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Volume 69 
Part 7 
Page o1094  
July 2013  

Received 4 June 2013
Accepted 10 June 2013
Online 15 June 2013

Key indicators
Single-crystal X-ray study
T = 291 K
Mean [sigma](C-C) = 0.003 Å
R = 0.040
wR = 0.116
Data-to-parameter ratio = 16.0
Details
Open access

3-Methyl-2-(3,3,3-trichloro-2-hydroxypropyl)quinazolin-4(3H)-one

aS.Yunusov Institute of the Chemistry of Plant Substances, Academy of Sciences of Uzbekistan, Mirzo Ulugbek Str. 77, Tashkent 100170, Uzbekistan
Correspondence e-mail: raxul@mail.ru

The title molecule, C12H11Cl3N2O2, contains planar quinazolin-4(3H)-one (r.m.s. deviation = 0.0257 Å) and propyl fragments, forming a dihedral angle of 10.4 (2)°. An intramolecular O-H...N hydorgen bond occurs. In the crystal, O-H...O hydrogen bonds link the molecules into an infinite chain running parallel to the b axis.

Related literature

For the biological properties of quinazolin-4(3H)-one derivatives, see: Yang et al. (2009[Yang, X.-H., Chen, X.-B. & Zhou, S.-X. (2009). Acta Cryst. E65, o185-o186.]). For the fungicidal and insecticidal activity and syntheses of quinazolin-4(3H)-one derivatives, see: Shakhidoyatov (1988[Shakhidoyatov, Kh. M. (1988). Quinazolin-4-one and their biological activity., edited by M. S. Yunusov, S. R. Tulyaganov & M. M. Yunusov, p. 99. Tashkent: Fan.]). For related structures of quinazolin-4(3H)-one derivatives, see: Tashkhodjaev et al. (2001[Tashkhodjaev, B., Turgunov, K. K. & Shakhidoyatov, Kh. M. (2001). J. Struct. Chem. 42, 1040-1043.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C12H11Cl3N2O2

  • Mr = 321.58

  • Orthorhombic, P b c a

  • a = 9.3440 (19) Å

  • b = 11.352 (2) Å

  • c = 25.719 (5) Å

  • V = 2728.2 (10) Å3

  • Z = 8

  • Cu K[alpha] radiation

  • [mu] = 6.09 mm-1

  • T = 291 K

  • 0.23 × 0.20 × 0.18 mm

Data collection
  • Oxford Diffraction Xcalibur Ruby diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.284, Tmax = 0.334

  • 8631 measured reflections

  • 2833 independent reflections

  • 2273 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.040

  • wR(F2) = 0.116

  • S = 1.03

  • 2833 reflections

  • 177 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.34 e Å-3

  • [Delta][rho]min = -0.43 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O2-H2...N1 0.79 (3) 2.47 (3) 2.924 (2) 118 (3)
O2-H2...O1i 0.79 (3) 2.13 (3) 2.842 (2) 149 (3)
Symmetry code: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2009[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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: XP in SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PV2636 ).


Acknowledgements

We thank the Academy of Sciences of the Republic of Uzbekistan for supporting this study (grant FA-F7-T185).

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Shakhidoyatov, Kh. M. (1988). Quinazolin-4-one and their biological activity., edited by M. S. Yunusov, S. R. Tulyaganov & M. M. Yunusov, p. 99. Tashkent: Fan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Tashkhodjaev, B., Turgunov, K. K. & Shakhidoyatov, Kh. M. (2001). J. Struct. Chem. 42, 1040-1043.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Yang, X.-H., Chen, X.-B. & Zhou, S.-X. (2009). Acta Cryst. E65, o185-o186.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1094  [ doi:10.1107/S1600536813016073 ]

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