organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

2-(1-Benzo­thio­phen-2-yl)-4H-1,3,4-oxa­diazin-5(6H)-one

aChemical Engineering Department, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China, and bCollege of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China
*Correspondence e-mail: njutshs@126.com

(Received 27 November 2013; accepted 9 December 2013; online 14 December 2013)

In the title compound, C11H8N2O2S, the oxadiazinone ring is nearly planar [maximum deviation = 0.016 (4) Å], and is approximately coplanar with the benzo­thio­phene ring system [dihedral angle = 3.1 (5)°]. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming chains running along the b-axis direction.

Related literature

For applications of oxadiazin derivatives, see: De Sarro et al. (2005[De Sarro, G., Gitto, R., Russo, E., Ibbadu, G. F., Barreca, M. L., De Luca, L. & Chimirri, A. (2005). Curr. Top. Med. Chem. 5, 31-42.]); Shigeki et al. (2012[Shigeki, H., Koshi, U., Satoshi, N., Koki, K., Koichi, I., Yoshikiko, N., Osamu, T., Takahisa, H. & Masahiro, Y. (2012). J. Med. Chem. 55, 10584-10600.]).

[Scheme 1]

Experimental

Crystal data
  • C11H8N2O2S

  • Mr = 232.25

  • Monoclinic, P 21 /n

  • a = 7.4950 (15) Å

  • b = 6.0350 (12) Å

  • c = 22.412 (5) Å

  • β = 93.08 (3)°

  • V = 1012.3 (4) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.30 mm−1

  • T = 293 K

  • 0.30 × 0.20 × 0.10 mm

Data collection
  • Enraf–Nonius CAD-4 diffractometer

  • Absorption correction: ψ scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.915, Tmax = 0.970

  • 1999 measured reflections

  • 1848 independent reflections

  • 1167 reflections with I > 2σ(I)

  • Rint = 0.064

  • 3 standard reflections every 200 reflections intensity decay: 1%

Refinement
  • R[F2 > 2σ(F2)] = 0.064

  • wR(F2) = 0.192

  • S = 1.00

  • 1848 reflections

  • 145 parameters

  • 1 restraint

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1A⋯O2i 0.86 2.03 2.848 (5) 158
Symmetry code: (i) [-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{5\over 2}}].

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Noncompetitive α-amino-3-hydroxy-5-methyl-4-isoxazolepropanoic acid (AMPA) receptor antagonists have actively been explored, driven by the belief that such drugs would exercise effectiveness independent of glutamatelevels and the synaptic membrane polarization state, with minor influence on normal glutamatergic activity compared with competitive antagonists (De Sarro et al., 2005). Commercially available 2,4-diphenyl-4H-1,3,4-oxadiazin-5-one was selected as a suitable starting compound with a novel structure versus other HTS (high throughput screening) hit compounds and known noncompetitive AMPA antagonists (Shigeki et al., 2012). The title compound is a new oxadiazin compound with a similar structure to it. We synthesized it and report here its crystal structure.

The molecular structure of the title compound is shown in Fig. 1. The benzothiophene ring makes a dihedral angle of 3.1 (5)° to oxadiazin ring.

As shown in Figure 2, the molecules are linked by N—H···O and weak S···S (Table 1) bonds into a three-dimensional network, which consolidate the crystal packing.

Related literature top

For applications of oxadiazin derivatives, see: De Sarro et al. (2005); Shigeki et al. (2012).

Experimental top

N'-(2-chloroacetyl)benzo[b]thiophene-2-carbohydrazide (0.27 g, 1 mmol) was dissolved in 10 ml acetonitrile, after which potassium carbonate (0.28 g, 2.0 mmol) was added and the mixture was refluxed for 3 h under heating. The reaction solution was left and cooled to room temperature, evaporated, diluted with EtOAc, washed with water and brine, and then dried over MgSO4. After the drying agent was filtered off, the product was evaporated and the resulting crystalline residues were recrystallized from n-hexane and EtOAc to give the compound (0.19 g, 0.8 mmol, 80.0%) as a yellow crystal suitable for X-ray analysis.

Refinement top

H atoms were positioned geometrically, with N— H = 0.86 Å and C—H = 0.93, and 0.97 Å for aromatic and methylene H, respectively, and constrained to ride on their parent atoms, Uiso(H) = 1.2Ueq(C,N).

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme and displacement ellipsoids at the 30% probability level.
[Figure 2] Fig. 2. A packing diagram of (I). Intermolecular hydrogen bonds are shown as dashed lines.
2-(1-Benzothiophen-2-yl)-4H-1,3,4-oxadiazin-5(6H)-one top
Crystal data top
C11H8N2O2SF(000) = 480
Mr = 232.25Dx = 1.524 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 25 reflections
a = 7.4950 (15) Åθ = 9–12°
b = 6.0350 (12) ŵ = 0.30 mm1
c = 22.412 (5) ÅT = 293 K
β = 93.08 (3)°Block, colorless
V = 1012.3 (4) Å30.30 × 0.20 × 0.10 mm
Z = 4
Data collection top
Enraf–Nonius CAD-4
diffractometer
1167 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.064
Graphite monochromatorθmax = 25.4°, θmin = 1.8°
ω/2θ scansh = 09
Absorption correction: ψ scan
(North et al., 1968)
k = 07
Tmin = 0.915, Tmax = 0.970l = 2727
1999 measured reflections3 standard reflections every 200 reflections
1848 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.064Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.192H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.1P)2 + 0.650P]
where P = (Fo2 + 2Fc2)/3
1848 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.39 e Å3
1 restraintΔρmin = 0.39 e Å3
Crystal data top
C11H8N2O2SV = 1012.3 (4) Å3
Mr = 232.25Z = 4
Monoclinic, P21/nMo Kα radiation
a = 7.4950 (15) ŵ = 0.30 mm1
b = 6.0350 (12) ÅT = 293 K
c = 22.412 (5) Å0.30 × 0.20 × 0.10 mm
β = 93.08 (3)°
Data collection top
Enraf–Nonius CAD-4
diffractometer
1167 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.064
Tmin = 0.915, Tmax = 0.9703 standard reflections every 200 reflections
1999 measured reflections intensity decay: 1%
1848 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0641 restraint
wR(F2) = 0.192H-atom parameters constrained
S = 1.00Δρmax = 0.39 e Å3
1848 reflectionsΔρmin = 0.39 e Å3
145 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.66885 (16)0.2027 (2)0.99910 (5)0.0507 (4)
O20.8714 (5)0.7881 (6)1.23337 (14)0.0632 (10)
O10.8545 (5)0.7527 (5)1.07326 (14)0.0606 (10)
C10.6558 (5)0.2443 (8)0.92291 (17)0.0391 (10)
N10.7891 (5)0.5094 (6)1.17093 (15)0.0442 (9)
H1A0.76850.42641.20100.053*
C20.5909 (6)0.0894 (8)0.8802 (2)0.0491 (12)
H2B0.54960.04880.89170.059*
N20.7558 (5)0.4203 (6)1.11441 (15)0.0430 (9)
C30.5905 (6)0.1488 (9)0.8209 (2)0.0540 (13)
H3B0.54540.05080.79180.065*
C40.6552 (6)0.3490 (9)0.8041 (2)0.0555 (13)
H4A0.65660.38170.76360.067*
C50.7186 (6)0.5054 (8)0.84494 (19)0.0514 (12)
H5A0.75900.64270.83250.062*
C60.7203 (6)0.4501 (8)0.90646 (18)0.0429 (11)
C70.7809 (5)0.5961 (8)0.95690 (16)0.0371 (10)
H7A0.82560.73950.95500.044*
C80.7548 (5)0.4656 (7)1.00939 (17)0.0379 (10)
C90.7923 (5)0.5458 (7)1.07104 (17)0.0342 (9)
C100.8941 (6)0.8522 (7)1.13060 (19)0.0461 (11)
H10A0.82840.99031.13260.055*
H10B1.02040.88781.13410.055*
C110.8500 (6)0.7115 (8)1.18252 (19)0.0446 (11)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0665 (8)0.0529 (7)0.0334 (7)0.0047 (6)0.0096 (5)0.0009 (6)
O20.076 (2)0.082 (3)0.0322 (18)0.002 (2)0.0036 (15)0.0179 (18)
O10.104 (3)0.049 (2)0.0293 (18)0.0176 (18)0.0092 (17)0.0028 (14)
C10.038 (2)0.056 (3)0.024 (2)0.0058 (19)0.0081 (17)0.0047 (19)
N10.059 (2)0.052 (2)0.0225 (18)0.0017 (19)0.0104 (16)0.0012 (16)
C20.054 (3)0.057 (3)0.037 (3)0.001 (2)0.005 (2)0.006 (2)
N20.062 (2)0.043 (2)0.0248 (18)0.0046 (18)0.0097 (16)0.0007 (16)
C30.052 (3)0.078 (4)0.031 (2)0.012 (3)0.002 (2)0.013 (3)
C40.064 (3)0.079 (4)0.024 (2)0.019 (3)0.007 (2)0.003 (2)
C50.071 (3)0.051 (3)0.034 (3)0.013 (2)0.016 (2)0.008 (2)
C60.046 (2)0.053 (3)0.031 (2)0.009 (2)0.0105 (18)0.002 (2)
C70.0324 (19)0.060 (3)0.0186 (19)0.013 (2)0.0016 (15)0.0124 (19)
C80.049 (2)0.041 (2)0.024 (2)0.007 (2)0.0071 (17)0.0004 (18)
C90.042 (2)0.036 (2)0.026 (2)0.0013 (18)0.0036 (17)0.0014 (18)
C100.057 (3)0.046 (3)0.036 (2)0.005 (2)0.005 (2)0.007 (2)
C110.047 (2)0.058 (3)0.029 (2)0.012 (2)0.0056 (19)0.011 (2)
Geometric parameters (Å, º) top
S—C81.723 (5)C3—C41.363 (7)
S—C11.723 (4)C3—H3B0.9300
O2—C111.232 (5)C4—C51.382 (7)
O1—C91.333 (5)C4—H4A0.9300
O1—C101.435 (5)C5—C61.418 (6)
C1—C61.390 (6)C5—H5A0.9300
C1—C21.406 (6)C6—C71.485 (6)
N1—C111.323 (6)C7—C81.438 (6)
N1—N21.387 (5)C7—H7A0.9300
N1—H1A0.8600C8—C91.477 (5)
C2—C31.377 (6)C10—C111.492 (6)
C2—H2B0.9300C10—H10A0.9700
N2—C91.274 (5)C10—H10B0.9700
C8—S—C190.0 (2)C1—C6—C5118.9 (4)
C9—O1—C10118.7 (3)C1—C6—C7115.1 (4)
C6—C1—C2121.8 (4)C5—C6—C7125.9 (4)
C6—C1—S113.0 (3)C8—C7—C6104.4 (4)
C2—C1—S125.2 (4)C8—C7—H7A127.8
C11—N1—N2125.5 (4)C6—C7—H7A127.8
C11—N1—H1A117.3C7—C8—C9124.0 (4)
N2—N1—H1A117.3C7—C8—S117.5 (3)
C3—C2—C1117.8 (5)C9—C8—S118.6 (3)
C3—C2—H2B121.1N2—C9—O1128.1 (4)
C1—C2—H2B121.1N2—C9—C8118.8 (4)
C9—N2—N1115.5 (4)O1—C9—C8113.0 (3)
C4—C3—C2121.1 (5)O1—C10—C11114.6 (4)
C4—C3—H3B119.5O1—C10—H10A108.6
C2—C3—H3B119.5C11—C10—H10A108.6
C3—C4—C5122.5 (4)O1—C10—H10B108.6
C3—C4—H4A118.8C11—C10—H10B108.6
C5—C4—H4A118.8H10A—C10—H10B107.6
C4—C5—C6117.9 (5)O2—C11—N1123.6 (4)
C4—C5—H5A121.0O2—C11—C10119.0 (4)
C6—C5—H5A121.0N1—C11—C10117.4 (4)
C8—S—C1—C61.8 (3)C6—C7—C8—S0.0 (4)
C8—S—C1—C2179.4 (4)C1—S—C8—C71.0 (3)
C6—C1—C2—C30.9 (6)C1—S—C8—C9177.3 (3)
S—C1—C2—C3179.7 (3)N1—N2—C9—O11.6 (6)
C11—N1—N2—C91.8 (6)N1—N2—C9—C8178.0 (3)
C1—C2—C3—C41.7 (7)C10—O1—C9—N22.6 (7)
C2—C3—C4—C52.2 (7)C10—O1—C9—C8179.1 (4)
C3—C4—C5—C61.9 (7)C7—C8—C9—N2176.5 (4)
C2—C1—C6—C50.7 (6)S—C8—C9—N21.7 (5)
S—C1—C6—C5179.5 (3)C7—C8—C9—O10.4 (6)
C2—C1—C6—C7178.9 (4)S—C8—C9—O1178.6 (3)
S—C1—C6—C72.2 (4)C9—O1—C10—C113.3 (6)
C4—C5—C6—C11.1 (6)N2—N1—C11—O2177.0 (4)
C4—C5—C6—C7179.1 (4)N2—N1—C11—C102.8 (6)
C1—C6—C7—C81.4 (4)O1—C10—C11—O2176.5 (4)
C5—C6—C7—C8179.5 (4)O1—C10—C11—N13.4 (6)
C6—C7—C8—C9178.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.032.848 (5)158
Symmetry code: (i) x+3/2, y1/2, z+5/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O2i0.862.032.848 (5)158
Symmetry code: (i) x+3/2, y1/2, z+5/2.
 

Acknowledgements

The work was supported by Nanjing College of Chemical Technology, China (NHKY-2013–02).

References

First citationDe Sarro, G., Gitto, R., Russo, E., Ibbadu, G. F., Barreca, M. L., De Luca, L. & Chimirri, A. (2005). Curr. Top. Med. Chem. 5, 31–42.  Web of Science PubMed CAS
First citationEnraf–Nonius (1994). CAD-4 EXPRESS. Enraf–Nonius, Delft, The Netherlands.
First citationHarms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
First citationNorth, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.  CrossRef IUCr Journals Web of Science
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationShigeki, H., Koshi, U., Satoshi, N., Koki, K., Koichi, I., Yoshikiko, N., Osamu, T., Takahisa, H. & Masahiro, Y. (2012). J. Med. Chem. 55, 10584–10600.  Web of Science PubMed

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ISSN: 2056-9890
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