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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 [sigma](C-C) = 0.002 Å
R = 0.029
wR = 0.083
Data-to-parameter ratio = 13.4
Details
Open access

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

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-H...O hydrogen bonds, in which O atoms serve as double or triple acceptors.

Related literature

For related literature, see: Allen et al. (1987[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 & Melzer (1979[Baloniak, S. & Melzer, E. (1979). Acta Pol. Pharm. 36, 147-154.]); Katrusiak et al. (2002[Katrusiak, A. A., Katrusiak, A., Baloniak, S. & Zielinska, K. (2002). Pol. J. Chem. 76, 45-56.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19N3O3

  • Mr = 301.34

  • Monoclinic, P 21

  • a = 5.6246 (6) Å

  • b = 8.8923 (6) Å

  • c = 15.0842 (10) Å

  • [beta] = 99.530 (7)°

  • V = 744.03 (11) Å3

  • Z = 2

  • Cu K[alpha] radiation

  • [mu] = 0.78 mm-1

  • T = 293 (2) K

  • 0.38 × 0.35 × 0.30 mm

Data collection
  • Kuma Diffraction KM-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.716, Tmax = 0.794

  • 2796 measured reflections

  • 2705 independent reflections

  • 2646 reflections with I > 2[sigma](I)

  • Rint = 0.025

  • 2 standard reflections every 100 reflections intensity decay: <2%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.029

  • wR(F2) = 0.082

  • S = 1.06

  • 2705 reflections

  • 202 parameters

  • 1 restraint

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.13 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]); 1249 Friedel pairs

  • Flack parameter: 0.07 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17A...O15 0.97 2.21 2.8636 (18) 124
C10-H10...O15i 0.93 2.53 3.3508 (19) 148
C14-H14C...O15i 0.96 2.53 3.419 (2) 155
C5-H5...O19ii 0.93 2.49 3.4124 (19) 174
C21-H21B...O19ii 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[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


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.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Katrusiak, A. A., Katrusiak, A., Baloniak, S. & Zielinska, K. (2002). Pol. J. Chem. 76, 45-56.  [ChemPort]
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.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2008). E64, o435  [ doi:10.1107/S1600536808000111 ]

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