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Volume 69 
Part 11 
Pages o1617-o1618  
November 2013  

Received 28 September 2013
Accepted 2 October 2013
Online 5 October 2013

Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.006 Å
Disorder in main residue
R = 0.079
wR = 0.164
Data-to-parameter ratio = 14.2
Details
Open access

N-[2-(2,2-Di­methyl­propanamido)­pyrimidin-4-yl]-2,2-di­methyl­propanamide n-hexane 0.25-solvate hemihydrate

aFaculty of Technology and Chemical Engineering, University of Technology and Life Sciences, Seminaryjna 3, PL-85-326 Bydgoszcz, Poland,bDepartment of Chemistrycv5431, University of Jyväskylä, P.O. Box 35, FI-40014 Jyväskylä, Finland, and cStructural Chemistry and Crystallography Group, University of Lodz, Pomorska 163/165, PL-90-236 Lódz, Poland
Correspondence e-mail: lilach@uni.lodz.pl

The asymmetric unit of the title compound, C14H22N4O2·0.25C6H14·0.5H2O, contains two independent mol­ecules of 2,4-bis­(pivaloyl­amino)­pyrimidine (M) with similar conformations, one water mol­ecule and one-half n-hexane solvent mol­ecule situated on an inversion center. In one independent M mol­ecule, one of the two tert-butyl groups is rotationally disordered between two orientations in a 3:2 ratio. The n-hexane solvent mol­ecule is disordered between two conformations in the same ratio. The water mol­ecule bridges two independent M mol­ecules via O-H...O, N-H...O and O-H...N hydrogen bonds into a 2M·H2O unit, and these units are further linked by N-H...N hydrogen bonds into chains running in the [010] direction. Weak C-H...O inter­actions are observed between the adjacent chains.

Related literature

For the related structures of 2,4-bis­(acyl­oamino)­pyrimidines in the solid state and in solution, see: Osmialowski et al. (2012[Osmialowski, B., Kolehmainen, E., Ikonen, S., Valkonen, A., Kwiatkowski, A., Grela, I. & Haapaniemi, E. (2012). J. Org. Chem. 77, 9609-9619.]). For the related structures of 2,6-bis­(acyl­oamino)­pyridines, see: Osmialowski et al. (2010[Osmialowski, B., Kolehmainen, E., Gawinecki, R., Dobosz, R. & Kaupinen, R. (2010). J. Phys. Chem. A, 114, 12881-12887.]); Crane (2003[Crane, J. D. (2003). Acta Cryst. E59, o1854-o1855.]).

[Scheme 1]

Experimental

Crystal data
  • 2C14H22N4O2·0.5C6H14·H2O

  • Mr = 617.81

  • Triclinic, [P \overline 1]

  • a = 10.6055 (5) Å

  • b = 12.2181 (6) Å

  • c = 14.9774 (7) Å

  • [alpha] = 88.060 (3)°

  • [beta] = 73.093 (4)°

  • [gamma] = 74.179 (3)°

  • V = 1784.36 (16) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 123 K

  • 0.30 × 0.05 × 0.04 mm

Data collection
  • Bruker-Nonius KappaCCD diffractometer with an APEXII detector

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004[Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.]) Tmin = 0.977, Tmax = 0.997

  • 21621 measured reflections

  • 6422 independent reflections

  • 3597 reflections with I > 2[sigma](I)

  • Rint = 0.100

Refinement
  • R[F2 > 2[sigma](F2)] = 0.079

  • wR(F2) = 0.164

  • S = 1.04

  • 6422 reflections

  • 451 parameters

  • 101 restraints

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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1A...O8A 0.84 (2) 2.08 (2) 2.910 (3) 167 (4)
O1-H1A...N1A 0.84 (2) 2.51 (4) 2.958 (4) 115 (3)
O1-H1B...O8 0.83 (2) 2.13 (2) 2.943 (3) 168 (4)
O1-H1B...N1 0.83 (2) 2.48 (4) 2.931 (4) 115 (3)
N7-H7...N3Ai 0.88 (2) 2.32 (2) 3.144 (4) 156 (3)
N13-H13...O1 0.87 (2) 2.02 (2) 2.864 (4) 162 (4)
N7A-H7A...N3ii 0.87 (2) 2.16 (2) 2.958 (4) 152 (3)
N13A-H13A...O1 0.89 (2) 2.02 (2) 2.882 (4) 164 (4)
C5-H5...O14iii 0.95 2.37 3.205 (5) 147
Symmetry codes: (i) x, y+1, z; (ii) x, y-1, z; (iii) -x+1, -y+1, -z+1.

Data collection: COLLECT (Bruker, 2008[Bruker (2008). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR2004 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL2013 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: CV5431 ).


Acknowledgements

The financial support from the National Science Centre in Kraków (grant No. NCN204 356840) is gratefully acknowledged. Academy Professor Kari Rissanen is also gratefully acknowledged for financial support (Academy of Finland grant Nos. 122350, 140718, 265328 and 263256).

References

Bruker (2008). COLLECT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Crane, J. D. (2003). Acta Cryst. E59, o1854-o1855.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Osmialowski, B., Kolehmainen, E., Gawinecki, R., Dobosz, R. & Kaupinen, R. (2010). J. Phys. Chem. A, 114, 12881-12887.  [Web of Science] [PubMed]
Osmialowski, B., Kolehmainen, E., Ikonen, S., Valkonen, A., Kwiatkowski, A., Grela, I. & Haapaniemi, E. (2012). J. Org. Chem. 77, 9609-9619.  [PubMed]
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany.
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]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1617-o1618   [ doi:10.1107/S160053681302713X ]

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