms. The dihedral angle between the phenyl and furan ring planes is 88.45 (7)°.

3. Supramolecular features

The extended structure of 1 (Table 1, Fig. 3) features C7—H7⋯O1 hydrogen bonds forming molecular chains along the c-axis direction and C3—H3B⋯N2 hydrogen bonds forming chains along the a-axis direction. No π–π stacking interactions or layering of any kind is observed in the extended structure. The crystal of 2 on the other hand (Fig. 4) is brought about by a continuous and extensive network of intermolecular hydrogen bonds (Table 2). These include the oxygen atom on the substituted thiazine ring acting as a double acceptor for the C13—H13⋯O2 and C14—H14⋯O2 bonds and also between symmetry-related furan rings (C12—H12⋯O1). These interactions result in infinite layers of furan and thiazine moieties lying parallel to the (100) plane. Additional interaction between a carbon atom of the phenyl ring and the oxygen atom on the thiazine ring (C10—H10⋯O2) and the π–π stacking of the phenyl rings between pairs of molecules further consolidate the packing. Alternating layers of amphiphilic (furan and thiazine) and hydrophobic (phenyl) entities, parallel to the (100) plane are a feature of this structure.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3B⋯N2ⁱ	0.99	2.53	3.503 (4)	169
C7—H7⋯O1ⁱⁱ	0.95	2.62	3.495 (3)	154
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, -z+1]$ ; (ii) $[-x+{\script{3\over 2}}, -y+2, z-{\script{1\over 2}}]$ .

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O2ⁱ	0.95	2.54	3.4276 (16)	155
C12—H12⋯O1ⁱⁱ	0.95	2.58	3.4583 (16)	153
C14—H14⋯O2ⁱⁱⁱ	0.95	2.50	3.4252 (16)	166
C13—H13⋯O2^iv	0.95	2.43	3.3641 (16)	168
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iv) .

Figure 3
Crystal packing diagram of 1 with red dotted lines for C—H⋯O contacts and blue dotted lines for the C—H⋯N contacts.

Figure 4
Crystal packing diagram of 2 showing alternating layers of amphiphilic and hydrophobic regions. Red dotted lines represent the C—H⋯O contacts.

4. Database survey

We have previously reported the crystal structures of 2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one (Yennawar & Silverberg, 2014 , 2015 ), N-[(2S,5R)-4-oxo-2,3-diphenyl-1,3-thiazinan-5-yl] acetamide 0.375 hydrate (Yennawar et al., 2015 ), (2S)-2-(3-nitrophenyl)-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one (Yennawar, Bradley et al., 2018), rac-2-(4-nitrophenyl)-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one (Yennawar, Bradley et al., 2018), racemic (R*,R*)-2,2′-(1,4-phenylene)bis(3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one) (Yennawar et al., 2021 ), and meso-3,3′-(1,4-phenylene)bis(2-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one) (Yennawar, Moyer & Silverberg, 2018 ). A literature survey did not reveal crystal structures of any other 2,3-diaryl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-ones.

5. Synthesis and crystallization

TLC plates (silica gel GF, 250-micron, 10 × 20 cm, cat. No. P21521) were purchased from Miles Scientific. TLCs were visualized under short wave UV, and then with I₂, and then by spraying with ceric ammonium nitrate/sulfuric acid and heating. Infrared spectra were run on a Thermo-Fisher NICOLET iS50 FT-IR using a diamond-ATR attachment for direct powder analysis (Penn State Schuylkill). ¹H and ¹³C NMR experiments (Penn State's shared NMR facility, University Park) were carried out on a Bruker Avance-III-HD 500.20-MHz (1H frequency) instrument using a 5 mm Prodigy (liquid nitrogen cooled) BBOBB-1H/19F/D Z-GRD cryoprobe. Samples were dissolved in pyridine-d5 and analyzed at RT. Typical conditions for ¹H acquisition were 1 s relaxation delay, the acquisition time of 3.28 s, the spectral width of 10 kHz, 32 scans. Spectra were zero-filled to 128k points, and multiplied by exponential multiplication (EM with LB = 0.3 Hz) prior to FT. For ¹³C experiments, data were acquired with power-gated ¹H decoupling using a 2 s relaxation delay, with an acquisition time of 1.1 s, spectral width of 29.8 kHz, and 256 scans. Spectra were zero-filled once, and multiplied by EM with LB = 2 Hz prior to FT. MS samples were analyzed for accurate mass by LCMS on a SCIEX Exion LC with a SCIEX 5600+ TripleTOF MS. Separation was achieved on an Agilent Infinity LabPoroshell column 120 EC-C18, 2.1 X 50mm, 2.7-micron particle (p/n 699775-902), column maintained at 313 K. Elution using a reversed phase gradient of 100% (water with 0.1% formic acid) ramped to 100% (acetonitrile with 0.1% formic acid) over 10 min at a flowrate of 0.4 mL min⁻¹. The MS was scanned over 50–1200 Da and calibrated with the SCIEX APCI positive calibrant solution (Part 4460131) prior to sample analysis. Samples were analyzed in ESI positive mode with a DP = 100 V, CE = 10, GAS1 = GAS2 = 60 psi, curtain = 30 psi, ISV = 5500 V, and source temperature of 773 K (Villanova University). Melting points were performed on a Vernier Melt Station (Penn State Schuylkill). Suitable crystals were selected and sequentially mounted using a nylon loop and a dab of paratone oil.

2-Phenyl-3-(thiazol-2-yl)-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one, 1: A two-necked 25 ml round-bottom flask was oven-dried, cooled under N₂, and charged with a stir bar. 2-Aminothiazole (0.6005 g, 6.00 mmol) and benzaldehyde (0.6369 g, 6.00 mmol) were added. 2-Methyltetrahydrofuran (2.3 ml) was added and the solution was stirred for five minutes. 3-Mercaptopropionic acid (0.6379 g, 6.00 mmol) was added followed by pyridine (2.9 ml, 36 mmol). Finally, 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) in 2-methyltetrahydrofuran (50 weight percent; 11 ml, 18 mmol) was added. The reaction was stirred at room temperature and followed by TLC, then poured into a separatory funnel with dichloromethane (20 ml). The mixture was washed with water (10 ml). The aqueous was then extracted twice with dichloromethane (10 ml each). The organics were combined and washed with saturated sodium bicarbonate (10 ml) and then saturated sodium chloride (10 ml). The organic extract was dried over sodium sulfate and concentrated under vacuum to give a crude mixture. After chromatography on 30 g silica gel with mixtures of ethyl acetate and hexanes (gradient from 30% ethyl acetate to 70%), recrystallization from methanol solution gave an off-white solid (0.1186 g, 7% yield). m.p.: 426–427 K. Colorless blocks of 1 for crystallography were grown by slow evaporation from methanol solution. ¹H NMR (d5-pyridine) δ 7.65 (s, 1H), 7.47 (d, J = 3.7 Hz, 1H), 7.39 (d, J = 7.8 Hz, 2H), 7.26 (t, J = 7.6 Hz, 2H), 7.21 (d, J = 7.2 Hz, 1H), 7.12 (d, J = 3.7 Hz, 1H), 3.16–2.93 (m, 2H), 2.83–2.73 (m, 1H), 2.65–2.55 (m, 1H). ¹³C NMR (d5-pyridine) δ 168.5, 158.4, 140.1, 137.4, 128.7, 127.8, 126.4, 115.9, 61.7, 34.4, 20.8. HRMS (m/z): [M + H⁺] of 277.0465 is consistent with calculated [M + H]⁺ of 277.0464. IR (neat, cm⁻¹): 1647 (C=O).

2-(Furan-2-yl)-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one, 2: A two-necked 25 ml round-bottom flask was oven-dried, cooled under N₂, and charged with a stir bar. Aniline (0.5585 g, 6.00 mmol) and furfural (0.5764 g, 6.00 mmol) were added. 2-Methyltetrahydrofuran (2.3 ml) was added and the solution was stirred for five minutes. Pyridine (2.9 ml, 36 mmol) and 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphorinane-2,4,6-trioxide (T3P) in 2-methyltetrahydrofuran (50 weight percent; 11 ml, 18 mmol) were added. Lastly, 3-mercaptopropionic acid (0.52 ml, 6.00 mmol) was added dropwise. The reaction was stirred at room temperature and followed by TLC, then poured into a separatory funnel with ethyl acetate (20 ml). The mixture was washed with water (10 ml). The aqueous layer was then extracted twice with ethyl acetate (10 ml each). The organics were combined and washed with saturated sodium bicarbonate (10 ml) and then saturated sodium chloride (10 ml). The organic extract was dried over sodium sulfate and concentrated under vacuum to give a crude mixture. After chromatography on 30 g silica gel with mixtures of ethyl acetate and hexanes (gradient from 30% ethyl acetate to 70%), recrystallization from ethanol gave a light orange solid (0.538 g, 35% yield). m.p.: 380.1–380.9 K (decomposition). Yellow blocks of 2 were grown by slow evaporation from ethanol solution. ¹H NMR (d5-pyridine) δ 7.43 (d, J = 8.2 Hz, 2H), 7.30 (t, J = 7.9 Hz, 2H), 7.18 (d, J = 14.9 Hz, 2H), 6.49 (d, J = 3.4 Hz, 1H), 6.38 (dd, J = 3.3, 1.8 Hz, 1H), 6.32 (s, 1H), 3.23–3.13 (m, 1H), 3.07–2.92 (m, 2H), 2.88–2.79 (m, 1H). ¹³C NMR (d5-pyridine) δ 168.7, 152.1, 143.2, 143.1, 129.1, 127.6, 127.2, 110.8, 109.1, 59.7, 34.7, 23.3. HRMS (m/z): [M + H⁺] of 260.0737 is consistent with calculated [M + H]⁺ of 260.0739. IR (neat, cm⁻¹): 1623 (C=O).

6. 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 0.95 Å (aromatic), 0.97 Å (methylene) and 1.0 Å (methyne) and 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	C₁₃H₁₂N₂OS₂	C₁₄H₁₃NO₂S
M_r	276.37	259.31
Crystal system, space group	Orthorhombic, P2₁2₁2₁	Monoclinic, P2₁/c
Temperature (K)	173	173
a, b, c (Å)	9.71506 (15), 10.04091 (13), 13.06169 (18)	14.0188 (2), 8.0422 (1), 11.3223 (2)
α, β, γ (°)	90, 90, 90	90, 104.066 (1), 90
V (Å³)	1274.14 (3)	1238.22 (3)
Z	4	4
Radiation type	Cu Kα	Cu Kα
μ (mm⁻¹)	3.69	2.27
Crystal size (mm)	0.15 × 0.10 × 0.05	0.19 × 0.18 × 0.09

Data collection
Diffractometer	ROD, SynergyCustom system, HyPix-Arc 150	ROD, SynergyCustom system, HyPix-Arc 150
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2025 )	Multi-scan (CrysAlis PRO; Rigaku OD, 2025)
T_min, T_max	0.820, 1.000	0.813, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	15582, 2577, 2456	7838, 2435, 2322
R_int	0.037	0.021
(sin θ/λ)_max (Å⁻¹)	0.631	0.630

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.073, 1.05	0.029, 0.080, 1.08
No. of reflections	2577	2435
No. of parameters	164	164
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18	0.28, −0.30
Absolute structure	Flack x determined using 979 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )	–
Absolute structure parameter	0.013 (9)	–
Computer programs: CrysAlis PRO (Rigaku OD, 2025), SHELXT (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC references: 2496686; 2496685

Crystal structure: contains datablocks 1, 2. DOI: https://doi.org/10.1107/S2056989025009193/hb8168sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989025009193/hb81681sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989025009193/hb81682sup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989025009193/hb81681sup4.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989025009193/hb81682sup5.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989025009193/hb81681sup6.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989025009193/hb81682sup7.cml

checkCIF report

Computing details top

(2S)-2-Phenyl-3-(thiazol-2-yl)-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one (1) top

Crystal data top

C₁₃H₁₂N₂OS₂	D_x = 1.441 Mg m⁻³
M_r = 276.37	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 8550 reflections
a = 9.71506 (15) Å	θ = 3.4–73.4°
b = 10.04091 (13) Å	µ = 3.69 mm⁻¹
c = 13.06169 (18) Å	T = 173 K
V = 1274.14 (3) Å³	Block, colorless
Z = 4	0.15 × 0.10 × 0.05 mm
F(000) = 576

Data collection top

ROD, SynergyCustom system, HyPix-Arc 150 diffractometer	2577 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	2456 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.037
Detector resolution: 10.0000 pixels mm^-1	θ_max = 76.5°, θ_min = 5.6°
ω scans	h = −10→12
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2025)	k = −12→12
T_min = 0.820, T_max = 1.000	l = −16→16
15582 measured reflections

Refinement top

Refinement on F²	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ²(F_o²) + (0.0356P)² + 0.1897P] where P = (F_o² + 2F_c²)/3
R[F² > 2σ(F²)] = 0.028	(Δ/σ)_max < 0.001
wR(F²) = 0.073	Δρ_max = 0.14 e Å⁻³
S = 1.05	Δρ_min = −0.18 e Å⁻³
2577 reflections	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
164 parameters	Extinction coefficient: 0.0019 (4)
0 restraints	Absolute structure: Flack x determined using 979 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
Hydrogen site location: inferred from neighbouring sites	Absolute structure parameter: 0.013 (9)

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	0.89569 (8)	0.55653 (7)	0.61560 (5)	0.0551 (2)
S2	0.80954 (8)	0.91269 (7)	0.30808 (6)	0.0584 (2)
O1	0.7233 (2)	0.91808 (17)	0.49817 (15)	0.0560 (5)
N1	0.8157 (2)	0.71837 (18)	0.45942 (14)	0.0372 (4)
N2	0.8863 (2)	0.6695 (2)	0.29155 (16)	0.0492 (5)
C1	0.8492 (2)	0.5775 (2)	0.48283 (18)	0.0403 (5)
H1	0.932918	0.554839	0.441811	0.048*
C8	0.7369 (3)	0.4831 (2)	0.44846 (17)	0.0394 (5)
C2	0.7542 (2)	0.8056 (2)	0.52664 (19)	0.0410 (5)
C9	0.6083 (3)	0.5254 (3)	0.4168 (2)	0.0533 (7)
H9	0.586998	0.617694	0.417852	0.064*
C5	0.8384 (2)	0.7550 (2)	0.35675 (18)	0.0381 (5)
C6	0.9008 (3)	0.7284 (3)	0.1967 (2)	0.0548 (7)
H6	0.933586	0.680501	0.138953	0.066*
C13	0.7641 (4)	0.3466 (3)	0.4476 (2)	0.0536 (7)
H13	0.851329	0.314590	0.469296	0.064*
C4	0.7364 (3)	0.6209 (3)	0.6645 (2)	0.0511 (7)
H4A	0.657947	0.571637	0.634444	0.061*
H4B	0.733136	0.610383	0.739804	0.061*
C3	0.7273 (3)	0.7666 (3)	0.6364 (2)	0.0488 (6)
H3A	0.793298	0.815724	0.680090	0.059*
H3B	0.633938	0.798117	0.654775	0.059*
C12	0.6630 (5)	0.2569 (3)	0.4149 (2)	0.0687 (10)
H12	0.681842	0.164056	0.415077	0.082*
C7	0.8660 (3)	0.8566 (3)	0.1911 (2)	0.0600 (8)
H7	0.871548	0.909530	0.130911	0.072*
C10	0.5096 (3)	0.4347 (3)	0.3836 (3)	0.0681 (9)
H10	0.422186	0.465784	0.361365	0.082*
C11	0.5374 (4)	0.3017 (3)	0.3825 (3)	0.0682 (9)
H11	0.469717	0.240301	0.359493	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0709 (4)	0.0553 (4)	0.0391 (3)	0.0174 (3)	−0.0116 (3)	0.0017 (3)
S2	0.0820 (5)	0.0416 (4)	0.0515 (4)	0.0087 (3)	0.0069 (4)	0.0116 (3)
O1	0.0800 (13)	0.0353 (9)	0.0527 (10)	0.0115 (9)	0.0006 (9)	−0.0027 (8)
N1	0.0463 (10)	0.0299 (9)	0.0354 (10)	0.0011 (8)	0.0000 (9)	−0.0002 (8)
N2	0.0680 (14)	0.0432 (12)	0.0364 (11)	−0.0006 (11)	0.0043 (10)	−0.0001 (9)
C1	0.0505 (13)	0.0361 (12)	0.0343 (11)	0.0096 (10)	0.0023 (9)	0.0018 (10)
C8	0.0581 (14)	0.0317 (11)	0.0284 (10)	0.0009 (10)	0.0081 (10)	−0.0006 (9)
C2	0.0458 (12)	0.0363 (12)	0.0409 (12)	0.0014 (10)	−0.0022 (10)	−0.0055 (10)
C9	0.0532 (15)	0.0405 (13)	0.0660 (18)	−0.0014 (12)	0.0024 (13)	−0.0090 (12)
C5	0.0424 (11)	0.0350 (11)	0.0369 (12)	−0.0034 (9)	−0.0027 (9)	0.0022 (9)
C6	0.0694 (17)	0.0591 (17)	0.0359 (13)	−0.0055 (14)	0.0043 (13)	0.0028 (12)
C13	0.088 (2)	0.0378 (13)	0.0352 (13)	0.0093 (13)	0.0069 (13)	0.0027 (10)
C4	0.0691 (17)	0.0500 (15)	0.0341 (12)	−0.0018 (13)	0.0029 (12)	0.0007 (11)
C3	0.0583 (15)	0.0479 (14)	0.0401 (13)	0.0051 (12)	0.0069 (11)	−0.0044 (11)
C12	0.131 (3)	0.0312 (14)	0.0434 (15)	−0.0125 (17)	0.0188 (18)	−0.0030 (11)
C7	0.0734 (19)	0.0614 (18)	0.0452 (15)	−0.0007 (14)	0.0053 (14)	0.0158 (14)
C10	0.0595 (17)	0.0628 (19)	0.082 (2)	−0.0120 (15)	0.0055 (16)	−0.0157 (19)
C11	0.089 (2)	0.0566 (18)	0.0594 (18)	−0.0269 (17)	0.0190 (18)	−0.0084 (17)

Geometric parameters (Å, º) top

S1—C1	1.804 (2)	C9—C10	1.392 (4)
S1—C4	1.795 (3)	C6—H6	0.9500
S2—C5	1.730 (2)	C6—C7	1.333 (4)
S2—C7	1.718 (3)	C13—H13	0.9500
O1—C2	1.226 (3)	C13—C12	1.400 (5)
N1—C1	1.484 (3)	C4—H4A	0.9900
N1—C2	1.377 (3)	C4—H4B	0.9900
N1—C5	1.408 (3)	C4—C3	1.510 (4)
N2—C5	1.295 (3)	C3—H3A	0.9900
N2—C6	1.380 (3)	C3—H3B	0.9900
C1—H1	1.0000	C12—H12	0.9500
C1—C8	1.513 (3)	C12—C11	1.368 (5)
C8—C9	1.383 (4)	C7—H7	0.9500
C8—C13	1.395 (3)	C10—H10	0.9500
C2—C3	1.510 (4)	C10—C11	1.363 (5)
C9—H9	0.9500	C11—H11	0.9500

C4—S1—C1	94.83 (12)	C8—C13—H13	119.9
C7—S2—C5	88.58 (13)	C8—C13—C12	120.1 (3)
C2—N1—C1	124.80 (19)	C12—C13—H13	119.9
C2—N1—C5	120.63 (19)	S1—C4—H4A	110.0
C5—N1—C1	114.25 (18)	S1—C4—H4B	110.0
C5—N2—C6	110.1 (2)	H4A—C4—H4B	108.4
S1—C1—H1	106.6	C3—C4—S1	108.26 (19)
N1—C1—S1	111.35 (16)	C3—C4—H4A	110.0
N1—C1—H1	106.6	C3—C4—H4B	110.0
N1—C1—C8	112.22 (19)	C2—C3—C4	118.2 (2)
C8—C1—S1	113.11 (16)	C2—C3—H3A	107.8
C8—C1—H1	106.6	C2—C3—H3B	107.8
C9—C8—C1	123.2 (2)	C4—C3—H3A	107.8
C9—C8—C13	118.0 (3)	C4—C3—H3B	107.8
C13—C8—C1	118.8 (3)	H3A—C3—H3B	107.1
O1—C2—N1	119.9 (2)	C13—C12—H12	119.7
O1—C2—C3	119.0 (2)	C11—C12—C13	120.6 (3)
N1—C2—C3	121.0 (2)	C11—C12—H12	119.7
C8—C9—H9	119.5	S2—C7—H7	124.8
C8—C9—C10	121.0 (3)	C6—C7—S2	110.4 (2)
C10—C9—H9	119.5	C6—C7—H7	124.8
N1—C5—S2	124.30 (17)	C9—C10—H10	119.7
N2—C5—S2	115.03 (17)	C11—C10—C9	120.5 (3)
N2—C5—N1	120.7 (2)	C11—C10—H10	119.7
N2—C6—H6	122.0	C12—C11—H11	120.1
C7—C6—N2	116.0 (3)	C10—C11—C12	119.7 (3)
C7—C6—H6	122.0	C10—C11—H11	120.1

S1—C1—C8—C9	115.7 (2)	C2—N1—C5—S2	6.7 (3)
S1—C1—C8—C13	−64.8 (3)	C2—N1—C5—N2	−174.5 (2)
S1—C4—C3—C2	49.7 (3)	C9—C8—C13—C12	0.4 (4)
O1—C2—C3—C4	166.8 (3)	C9—C10—C11—C12	0.2 (5)
N1—C1—C8—C9	−11.3 (3)	C5—S2—C7—C6	0.1 (2)
N1—C1—C8—C13	168.2 (2)	C5—N1—C1—S1	153.07 (17)
N1—C2—C3—C4	−14.8 (4)	C5—N1—C1—C8	−79.0 (2)
N2—C6—C7—S2	−0.5 (4)	C5—N1—C2—O1	−2.7 (4)
C1—S1—C4—C3	−65.9 (2)	C5—N1—C2—C3	179.0 (2)
C1—N1—C2—O1	−175.7 (2)	C5—N2—C6—C7	0.8 (4)
C1—N1—C2—C3	5.9 (4)	C6—N2—C5—S2	−0.7 (3)
C1—N1—C5—S2	−179.52 (17)	C6—N2—C5—N1	−179.5 (2)
C1—N1—C5—N2	−0.8 (3)	C13—C8—C9—C10	−1.0 (4)
C1—C8—C9—C10	178.4 (3)	C13—C12—C11—C10	−0.9 (5)
C1—C8—C13—C12	−179.1 (2)	C4—S1—C1—N1	58.12 (18)
C8—C9—C10—C11	0.7 (5)	C4—S1—C1—C8	−69.34 (18)
C8—C13—C12—C11	0.6 (4)	C7—S2—C5—N1	179.1 (2)
C2—N1—C1—S1	−33.5 (3)	C7—S2—C5—N2	0.3 (2)
C2—N1—C1—C8	94.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3B···N2ⁱ	0.99	2.53	3.503 (4)	169
C7—H7···O1ⁱⁱ	0.95	2.62	3.495 (3)	154

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

2-(Furan-2-yl)-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one (2) top

Crystal data top

C₁₄H₁₃NO₂S	F(000) = 544
M_r = 259.31	D_x = 1.391 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 14.0188 (2) Å	Cell parameters from 5692 reflections
b = 8.0422 (1) Å	θ = 3.2–76.2°
c = 11.3223 (2) Å	µ = 2.27 mm⁻¹
β = 104.066 (1)°	T = 173 K
V = 1238.22 (3) Å³	Block, yellow
Z = 4	0.19 × 0.18 × 0.09 mm

Data collection top

ROD, SynergyCustom system, HyPix-Arc 150 diffractometer	2322 reflections with I > 2σ(I)
Detector resolution: 10.0000 pixels mm^-1	R_int = 0.021
ω scans	θ_max = 76.3°, θ_min = 3.3°
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2025)	h = −17→15
T_min = 0.813, T_max = 1.000	k = −9→9
7838 measured reflections	l = −12→13
2435 independent reflections

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.029	w = 1/[σ²(F_o²) + (0.0403P)² + 0.4195P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.080	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.28 e Å⁻³
2435 reflections	Δρ_min = −0.30 e Å⁻³
164 parameters	Extinction correction: SHELXL-2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0077 (5)

Special details top

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

	x	y	z	U_iso*/U_eq
S1	0.07806 (2)	0.43110 (4)	0.36542 (3)	0.02744 (13)
O2	0.23770 (7)	0.25789 (11)	0.10605 (8)	0.0256 (2)
O1	0.21764 (7)	0.77273 (11)	0.44109 (8)	0.0254 (2)
N1	0.24650 (7)	0.38603 (13)	0.28567 (9)	0.0190 (2)
C11	0.21704 (8)	0.66614 (15)	0.34668 (10)	0.0194 (3)
C5	0.35291 (8)	0.37345 (15)	0.31819 (11)	0.0202 (3)
C4	0.19546 (9)	0.32966 (15)	0.17485 (11)	0.0200 (3)
C1	0.20443 (8)	0.48549 (15)	0.37027 (10)	0.0196 (3)
H1	0.244178	0.461383	0.454540	0.024*
C10	0.39909 (9)	0.29220 (16)	0.42481 (11)	0.0240 (3)
H10	0.361323	0.242939	0.474755	0.029*
C12	0.22949 (10)	0.75125 (16)	0.24929 (12)	0.0272 (3)
H12	0.231244	0.706306	0.172252	0.033*
C6	0.40772 (9)	0.44727 (16)	0.24559 (12)	0.0254 (3)
H6	0.375659	0.503820	0.173134	0.030*
C14	0.23214 (10)	0.92929 (16)	0.39920 (13)	0.0288 (3)
H14	0.236273	1.028377	0.445845	0.035*
C3	0.08435 (9)	0.34646 (18)	0.13502 (12)	0.0280 (3)
H3A	0.067243	0.381193	0.048541	0.034*
H3B	0.055757	0.234554	0.138570	0.034*
C9	0.50141 (10)	0.28352 (17)	0.45798 (12)	0.0293 (3)
H9	0.533662	0.227828	0.530735	0.035*
C8	0.55618 (9)	0.35590 (18)	0.38510 (13)	0.0310 (3)
H8	0.625913	0.349154	0.407707	0.037*
C7	0.50956 (10)	0.43809 (18)	0.27934 (13)	0.0305 (3)
H7	0.547376	0.488261	0.229822	0.037*
C2	0.03348 (9)	0.46475 (18)	0.20431 (12)	0.0297 (3)
H2A	−0.038455	0.446094	0.180119	0.036*
H2B	0.046518	0.581040	0.184200	0.036*
C13	0.23958 (10)	0.92243 (16)	0.28411 (14)	0.0299 (3)
H13	0.249607	1.013374	0.234946	0.036*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.02374 (18)	0.0304 (2)	0.0316 (2)	−0.00259 (12)	0.01330 (13)	0.00038 (12)
O2	0.0287 (5)	0.0262 (5)	0.0225 (5)	0.0000 (4)	0.0073 (3)	−0.0041 (4)
O1	0.0306 (5)	0.0235 (5)	0.0217 (5)	−0.0001 (4)	0.0056 (3)	−0.0048 (3)
N1	0.0185 (5)	0.0189 (5)	0.0200 (5)	0.0004 (4)	0.0053 (4)	−0.0012 (4)
C11	0.0191 (5)	0.0204 (6)	0.0188 (6)	0.0008 (4)	0.0045 (4)	−0.0031 (4)
C5	0.0195 (6)	0.0183 (6)	0.0223 (6)	0.0006 (4)	0.0042 (4)	−0.0036 (5)
C4	0.0233 (6)	0.0162 (5)	0.0200 (6)	−0.0008 (4)	0.0047 (5)	0.0027 (4)
C1	0.0205 (5)	0.0206 (6)	0.0186 (6)	0.0005 (5)	0.0066 (4)	0.0004 (5)
C10	0.0254 (6)	0.0225 (6)	0.0238 (6)	0.0012 (5)	0.0053 (5)	0.0000 (5)
C12	0.0364 (7)	0.0220 (6)	0.0263 (7)	0.0014 (5)	0.0140 (5)	0.0011 (5)
C6	0.0243 (6)	0.0275 (7)	0.0245 (6)	−0.0001 (5)	0.0063 (5)	0.0015 (5)
C14	0.0271 (7)	0.0198 (6)	0.0389 (8)	−0.0013 (5)	0.0068 (6)	−0.0056 (5)
C3	0.0218 (6)	0.0325 (7)	0.0272 (7)	−0.0019 (5)	0.0013 (5)	−0.0023 (5)
C9	0.0279 (7)	0.0290 (7)	0.0273 (7)	0.0057 (5)	−0.0004 (5)	−0.0023 (5)
C8	0.0193 (6)	0.0355 (8)	0.0363 (7)	0.0025 (5)	0.0031 (5)	−0.0088 (6)
C7	0.0237 (6)	0.0367 (8)	0.0332 (7)	−0.0033 (5)	0.0110 (5)	−0.0034 (6)
C2	0.0189 (6)	0.0346 (7)	0.0335 (7)	0.0017 (5)	0.0023 (5)	0.0002 (6)
C13	0.0314 (7)	0.0198 (6)	0.0415 (8)	0.0014 (5)	0.0148 (6)	0.0041 (5)

Geometric parameters (Å, º) top

S1—C1	1.8125 (12)	C12—C13	1.4295 (18)
S1—C2	1.7992 (14)	C6—H6	0.9500
O2—C4	1.2308 (15)	C6—C7	1.3874 (18)
O1—C11	1.3687 (14)	C14—H14	0.9500
O1—C14	1.3779 (16)	C14—C13	1.333 (2)
N1—C5	1.4505 (15)	C3—H3A	0.9900
N1—C4	1.3621 (15)	C3—H3B	0.9900
N1—C1	1.4765 (15)	C3—C2	1.5169 (19)
C11—C1	1.4954 (17)	C9—H9	0.9500
C11—C12	1.3448 (18)	C9—C8	1.385 (2)
C5—C10	1.3870 (17)	C8—H8	0.9500
C5—C6	1.3876 (18)	C8—C7	1.385 (2)
C4—C3	1.5188 (16)	C7—H7	0.9500
C1—H1	1.0000	C2—H2A	0.9900
C10—H10	0.9500	C2—H2B	0.9900
C10—C9	1.3935 (18)	C13—H13	0.9500
C12—H12	0.9500

C2—S1—C1	95.20 (6)	C7—C6—H6	120.2
C11—O1—C14	106.07 (10)	O1—C14—H14	124.7
C5—N1—C1	114.93 (9)	C13—C14—O1	110.60 (11)
C4—N1—C5	119.22 (10)	C13—C14—H14	124.7
C4—N1—C1	125.08 (10)	C4—C3—H3A	107.7
O1—C11—C1	116.58 (10)	C4—C3—H3B	107.7
C12—C11—O1	110.14 (11)	H3A—C3—H3B	107.1
C12—C11—C1	133.28 (11)	C2—C3—C4	118.65 (11)
C10—C5—N1	119.18 (11)	C2—C3—H3A	107.7
C10—C5—C6	120.58 (11)	C2—C3—H3B	107.7
C6—C5—N1	120.21 (11)	C10—C9—H9	119.9
O2—C4—N1	120.88 (11)	C8—C9—C10	120.13 (12)
O2—C4—C3	118.05 (11)	C8—C9—H9	119.9
N1—C4—C3	121.01 (11)	C9—C8—H8	119.9
S1—C1—H1	107.2	C9—C8—C7	120.17 (12)
N1—C1—S1	113.03 (8)	C7—C8—H8	119.9
N1—C1—C11	109.10 (9)	C6—C7—H7	120.0
N1—C1—H1	107.2	C8—C7—C6	120.09 (13)
C11—C1—S1	112.71 (8)	C8—C7—H7	120.0
C11—C1—H1	107.2	S1—C2—H2A	109.7
C5—C10—H10	120.3	S1—C2—H2B	109.7
C5—C10—C9	119.36 (12)	C3—C2—S1	109.81 (9)
C9—C10—H10	120.3	C3—C2—H2A	109.7
C11—C12—H12	126.6	C3—C2—H2B	109.7
C11—C12—C13	106.73 (12)	H2A—C2—H2B	108.2
C13—C12—H12	126.6	C12—C13—H13	126.8
C5—C6—H6	120.2	C14—C13—C12	106.46 (12)
C5—C6—C7	119.67 (12)	C14—C13—H13	126.8

O2—C4—C3—C2	−167.11 (12)	C4—N1—C1—C11	−92.17 (13)
O1—C11—C1—S1	77.57 (11)	C4—C3—C2—S1	−47.73 (15)
O1—C11—C1—N1	−156.00 (9)	C1—S1—C2—C3	61.81 (10)
O1—C11—C12—C13	0.57 (15)	C1—N1—C5—C10	64.62 (14)
O1—C14—C13—C12	−0.11 (16)	C1—N1—C5—C6	−113.03 (12)
N1—C5—C10—C9	−178.37 (11)	C1—N1—C4—O2	174.61 (11)
N1—C5—C6—C7	178.32 (11)	C1—N1—C4—C3	−8.21 (17)
N1—C4—C3—C2	15.63 (18)	C1—C11—C12—C13	−178.65 (13)
C11—O1—C14—C13	0.45 (14)	C10—C5—C6—C7	0.71 (19)
C11—C12—C13—C14	−0.28 (16)	C10—C9—C8—C7	0.4 (2)
C5—N1—C4—O2	5.23 (17)	C12—C11—C1—S1	−103.25 (15)
C5—N1—C4—C3	−177.59 (11)	C12—C11—C1—N1	23.17 (18)
C5—N1—C1—S1	−156.14 (8)	C6—C5—C10—C9	−0.74 (19)
C5—N1—C1—C11	77.62 (12)	C14—O1—C11—C1	178.73 (10)
C5—C10—C9—C8	0.2 (2)	C14—O1—C11—C12	−0.63 (13)
C5—C6—C7—C8	−0.1 (2)	C9—C8—C7—C6	−0.4 (2)
C4—N1—C5—C10	−124.95 (12)	C2—S1—C1—N1	−55.69 (9)
C4—N1—C5—C6	57.40 (16)	C2—S1—C1—C11	68.60 (9)
C4—N1—C1—S1	34.08 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O2ⁱ	0.95	2.54	3.4276 (16)	155
C12—H12···O1ⁱⁱ	0.95	2.58	3.4583 (16)	153
C14—H14···O2ⁱⁱⁱ	0.95	2.50	3.4252 (16)	166
C13—H13···O2^iv	0.95	2.43	3.3641 (16)	168

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

Acknowledgements

This work was supported by a Major Research Instrumentation Grant from the National Science Foundation to Villanova University (CHE-1827930) for the mass spectrometer; NIH S10 grants (1S10-OD028589 and 1S10-RR023439) to Dr Neela Yennawar (PSU, University Park) for the X-ray diffractometer; and by a research development grant at Penn State Schuylkill.

Funding information

Funding for this research was provided by: National Science Foundation, Directorate for Mathematical and Physical Sciences (grant No. CHE-1827930 to Villanova University); National Institutes of Health (grant No. 1S10-OD028589 to Neela Yennawar; grant No. 1S10-RR023439 to Neela Yennawar); Penn State Schuylkill (grant to Lee J. Silverberg).

References

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Volume 81| Part 11| November 2025| Pages 1044-1049

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

Syntheses and structures of spontaneously resolved (2S)-2-phenyl-3-(thia­zol-2-yl)-2,3,5,6-tetra­hydro-4H-1,3-thia­zin-4-one and racemic 2-(furan-2-yl)-3-phenyl-2,3,5,6-tetra­hydro-4H-1,3-thia­zin-4-one

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Acknowledgements

Funding information

References

research communications

Syntheses and structures of spontaneously resolved (2S)-2-phenyl-3-(thiazol-2-yl)-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one and racemic 2-(furan-2-yl)-3-phenyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one

3. Supramolecular features