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

Li, W.; Yin, H.; Wen, L.; Cui, J.; Wang, D.

doi:10.1107/S1600536809038884

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2594

doi:10.1107/S1600536809038884

Open

access

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

Wenkuan Li,^a Handong Yin,^a ^* Liyuan Wen,^a Jichun Cui ^a and Daqi Wang ^a

^aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
^*Correspondence e-mail: handongyin@163.com

(Received 13 September 2009; accepted 25 September 2009; online 30 September 2009)

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 ). For hybridization, see: Beddoes et al. (1986 ).

Experimental

Crystal data

C₁₃H₁₂N₂O₂S
M_r = 260.31
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.117
S = 1.04
2236 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.24 e Å⁻³

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

Supporting information

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

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

(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

Computing details top

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

Figures top

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

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

Crystal data top

C₁₃H₁₂N₂O₂S	F(000) = 544
M_r = 260.31	D_x = 1.374 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2091 reflections
a = 8.0933 (11) Å	θ = 2.5–26.6°
b = 9.1406 (14) Å	µ = 0.25 mm⁻¹
c = 17.2077 (19) Å	T = 298 K
β = 98.720 (1)°	Block, colourless
V = 1258.3 (3) Å³	0.50 × 0.49 × 0.47 mm
Z = 4

Data collection top

Siemens SMART CCD area-detector diffractometer	2236 independent reflections
Radiation source: fine-focus sealed tube	1554 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −9→9
T_min = 0.884, T_max = 0.891	k = −10→8
6305 measured reflections	l = −20→18

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0456P)² + 0.5551P] where P = (F_o² + 2F_c²)/3
2236 reflections	(Δ/σ)_max < 0.001
164 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₃H₁₂N₂O₂S	V = 1258.3 (3) Å³
M_r = 260.31	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.0933 (11) Å	µ = 0.25 mm⁻¹
b = 9.1406 (14) Å	T = 298 K
c = 17.2077 (19) Å	0.50 × 0.49 × 0.47 mm
β = 98.720 (1)°

Data collection top

Siemens SMART CCD area-detector diffractometer	2236 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1554 reflections with I > 2σ(I)
T_min = 0.884, T_max = 0.891	R_int = 0.031
6305 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.04	Δρ_max = 0.20 e Å⁻³
2236 reflections	Δρ_min = −0.24 e Å⁻³
164 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.40181 (10)	0.62694 (9)	0.23706 (4)	0.0734 (3)
N1	0.5832 (2)	0.5184 (2)	0.14152 (12)	0.0558 (6)
N2	0.3056 (2)	0.4365 (2)	0.11652 (11)	0.0482 (5)
O1	0.0910 (2)	0.5044 (2)	0.18270 (11)	0.0663 (5)
O2	0.44903 (19)	0.23876 (18)	0.06204 (9)	0.0515 (4)
C1	0.4324 (3)	0.5174 (3)	0.15857 (14)	0.0479 (6)
C2	0.6825 (3)	0.6082 (3)	0.19276 (15)	0.0603 (7)
H2	0.7953	0.6217	0.1899	0.072*
C3	0.6079 (4)	0.6747 (4)	0.24650 (17)	0.0713 (8)
H3	0.6608	0.7387	0.2843	0.086*
C4	0.1397 (3)	0.4400 (3)	0.12897 (15)	0.0517 (6)
C5	0.0457 (3)	0.3538 (3)	0.06545 (14)	0.0491 (6)
C6	0.1552 (3)	0.3004 (3)	0.01772 (14)	0.0484 (6)
C7	0.3314 (3)	0.3506 (3)	0.04657 (13)	0.0463 (6)
H7	0.3668	0.4169	0.0075	0.056*
C8	−0.1242 (3)	0.3255 (3)	0.04990 (16)	0.0580 (7)
H8	−0.1971	0.3625	0.0819	0.070*
C9	−0.1811 (3)	0.2406 (3)	−0.01463 (18)	0.0677 (8)
H9	−0.2947	0.2200	−0.0265	0.081*
C10	−0.0725 (4)	0.1850 (3)	−0.06238 (18)	0.0689 (8)
H10	−0.1140	0.1277	−0.1056	0.083*
C11	0.0976 (3)	0.2142 (3)	−0.04631 (16)	0.0605 (7)
H11	0.1708	0.1764	−0.0780	0.073*
C12	0.4196 (4)	0.1366 (3)	0.12151 (17)	0.0682 (8)
H12A	0.3049	0.1023	0.1115	0.082*
H12B	0.4381	0.1833	0.1727	0.082*
C13	0.5357 (4)	0.0121 (3)	0.12016 (18)	0.0747 (9)
H13A	0.5135	−0.0360	0.0701	0.112*
H13B	0.5203	−0.0559	0.1610	0.112*
H13C	0.6488	0.0473	0.1286	0.112*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0675 (5)	0.0909 (6)	0.0664 (5)	0.0092 (4)	0.0252 (4)	−0.0195 (4)
N1	0.0455 (12)	0.0655 (14)	0.0595 (13)	0.0005 (10)	0.0185 (10)	−0.0066 (11)
N2	0.0414 (11)	0.0518 (12)	0.0558 (12)	0.0053 (9)	0.0216 (9)	0.0009 (10)
O1	0.0562 (11)	0.0790 (13)	0.0707 (12)	0.0133 (10)	0.0320 (9)	−0.0043 (10)
O2	0.0436 (9)	0.0534 (10)	0.0618 (10)	0.0085 (8)	0.0218 (8)	0.0015 (8)
C1	0.0495 (14)	0.0485 (14)	0.0489 (13)	0.0101 (11)	0.0179 (11)	0.0071 (11)
C2	0.0508 (15)	0.0687 (18)	0.0615 (16)	−0.0015 (13)	0.0088 (13)	−0.0059 (14)
C3	0.0709 (19)	0.082 (2)	0.0600 (17)	0.0074 (16)	0.0064 (14)	−0.0130 (16)
C4	0.0445 (14)	0.0542 (15)	0.0612 (15)	0.0114 (12)	0.0237 (12)	0.0133 (13)
C5	0.0424 (13)	0.0491 (14)	0.0590 (15)	0.0065 (11)	0.0177 (11)	0.0150 (12)
C6	0.0435 (14)	0.0473 (14)	0.0570 (15)	0.0023 (11)	0.0164 (11)	0.0109 (12)
C7	0.0408 (13)	0.0480 (14)	0.0536 (14)	0.0065 (11)	0.0183 (11)	0.0053 (11)
C8	0.0441 (15)	0.0623 (17)	0.0712 (18)	0.0083 (13)	0.0200 (13)	0.0185 (15)
C9	0.0441 (15)	0.076 (2)	0.084 (2)	−0.0033 (14)	0.0124 (14)	0.0152 (17)
C10	0.0607 (18)	0.0698 (19)	0.0747 (19)	−0.0109 (15)	0.0059 (14)	−0.0009 (16)
C11	0.0529 (16)	0.0644 (17)	0.0672 (17)	0.0014 (13)	0.0186 (13)	0.0014 (15)
C12	0.0670 (18)	0.0639 (18)	0.0779 (19)	0.0119 (14)	0.0242 (15)	0.0180 (15)
C13	0.078 (2)	0.0633 (19)	0.078 (2)	0.0156 (16)	−0.0028 (16)	0.0035 (16)

Geometric parameters (Å, º) top

S1—C3	1.708 (3)	C6—C11	1.377 (4)
S1—C1	1.729 (2)	C6—C7	1.509 (3)
N1—C1	1.298 (3)	C7—H7	0.9800
N1—C2	1.372 (3)	C8—C9	1.376 (4)
N2—C1	1.378 (3)	C8—H8	0.9300
N2—C4	1.392 (3)	C9—C10	1.388 (4)
N2—C7	1.478 (3)	C9—H9	0.9300
O1—C4	1.211 (3)	C10—C11	1.388 (4)
O2—C7	1.395 (3)	C10—H10	0.9300
O2—C12	1.432 (3)	C11—H11	0.9300
C2—C3	1.326 (4)	C12—C13	1.479 (4)
C2—H2	0.9300	C12—H12A	0.9700
C3—H3	0.9300	C12—H12B	0.9700
C4—C5	1.464 (4)	C13—H13A	0.9600
C5—C6	1.385 (3)	C13—H13B	0.9600
C5—C8	1.385 (3)	C13—H13C	0.9600

C3—S1—C1	88.22 (13)	O2—C7—H7	108.8
C1—N1—C2	109.8 (2)	N2—C7—H7	108.8
C1—N2—C4	124.5 (2)	C6—C7—H7	108.8
C1—N2—C7	121.80 (17)	C9—C8—C5	117.6 (2)
C4—N2—C7	113.3 (2)	C9—C8—H8	121.2
C7—O2—C12	115.58 (17)	C5—C8—H8	121.2
N1—C1—N2	122.4 (2)	C8—C9—C10	121.3 (3)
N1—C1—S1	115.1 (2)	C8—C9—H9	119.4
N2—C1—S1	122.52 (17)	C10—C9—H9	119.4
C3—C2—N1	116.0 (3)	C11—C10—C9	120.7 (3)
C3—C2—H2	122.0	C11—C10—H10	119.7
N1—C2—H2	122.0	C9—C10—H10	119.7
C2—C3—S1	111.0 (2)	C6—C11—C10	118.3 (2)
C2—C3—H3	124.5	C6—C11—H11	120.8
S1—C3—H3	124.5	C10—C11—H11	120.8
O1—C4—N2	124.2 (3)	O2—C12—C13	108.4 (2)
O1—C4—C5	129.8 (2)	O2—C12—H12A	110.0
N2—C4—C5	106.1 (2)	C13—C12—H12A	110.0
C6—C5—C8	121.7 (3)	O2—C12—H12B	110.0
C6—C5—C4	109.0 (2)	C13—C12—H12B	110.0
C8—C5—C4	129.3 (2)	H12A—C12—H12B	108.4
C11—C6—C5	120.4 (2)	C12—C13—H13A	109.5
C11—C6—C7	128.8 (2)	C12—C13—H13B	109.5
C5—C6—C7	110.8 (2)	H13A—C13—H13B	109.5
O2—C7—N2	114.23 (19)	C12—C13—H13C	109.5
O2—C7—C6	115.0 (2)	H13A—C13—H13C	109.5
N2—C7—C6	100.76 (17)	H13B—C13—H13C	109.5

Experimental details

Crystal data
Chemical formula	C₁₃H₁₂N₂O₂S
M_r	260.31
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	8.0933 (11), 9.1406 (14), 17.2077 (19)
β (°)	98.720 (1)
V (Å³)	1258.3 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.50 × 0.49 × 0.47

Data collection
Diffractometer	Siemens SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.884, 0.891
No. of measured, independent and observed [I > 2σ(I)] reflections	6305, 2236, 1554
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.117, 1.04
No. of reflections	2236
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.24

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Acknowledgements

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

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. CSD CrossRef Google Scholar
Gai, X., Grigg, R., Khamnaen, T., Rajviroongit, S., Sridharan, V., Zhang, L., Collard, S. & Keep, A. (2003). Tetrahedron Lett. 44, 7441–7443. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). SMART and SAINT. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar