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Tetrahydro-1, 4-Thiazine-3, 5-Dione molbank Short Note Tetrahydro-1,4-thiazine-3,5-dioneShort Note Tetrahydro-1,4-thiazine-3,5-dione R. Alan Aitken * , Alexandra M. Z. Slawin and Pei-pei Yeh R.EaStCHEM Alan Aitken School *, Alexandra of Chemistry, M. University Z. Slawin of Stand Andrews, Pei-pei North Yeh Haugh, St Andrews Fife KY16 9ST, UK; [email protected] (A.M.Z.S.); [email protected] (P.-p.Y.) EaStCHEM School of Chemistry, University of St Andrews, North Haugh, St Andrews Fife KY16 9ST, UK; * Correspondence: [email protected]; Tel.: +44-1334-463865 [email protected] (A.M.Z.S.); [email protected] (P.-p.Y.) * Correspondence: [email protected]; Tel.: +44-1334-463865 Received: 30 November 2018; Accepted: 12 December 2018; Published: 13 December 2018 Received: 30 November 2018; Accepted: 12 December 2018; Published: date Abstract: The X-ray structure of the title compound contains eight molecules in the unit cell which formAbstract: the basisThe X-ray of a herringbone structure of arrangement the title compound of hydrogen contains bonded eight ribbons. molecules in the unit cell which form the basis of a herringbone arrangement of hydrogen bonded ribbons. Keywords: tetrahydro-1,4-thiazine-3,5-dione; X-ray structure; hydrogen bonding Keywords: tetrahydro-1,4-thiazine-3,5-dione; X-ray structure; hydrogen bonding 1. Introduction The simplesimple heterocyclic heterocyclic compound compound tetrahydro-1,4-thiazine-3,5-dione tetrahydro-1,4-thiazine-3,5-dione (or thiomorpholine-3,5-dione) (or thiomorpholine-3,5- 1dione), the cyclic 1, the imide cyclic of imide thiodiglycolic of thiodiglycolic acid 2, was acid first 2 prepared, was first in prepared 1948 [1], andin 1948 IR and [1], NMR and spectroscopicIR and NMR dataspectroscopic were reported data were in 2001 reported [2]. in Following 2001 [2]. ourFollowing recent our report recent of report the first of generationthe first generation of the parent of the 1,4-oxazineparent 1,4-oxazine [3], we [3], were we interestedwere interested to explore to expl routesore routes to the to analogousthe analogous 1,4-thiazine 1,4-thiazine and and many many of theseof these attempts attempts have have involved involved starting starting from from1, although1, although we we have have so farso beenfar been unable unable to reproduce to reproduce the reportedthe reported [1] direct [1] direct reduction reduction of 1 to of 1,4-thiazine 1 to 1,4-thiazine over aluminium over aluminium powder. powder. In the courseIn the ofcourse these of studies, these compoundstudies, compound1 has been 1 preparedhas been in prepared large quantity in large and quantity we report and here we the report molecular here and thecrystal molecular structure and ofcrystal1 as determinedstructure of 1 by as X-ray determined diffraction. by X-ray The diffraction. observed crystal The observed structure crystal is discussed structure in comparisonis discussed within comparison those in similar with those previously in similar reported previously structures. reported structures. 2. Results Compound 11was was readily readily prepared prepared using theusing literature the literature method [ 1]method involving [1] heating involving commercially heating availablecommercially thiodiglycolic available thiodiglycolic acid 2 with an acid excess 2 with of aqueous an excess ammonia of aqueous and ammonia distilling and off the distilling water, firstoff the at atmosphericwater, first at pressure atmospheric and finallypressure under and vacuumfinally under (Scheme vacuum1). The (Scheme residue 1). was The subjected residue was to kugelrohr subjected distillationto kugelrohr to distillation give the product to give as the colourless product crystals as colourless which crystals were directly which suitable were directly for the suitable X-ray structure for the determination.X-ray structure Bothdetermination. IR and NMR Both (CD 3IRSOCD and 3NMR) spectra (CD were3SOCD in agreement3) spectra withwere previouslyin agreement reported with 1 13 valuespreviously [2], butreported we have values also recorded[2], but weH- have and alsoC-NMR recorded data in1H- CDCl and3 (see13C-NMR Experimental data in SectionCDCl3 and(see SupplementaryExperimental Section Material). and Supplementary Material). O 1. aq. NH3 S S S 2. heat, − H O 2 = HN CO2H CO2H O N O O H 2 1 Scheme 1. Synthetic route to 1 [[1].1]. In the X-ray structure there are two distinct moleculesmolecules (Figure 11,, TablesTables1 1and and2) 2) both both of of which which show anan “envelope”“envelope” structure structure with with the the sulfur sulfur atom atom above above the the plane plan containinge containing the imidethe imide function function and two CH groups. The molecular dimensions are similar but slightly different which reflects the different and two2 CH2 groups. The molecular dimensions are similar but slightly different which reflects the roledifferent of the role two of molecules the two inmolecules the hydrogen-bonding in the hydrog patternen-bonding (each pattern molecule (each is hydrogen-bonded molecule is hydrogen- to two ofbonded the opposite to two type).of the Inopposite the first type). molecule In the the first sulfur molecule atom isthe 0.865 sulfur Å aboveatom is the 0.865 mean Å planeabove formed the mean by plane formed by C(2), C(3), N(4), C(5) and C(6) and the plane containing C(2), S(1) and C(6) is at an Molbank 2018, 2018, M1036; doi:10.3390/M1036 www.mdpi.com/journal/molbank Molbank 2017, 2017, M9xx; doi: FOR PEER REVIEW www.mdpi.com/journal/molbank Molbank 2018, 2018, M1036 2 of 5 Molbank 2017, 2017, M9xx FOR PEER REVIEW 2 of 5 C(2), C(3), N(4), C(5) and C(6) and the plane containing C(2), S(1) and C(6) is at an angle of 46.27◦ to ° theangle first of plane. 46.27 Forto the the first second plane. molecule For the the second corresponding molecule the parameters corresponding are 0.897 parameters Å and 48.15 are◦ .0.897 In the Å ° unitand cell48.15 there. In are the eight unit molecules,cell there are four eight of each molecules, type, and four these of areeach arranged type, and ina these “herringbone” are arranged pattern in a when“herringbone” viewed along pattern the when a axis viewed (Figure 2along). the a axis (Figure 2). Figure 1. The two distinct molecules in the molecular structure of 1 with numbering scheme. Figure 1. The two distinct molecules in the molecular structure of 1 with numbering scheme. Table 1. Selected bond lengths. Bond Length/ÅTable 1. Selected bond lengths. Bond Length/Å S(1)–C(2)Bond 1.804(2)Length/Å Bond S(11)–C(12) Length/Å 1.799(2) S(1)–C(6)S(1)–C(2) 1.807(3)1.804(2) S(11)–C(12) S(11)–C(16) 1.799(2) 1.797(3) O(3)–C(3) 1.230(3) O(13)–C(13) 1.231(3) S(1)–C(6) 1.807(3) S(11)–C(16) 1.797(3) O(5)–C(5) 1.227(3) O(15–C(15) 1.223(3) N(4)–C(3)O(3)–C(3) 1.375(3)1.230(3) O(13)–C(13) N(14)–C(13) 1.231(3) 1.370(3) N(4)–C(5)O(5)–C(5) 1.400(3)1.227(3) O(15–C(15) N(14)–C(15) 1.223(3) 1.396(3) N(4)–H(4N)N(4)–C(3) 0.975(5)1.375(3) N(14)–C(13) N(14)–H(14N) 1.370(3) 0.976(5) C(2)–C(3)N(4)–C(5) 1.500(3)1.400(3) N(14)–C(15) C(12)–C(13) 1.396(3) 1.503(3) C(5)–C(6) 1.496(3) C(15)–C(16) 1.503(3) N(4)–H(4N) 0.975(5) N(14)–H(14N) 0.976(5) C(2)–C(3) 1.500(3) C(12)–C(13) 1.503(3) Table 2. Selected angles. C(5)–C(6) 1.496(3) C(15)–C(16) 1.503(3) Angle Value/◦ Angle Value/◦ C(2)–S(1)–C(6) 97.48(11)Table 2. Selected C(12)–S(11)–C(16) angles. 96.37(11) C(3)–N(4)–C(5)Angle 129.08(19)Value/° C(13)–N(14)–C(15)Angle Value/° 128.60(19) C(3)–N(4)–H(4N) 113.0(13) C(13)–N(14)–H(14N) 114.6(15) C(5)–N(4)–H(4N)C(2)–S(1)–C(6) 117.4(13)97.48(11) C(12)–S(11)–C(16) C(15)–N(14)–H(14N) 96.37(11) 116.6(15) C(3)–C(2)–S(1)C(3)–N(4)–C(5) 112.69(16)129.08(19) C(13)–N(14)–C(15) C(13)–C(12)–S(11) 128.60(19) 113.30(16) O(3)–C(3)–N(4)C(3)–N(4)–H(4N) 118.8(2)113.0(13) C(13)–N(14)–H(14N) O(13)–C(13)–N(14) 114.6(15) 119.0(2) O(3)–C(3)–C(2)C(5)–N(4)–H(4N) 122.1(2)117.4(13) C(15)–N(14)–H(14N) O(13)–C(13)–C(12) 116.6(15) 122.1(2) N(4)–C(3)–C(2) 119.03(19) N(14)–C(13)–C(12) 118.85(19) O(5)–C(5)–N(4)C(3)–C(2)–S(1) 119.2(2)112.69(16) C(13)–C(12)–S(11) O(15)–C(15)–N(14) 113.30(16) 118.6(2) O(5)–C(5)–C(6)O(3)–C(3)–N(4) 121.6(2)118.8(2) O(13)–C(13)–N(14) O(15)–C(15)–C(16) 119.0(2) 121.8(2) N(4)–C(5)–C(6)O(3)–C(3)–C(2) 119.2(2)122.1(2) O(13)–C(13)–C(12) N(14)–C(15)–C(16) 122.1(2) 119.5(2) C(5)–C(6)–S(1)N(4)–C(3)–C(2) 115.51(16)119.03(19) N(14)–C(13)–C(12) C(15)–C(16)–S(11) 118.85(19) 114.20(17) O(5)–C(5)–N(4) 119.2(2) O(15)–C(15)–N(14) 118.6(2) O(5)–C(5)–C(6) 121.6(2) O(15)–C(15)–C(16) 121.8(2) N(4)–C(5)–C(6) 119.2(2) N(14)–C(15)–C(16) 119.5(2) C(5)–C(6)–S(1) 115.51(16) C(15)–C(16)–S(11) 114.20(17) Molbank 2017, 2017, M9xx FOR PEER REVIEW 3 of 5 Molbank 2018, 2018, M1036 3 of 5 Molbank 2017, 2017, M9xx FOR PEER REVIEW 3 of 5 Figure 2.
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