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Volume 70 
Part 1 
Pages o1-o2  
January 2014  

Received 19 November 2013
Accepted 26 November 2013
Online 4 December 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.059
wR = 0.157
Data-to-parameter ratio = 16.4
Details
Open access

Ethyl 6-methyl-2-oxo-4-[4-(1H-tetra­zol-5-yl)phen­yl]-1,2,3,4-tetra­hydro­pyrimidine-5-carboxyl­ate-di­methyl­formamide-water (2/1/1)

aDepartment of Chemical Engineering, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China, and bDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
Correspondence e-mail: ouyanghuay@126.com

The asymmetric unit of the title compound, 2C15H16N6O3·C3H7NO·H2O, contains two independent ethyl 6-methyl-2-oxo-4-[4-(1H-tetra­zol-5-yl)phen­yl]-1,2,3,4-tetra­hydro­pyrim­id­ine-5-carboxyl­ate mol­ecules, in which the dihedral angles between the tetra­zole and benzene rings are 20.54 (12) and 12.13 (12)°. An intra­molecular C-H...O hydrogen bond occurs in each mol­ecule. In the crystal, N-H...O, N-H...N, O-H...O and O-H...N hydrogen bonds, as well as weak C-H...O and C-H...N hydrogen bonds, link the mol­ecules into a three-dimensional supra­molecular architecture. [pi]-[pi] stacking is also observed between parallel tetra­zole rings of adjacent mol­ecules, the centroid-centroid distance being 3.482 (6) Å.

Related literature

For applications of hydro­pyrimidine derivatives and related compounds, see: Atwal et al. (1990[Atwal, K. S., Rovnyak, G. C., Schwartz, J., Moreland, S., Hedberg, A., Gougoutas, J. Z., Malley, M. F. & Floyd, D. M. (1990). J. Med. Chem. A33, 1510-1515.]); Kappe & Stadler (2004[Kappe, C. O. & Stadler, A. (2004). Org. React., A63, 1-116.]).

[Scheme 1]

Experimental

Crystal data
  • 2C15H16N6O3·C3H7NO·H2O

  • Mr = 747.79

  • Triclinic, [P \overline 1]

  • a = 10.198 (2) Å

  • b = 13.262 (3) Å

  • c = 13.771 (3) Å

  • [alpha] = 81.14 (3)°

  • [beta] = 73.32 (3)°

  • [gamma] = 81.14 (3)°

  • V = 1750.9 (6) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.40 × 0.30 × 0.20 mm

Data collection
  • Rigaku Mercury2 diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.832, Tmax = 1.000

  • 18496 measured reflections

  • 7997 independent reflections

  • 5573 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.157

  • S = 1.12

  • 7997 reflections

  • 487 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.38 e Å-3

  • [Delta][rho]min = -0.29 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N5-H5A...O1W 0.86 1.80 2.646 (3) 170
N9-H9A...O7 0.86 1.82 2.683 (3) 176
N10-H10B...O2 0.86 1.98 2.801 (2) 160
N11-H11B...N2i 0.86 2.26 3.014 (3) 147
N12-H12A...O1 0.86 2.04 2.884 (2) 165
N13-H13B...O7ii 0.86 2.44 3.176 (3) 144
O1W-H1WA...N8ii 0.85 2.17 2.985 (3) 160
O1W-H1WB...O1iii 0.85 2.01 2.677 (2) 135
C5-H5D...O3 0.96 2.07 2.817 (3) 133
C16-H16A...O5 0.96 2.03 2.781 (3) 133
C26-H26A...O7 0.93 2.59 3.431 (3) 151
C32-H32A...N3iv 0.96 2.53 3.463 (4) 164
C33-H33A...N3iv 1.00 2.53 3.506 (3) 164
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y, -z+1; (iii) x, y, z-1; (iv) x+1, y-1, z+1.

Data collection: CrystalClear (Rigaku, 2005[Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: XU5754 ).


References

Atwal, K. S., Rovnyak, G. C., Schwartz, J., Moreland, S., Hedberg, A., Gougoutas, J. Z., Malley, M. F. & Floyd, D. M. (1990). J. Med. Chem. A33, 1510-1515.  [CSD] [CrossRef] [Web of Science]
Kappe, C. O. & Stadler, A. (2004). Org. React., A63, 1-116.
Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2014). E70, o1-o2   [ doi:10.1107/S1600536813032224 ]

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