Crystal structures of rac-2,3-diphenyl-2,3,5,6-tetra­hydro-4H-1,3-thia­zine-1,1,4-trione and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thia­zinan-5-yl]acet­amide

Yennawar, H.P.; Lowe, S.L.; Mammen, M.M.; Verhagen, C.R.; Silverberg, L.J.

doi:10.1107/S2056989023000695

research communications

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ISSN: 2056-9890

Volume 79| Part 2| February 2023| Pages 120-123

https://doi.org/10.1107/S2056989023000695

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Crystal structures of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide

Hemant P. Yennawar,^a Saige L. Lowe,^b Matthew M. Mammen,^b Connor R. Verhagen ^b and Lee J. Silverberg ^b ^*

^aDepartment of Biochemistry and Molecular Biology, Pennsylvania State University, University Park, PA 16802, USA, and ^bPennsylvania State University, Schuylkill Campus, 200 University Drive, Schuylkill Haven, PA 17972, USA
^*Correspondence e-mail: ljs43@psu.edu

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 13 January 2023; accepted 25 January 2023; online 31 January 2023)

The syntheses and crystal structures of two thiazinone compounds, namely, rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione, C₁₆H₁₅NO₃S, in its racemic form, and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide, C₁₈H₁₈N₂O₄S, in an enantiopure form, are reported. The thiazine rings in the two structures differ in their puckering, as a half-chair in the first and a boat pucker in the second. The extended structures for both compounds have only C—H⋯O-type interactions between symmetry-related molecules, and exhibit no π–π stacking interactions in spite of each having two phenyl rings.

Keywords: crystal structure; thiazinone; sulfone; enantiopure.

CCDC references: 2238010; 2238009

1. Chemical context

The 2,3-dihydro-4H-1,3-thiazin-4-ones are a group of six-membered heterocycles with a wide range of biological activity (Ryabukhin et al., 1996 ; Silverberg & Moyer, 2019 ). Surrey's research (Surrey et al., 1958 ; Surrey, 1963a ,b ) resulted in the discovery of two drugs, the antianxiety and muscle relaxant chlormezanone, C₁₁H₁₂ClNO₃S, [2-(4-chlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide] (O'Neil, 2006 ; Tanaka & Horayama, 2005 ) and the muscle relaxant dichlormezanone, C₁₁H₁₁Cl₂NO₃S, [2-(3,4-dichlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide] (Elks & Ganellin, 1990 ). These sulfones showed greater activity than the sulfides from which they were synthesized (Surrey et al., 1958).

We have previously reported the preparation of the sulfones rac-2,3-dihydro-2,3-diphenyl-4H-1,3-thiazin-4-one 1,1-dioxide and N-[(2S,5R)-1,1-dioxido-4-oxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide (Silverberg, 2020 ). We have also reported X-ray crystal structures of the corresponding sulfides and sulfoxides (Yennawar & Silverberg, 2014 , 2015 ; Yennawar et al., 2015 , 2016 , 2017 ). The crystal structure of chlormezanone has been reported (Tanaka & Horayama, 2005). Herein we report the crystal structures of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione, 1, and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide, 2.

2. Structural commentary

Compound 1 has one chiral center at C1 with an S configuration in the arbitrarily chosen asymmetric unit but crystal symmetry generates a racemic mixture (space group P2₁/c). Compound 2 has two chiral centers, at C1 and C3 (S and R respectively), synthesized as such, and crystallizes in space group P2₁2₁2₁. In 1, the dihedral angles between the thiazine ring (all atoms) and the pendant C5–C10 and C11–C16 phenyl groups are 84.02 (14) and 79.56 (12)°, respectively; the dihedral angle between the pendant rings is 61.26 (15)°. The equivalent angles in 2 are 81.25 (15), 82.58 (13) and 50.40 (15)°, respectively.

The structure of 1 (Fig. 1) has a half-chair puckering of the thiazine ring with puckering amplitude Q = 0.605 (2) Å, θ = 47.2 (2)°, φ = 346.7 (3)°, while in 2 (Fig. 2) the ring has a boat pucker [Q = 0.770 (2) Å, θ = 85.31 (15)°, φ = 61.89 (17)°]. This change in the puckering of the central ring system of the two molecules leads to differing orientations of one of the phenyl rings, which is clear from the overlay diagram (Fig. 3).

Figure 1
The asymmetric unit of 1 with displacement ellipsoids drawn at 50% probability level.

Figure 2
The asymmetric unit of 2 with displacement ellipsoids drawn at 50% probability level.

Figure 3
Overlay plot of 1 and 2 where the three atoms S1, N1, and C11 are matched. Atoms C3 and C8 of compound 1 are labeled.

3. Supramolecular features

In both structures, only C—H⋯O-type hydrogen-bond interactions between symmetry-related molecules are observed (Tables 1 and 2). In 1, a single hydrogen bond [C12—H12⋯O1 = 3.454 (4) Å, 157°] and its symmetry-equivalent form a pair of parallel interactions (Fig. 4). In 2 (Fig. 5), the carbon atoms C1 and C4, both of the thiazine ring, as well as C8 of one of the phenyl rings each donate an H atom for three distinct interactions involving three of the four oxygen atoms in the molecule. Although both compounds each have two phenyl rings, neither of the lattices exhibit any π–π stacking interactions.

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C12—H12⋯O1ⁱ	0.95	2.56	3.454 (4)	157
Symmetry code: (i) .

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯O2ⁱ	0.98	2.39	3.365 (3)	173
C4—H4A⋯O4ⁱⁱ	0.97	2.29	3.185 (4)	153
C8—H8⋯O3ⁱⁱⁱ	0.93	2.51	3.378 (5)	155
Symmetry codes: (i) ; (ii) x+1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 4
Crystal packing diagram for 1 showing intermolecular pairs of C—H⋯O hydrogen bonds.

Figure 5
Crystal packing diagram for 2 showing intermolecular C—H⋯O hydrogen bonds.

4. Database survey

Searches undertaken using the American Chemical Society's Chemical Abstract Service (CAS) Scifinder platform did not find crystal structures of any 1,3-thiazin-4-one sulfones other than chlormezanone (CSD refcode KAPNAR; Tanaka & Horayama, 2005).

5. Synthesis and crystallization

General oxidation procedure (Surrey et al., 1958; Silverberg, 2020; Cannon et al. 2015 ): the heterocycle (0.267 mmol) was dissolved in glacial acetic acid (1.2 ml). An aqueous solution of KMnO₄ (0.535 mmol in 1.45 ml water) was added dropwise at room temperature with vigorous stirring. The reaction was followed by TLC. Solid sodium bisulfite (NaHSO₃/Na₂S₂O₅) was added until the mixture remained colorless and then 1.45 ml of water were added and stirred for 10 min. The mixture was extracted with CH₂Cl₂ (3 × 5 ml). The organics were combined and washed once with sat. NaCl. The solution was dried over Na₂SO₄ and filtered. The product was purified by chromatography in a silica gel micro-column.

rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione, 1: Eluted with mixtures of ethyl acetate and hexanes. White solid (0.053 g, 70%). m.p.: 418–421 K. Crystals for X-ray diffraction studies were grown by slow evaporation from toluene solution.

N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide, 2: Eluted with a mixture of 10% acetone and 90% ethyl acetate. White solid (0.076 g, 80%). m.p.: 443–467 K (decomposition). Crystals were grown by slow evaporation from ethanol solution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The hydrogen atoms were placed in their geometrically calculated positions and their coordinates refined using the riding model with parent-atom—H lengths of 0.93 Å (CH), 0.98 Å (chiral-CH), 0.96 Å (CH₃), 0.97 Å (CH₂). Isotropic displacement parameters for these atoms were set to 1.2 (CH) or 1.5 (CH₃) times U_eq of the parent atom.

Table 3
Experimental details

	1	2
Crystal data
Chemical formula	C₁₆H₁₅NO₃S	C₁₈H₁₈N₂O₄S
M_r	301.35	358.40
Crystal system, space group	Monoclinic, P2₁/c	Orthorhombic, P2₁2₁2₁
Temperature (K)	173	298
a, b, c (Å)	14.4485 (6), 10.2031 (5), 10.4950 (4)	5.5230 (4), 10.6857 (9), 28.430 (2)
α, β, γ (°)	90, 107.179 (4), 90	90, 90, 90
V (Å³)	1478.13 (11)	1677.8 (2)
Z	4	4
Radiation type	Cu Kα	Mo Kα
μ (mm⁻¹)	2.03	0.22
Crystal size (mm)	0.2 × 0.18 × 0.09	0.22 × 0.06 × 0.06

Data collection
Diffractometer	Rigaku Oxford Diffraction Synergy Custom system, HyPix-Arc 150	Bruker SMART CCD area detector
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.668, 1.000	0.656, 0.900
No. of measured, independent and observed [I > 2σ(I)] reflections	7437, 2856, 2139	13301, 4037, 3460
R_int	0.056	0.035
(sin θ/λ)_max (Å⁻¹)	0.628	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.150, 1.10	0.042, 0.103, 1.04
No. of reflections	2856	4037
No. of parameters	191	231
H-atom treatment	H-atom parameters constrained	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.34	0.24, −0.14
Absolute structure	–	Flack x determined using 1213 quotients [(I⁺)−(I⁻)]/[(I⁺)+(I⁻)] (Parsons et al., 2013 )
Absolute structure parameter	–	0.07 (4)
Computer programs: CrysAlis PRO (Rigaku OD, 2022 $[Rigaku OD (2022). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SMART and SAINT (Bruker, 2016 ), SHELXT (Sheldrick, 2015a ), SHELXS (Sheldrick, 2008 ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC references: 2238010; 2238009

Crystal structure: contains datablocks 1, 2. DOI: https://doi.org/10.1107/S2056989023000695/hb8050sup1.cif

Structure factors: contains datablock 1. DOI: https://doi.org/10.1107/S2056989023000695/hb80501sup2.hkl

Structure factors: contains datablock 2. DOI: https://doi.org/10.1107/S2056989023000695/hb80502sup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989023000695/hb80501sup4.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989023000695/hb80502sup5.mol

Supporting information file. DOI: https://doi.org/10.1107/S2056989023000695/hb80501sup6.cml

Supporting information file. DOI: https://doi.org/10.1107/S2056989023000695/hb80502sup7.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2022) for (1); SMART (Bruker, 2016) for (2). Cell refinement: CrysAlis PRO (Rigaku OD, 2022) for (1); SAINT (Bruker, 2016) for (2). Data reduction: CrysAlis PRO (Rigaku OD, 2022) for (1); SAINT (Bruker, 2016) for (2). Program(s) used to solve structure: SHELXT (Sheldrick, 2015a) for (1); SHELXS (Sheldrick, 2008) for (2). For both structures, program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

rac-2,3-Diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione (1) top

Crystal data top

C₁₆H₁₅NO₃S	F(000) = 632
M_r = 301.35	D_x = 1.354 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54184 Å
a = 14.4485 (6) Å	Cell parameters from 3416 reflections
b = 10.2031 (5) Å	θ = 3.2–73.3°
c = 10.4950 (4) Å	µ = 2.03 mm⁻¹
β = 107.179 (4)°	T = 173 K
V = 1478.13 (11) Å³	Block, clear colourless
Z = 4	0.2 × 0.18 × 0.09 mm

Data collection top

Rigaku Oxford Diffraction Synergy Custom system, HyPix-Arc 150 diffractometer	2856 independent reflections
Radiation source: Rotating-anode X-ray tube, Rigaku (Cu) X-ray Source	2139 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.056
Detector resolution: 10.0000 pixels mm^-1	θ_max = 75.6°, θ_min = 3.2°
ω scans	h = −15→17
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −11→12
T_min = 0.668, T_max = 1.000	l = −12→13
7437 measured 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)] = 0.052	w = 1/[σ²(F_o²) + (0.0712P)² + 0.268P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.150	(Δ/σ)_max < 0.001
S = 1.10	Δρ_max = 0.32 e Å⁻³
2856 reflections	Δρ_min = −0.34 e Å⁻³
191 parameters	Extinction correction: SHELXL2018/3 (Sheldrick 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0023 (5)
Primary atom site location: dual

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	0.45082 (4)	0.66477 (7)	0.66401 (5)	0.0380 (2)
O1	0.52700 (12)	0.5704 (2)	0.67907 (19)	0.0514 (6)
O2	0.41925 (14)	0.6961 (2)	0.77812 (16)	0.0519 (6)
O3	0.22170 (13)	0.91599 (19)	0.44575 (18)	0.0455 (5)
N1	0.27444 (13)	0.7076 (2)	0.48536 (18)	0.0306 (5)
C1	0.35000 (16)	0.6063 (3)	0.5290 (2)	0.0310 (5)
H1	0.374440	0.583984	0.451921	0.037*
C4	0.47674 (18)	0.8100 (3)	0.5937 (2)	0.0396 (6)
H4A	0.532525	0.854461	0.656910	0.048*
H4B	0.493981	0.790381	0.511127	0.048*
C3	0.38813 (19)	0.8988 (3)	0.5617 (3)	0.0425 (6)
H3A	0.399282	0.971486	0.505438	0.051*
H3B	0.384838	0.938047	0.646531	0.051*
C2	0.28912 (18)	0.8402 (3)	0.4920 (2)	0.0348 (6)
C5	0.18322 (17)	0.6594 (3)	0.3978 (2)	0.0333 (6)
C6	0.17961 (19)	0.6182 (3)	0.2711 (2)	0.0440 (7)
H6	0.235336	0.625452	0.241121	0.053*
C7	0.0947 (2)	0.5664 (4)	0.1879 (3)	0.0559 (9)
H7	0.091908	0.537900	0.100655	0.067*
C8	0.0141 (2)	0.5563 (4)	0.2324 (3)	0.0633 (10)
H8	−0.044126	0.519958	0.175939	0.076*
C9	0.0179 (2)	0.5990 (4)	0.3588 (3)	0.0682 (11)
H9	−0.038042	0.592964	0.388363	0.082*
C10	0.10296 (19)	0.6506 (3)	0.4427 (3)	0.0496 (8)
H10	0.105807	0.679455	0.529797	0.060*
C11	0.31292 (16)	0.4818 (3)	0.5756 (2)	0.0334 (6)
C12	0.3255 (2)	0.3631 (3)	0.5188 (3)	0.0437 (7)
H12	0.356067	0.360439	0.450153	0.052*
C13	0.2933 (2)	0.2481 (3)	0.5624 (3)	0.0550 (8)
H13	0.301505	0.166705	0.523015	0.066*
C14	0.2495 (2)	0.2515 (3)	0.6624 (3)	0.0541 (8)
H14	0.227909	0.172599	0.692365	0.065*
C15	0.2371 (2)	0.3693 (3)	0.7189 (3)	0.0468 (7)
H15	0.207209	0.371115	0.788272	0.056*
C16	0.26749 (17)	0.4849 (3)	0.6758 (2)	0.0391 (6)
H16	0.257539	0.566039	0.714104	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0329 (4)	0.0492 (5)	0.0252 (3)	−0.0062 (3)	−0.0018 (2)	0.0054 (3)
O1	0.0332 (10)	0.0563 (14)	0.0540 (11)	0.0048 (9)	−0.0038 (8)	0.0172 (10)
O2	0.0568 (12)	0.0699 (15)	0.0249 (9)	−0.0242 (11)	0.0060 (8)	−0.0045 (9)
O3	0.0431 (11)	0.0385 (11)	0.0531 (11)	0.0069 (9)	0.0117 (8)	0.0068 (9)
N1	0.0264 (10)	0.0339 (12)	0.0271 (9)	0.0014 (9)	0.0010 (7)	0.0010 (9)
C1	0.0288 (12)	0.0369 (14)	0.0242 (11)	0.0019 (11)	0.0029 (8)	0.0001 (10)
C4	0.0332 (13)	0.0488 (18)	0.0306 (12)	−0.0078 (12)	−0.0002 (9)	−0.0007 (12)
C3	0.0429 (15)	0.0410 (16)	0.0409 (13)	−0.0035 (13)	0.0085 (11)	−0.0046 (12)
C2	0.0387 (13)	0.0361 (15)	0.0287 (12)	0.0004 (12)	0.0088 (9)	0.0008 (11)
C5	0.0266 (12)	0.0412 (16)	0.0273 (11)	0.0008 (11)	0.0006 (9)	0.0025 (11)
C6	0.0344 (13)	0.061 (2)	0.0318 (13)	0.0004 (13)	0.0024 (10)	−0.0038 (13)
C7	0.0457 (16)	0.075 (2)	0.0375 (14)	−0.0016 (16)	−0.0020 (11)	−0.0111 (15)
C8	0.0393 (16)	0.083 (3)	0.0542 (18)	−0.0118 (17)	−0.0070 (13)	−0.0056 (18)
C9	0.0319 (15)	0.118 (3)	0.0511 (18)	−0.0105 (19)	0.0072 (12)	0.003 (2)
C10	0.0347 (14)	0.079 (2)	0.0340 (13)	−0.0036 (15)	0.0083 (10)	−0.0019 (14)
C11	0.0284 (12)	0.0365 (15)	0.0299 (11)	0.0023 (11)	0.0005 (9)	0.0008 (11)
C12	0.0441 (15)	0.0421 (17)	0.0402 (14)	0.0065 (13)	0.0051 (11)	−0.0036 (13)
C13	0.063 (2)	0.0324 (17)	0.0579 (18)	0.0028 (15)	0.0007 (15)	0.0000 (14)
C14	0.0525 (17)	0.0420 (19)	0.0573 (18)	−0.0064 (15)	−0.0001 (14)	0.0102 (15)
C15	0.0428 (15)	0.0516 (19)	0.0431 (15)	−0.0038 (14)	0.0083 (11)	0.0098 (14)
C16	0.0398 (14)	0.0400 (16)	0.0360 (13)	−0.0006 (12)	0.0089 (10)	0.0013 (12)

Geometric parameters (Å, º) top

S1—O1	1.435 (2)	C6—C7	1.383 (4)
S1—O2	1.438 (2)	C7—H7	0.9500
S1—C1	1.807 (2)	C7—C8	1.381 (4)
S1—C4	1.744 (3)	C8—H8	0.9500
O3—C2	1.226 (3)	C8—C9	1.382 (5)
N1—C1	1.475 (3)	C9—H9	0.9500
N1—C2	1.368 (3)	C9—C10	1.387 (4)
N1—C5	1.451 (3)	C10—H10	0.9500
C1—H1	1.0000	C11—C12	1.385 (4)
C1—C11	1.514 (4)	C11—C16	1.394 (3)
C4—H4A	0.9900	C12—H12	0.9500
C4—H4B	0.9900	C12—C13	1.389 (4)
C4—C3	1.523 (4)	C13—H13	0.9500
C3—H3A	0.9900	C13—C14	1.377 (5)
C3—H3B	0.9900	C14—H14	0.9500
C3—C2	1.524 (4)	C14—C15	1.375 (4)
C5—C6	1.381 (3)	C15—H15	0.9500
C5—C10	1.377 (4)	C15—C16	1.381 (4)
C6—H6	0.9500	C16—H16	0.9500

O1—S1—O2	118.62 (12)	C5—C6—H6	120.0
O1—S1—C1	106.20 (12)	C5—C6—C7	119.9 (3)
O1—S1—C4	111.28 (13)	C7—C6—H6	120.0
O2—S1—C1	110.23 (11)	C6—C7—H7	120.2
O2—S1—C4	108.92 (14)	C8—C7—C6	119.6 (3)
C4—S1—C1	99.96 (11)	C8—C7—H7	120.2
C2—N1—C1	126.0 (2)	C7—C8—H8	119.9
C2—N1—C5	117.7 (2)	C7—C8—C9	120.2 (3)
C5—N1—C1	114.2 (2)	C9—C8—H8	119.9
S1—C1—H1	108.3	C8—C9—H9	119.8
N1—C1—S1	111.31 (17)	C8—C9—C10	120.4 (3)
N1—C1—H1	108.3	C10—C9—H9	119.8
N1—C1—C11	112.84 (19)	C5—C10—C9	119.1 (3)
C11—C1—S1	107.70 (15)	C5—C10—H10	120.5
C11—C1—H1	108.3	C9—C10—H10	120.5
S1—C4—H4A	109.9	C12—C11—C1	119.3 (2)
S1—C4—H4B	109.9	C12—C11—C16	119.7 (3)
H4A—C4—H4B	108.3	C16—C11—C1	121.0 (2)
C3—C4—S1	109.11 (19)	C11—C12—H12	120.1
C3—C4—H4A	109.9	C11—C12—C13	119.8 (3)
C3—C4—H4B	109.9	C13—C12—H12	120.1
C4—C3—H3A	107.6	C12—C13—H13	119.9
C4—C3—H3B	107.6	C14—C13—C12	120.2 (3)
C4—C3—C2	118.7 (2)	C14—C13—H13	119.9
H3A—C3—H3B	107.1	C13—C14—H14	120.0
C2—C3—H3A	107.6	C15—C14—C13	119.9 (3)
C2—C3—H3B	107.6	C15—C14—H14	120.0
O3—C2—N1	120.7 (2)	C14—C15—H15	119.7
O3—C2—C3	117.7 (2)	C14—C15—C16	120.7 (3)
N1—C2—C3	121.5 (2)	C16—C15—H15	119.7
C6—C5—N1	118.8 (2)	C11—C16—H16	120.2
C10—C5—N1	120.3 (2)	C15—C16—C11	119.6 (3)
C10—C5—C6	120.9 (2)	C15—C16—H16	120.2

S1—C1—C11—C12	−111.1 (2)	C4—C3—C2—O3	−167.2 (2)
S1—C1—C11—C16	68.1 (2)	C4—C3—C2—N1	15.3 (4)
S1—C4—C3—C2	−45.9 (3)	C2—N1—C1—S1	29.3 (3)
O1—S1—C1—N1	−168.32 (16)	C2—N1—C1—C11	150.5 (2)
O1—S1—C1—C11	67.50 (19)	C2—N1—C5—C6	96.5 (3)
O1—S1—C4—C3	172.01 (17)	C2—N1—C5—C10	−86.0 (3)
O2—S1—C1—N1	62.00 (19)	C5—N1—C1—S1	−167.57 (16)
O2—S1—C1—C11	−62.2 (2)	C5—N1—C1—C11	−46.3 (3)
O2—S1—C4—C3	−55.4 (2)	C5—N1—C2—O3	13.2 (3)
N1—C1—C11—C12	125.6 (2)	C5—N1—C2—C3	−169.4 (2)
N1—C1—C11—C16	−55.2 (3)	C5—C6—C7—C8	0.0 (5)
N1—C5—C6—C7	177.1 (3)	C6—C5—C10—C9	0.3 (5)
N1—C5—C10—C9	−177.2 (3)	C6—C7—C8—C9	0.7 (6)
C1—S1—C4—C3	60.16 (19)	C7—C8—C9—C10	−0.9 (6)
C1—N1—C2—O3	175.8 (2)	C8—C9—C10—C5	0.4 (6)
C1—N1—C2—C3	−6.8 (3)	C10—C5—C6—C7	−0.5 (4)
C1—N1—C5—C6	−68.1 (3)	C11—C12—C13—C14	−0.4 (4)
C1—N1—C5—C10	109.4 (3)	C12—C11—C16—C15	1.1 (4)
C1—C11—C12—C13	178.9 (2)	C12—C13—C14—C15	0.4 (4)
C1—C11—C16—C15	−178.1 (2)	C13—C14—C15—C16	0.4 (4)
C4—S1—C1—N1	−52.56 (18)	C14—C15—C16—C11	−1.2 (4)
C4—S1—C1—C11	−176.73 (18)	C16—C11—C12—C13	−0.3 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12···O1ⁱ	0.95	2.56	3.454 (4)	157

Symmetry code: (i) −x+1, −y+1, −z+1.

N-[(2S,5R)-1,1,4-Trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide (2) top

Crystal data top

C₁₈H₁₈N₂O₄S	D_x = 1.419 Mg m⁻³
M_r = 358.40	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 4224 reflections
a = 5.5230 (4) Å	θ = 2.4–25.0°
b = 10.6857 (9) Å	µ = 0.22 mm⁻¹
c = 28.430 (2) Å	T = 298 K
V = 1677.8 (2) Å³	Rod, colorless
Z = 4	0.22 × 0.06 × 0.06 mm
F(000) = 752

Data collection top

Bruker SMART CCD area detector diffractometer	3460 reflections with I > 2σ(I)
phi and ω scans	R_int = 0.035
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	θ_max = 28.3°, θ_min = 1.4°
T_min = 0.656, T_max = 0.900	h = −7→5
13301 measured reflections	k = −12→14
4037 independent reflections	l = −36→37

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.042	w = 1/[σ²(F_o²) + (0.0564P)² + 0.035P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.103	(Δ/σ)_max < 0.001
S = 1.04	Δρ_max = 0.24 e Å⁻³
4037 reflections	Δρ_min = −0.14 e Å⁻³
231 parameters	Absolute structure: Flack x determined using 1213 quotients [(I⁺)-(I^-)]/[(I⁺)+(I^-)] (Parsons et al., 2013)
0 restraints	Absolute structure parameter: 0.07 (4)
Primary atom site location: structure-invariant direct methods

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.

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

	x	y	z	U_iso*/U_eq
S1	0.29097 (13)	0.61561 (6)	0.04750 (2)	0.04039 (18)
O1	0.2013 (5)	0.5960 (2)	0.00084 (6)	0.0665 (7)
O2	0.5430 (4)	0.5943 (2)	0.05600 (8)	0.0655 (6)
O3	0.0948 (4)	0.72050 (18)	0.18769 (6)	0.0575 (6)
O4	−0.3983 (4)	0.8940 (2)	0.13514 (8)	0.0659 (6)
N1	0.1594 (4)	0.56459 (18)	0.13538 (6)	0.0394 (5)
N2	0.0062 (5)	0.8977 (2)	0.12438 (9)	0.0485 (6)
C1	0.1124 (4)	0.5198 (2)	0.08754 (7)	0.0333 (5)
H1	−0.058432	0.536713	0.080716	0.040*
C2	0.0930 (5)	0.6841 (2)	0.14753 (8)	0.0409 (6)
C3	0.0251 (5)	0.7713 (2)	0.10656 (8)	0.0398 (6)
H3	−0.132274	0.745690	0.093867	0.048*
C4	0.2134 (6)	0.7692 (2)	0.06686 (8)	0.0424 (6)
H4A	0.359008	0.811013	0.077660	0.051*
H4B	0.150687	0.816206	0.040330	0.051*
C11	0.1560 (4)	0.3832 (2)	0.07738 (7)	0.0350 (5)
C16	0.3688 (5)	0.3203 (3)	0.08898 (9)	0.0448 (6)
H16	0.493371	0.362002	0.104412	0.054*
C15	0.3932 (6)	0.1953 (3)	0.07738 (10)	0.0559 (8)
H15	0.533040	0.152566	0.085968	0.067*
C14	0.2132 (7)	0.1331 (3)	0.05326 (10)	0.0596 (9)
H14	0.232717	0.049213	0.045356	0.072*
C13	0.0065 (7)	0.1949 (3)	0.04104 (10)	0.0565 (8)
H13	−0.114479	0.153289	0.024516	0.068*
C12	−0.0235 (5)	0.3194 (2)	0.05317 (8)	0.0434 (6)
H12	−0.165681	0.360621	0.044990	0.052*
C5	0.2702 (5)	0.4889 (2)	0.17177 (7)	0.0393 (6)
C6	0.1536 (6)	0.3843 (3)	0.18873 (9)	0.0535 (8)
H6	0.004073	0.360301	0.176670	0.064*
C7	0.2639 (10)	0.3152 (3)	0.22429 (10)	0.0815 (13)
H7	0.188747	0.243530	0.235747	0.098*
C8	0.4806 (12)	0.3516 (5)	0.24243 (12)	0.0976 (17)
H8	0.553113	0.304469	0.266063	0.117*
C9	0.5929 (8)	0.4575 (5)	0.22597 (12)	0.0839 (13)
H9	0.738587	0.483351	0.239181	0.101*
C10	0.4902 (6)	0.5261 (3)	0.18983 (10)	0.0560 (8)
H10	0.568552	0.596319	0.177902	0.067*
C17	−0.2027 (7)	0.9434 (3)	0.14185 (9)	0.0490 (7)
C18	−0.1753 (8)	1.0631 (3)	0.16996 (11)	0.0678 (10)
H18A	−0.330040	1.103268	0.172852	0.102*
H18B	−0.064566	1.118103	0.154150	0.102*
H18C	−0.113853	1.043699	0.200700	0.102*
H2	0.139 (5)	0.924 (3)	0.1348 (9)	0.042 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0452 (4)	0.0358 (3)	0.0402 (3)	0.0022 (3)	0.0046 (3)	0.0016 (2)
O1	0.1092 (19)	0.0556 (12)	0.0347 (9)	−0.0001 (14)	0.0030 (11)	−0.0010 (8)
O2	0.0404 (11)	0.0512 (13)	0.1048 (17)	0.0035 (10)	0.0137 (12)	0.0130 (11)
O3	0.0835 (16)	0.0502 (12)	0.0387 (9)	0.0055 (11)	0.0013 (10)	−0.0095 (8)
O4	0.0562 (14)	0.0671 (15)	0.0742 (14)	0.0093 (13)	−0.0051 (11)	−0.0223 (12)
N1	0.0536 (15)	0.0329 (10)	0.0317 (9)	0.0008 (10)	−0.0029 (9)	−0.0018 (8)
N2	0.0530 (16)	0.0315 (12)	0.0611 (14)	−0.0018 (12)	−0.0034 (12)	−0.0078 (10)
C1	0.0321 (12)	0.0353 (12)	0.0324 (10)	0.0017 (10)	−0.0035 (9)	−0.0027 (9)
C2	0.0461 (16)	0.0349 (13)	0.0415 (12)	−0.0033 (12)	0.0008 (12)	−0.0033 (10)
C3	0.0431 (15)	0.0303 (12)	0.0460 (13)	−0.0002 (11)	−0.0029 (11)	−0.0054 (10)
C4	0.0506 (15)	0.0347 (12)	0.0419 (12)	−0.0013 (13)	−0.0016 (12)	0.0019 (9)
C11	0.0406 (14)	0.0327 (11)	0.0317 (10)	−0.0004 (11)	0.0015 (9)	−0.0009 (9)
C16	0.0480 (16)	0.0434 (14)	0.0431 (13)	0.0080 (13)	−0.0010 (11)	0.0002 (11)
C15	0.072 (2)	0.0458 (16)	0.0498 (15)	0.0223 (16)	0.0092 (15)	0.0110 (12)
C14	0.095 (3)	0.0319 (13)	0.0516 (15)	−0.0005 (17)	0.0225 (18)	0.0014 (11)
C13	0.072 (2)	0.0451 (16)	0.0521 (15)	−0.0183 (17)	0.0068 (15)	−0.0108 (12)
C12	0.0463 (15)	0.0445 (15)	0.0394 (12)	−0.0049 (13)	0.0010 (12)	−0.0051 (11)
C5	0.0445 (15)	0.0420 (13)	0.0315 (10)	0.0043 (12)	−0.0011 (11)	−0.0019 (9)
C6	0.071 (2)	0.0473 (15)	0.0422 (13)	−0.0011 (16)	0.0077 (13)	0.0033 (12)
C7	0.138 (4)	0.060 (2)	0.0462 (16)	0.015 (3)	0.012 (2)	0.0154 (14)
C8	0.147 (5)	0.100 (4)	0.0458 (18)	0.058 (3)	−0.020 (2)	0.0019 (19)
C9	0.073 (3)	0.118 (4)	0.060 (2)	0.039 (3)	−0.0289 (19)	−0.029 (2)
C10	0.0483 (18)	0.071 (2)	0.0483 (14)	0.0058 (16)	−0.0050 (13)	−0.0119 (14)
C17	0.065 (2)	0.0384 (14)	0.0435 (13)	0.0077 (15)	−0.0061 (15)	−0.0038 (10)
C18	0.095 (3)	0.0437 (16)	0.0649 (18)	0.0125 (19)	−0.0055 (19)	−0.0156 (13)

Geometric parameters (Å, º) top

S1—O1	1.431 (2)	C15—H15	0.9300
S1—O2	1.431 (2)	C15—C14	1.378 (5)
S1—C1	1.821 (2)	C14—H14	0.9300
S1—C4	1.783 (3)	C14—C13	1.364 (5)
O3—C2	1.206 (3)	C13—H13	0.9300
O4—C17	1.218 (4)	C13—C12	1.384 (4)
N1—C1	1.465 (3)	C12—H12	0.9300
N1—C2	1.373 (3)	C5—C6	1.377 (4)
N1—C5	1.449 (3)	C5—C10	1.378 (4)
N2—C3	1.446 (3)	C6—H6	0.9300
N2—C17	1.348 (4)	C6—C7	1.393 (5)
N2—H2	0.84 (3)	C7—H7	0.9300
C1—H1	0.9800	C7—C8	1.360 (7)
C1—C11	1.507 (3)	C8—H8	0.9300
C2—C3	1.538 (3)	C8—C9	1.373 (6)
C3—H3	0.9800	C9—H9	0.9300
C3—C4	1.535 (4)	C9—C10	1.384 (5)
C4—H4A	0.9700	C10—H10	0.9300
C4—H4B	0.9700	C17—C18	1.515 (4)
C11—C16	1.394 (4)	C18—H18A	0.9600
C11—C12	1.386 (3)	C18—H18B	0.9600
C16—H16	0.9300	C18—H18C	0.9600
C16—C15	1.382 (4)

O1—S1—C1	108.03 (13)	C16—C15—H15	119.5
O1—S1—C4	109.74 (13)	C14—C15—C16	121.0 (3)
O2—S1—O1	118.01 (15)	C14—C15—H15	119.5
O2—S1—C1	109.38 (12)	C15—C14—H14	120.1
O2—S1—C4	109.15 (14)	C13—C14—C15	119.8 (3)
C4—S1—C1	101.20 (11)	C13—C14—H14	120.1
C2—N1—C1	119.34 (19)	C14—C13—H13	119.9
C2—N1—C5	116.91 (18)	C14—C13—C12	120.2 (3)
C5—N1—C1	123.75 (19)	C12—C13—H13	119.9
C3—N2—H2	112 (2)	C11—C12—H12	119.6
C17—N2—C3	122.0 (3)	C13—C12—C11	120.7 (3)
C17—N2—H2	120 (2)	C13—C12—H12	119.6
S1—C1—H1	107.1	C6—C5—N1	120.4 (2)
N1—C1—S1	107.50 (16)	C10—C5—N1	118.5 (3)
N1—C1—H1	107.1	C10—C5—C6	121.1 (3)
N1—C1—C11	117.76 (19)	C5—C6—H6	120.7
C11—C1—S1	109.76 (16)	C5—C6—C7	118.7 (3)
C11—C1—H1	107.1	C7—C6—H6	120.7
O3—C2—N1	122.4 (2)	C6—C7—H7	119.7
O3—C2—C3	121.6 (2)	C8—C7—C6	120.6 (4)
N1—C2—C3	115.99 (19)	C8—C7—H7	119.7
N2—C3—C2	108.5 (2)	C7—C8—H8	119.9
N2—C3—H3	109.0	C7—C8—C9	120.2 (4)
N2—C3—C4	108.7 (2)	C9—C8—H8	119.9
C2—C3—H3	109.0	C8—C9—H9	119.8
C4—C3—C2	112.5 (2)	C8—C9—C10	120.3 (4)
C4—C3—H3	109.0	C10—C9—H9	119.8
S1—C4—H4A	108.8	C5—C10—C9	119.0 (4)
S1—C4—H4B	108.8	C5—C10—H10	120.5
C3—C4—S1	113.79 (17)	C9—C10—H10	120.5
C3—C4—H4A	108.8	O4—C17—N2	123.0 (2)
C3—C4—H4B	108.8	O4—C17—C18	122.5 (3)
H4A—C4—H4B	107.7	N2—C17—C18	114.5 (3)
C16—C11—C1	123.8 (2)	C17—C18—H18A	109.5
C12—C11—C1	117.2 (2)	C17—C18—H18B	109.5
C12—C11—C16	118.9 (2)	C17—C18—H18C	109.5
C11—C16—H16	120.3	H18A—C18—H18B	109.5
C15—C16—C11	119.5 (3)	H18A—C18—H18C	109.5
C15—C16—H16	120.3	H18B—C18—H18C	109.5

S1—C1—C11—C16	73.2 (2)	C2—N1—C5—C6	114.0 (3)
S1—C1—C11—C12	−103.8 (2)	C2—N1—C5—C10	−64.0 (3)
O1—S1—C1—N1	−165.13 (17)	C2—C3—C4—S1	50.6 (3)
O1—S1—C1—C11	65.65 (19)	C3—N2—C17—O4	−15.9 (4)
O1—S1—C4—C3	111.3 (2)	C3—N2—C17—C18	165.1 (2)
O2—S1—C1—N1	65.22 (19)	C4—S1—C1—N1	−49.88 (19)
O2—S1—C1—C11	−64.00 (19)	C4—S1—C1—C11	−179.10 (17)
O2—S1—C4—C3	−117.9 (2)	C11—C16—C15—C14	2.0 (4)
O3—C2—C3—N2	8.7 (4)	C16—C11—C12—C13	0.6 (4)
O3—C2—C3—C4	129.0 (3)	C16—C15—C14—C13	−0.7 (4)
N1—C1—C11—C16	−50.2 (3)	C15—C14—C13—C12	−0.6 (4)
N1—C1—C11—C12	132.9 (2)	C14—C13—C12—C11	0.7 (4)
N1—C2—C3—N2	−169.1 (2)	C12—C11—C16—C15	−1.9 (4)
N1—C2—C3—C4	−48.8 (3)	C5—N1—C1—S1	−117.4 (2)
N1—C5—C6—C7	−178.9 (3)	C5—N1—C1—C11	7.2 (3)
N1—C5—C10—C9	177.3 (3)	C5—N1—C2—O3	−9.9 (4)
N2—C3—C4—S1	170.82 (19)	C5—N1—C2—C3	167.9 (2)
C1—S1—C4—C3	−2.7 (2)	C5—C6—C7—C8	1.1 (5)
C1—N1—C2—O3	169.2 (3)	C6—C5—C10—C9	−0.8 (4)
C1—N1—C2—C3	−13.1 (4)	C6—C7—C8—C9	0.3 (6)
C1—N1—C5—C6	−64.9 (3)	C7—C8—C9—C10	−2.0 (6)
C1—N1—C5—C10	117.0 (3)	C8—C9—C10—C5	2.2 (5)
C1—C11—C16—C15	−178.8 (2)	C10—C5—C6—C7	−0.9 (4)
C1—C11—C12—C13	177.7 (2)	C17—N2—C3—C2	−88.7 (3)
C2—N1—C1—S1	63.7 (3)	C17—N2—C3—C4	148.7 (3)
C2—N1—C1—C11	−171.8 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···O2ⁱ	0.98	2.39	3.365 (3)	173
C4—H4A···O4ⁱⁱ	0.97	2.29	3.185 (4)	153
C8—H8···O3ⁱⁱⁱ	0.93	2.51	3.378 (5)	155

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

Funding information

Research reported here was conducted on instrumentation funded by NSF (for Bruker AXS system) CHEM-0131112, and SIG S10 grants of the National Institutes of Health (for the Rigaku rotating anode system) under award numbers 1S10OD028589–01 and 1S10RR023439–01 to Dr Neela Yennawar.

References

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Volume 79| Part 2| February 2023| Pages 120-123

https://doi.org/10.1107/S2056989023000695

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

Crystal structures of rac-2,3-di­phenyl-2,3,5,6-tetra­hydro-4H-1,3-thia­zine-1,1,4-trione and N-[(2S,5R)-1,1,4-trioxo-2,3-di­phenyl-1,3-thia­zinan-5-yl]acet­amide

1. Chemical context

2. Structural commentary

3. Supra­molecular features

4. Database survey

5. Synthesis and crystallization

6. Refinement

Supporting information

Funding information

References

research communications

Crystal structures of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide

3. Supramolecular features