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The title compound, C12H10O2N2S, is a potential antitumor agent. The compound, obtained by the reaction of 2,4-di­amino-1-thia-3-aza­buta­diene with ketene, crystallizes with monoclinic symmetry in space group P21.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002726/dn6022sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002726/dn6022Isup2.hkl
Contains datablock I

CCDC reference: 182622

Key indicators

  • Single-crystal X-ray study
  • T = 300 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.045
  • wR factor = 0.119
  • Data-to-parameter ratio = 24.9

checkCIF results

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ADDSYM reports no extra symmetry








Comment top

Heterocyclic compounds containing S and N atoms have attracted much attention because of their broad spectrum of biological activities (Wishka et al., 1998). In particular, 1,3-thiazinones and pyrimidinethiones have been explored as antitumor (Mayer et al., 1999), antibacterial agents (Vig et al., 1998), as well as antiviral agents for human immunodeficiency virus (HIV) (Danel et al., 1997). We report here the structure of one such thiazinone, 2-(N-phenylacetamido)-6H-1,3-thiazin-6-one, (I), which is a useful intermediate for the synthesis of N-deacylated 2-amino-1,3-thiazine-6-thione. The thiazinic ring and amide group are nearly planar. The phenyl substituent is approximately perpendicular to the acetamidothiazin-6-one ring with a bond angle of 79.04 (4)°.

Experimental top

Synthesis was carried out starting from 2,4-diamino-1-thia-3-azabutadiene and ketene (Landreau et al., 2000). Ketene, formed by cracking of acetone, was passed through a solution of azabutadiene (4 mmol) in anhydrous dichloromethane (150 ml) until starting product had disappeared. The mixture was cautiously evaporated and the residue was purified twice by flash chromatography (silica gel, dichloromethane/ethyl acetate, 9/1). Single crystals suitable for X-ray analysis were obtained by slow evaporation at room temperature from diethyl ether.

Refinement top

The positions of the CH3 group H atoms were refined. Other H atoms were fixed at calculated positions. Riding isotropic displacement parameter was used for all H atoms.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXTL (Sheldrick, 1995); program(s) used to refine structure: JANA2000 (Petricek & Dusek, 2000); molecular graphics: DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: JANA2000.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids. H have been omitted for clarity.
2-N-Phenylacetamido-6H-1,3-thiazin-6-one top
Crystal data top
C12H10N2O2SF(000) = 512
Mr = 246.3Dx = 1.39 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ybcCell parameters from 11369 reflections
a = 6.0696 (5) Åθ = 4.1–32.1°
b = 18.0716 (9) ŵ = 0.27 mm1
c = 10.8780 (8) ÅT = 300 K
β = 99.579 (10)°Block, colourless
V = 1176.54 (15) Å30.31 × 0.23 × 0.15 mm
Z = 4
Data collection top
Nonius KappaCCD
diffractometer
2758 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 32.1°, θmin = 4.1°
ϕ and ω scansh = 99
27839 measured reflectionsk = 2626
4086 independent reflectionsl = 1616
Refinement top
Refinement on F2Weighting scheme based on measured s.u.'s w = 1/[σ2(I) + 0.001024I2]
R[F2 > 2σ(F2)] = 0.045(Δ/σ)max = 0.001
wR(F2) = 0.119Δρmax = 0.33 e Å3
S = 1.65Δρmin = 0.27 e Å3
4086 reflectionsExtinction correction: B-C type 1 Lorentzian isotropic
164 parametersExtinction coefficient: 0.413964
H atoms treated by a mixture of independent and constrained refinement
Crystal data top
C12H10N2O2SV = 1176.54 (15) Å3
Mr = 246.3Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.0696 (5) ŵ = 0.27 mm1
b = 18.0716 (9) ÅT = 300 K
c = 10.8780 (8) Å0.31 × 0.23 × 0.15 mm
β = 99.579 (10)°
Data collection top
Nonius KappaCCD
diffractometer
2758 reflections with I > 2σ(I)
27839 measured reflectionsRint = 0.039
4086 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.045164 parameters
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.65Δρmax = 0.33 e Å3
4086 reflectionsΔρmin = 0.27 e Å3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S10.22543 (6)0.733745 (17)0.58282 (3)0.05627 (14)
C20.2524 (2)0.63925 (6)0.61524 (11)0.0442 (4)
N30.37751 (19)0.59342 (6)0.56705 (9)0.0518 (4)
C40.5097 (3)0.61647 (8)0.48423 (13)0.0599 (5)
C50.5336 (2)0.68528 (8)0.44156 (13)0.0578 (5)
C60.4144 (2)0.74718 (7)0.47600 (12)0.0520 (4)
O10.42375 (19)0.81081 (5)0.43808 (10)0.0698 (4)
N70.12890 (17)0.60939 (5)0.70061 (9)0.0460 (3)
C80.0078 (2)0.65187 (8)0.76539 (13)0.0556 (5)
C90.0940 (3)0.61469 (11)0.8707 (2)0.0772 (7)
O20.0488 (2)0.71535 (6)0.73850 (11)0.0824 (5)
C100.1646 (2)0.53204 (6)0.73286 (11)0.0432 (4)
C110.3467 (2)0.51184 (7)0.81798 (12)0.0501 (4)
C120.3742 (2)0.43867 (7)0.85436 (13)0.0574 (5)
C130.2189 (3)0.38676 (7)0.80678 (13)0.0581 (5)
C140.0388 (3)0.40703 (8)0.72054 (14)0.0664 (5)
C150.0100 (2)0.48024 (8)0.68232 (13)0.0602 (5)
H9a0.029 (4)0.6001 (13)0.931 (2)0.1225*
H9b0.191 (4)0.6503 (13)0.8996 (19)0.1225*
H9c0.162 (4)0.5693 (13)0.843 (2)0.1225*
H40.59970.57880.45090.0916*
H50.64080.69010.38390.0883*
H110.45620.54910.85290.0745*
H120.50510.42340.91410.0850*
H130.23620.33520.83370.0879*
H140.07010.36910.68660.0979*
H150.11740.49490.61990.0872*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0719 (3)0.03283 (19)0.0679 (2)0.00403 (14)0.02273 (17)0.00298 (13)
C20.0508 (7)0.0347 (6)0.0463 (6)0.0018 (5)0.0060 (5)0.0004 (5)
N30.0678 (7)0.0375 (6)0.0531 (6)0.0081 (5)0.0188 (5)0.0011 (4)
C40.0733 (9)0.0532 (8)0.0568 (8)0.0114 (7)0.0216 (7)0.0029 (6)
C50.0656 (9)0.0537 (8)0.0574 (8)0.0010 (6)0.0198 (6)0.0013 (6)
C60.0560 (8)0.0429 (7)0.0557 (7)0.0096 (6)0.0050 (6)0.0008 (5)
O10.0834 (7)0.0426 (6)0.0867 (7)0.0115 (5)0.0237 (6)0.0092 (4)
N70.0524 (6)0.0328 (5)0.0541 (6)0.0032 (4)0.0126 (4)0.0006 (4)
C80.0553 (8)0.0439 (8)0.0707 (8)0.0050 (6)0.0198 (6)0.0003 (6)
C90.0763 (12)0.0592 (10)0.1096 (14)0.0034 (8)0.0545 (10)0.0037 (9)
O20.1000 (9)0.0516 (6)0.1069 (8)0.0312 (6)0.0498 (7)0.0156 (6)
C100.0526 (7)0.0319 (6)0.0463 (6)0.0004 (5)0.0119 (5)0.0010 (5)
C110.0526 (7)0.0414 (7)0.0551 (7)0.0049 (5)0.0057 (5)0.0007 (5)
C120.0688 (8)0.0461 (7)0.0552 (7)0.0051 (6)0.0044 (6)0.0058 (6)
C130.0855 (10)0.0355 (6)0.0549 (7)0.0006 (6)0.0162 (7)0.0004 (5)
C140.0836 (10)0.0401 (8)0.0722 (9)0.0155 (7)0.0030 (8)0.0068 (6)
C150.0665 (8)0.0429 (7)0.0650 (8)0.0064 (6)0.0067 (6)0.0009 (6)
Geometric parameters (Å, º) top
S1—C21.7459 (12)C9—H9a0.95 (2)
S1—C61.7799 (15)C9—H9b0.96 (2)
C2—N31.2921 (17)C9—H9c0.94 (2)
C2—N71.3955 (17)C10—C111.3685 (16)
N3—C41.3672 (19)C10—C151.3739 (18)
C4—C51.344 (2)C11—C121.3824 (18)
C4—H40.98C11—H110.98
C5—C61.416 (2)C12—C131.3690 (19)
C5—H50.98C12—H120.98
C6—O11.2263 (16)C13—C141.367 (2)
N7—C81.4033 (18)C13—H130.98
N7—C101.4486 (15)C14—C151.389 (2)
C8—C91.496 (3)C14—H140.98
C8—O21.1997 (18)C15—H150.98
C2—S1—C6102.49 (6)C8—C9—H9c109.8 (15)
S1—C2—N3125.93 (10)H9a—C9—H9b114.6 (19)
S1—C2—N7118.02 (9)H9a—C9—H9c103 (2)
N3—C2—N7116.05 (11)H9b—C9—H9c115 (2)
C2—N3—C4121.39 (11)N7—C10—C11119.51 (10)
N3—C4—C5128.22 (14)N7—C10—C15119.74 (10)
N3—C4—H4117.18C11—C10—C15120.67 (11)
C5—C4—H4114.60C10—C11—C12119.61 (11)
C4—C5—C6123.38 (14)C10—C11—H11119.97
C4—C5—H5115.21C12—C11—H11120.41
C6—C5—H5121.41C11—C12—C13120.31 (12)
S1—C6—C5118.56 (10)C11—C12—H12120.39
S1—C6—O1114.74 (11)C13—C12—H12119.30
C5—C6—O1126.69 (14)C12—C13—C14119.84 (12)
C2—N7—C8123.42 (10)C12—C13—H13120.48
C2—N7—C10117.33 (10)C14—C13—H13119.68
C8—N7—C10118.90 (11)C13—C14—C15120.48 (13)
N7—C8—C9116.77 (13)C13—C14—H14118.92
N7—C8—O2121.11 (14)C15—C14—H14120.60
C9—C8—O2122.11 (15)C10—C15—C14119.05 (12)
C8—C9—H9a108.7 (15)C10—C15—H15120.11
C8—C9—H9b105.2 (14)C14—C15—H15120.83

Experimental details

Crystal data
Chemical formulaC12H10N2O2S
Mr246.3
Crystal system, space groupMonoclinic, P21/c
Temperature (K)300
a, b, c (Å)6.0696 (5), 18.0716 (9), 10.8780 (8)
β (°) 99.579 (10)
V3)1176.54 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.27
Crystal size (mm)0.31 × 0.23 × 0.15
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
27839, 4086, 2758
Rint0.039
(sin θ/λ)max1)0.747
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.119, 1.65
No. of reflections4086
No. of parameters164
No. of restraints?
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.33, 0.27

Computer programs: COLLECT (Hooft, 1998), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN, SHELXTL (Sheldrick, 1995), JANA2000 (Petricek & Dusek, 2000), DIAMOND (Brandenburg & Berndt, 1999), JANA2000.

 

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