Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802002726/dn6022sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802002726/dn6022Isup2.hkl |
CCDC reference: 182622
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.
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.
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.
Fig. 1. The molecular structure of (I) showing 50% probability displacement ellipsoids. H have been omitted for clarity. |
C12H10N2O2S | F(000) = 512 |
Mr = 246.3 | Dx = 1.39 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ybc | Cell parameters from 11369 reflections |
a = 6.0696 (5) Å | θ = 4.1–32.1° |
b = 18.0716 (9) Å | µ = 0.27 mm−1 |
c = 10.8780 (8) Å | T = 300 K |
β = 99.579 (10)° | Block, colourless |
V = 1176.54 (15) Å3 | 0.31 × 0.23 × 0.15 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 2758 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.039 |
Graphite monochromator | θmax = 32.1°, θmin = 4.1° |
ϕ and ω scans | h = −9→9 |
27839 measured reflections | k = −26→26 |
4086 independent reflections | l = −16→16 |
Refinement on F2 | Weighting 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) = 0.119 | Δρmax = 0.33 e Å−3 |
S = 1.65 | Δρmin = −0.27 e Å−3 |
4086 reflections | Extinction correction: B-C type 1 Lorentzian isotropic |
164 parameters | Extinction coefficient: 0.413964 |
H atoms treated by a mixture of independent and constrained refinement |
C12H10N2O2S | V = 1176.54 (15) Å3 |
Mr = 246.3 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 6.0696 (5) Å | µ = 0.27 mm−1 |
b = 18.0716 (9) Å | T = 300 K |
c = 10.8780 (8) Å | 0.31 × 0.23 × 0.15 mm |
β = 99.579 (10)° |
Nonius KappaCCD diffractometer | 2758 reflections with I > 2σ(I) |
27839 measured reflections | Rint = 0.039 |
4086 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 164 parameters |
wR(F2) = 0.119 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.65 | Δρmax = 0.33 e Å−3 |
4086 reflections | Δρmin = −0.27 e Å−3 |
x | y | z | Uiso*/Ueq | ||
S1 | 0.22543 (6) | 0.733745 (17) | 0.58282 (3) | 0.05627 (14) | |
C2 | 0.2524 (2) | 0.63925 (6) | 0.61524 (11) | 0.0442 (4) | |
N3 | 0.37751 (19) | 0.59342 (6) | 0.56705 (9) | 0.0518 (4) | |
C4 | 0.5097 (3) | 0.61647 (8) | 0.48423 (13) | 0.0599 (5) | |
C5 | 0.5336 (2) | 0.68528 (8) | 0.44156 (13) | 0.0578 (5) | |
C6 | 0.4144 (2) | 0.74718 (7) | 0.47600 (12) | 0.0520 (4) | |
O1 | 0.42375 (19) | 0.81081 (5) | 0.43808 (10) | 0.0698 (4) | |
N7 | 0.12890 (17) | 0.60939 (5) | 0.70061 (9) | 0.0460 (3) | |
C8 | −0.0078 (2) | 0.65187 (8) | 0.76539 (13) | 0.0556 (5) | |
C9 | −0.0940 (3) | 0.61469 (11) | 0.8707 (2) | 0.0772 (7) | |
O2 | −0.0488 (2) | 0.71535 (6) | 0.73850 (11) | 0.0824 (5) | |
C10 | 0.1646 (2) | 0.53204 (6) | 0.73286 (11) | 0.0432 (4) | |
C11 | 0.3467 (2) | 0.51184 (7) | 0.81798 (12) | 0.0501 (4) | |
C12 | 0.3742 (2) | 0.43867 (7) | 0.85436 (13) | 0.0574 (5) | |
C13 | 0.2189 (3) | 0.38676 (7) | 0.80678 (13) | 0.0581 (5) | |
C14 | 0.0388 (3) | 0.40703 (8) | 0.72054 (14) | 0.0664 (5) | |
C15 | 0.0100 (2) | 0.48024 (8) | 0.68232 (13) | 0.0602 (5) | |
H9a | 0.029 (4) | 0.6001 (13) | 0.931 (2) | 0.1225* | |
H9b | −0.191 (4) | 0.6503 (13) | 0.8996 (19) | 0.1225* | |
H9c | −0.162 (4) | 0.5693 (13) | 0.843 (2) | 0.1225* | |
H4 | 0.5997 | 0.5788 | 0.4509 | 0.0916* | |
H5 | 0.6408 | 0.6901 | 0.3839 | 0.0883* | |
H11 | 0.4562 | 0.5491 | 0.8529 | 0.0745* | |
H12 | 0.5051 | 0.4234 | 0.9141 | 0.0850* | |
H13 | 0.2362 | 0.3352 | 0.8337 | 0.0879* | |
H14 | −0.0701 | 0.3691 | 0.6866 | 0.0979* | |
H15 | −0.1174 | 0.4949 | 0.6199 | 0.0872* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0719 (3) | 0.03283 (19) | 0.0679 (2) | 0.00403 (14) | 0.02273 (17) | 0.00298 (13) |
C2 | 0.0508 (7) | 0.0347 (6) | 0.0463 (6) | 0.0018 (5) | 0.0060 (5) | −0.0004 (5) |
N3 | 0.0678 (7) | 0.0375 (6) | 0.0531 (6) | 0.0081 (5) | 0.0188 (5) | 0.0011 (4) |
C4 | 0.0733 (9) | 0.0532 (8) | 0.0568 (8) | 0.0114 (7) | 0.0216 (7) | 0.0029 (6) |
C5 | 0.0656 (9) | 0.0537 (8) | 0.0574 (8) | −0.0010 (6) | 0.0198 (6) | 0.0013 (6) |
C6 | 0.0560 (8) | 0.0429 (7) | 0.0557 (7) | −0.0096 (6) | 0.0050 (6) | 0.0008 (5) |
O1 | 0.0834 (7) | 0.0426 (6) | 0.0867 (7) | −0.0115 (5) | 0.0237 (6) | 0.0092 (4) |
N7 | 0.0524 (6) | 0.0328 (5) | 0.0541 (6) | 0.0032 (4) | 0.0126 (4) | 0.0006 (4) |
C8 | 0.0553 (8) | 0.0439 (8) | 0.0707 (8) | 0.0050 (6) | 0.0198 (6) | −0.0003 (6) |
C9 | 0.0763 (12) | 0.0592 (10) | 0.1096 (14) | 0.0034 (8) | 0.0545 (10) | 0.0037 (9) |
O2 | 0.1000 (9) | 0.0516 (6) | 0.1069 (8) | 0.0312 (6) | 0.0498 (7) | 0.0156 (6) |
C10 | 0.0526 (7) | 0.0319 (6) | 0.0463 (6) | 0.0004 (5) | 0.0119 (5) | −0.0010 (5) |
C11 | 0.0526 (7) | 0.0414 (7) | 0.0551 (7) | −0.0049 (5) | 0.0057 (5) | −0.0007 (5) |
C12 | 0.0688 (8) | 0.0461 (7) | 0.0552 (7) | 0.0051 (6) | 0.0044 (6) | 0.0058 (6) |
C13 | 0.0855 (10) | 0.0355 (6) | 0.0549 (7) | 0.0006 (6) | 0.0162 (7) | 0.0004 (5) |
C14 | 0.0836 (10) | 0.0401 (8) | 0.0722 (9) | −0.0155 (7) | 0.0030 (8) | −0.0068 (6) |
C15 | 0.0665 (8) | 0.0429 (7) | 0.0650 (8) | −0.0064 (6) | −0.0067 (6) | −0.0009 (6) |
S1—C2 | 1.7459 (12) | C9—H9a | 0.95 (2) |
S1—C6 | 1.7799 (15) | C9—H9b | 0.96 (2) |
C2—N3 | 1.2921 (17) | C9—H9c | 0.94 (2) |
C2—N7 | 1.3955 (17) | C10—C11 | 1.3685 (16) |
N3—C4 | 1.3672 (19) | C10—C15 | 1.3739 (18) |
C4—C5 | 1.344 (2) | C11—C12 | 1.3824 (18) |
C4—H4 | 0.98 | C11—H11 | 0.98 |
C5—C6 | 1.416 (2) | C12—C13 | 1.3690 (19) |
C5—H5 | 0.98 | C12—H12 | 0.98 |
C6—O1 | 1.2263 (16) | C13—C14 | 1.367 (2) |
N7—C8 | 1.4033 (18) | C13—H13 | 0.98 |
N7—C10 | 1.4486 (15) | C14—C15 | 1.389 (2) |
C8—C9 | 1.496 (3) | C14—H14 | 0.98 |
C8—O2 | 1.1997 (18) | C15—H15 | 0.98 |
C2—S1—C6 | 102.49 (6) | C8—C9—H9c | 109.8 (15) |
S1—C2—N3 | 125.93 (10) | H9a—C9—H9b | 114.6 (19) |
S1—C2—N7 | 118.02 (9) | H9a—C9—H9c | 103 (2) |
N3—C2—N7 | 116.05 (11) | H9b—C9—H9c | 115 (2) |
C2—N3—C4 | 121.39 (11) | N7—C10—C11 | 119.51 (10) |
N3—C4—C5 | 128.22 (14) | N7—C10—C15 | 119.74 (10) |
N3—C4—H4 | 117.18 | C11—C10—C15 | 120.67 (11) |
C5—C4—H4 | 114.60 | C10—C11—C12 | 119.61 (11) |
C4—C5—C6 | 123.38 (14) | C10—C11—H11 | 119.97 |
C4—C5—H5 | 115.21 | C12—C11—H11 | 120.41 |
C6—C5—H5 | 121.41 | C11—C12—C13 | 120.31 (12) |
S1—C6—C5 | 118.56 (10) | C11—C12—H12 | 120.39 |
S1—C6—O1 | 114.74 (11) | C13—C12—H12 | 119.30 |
C5—C6—O1 | 126.69 (14) | C12—C13—C14 | 119.84 (12) |
C2—N7—C8 | 123.42 (10) | C12—C13—H13 | 120.48 |
C2—N7—C10 | 117.33 (10) | C14—C13—H13 | 119.68 |
C8—N7—C10 | 118.90 (11) | C13—C14—C15 | 120.48 (13) |
N7—C8—C9 | 116.77 (13) | C13—C14—H14 | 118.92 |
N7—C8—O2 | 121.11 (14) | C15—C14—H14 | 120.60 |
C9—C8—O2 | 122.11 (15) | C10—C15—C14 | 119.05 (12) |
C8—C9—H9a | 108.7 (15) | C10—C15—H15 | 120.11 |
C8—C9—H9b | 105.2 (14) | C14—C15—H15 | 120.83 |
Experimental details
Crystal data | |
Chemical formula | C12H10N2O2S |
Mr | 246.3 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 300 |
a, b, c (Å) | 6.0696 (5), 18.0716 (9), 10.8780 (8) |
β (°) | 99.579 (10) |
V (Å3) | 1176.54 (15) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.27 |
Crystal size (mm) | 0.31 × 0.23 × 0.15 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27839, 4086, 2758 |
Rint | 0.039 |
(sin θ/λ)max (Å−1) | 0.747 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.119, 1.65 |
No. of reflections | 4086 |
No. of parameters | 164 |
No. of restraints | ? |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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.
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)°.