3-(4-Methyl­piperazin-1-yl)isobenzofuran-1(3H)-one3-Substituted phthalides. XXXVI.

Odabaşoğlu, M.; Büyükgüngör, O.

doi:10.1107/S1600536808008209

Volume 64
Part 5
Page o779
May 2008

Received 26 March 2008
Accepted 26 March 2008
Online 2 April 2008

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.037
wR = 0.091
Data-to-parameter ratio = 15.4
Details

3-(4-Methylpiperazin-1-yl)isobenzofuran-1(3H)-one¹

Mustafa Odabasoglu ^a and Orhan Büyükgüngör ^b ^*

^aDepartment of Chemistry, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Kurupelit Samsun, Turkey, and ^bDepartment of Physics, Faculty of Arts and Sciences, Ondokuz Mayis University, TR-55139 Kurupelit Samsun, Turkey
Correspondence e-mail: orhanb@omu.edu.tr

In the molecule of the title compound, C₁₃H₁₆N₂O₂, the phthalide ring system is virtually planar, with a dihedral angle between the fused five- and six-membered rings of 1.17 (4)°. The methylpiperazine ring adopts a chair conformation. In the crystal structure, intermolecular C-HO and C-HN hydrogen bonds link the molecules, generating edge-fused R₃³(17) ring motifs, to form a three-dimensional network.

Related literature

For a related structure, see: Odabasoglu & Büyükgüngör (2006). For ring motif details, see: Bernstein et al. (1995); Etter (1990). For ring conformation puckering parameters, see: Cremer & Pople (1975).

Experimental

Crystal data

C₁₃H₁₆N₂O₂
M_r = 232.28
Monoclinic, P 2₁ /c
a = 13.1442 (7) Å
b = 6.0567 (4) Å
c = 15.7845 (10) Å
= 104.022 (5)°
V = 1219.17 (13) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.56 × 0.49 × 0.37 mm

Data collection

Stoe IPDSII diffractometer
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) T_min = 0.952, T_max = 0.969
14223 measured reflections
2394 independent reflections
1890 reflections with I > 2(I)
R_int = 0.035

Refinement

R[F² > 2(F²)] = 0.036
wR(F²) = 0.091
S = 1.04
2394 reflections
155 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.11 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C8-H8O1ⁱ	0.98	2.69	3.6135 (18)	157
C10-H10AN2ⁱⁱ	0.97	2.60	3.5315 (17)	160
Symmetry codes: (i) x, y-1, z; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2441 ).

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayis University, Turkey, for the use of the Stoe IPDSII diffractometer (purchased under grant F.279 of the University Research Fund).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.
Etter, M. C. (1990). Acc. Chem. Res. 23, 120-126.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Odabasoglu, M. & Büyükgüngör, O. (2006). Acta Cryst. E62, o1879-o1881.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie, Darmstadt, Germany.

organic compounds

3-(4-Methylpiperazin-1-yl)isobenzofuran-1(3H)-one1