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

Hu, H.-L.; Wu, C.-J.; Yeh, C.-W.; Chen, J.-D.

doi:10.1107/S1600536812032102

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 (C-C) = 0.005 Å
R = 0.034
wR = 0.076
Data-to-parameter ratio = 11.8
Details

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

Hui-Ling Hu,^a Chia-Jun Wu,^a Chun-Wei Yeh ^a and Jhy-Der Chen ^a ^*

^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-HN hydrogen bonds, generating an R₂²(8) motif. The dimers are further connected through a C-BrO interaction [3.136 (1) Å and 169.31 (1)°] into a chain along [110]. Weak C-HN 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). For the conformation of related amides, see Forbes et al. (2001); Oertli et al. (1992); Lu et al. (2011a,b). For C-BrO interactions, see: Rowland & Taylor (1996).

Experimental

Crystal data

C₁₃H₁₀BrN₃O₃
M_r = 336.15
Triclinic, $[P \overline 1]$
a = 5.9398 (6) Å
b = 7.4137 (7) Å
c = 15.897 (2) Å
= 77.846 (9)°
= 81.613 (7)°
= 68.185 (9)°
V = 633.58 (12) Å³
Z = 2
Mo K radiation
= 3.26 mm^-1
T = 295 K
0.4 × 0.3 × 0.2 mm

Data collection

Siemens P4 diffractometer
Absorption correction: scan (XSCANS; Siemens, 1995) T_min = 0.953, T_max = 0.984
2880 measured reflections
2192 independent reflections
1841 reflections with I > 2(I)
R_int = 0.027
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F² > 2(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
_max = 0.30 e Å^-3
_min = -0.41 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N3-H3AN1ⁱ	0.84 (4)	2.14 (1)	2.98 (1)	175 (1)
C13-H13BN2ⁱⁱ	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); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); 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.
Lu, C.-H., Wu, C.-J., Yeh, C.-W. & Chen, J.-D. (2011a). Acta Cryst. E67, o1872.
Lu, C.-H., Wu, C.-J., Yeh, C.-W., Hu, H.-L. & Chen, J.-D. (2011b). Acta Cryst. E67, o1858.
Oertli, G., Meyer, W. R., Suter, U. W., Joho, F. B., Gramlich, V. & Petter, W. (1992). Helv. Chim. Acta, 75, 184-189.
Rowland, R. S. & Taylor, R. (1996). J. Phys. Chem. 100, 7384-7391.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.

organic compounds