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Volume 69 
Part 12 
Pages o1766-o1767  
December 2013  

Received 28 October 2013
Accepted 7 November 2013
Online 13 November 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.007 Å
Disorder in solvent or counterion
R = 0.047
wR = 0.157
Data-to-parameter ratio = 11.8
Details
Open access

5-Acetyl-4-(3-hy­droxy­phen­yl)-6-methyl-1,2,3,4-tetra­hydro­pyrimidin-2-one-tris­(hy­droxy­meth­yl)ammonium chloride (2/1)

aPG & Research Department of Chemistry, The New College (Autonomous), Chennai 600 014, Tamilnadu, India, and bDepartment of Physics, The New College (Autonomous), Chennai 600 014, Tamilnadu, India
Correspondence e-mail: mnizam_new@yahoo.in

The asymmetric unit of the title compound, 2C13H14N2O3·C3H10NO3+·Cl-, contains two independent mol­ecules (A and B) of the title pyrimidine derivative and one ion-pair of tris­(hy­droxy­meth­yl)ammonium chloride. The pyrimidine ring in each pyrimidine derivative has a half-chair conformation. Its mean plane is inclined to the benzene ring by 87.2 (3)° in mol­ecule A and 85.7 (2)° in mol­ecule B. In the crystal, the pyrimidine derivatives are connected to each other by N-H...O hydrogen bonds, forming chains propagating along the b-axis direction. The chains are linked via O-H-Cl hydrogen bonds, forming corrugated sheets lying parallel to the bc plane. The sheets are linked via C-H...O hydrogen bonds, forming a three-dimensional framework. The tris­(hy­droxy­meth­yl)ammonium chloride mol­ecules are located in the cages of the framework. There are also further C-H...O hydrogen bonds and C-H...[pi] inter­actions present in the three-dimensional framework structure. Both the cation and chloride anion of the tris­(hy­droxy­meth­yl)ammonium chloride ion pair are disordered over two positions, with a refined occupancy ratio of 0.418 (8):0.582 (8) for the cation and 0.71 (4):0.29 (4) for the anion.

Related literature

For the crystal structures of related pyrimidine derivatives, see: NizamMohideen et al. (2008a[Nizam Mohideen, M., Rasheeth, A., Huq, C. A. M. A. & Nizar, S. S. (2008a). Acta Cryst. E64, o1752.],b[Nizam Mohideen, M., Rasheeth, A. & Huq, C. A. M. A. (2008b). Acta Cryst. E64, o1812.]). For standard bond lengths, 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.]). For puckering parameters, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]). For asymmetry parameters, see: Nardelli (1983[Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.]). For graph-set analysis, 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
  • 2C13H14N2O3·C3H10NO3+·Cl-

  • Mr = 636.09

  • Orthorhombic, P n a 21

  • a = 15.7317 (7) Å

  • b = 7.2634 (12) Å

  • c = 28.8121 (3) Å

  • V = 3292.2 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.17 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.950, Tmax = 0.966

  • 27037 measured reflections

  • 5759 independent reflections

  • 4284 reflections with I > 2[sigma](I)

  • Rint = 0.038

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.157

  • S = 0.88

  • 5759 reflections

  • 489 parameters

  • 270 restraints

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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C8-C13 and C21-C26 rings, respectively.

D-H...A D-H H...A D...A D-H...A
N1-H1A...O4i 0.90 (3) 2.06 (4) 2.882 (6) 151 (4)
N2-H2A...O2ii 0.88 (2) 1.99 (3) 2.865 (5) 170 (5)
O3-H3...Cl1iii 0.82 2.26 3.044 (8) 161
N3-H3A...O5ii 0.87 (3) 1.97 (3) 2.839 (5) 175 (3)
N4-H4A...O1 0.88 (3) 2.03 (3) 2.836 (6) 152 (3)
O6-H6...Cl1 0.82 2.27 3.090 (7) 173
C13-H13...O1i 0.93 2.58 3.496 (7) 171
C18-H18B...O1iv 0.96 2.48 3.411 (7) 164
C22-H22...O4i 0.93 2.56 3.485 (6) 171
C28'-H28D...Cg1v 0.97 2.65 3.598 (17) 166
C27-H27A...Cg2vi 0.97 2.73 3.444 (19) 131
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) [-x+{\script{5\over 2}}, y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (iv) [x+{\script{1\over 2}}, -y-{\script{1\over 2}}, z]; (v) [-x+2, -y+1, z-{\script{1\over 2}}]; (vi) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z].

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); 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.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: SU2662 ).


Acknowledgements

The authors are grateful to the SAIF, IIT Madras, for the data collection.

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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [Web of Science]
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [Web of Science]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Nardelli, M. (1983). Acta Cryst. C39, 1141-1142.  [CrossRef] [IUCr Journals]
Nizam Mohideen, M., Rasheeth, A. & Huq, C. A. M. A. (2008b). Acta Cryst. E64, o1812.  [CSD] [CrossRef] [IUCr Journals]
Nizam Mohideen, M., Rasheeth, A., Huq, C. A. M. A. & Nizar, S. S. (2008a). Acta Cryst. E64, o1752.  [CSD] [CrossRef] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1766-o1767   [ doi:10.1107/S1600536813030559 ]

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