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Volume 69 
Part 5 
Page o778  
May 2013  

Received 20 March 2013
Accepted 17 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.051
wR = 0.158
Data-to-parameter ratio = 18.6
Details
Open access

3-Hydroxy-1-[(morpholin-4-yl)methyl]pyridazin-6(1H)-one

aDepartment of Chemistry, AVC College (Autonomous), Mannampandal 609 305, Tamilnadu, India,bDepartment of Chemistry, Government Arts College for Men (Autonomous), Nandanam, Chennai-35, Tamilnadu, India, and cCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C9H13N3O3, the morpholine ring adopts a chair conformation and its mean plane makes a dihedral angle of 68.00 (11)° with the pyridazine ring. The carbonyl O atom deviates from the plane of the pyridazine ring by 0.0482 (12) Å. An intramolecular C-H...O hydrogen bond occurs. In the crystal, molecules are linked by O-H...O and C-H...O hydrogen bonds, forming chains along [1-10].

Related literature

For the biological activity of morpholine derivatives, see: Lan et al. (2010[Lan, P., Chen, W. N., Xiao, G. K., Sun, P. H. & Chen, W. M. (2010). Bioorg. Med. Chem. Lett. 20, 6764-6772.]); Raparti et al. (2009[Raparti, V., Chitre, T., Bothara, K., Kumar, V., Dangre, S., Khachane, C., Gore, S. & Deshmane, B. (2009). Eur. J. Med. Chem. 44, 3954-3960.]). For a related structure, see: Wang et al. (2012[Wang, L.-J., Li, W.-W., Yang, S.-Y. & Yang, L. (2012). Acta Cryst. E68, o1235.]).

[Scheme 1]

Experimental

Crystal data
  • C9H13N3O3

  • Mr = 211.22

  • Triclinic, [P \overline 1]

  • a = 5.2110 (3) Å

  • b = 5.4165 (4) Å

  • c = 18.4544 (12) Å

  • [alpha] = 87.232 (2)°

  • [beta] = 83.993 (6)°

  • [gamma] = 80.862 (4)°

  • V = 511.18 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.979

  • 8839 measured reflections

  • 2530 independent reflections

  • 1679 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.051

  • wR(F2) = 0.158

  • S = 1.07

  • 2530 reflections

  • 136 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1...O2i 0.82 1.77 2.5777 (16) 167
C2-H2...O1ii 0.93 2.55 3.478 (2) 175
C5-H5A...O2 0.97 2.44 2.772 (2) 100
Symmetry codes: (i) x-1, y+1, z; (ii) -x, -y+1, -z.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2627 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS thanks the DST for an Inspire fellowship. The UGC (SAP-CAS) is acknowleged for departmental facilities.

References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lan, P., Chen, W. N., Xiao, G. K., Sun, P. H. & Chen, W. M. (2010). Bioorg. Med. Chem. Lett. 20, 6764-6772.  [CrossRef] [ChemPort] [PubMed]
Raparti, V., Chitre, T., Bothara, K., Kumar, V., Dangre, S., Khachane, C., Gore, S. & Deshmane, B. (2009). Eur. J. Med. Chem. 44, 3954-3960.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Wang, L.-J., Li, W.-W., Yang, S.-Y. & Yang, L. (2012). Acta Cryst. E68, o1235.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o778  [ doi:10.1107/S1600536813010477 ]

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