1-Methyl-2-(4-methyl­phen­yl)-4-morpholinopyridazine-3,6(1H,2H)-dione

Gzella, A.; Melzer, E.; Kaczmarek, M.S.; Woźniak, Z.

doi:10.1107/S1600536808000111

Volume 64
Part 2
Page o435
February 2008

Received 17 December 2007
Accepted 2 January 2008
Online 11 January 2008

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R = 0.029
wR = 0.083
Data-to-parameter ratio = 13.4
Details

1-Methyl-2-(4-methylphenyl)-4-morpholinopyridazine-3,6(1H,2H)-dione

Andrzej Gzella,^a ^* Ewa Melzer,^a Michal S. Kaczmarek ^b and Zenon Wozniak ^b

^aDepartment of Organic Chemistry, Poznan University of Medical Sciences, ul. Grunwaldzka 6, 60-780 Poznan, Poland, and ^bOptics Division, Faculty of Physics, A. Mickiewicz University, ul. Umultowska 85, 61-614 Poznan, Poland
Correspondence e-mail: akgzella@ump.edu.pl

The structure analysis of the title compound, C₁₆H₁₉N₃O₃, has been undertaken in order to facilitate the interpretation of ¹H and ¹³C NMR data and to determine the position of the morpholine residue in this nucleophilic substitution product. The main result is that the morpholine group, with a chair conformation, is connected at the 4-position of the pyridazine ring. The benzene and pyridazine rings make a dihedral angle of 62.17 (5)°. Molecules are linked into a two-dimensional network by non-classical C-HO hydrogen bonds, in which O atoms serve as double or triple acceptors.

Related literature

For related literature, see: Allen et al. (1987); Baloniak & Melzer (1979); Katrusiak et al. (2002).

Experimental

Crystal data

C₁₆H₁₉N₃O₃
M_r = 301.34
Monoclinic, P 2₁
a = 5.6246 (6) Å
b = 8.8923 (6) Å
c = 15.0842 (10) Å
= 99.530 (7)°
V = 744.03 (11) Å³
Z = 2
Cu K radiation
= 0.78 mm^-1
T = 293 (2) K
0.38 × 0.35 × 0.30 mm

Data collection

Kuma Diffraction KM-4 diffractometer
Absorption correction: scan (North et al., 1968) T_min = 0.716, T_max = 0.794
2796 measured reflections
2705 independent reflections
2646 reflections with I > 2(I)
R_int = 0.025
2 standard reflections every 100 reflections intensity decay: <2%

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.082
S = 1.06
2705 reflections
202 parameters
1 restraint
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.13 e Å^-3
Absolute structure: Flack (1983); 1249 Friedel pairs
Flack parameter: 0.07 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C17-H17AO15	0.97	2.21	2.8636 (18)	124
C10-H10O15ⁱ	0.93	2.53	3.3508 (19)	148
C14-H14CO15ⁱ	0.96	2.53	3.419 (2)	155
C5-H5O19ⁱⁱ	0.93	2.49	3.4124 (19)	174
C21-H21BO19ⁱⁱ	0.97	2.52	3.3036 (18)	137
Symmetry codes: (i) $[-x+1, y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+2, y+{\script{1\over 2}}, -z]$ .

Data collection: KM-4 Software (Kuma, 1996 $[Kuma (1996). KM-4 User's Guide. Version 8.0.1. Kuma Diffraction, Wroclaw, Poland.]$ ); cell refinement: KM-4 Software; data reduction: KM-4 Software; 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: CF2177 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Baloniak, S. & Melzer, E. (1979). Acta Pol. Pharm. 36, 147-154.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.
Flack, H. D. (1983). Acta Cryst. A39, 876-881.
Katrusiak, A. A., Katrusiak, A., Baloniak, S. & Zielinska, K. (2002). Pol. J. Chem. 76, 45-56.
Kuma (1996). KM-4 User's Guide. Version 8.0.1. Kuma Diffraction, Wroclaw, Poland.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds