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

Hui-Ling Hu; Chia-Jun Wu; Chun-Wei Yeh; Jhy-Der Chen

doi:10.1107/S1600536812032102

. 2012 Jul 18;68(Pt 8):o2497. doi: 10.1107/S1600536812032102

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

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

PMCID: PMC3414950 PMID: 22904937

Abstract

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 R ₂ ²(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 ▶). For the conformation of related amides, see Forbes et al. (2001 ▶); Oertli et al. (1992 ▶); Lu et al. (2011a ▶,b ▶). For C—Br⋯O interactions, see: Rowland & Taylor (1996 ▶).

Experimental

Crystal data

C₁₃H₁₀BrN₃O₃
M _r = 336.15
Triclinic,
a = 5.9398 (6) Å
b = 7.4137 (7) Å
c = 15.897 (2) Å
α = 77.846 (9)°
β = 81.613 (7)°
γ = 68.185 (9)°
V = 633.58 (12) Å³
Z = 2
Mo Kα radiation
μ = 3.26 mm⁻¹
T = 295 K
0.4 × 0.3 × 0.2 mm

Data collection

Siemens P4 diffractometer
Absorption correction: ψ scan (XSCANS; Siemens, 1995 ▶) T _min = 0.953, T _max = 0.984
2880 measured reflections
2192 independent reflections
1841 reflections with I > 2σ(I)
R _int = 0.027
3 standard reflections every 97 reflections intensity decay: none

Refinement

R[F ² > 2σ(F ²)] = 0.034
wR(F ²) = 0.076
S = 1.05
2192 reflections
186 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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 Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812032102/gw2122sup1.cif

e-68-o2497-sup1.cif^{(19.3KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812032102/gw2122Isup2.hkl

e-68-o2497-Isup2.hkl^{(107.7KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812032102/gw2122Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

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

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Symmetry codes: (i) Inline graphic ; (ii) .

Acknowledgments

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

supplementary crystallographic information

Comment

Several silver(I) complexes containg Methyl-4-(5-halopyrimidin-2-ylcarbamoyl)benzoate ligands have been reported, which show two-dimensional structures (Wu, et al., 2011). Within this project the crystal structure of the title compound was determined (Fig.1). The pyrimidyl and phenyl rings are not coplanar but twisted with an interplanar angle of 58.4 (1)°. Several C—O lengths are found in the title compound for amide [C5—O1 = 1.220 (4) Å] and methyl benzoate groups [C12—O3 = 1.200 (4), C12—O2 = 1.335 (4) and C13—O2 = 1.448 (4) Å], and the C—N—C angles in pyrimidyl group [C1—N1—C2 = 116.1 (3) and C1—N2—C4 = 116.5 (3)°] is smaller than that in amide group [C1—N3—C5 = 131.2 (3)°]. In its crystal structure intermolecular N—H···N hydrogen bonds are found (Tab. 1) and the molecules are also interlinked through C—Br···O van der Waals interactions [3.136 (1) Å and 169.31 (1) °] (Rowland et al., 1996). The weak C—H···N hydrogen bonds among the methyl benzoate and pyrimidyl rings are also found in the solid state (Fig. 2). In the crystal structure of the title compound the amide group adopts cis conformation with the H3A—N3—C5—O1 torsion angle of 14.8 (1) °, which is same as the chloro one (Lu, et al., 2011a). This conformation is different from that in the Ag complex, which is trans (Wu, et al., 2011; Lu, et al., 2011b).

Experimental

The title compound was prepared according to a published procedure (Wu et al., 2011). Block crystals suitable for X-ray crystallography were obtained by slow evaporization of the solvent from a solution of the title compound in methanol.