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Acta Crystallogr Sect E Struct Rep Online. 2009 October 1; 65(Pt 10): o2594.
Published online 2009 September 30. doi:  10.1107/S1600536809038884
PMCID: PMC2970224

3-Eth­oxy-2-(1,3-thia­zol-2-yl)isoindolin-1-one

Abstract

In the title compound, C13H12N2O2S, the dihedral angles between the isoindolone ring system and the thia­zole ring and the eth­oxy group are 6.50 (11) and 89.0 (2)°, respectively.

Related literature

For general background to isoindolin-1-one derivatives, see: Gai et al. (2003 [triangle]). For hybridization, see: Beddoes et al. (1986 [triangle]).

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Object name is e-65-o2594-scheme1.jpg

Experimental

Crystal data

  • C13H12N2O2S
  • M r = 260.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2594-efi1.jpg
  • a = 8.0933 (11) Å
  • b = 9.1406 (14) Å
  • c = 17.2077 (19) Å
  • β = 98.720 (1)°
  • V = 1258.3 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.25 mm−1
  • T = 298 K
  • 0.50 × 0.49 × 0.47 mm

Data collection

  • Siemens SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.884, T max = 0.891
  • 6305 measured reflections
  • 2236 independent reflections
  • 1554 reflections with I > 2σ(I)
  • R int = 0.031

Refinement

  • R[F 2 > 2σ(F 2)] = 0.042
  • wR(F 2) = 0.117
  • S = 1.04
  • 2236 reflections
  • 164 parameters
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809038884/bx2243sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809038884/bx2243Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We acknowledge financial support by the Natural Science Foundation of China (No. 20771053) and the Natural Science Foundation of Shandong Province (Y2008B48).

supplementary crystallographic information

Comment

The title compound, (I), was formed by accident, instead of the organotin compound containing schiff base which was expected. Isoindolin-1-one derivatives have been demonstrated to possess anxiolytic activity and are of interest as sedatives, hypnotics and muscle relaxants. In addition,the isoindolone moiety also features in anti-cancer drug candidates including protein kinase inhibitors(Gai et al. 2003). We have synthesized the title compound(I) and its crystal structure is reported herein.The molecular structure of (I) is shown in Fig.1. The dihedral angles between the isoindolone ring system and thiazole ring and oxyethyl group are 6.50 (11) and 89.0 (2)° respectively.The sum of bond angles around atom N1(359.6 °) indicates that the atom N1 is in sp2 hybridized state (Beddoes et al. 1986). The crystal packing is stabilized mainly by van der Waals interactions.

Experimental

(E)-2-((thiazol-2-ylimino)methyl)benzoic acid (4 mmol) and sodium ethoxide (4 mmol) were added to a stirred solution of ethanol (30 ml) in a Schlenk flask and stirred for 0.5 h. Chlorotriphenyltin (4 mmol) was then added to the reactor and the reaction mixture was heated under reflux for 6 h. The resulting clear solution was evaporated under vacuum. The product was crystallized from a mixed of dichloromethane/petroleum (1:1) to afford the title compound unexpectedly. Anal. Calcd (%) for C13H12N2O2S (Mr = 260.31): C, 59.98; H, 4.65; N, 10.76; O, 12.29; S, 12.32 Found (%): C, 60.00; H, 4.62; N, 10.74; O, 12.31; S, 12.30

Refinement

H atoms were positioned geometrically, with C—H = 0.93, 0.96, 0.97 and 0.98 Å for aromatic, methyl, methylene and methine H atoms, respectively, and constrained to ride on their parent atoms, with Uiso(H) = x Ueq(C) where x =1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

Fig. 1.
The molecular structure of the compound, showing 50% probability displacement ellipsoids. H atoms have been omitted for clarity.

Crystal data

C13H12N2O2SF(000) = 544
Mr = 260.31Dx = 1.374 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 2091 reflections
a = 8.0933 (11) Åθ = 2.5–26.6°
b = 9.1406 (14) ŵ = 0.25 mm1
c = 17.2077 (19) ÅT = 298 K
β = 98.720 (1)°Block, colourless
V = 1258.3 (3) Å30.50 × 0.49 × 0.47 mm
Z = 4

Data collection

Siemens SMART CCD area-detector diffractometer2236 independent reflections
Radiation source: fine-focus sealed tube1554 reflections with I > 2σ(I)
graphiteRint = 0.031
[var phi] and ω scansθmax = 25.1°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −9→9
Tmin = 0.884, Tmax = 0.891k = −10→8
6305 measured reflectionsl = −20→18

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0456P)2 + 0.5551P] where P = (Fo2 + 2Fc2)/3
2236 reflections(Δ/σ)max < 0.001
164 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = −0.24 e Å3

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

xyzUiso*/Ueq
S10.40181 (10)0.62694 (9)0.23706 (4)0.0734 (3)
N10.5832 (2)0.5184 (2)0.14152 (12)0.0558 (6)
N20.3056 (2)0.4365 (2)0.11652 (11)0.0482 (5)
O10.0910 (2)0.5044 (2)0.18270 (11)0.0663 (5)
O20.44903 (19)0.23876 (18)0.06204 (9)0.0515 (4)
C10.4324 (3)0.5174 (3)0.15857 (14)0.0479 (6)
C20.6825 (3)0.6082 (3)0.19276 (15)0.0603 (7)
H20.79530.62170.18990.072*
C30.6079 (4)0.6747 (4)0.24650 (17)0.0713 (8)
H30.66080.73870.28430.086*
C40.1397 (3)0.4400 (3)0.12897 (15)0.0517 (6)
C50.0457 (3)0.3538 (3)0.06545 (14)0.0491 (6)
C60.1552 (3)0.3004 (3)0.01772 (14)0.0484 (6)
C70.3314 (3)0.3506 (3)0.04657 (13)0.0463 (6)
H70.36680.41690.00750.056*
C8−0.1242 (3)0.3255 (3)0.04990 (16)0.0580 (7)
H8−0.19710.36250.08190.070*
C9−0.1811 (3)0.2406 (3)−0.01463 (18)0.0677 (8)
H9−0.29470.2200−0.02650.081*
C10−0.0725 (4)0.1850 (3)−0.06238 (18)0.0689 (8)
H10−0.11400.1277−0.10560.083*
C110.0976 (3)0.2142 (3)−0.04631 (16)0.0605 (7)
H110.17080.1764−0.07800.073*
C120.4196 (4)0.1366 (3)0.12151 (17)0.0682 (8)
H12A0.30490.10230.11150.082*
H12B0.43810.18330.17270.082*
C130.5357 (4)0.0121 (3)0.12016 (18)0.0747 (9)
H13A0.5135−0.03600.07010.112*
H13B0.5203−0.05590.16100.112*
H13C0.64880.04730.12860.112*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0675 (5)0.0909 (6)0.0664 (5)0.0092 (4)0.0252 (4)−0.0195 (4)
N10.0455 (12)0.0655 (14)0.0595 (13)0.0005 (10)0.0185 (10)−0.0066 (11)
N20.0414 (11)0.0518 (12)0.0558 (12)0.0053 (9)0.0216 (9)0.0009 (10)
O10.0562 (11)0.0790 (13)0.0707 (12)0.0133 (10)0.0320 (9)−0.0043 (10)
O20.0436 (9)0.0534 (10)0.0618 (10)0.0085 (8)0.0218 (8)0.0015 (8)
C10.0495 (14)0.0485 (14)0.0489 (13)0.0101 (11)0.0179 (11)0.0071 (11)
C20.0508 (15)0.0687 (18)0.0615 (16)−0.0015 (13)0.0088 (13)−0.0059 (14)
C30.0709 (19)0.082 (2)0.0600 (17)0.0074 (16)0.0064 (14)−0.0130 (16)
C40.0445 (14)0.0542 (15)0.0612 (15)0.0114 (12)0.0237 (12)0.0133 (13)
C50.0424 (13)0.0491 (14)0.0590 (15)0.0065 (11)0.0177 (11)0.0150 (12)
C60.0435 (14)0.0473 (14)0.0570 (15)0.0023 (11)0.0164 (11)0.0109 (12)
C70.0408 (13)0.0480 (14)0.0536 (14)0.0065 (11)0.0183 (11)0.0053 (11)
C80.0441 (15)0.0623 (17)0.0712 (18)0.0083 (13)0.0200 (13)0.0185 (15)
C90.0441 (15)0.076 (2)0.084 (2)−0.0033 (14)0.0124 (14)0.0152 (17)
C100.0607 (18)0.0698 (19)0.0747 (19)−0.0109 (15)0.0059 (14)−0.0009 (16)
C110.0529 (16)0.0644 (17)0.0672 (17)0.0014 (13)0.0186 (13)0.0014 (15)
C120.0670 (18)0.0639 (18)0.0779 (19)0.0119 (14)0.0242 (15)0.0180 (15)
C130.078 (2)0.0633 (19)0.078 (2)0.0156 (16)−0.0028 (16)0.0035 (16)

Geometric parameters (Å, °)

S1—C31.708 (3)C6—C111.377 (4)
S1—C11.729 (2)C6—C71.509 (3)
N1—C11.298 (3)C7—H70.9800
N1—C21.372 (3)C8—C91.376 (4)
N2—C11.378 (3)C8—H80.9300
N2—C41.392 (3)C9—C101.388 (4)
N2—C71.478 (3)C9—H90.9300
O1—C41.211 (3)C10—C111.388 (4)
O2—C71.395 (3)C10—H100.9300
O2—C121.432 (3)C11—H110.9300
C2—C31.326 (4)C12—C131.479 (4)
C2—H20.9300C12—H12A0.9700
C3—H30.9300C12—H12B0.9700
C4—C51.464 (4)C13—H13A0.9600
C5—C61.385 (3)C13—H13B0.9600
C5—C81.385 (3)C13—H13C0.9600
C3—S1—C188.22 (13)O2—C7—H7108.8
C1—N1—C2109.8 (2)N2—C7—H7108.8
C1—N2—C4124.5 (2)C6—C7—H7108.8
C1—N2—C7121.80 (17)C9—C8—C5117.6 (2)
C4—N2—C7113.3 (2)C9—C8—H8121.2
C7—O2—C12115.58 (17)C5—C8—H8121.2
N1—C1—N2122.4 (2)C8—C9—C10121.3 (3)
N1—C1—S1115.1 (2)C8—C9—H9119.4
N2—C1—S1122.52 (17)C10—C9—H9119.4
C3—C2—N1116.0 (3)C11—C10—C9120.7 (3)
C3—C2—H2122.0C11—C10—H10119.7
N1—C2—H2122.0C9—C10—H10119.7
C2—C3—S1111.0 (2)C6—C11—C10118.3 (2)
C2—C3—H3124.5C6—C11—H11120.8
S1—C3—H3124.5C10—C11—H11120.8
O1—C4—N2124.2 (3)O2—C12—C13108.4 (2)
O1—C4—C5129.8 (2)O2—C12—H12A110.0
N2—C4—C5106.1 (2)C13—C12—H12A110.0
C6—C5—C8121.7 (3)O2—C12—H12B110.0
C6—C5—C4109.0 (2)C13—C12—H12B110.0
C8—C5—C4129.3 (2)H12A—C12—H12B108.4
C11—C6—C5120.4 (2)C12—C13—H13A109.5
C11—C6—C7128.8 (2)C12—C13—H13B109.5
C5—C6—C7110.8 (2)H13A—C13—H13B109.5
O2—C7—N2114.23 (19)C12—C13—H13C109.5
O2—C7—C6115.0 (2)H13A—C13—H13C109.5
N2—C7—C6100.76 (17)H13B—C13—H13C109.5

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2243).

References

  • Beddoes, R. L., Dalton, L., Joule, T. A., Mills, O. S., Street, J. D. & Watt, C. I. F. (1986). J. Chem. Soc. Perkin Trans. 2, pp. 787–797.
  • Gai, X., Grigg, R., Khamnaen, T., Rajviroongit, S., Sridharan, V., Zhang, L., Collard, S. & Keep, A. (2003). Tetrahedron Lett 44, 7441–7443.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography