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Volume 68 
Part 8 
Page o2497  
August 2012  

Received 7 June 2012
Accepted 14 July 2012
Online 18 July 2012

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.005 Å
R = 0.034
wR = 0.076
Data-to-parameter ratio = 11.8
Details
Open access

Methyl 4-[N-(5-bromopyrimidin-2-yl)carbamoyl]benzoate

aDepartment of Chemistry, Chung-Yuan Christian University, Chung-Li 320, Taiwan
Correspondence e-mail: jdchen@cycu.edu.tw

In the title compound, C13H10BrN3O3, the pyrimidine and benzene rings are twisted with an interplanar angle of 58.4 (1)°. The secondary amide group adopts a cis conformation with an H-N-C-O torsion angle of 14.8 (1)°. In the crystal, molecules are connected into inversion dimers via pairs of N-H...N hydrogen bonds, generating an R22(8) motif. The dimers are further connected through a C-Br...O interaction [3.136 (1) Å and 169.31 (1)°] into a chain along [110]. Weak C-H...N hydrogen bonds between the methyl benzoate groups and pyrimidine rings are also observed in the crystal structure.

Related literature

For methyl-4-(5-bromopyrimidin-2-ylcarbamoyl)benzoate and its metal complexes, see: Wu et al. (2011[Wu, C.-J., Sie, M.-J., Hsiao, H.-L. & Chen, J.-D. (2011). CrystEngComm, 13, 4121-4130.]). For the conformation of related amides, see Forbes et al. (2001[Forbes, C. C., Beatty, A. M. & Smith, B. D. (2001). Org. Lett. 3, 3595-3598.]); Oertli et al. (1992[Oertli, G., Meyer, W. R., Suter, U. W., Joho, F. B., Gramlich, V. & Petter, W. (1992). Helv. Chim. Acta, 75, 184-189.]); Lu et al. (2011a[Lu, C.-H., Wu, C.-J., Yeh, C.-W. & Chen, J.-D. (2011a). Acta Cryst. E67, o1872.],b[Lu, C.-H., Wu, C.-J., Yeh, C.-W., Hu, H.-L. & Chen, J.-D. (2011b). Acta Cryst. E67, o1858.]). For C-Br...O interactions, see: Rowland & Taylor (1996[Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100, 7384-7391.]).

[Scheme 1]

Experimental

Crystal data
  • C13H10BrN3O3

  • Mr = 336.15

  • Triclinic, [P \overline 1]

  • a = 5.9398 (6) Å

  • b = 7.4137 (7) Å

  • c = 15.897 (2) Å

  • [alpha] = 77.846 (9)°

  • [beta] = 81.613 (7)°

  • [gamma] = 68.185 (9)°

  • V = 633.58 (12) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.26 mm-1

  • T = 295 K

  • 0.4 × 0.3 × 0.2 mm

Data collection
  • Siemens P4 diffractometer

  • Absorption correction: [psi] scan (XSCANS; Siemens, 1995[Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]) Tmin = 0.953, Tmax = 0.984

  • 2880 measured reflections

  • 2192 independent reflections

  • 1841 reflections with I > 2[sigma](I)

  • Rint = 0.027

  • 3 standard reflections every 97 reflections intensity decay: none

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.076

  • S = 1.05

  • 2192 reflections

  • 186 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.41 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...N1i 0.84 (4) 2.14 (1) 2.98 (1) 175 (1)
C13-H13B...N2ii 0.96 2.58 3.37 (1) 139
Symmetry codes: (i) -x+1, -y, -z+1; (ii) -x+1, -y+1, -z.

Data collection: XSCANS (Siemens, 1995[Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.]); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GW2122 ).


Acknowledgements

We are grateful to the National Science Council of the Republic of China for support.

References

Forbes, C. C., Beatty, A. M. & Smith, B. D. (2001). Org. Lett. 3, 3595-3598.  [ISI] [CSD] [CrossRef] [PubMed] [ChemPort]
Lu, C.-H., Wu, C.-J., Yeh, C.-W. & Chen, J.-D. (2011a). Acta Cryst. E67, o1872.  [CSD] [CrossRef] [details]
Lu, C.-H., Wu, C.-J., Yeh, C.-W., Hu, H.-L. & Chen, J.-D. (2011b). Acta Cryst. E67, o1858.  [CSD] [CrossRef] [details]
Oertli, G., Meyer, W. R., Suter, U. W., Joho, F. B., Gramlich, V. & Petter, W. (1992). Helv. Chim. Acta, 75, 184-189.  [CrossRef] [ChemPort]
Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100, 7384-7391.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Siemens (1995). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
Wu, C.-J., Sie, M.-J., Hsiao, H.-L. & Chen, J.-D. (2011). CrystEngComm, 13, 4121-4130.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o2497  [ doi:10.1107/S1600536812032102 ]

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